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The Volatile Oils Vol1 | E. Gildemeister



It is only within the last few decades that the former empiric manufacture of volatile oils has been placed on a scientific basis, which has enabled it to develop into an independent branch of chemical industry. During the period of transition in which this branch still finds itself, those factories which have done pioneer work, both scientifically and technically, as well as those which use the oils in various manufactures, are often compelled to suffer from the competition of inferior and adulterated products. As a matter of fact, the proper understanding of the estimation and appreciation of quality and purity of the much used volatile oils is not as common as is desirable for industry, commerce and the trades. The principal cause for this condition is the fact that the recent chemical investigations and their application to the arts have not yet been generally offered in suitable form...

TitleThe Volatile Oils Vol1
AuthorE. Gildemeister
PublisherJohn Wiley And Sons
Year1913
Copyright1913, E. Gildemeister
AmazonThe Volatile Oils
The Volatile Oils

The Volatile Oils Vol1

By E. Gildemeister.

Written under the auspices of the firm of Schimmel & Co., Miltitz Near Leipzig.

Authorized translation by Edward Kremers Madison, Wis.

First Volume. With Two Maps And Numerous Illustrations.

John Wiley And Sons, Inc., 432, Fourth Avenue, NEW YORK.

1913.

All rights reserved.

Schimmel & Co.'s Printing Office, Miltitz near Leipzig.

-Preface To The Second Edition
Eleven years have passed since the publication of the first edition. During this period enormous progress has been made, scientifically as well as practically, in the realm of the volatile oils. Numer...
-Preface
It is only within the last few decades that the former empiric manufacture of volatile oils has been placed on a scientific basis, which has enabled it to develop into an independent branch of chemica...
-Preface To The American Edition
In the work of Doctors Gildemeister and Hoffmann we find a happy blending of history with chemical science and technology that is quite unique in modern chemical literature. Moreover it covers a chapt...
-Historical Introduction. I. The Spice-Trade In Antiquity And During The Middle Ages
(With two maps.) Parts of plants as well as natural plant products which have been used since antiquity on account of their agreeable odor, their pleasant taste, or their medicinal virtue, enter the ...
-The Highways Of Comerce In Ancient Times
(Spicery and Grocery Trades inent Times and in the Middle Ages.) Bearbeitet v. Dr. Fr. Hoffmann. Druck v Rud.Loes, Leipzig Owing to the rise of the Persian empire, the inland commerce of wester...
-The Highways Of Comerce In Ancient Times. Continued
Arabian merchants also settled along the Malabar coast, in Ceylon and in the Indian sea ports. From the eighth to the tenth century, Daybal at the mouth of the Indus was the important commercial centr...
-II. General History Of The Volatile Oils
In the course of centuries various more or less independent branches have separated from the common trunk of natural science and have made a history of their own. This is true of the subject presented...
-II. General History Of The Volatile Oils. Part 2
J. F. Royle, An essay on the antiquity of Hindoo medicine. London 1837. Wallach and Heusinger, Das Altertum der indischen Medizin. Kassel 1839. p. 45. Allan Webb, The historical relations of ancient ...
-II. General History Of The Volatile Oils. Part 3
The principal works written by Dioscorides in the second half of the first century are the five books, of his De materia medica, also his Alexipharmaca et theriaca (Remedies against plant and animal p...
-II. General History Of The Volatile Oils. Part 4
With the development of the traditional knowledge, the Arabians also fostered the process of distillation in connection with the hermetic art2). As early as the fourth century, the 1) Gebri Summa per...
-II. General History Of The Volatile Oils. Part 5
It was during this earlier period of almost four centuries, devoted largely to medical research, that the Arabians acquired considerable skill in the art of distillation and the preparation of distill...
-II. General History Of The Volatile Oils. Part 6
1) Describuntur in hoc libro praeter alia, destillationis modus triplex, aquae, aceti et vini destillatio, alembici et cucurbitae quatuor generum, vitrei, fictiles vitro incrustati, plumbei et aerei ...
-II. General History Of The Volatile Oils. Part 7
In the same treatise Marcus Grascus also describes the distillation of turpentine oil from turpentine in an alembic.1) Supposing it to closely resemble the spirit of wine, he likewise designates it as...
-II. General History Of The Volatile Oils. Part 8
4) Raimundi Lulli Testamentum novissimum. In Mangets Bibliotheca chemica curiosa. Basiliae 1572. Vol. 1, p. 792 and 808. 5) Henrici Christiani Senckenberg Selecta juris et historiarum. Franco-furti 1...
-II. General History Of The Volatile Oils. Part 9
It was with the gradual introduction of printed books during the beginning of the sixteenth century, that the treatises of the past became more and more the common property of those versed in science ...
-II. General History Of The Volatile Oils. Part 10
Although, in all probability, the Indians, the Babylonians, and especially the Egyptians were acquainted with the art of distillation, also with volatile oils, a sharp distinction between true distill...
-II. General History Of The Volatile Oils. Part 11
Michael Schrick, Niitzlich Buchlein von Kunst und Tugend der ge-prenten Wassern. getruckt am 28. Mai zu Nurnberg 1517. New editions appeared in 1529 and 1601. By Hubertus Barlandius in Namur: Epistol...
-II. General History Of The Volatile Oils. Part 12
1) Liber de arte destillandi. Vol. I, vol. 18 and 19. Brunschwig was well acquainted with the preparation of spirit of wine, not only by the distillation of wine, but also by that of fermented honey (...
-II. General History Of The Volatile Oils. Part 13
The French translation which appeared in Paris in 1547 bears the title: Le del des philosophes ou secrets de la nature. Paris 1547. For the preparation of this spirit and that of a number of farfam...
-II. General History Of The Volatile Oils. Part 14
Under spike and lavender oils (fol. 186) he mentions that these oils are commonly imported from France in small bottles and sold at a high price.1) How little Ryff knew about the nature of volatile o...
-II. General History Of The Volatile Oils. Part 15
These Annotationes of Cordus are of special importance in the history of volatile oils, partly on account of the reputation of the author, partly because of his knowledge of the subject and also bec...
-II. General History Of The Volatile Oils. Part 16
Ander Theil des Schatzes Euonymi von allerhand kunstlichen und bewerten Qlen, wasseren und heymlichen Arzneyen, sampt ihrer ordentlichen bereytung und dienstlichen Figuren. Erstlich zusammen getragen ...
-II. General History Of The Volatile Oils. Part 17
For the distillation of the ethereal oil of flowers Philiatrus gives the following directions: 1) Ein kostlicher theurer Schatz etc. Edition of 1555, fol. 215-217. Die Bliimen der Spicken ode...
-II. General History Of The Volatile Oils. Part 18
This compilation, and still more his lectures on the materia medica of Dioscorides as well as his Historia Plantarum published in 1540, had established the fame of the young scholar. On one of his bot...
-Distilled Oils Known And In Use
2) Up to the beginning of the sixteenth century: The oils of benzoin, calamus, cedarwood, costus root, mastix, rose, rosemary, sage, spike, turpentine, juniperwood, frankincense, cinnamon. To These ...
-Distilled Oils Known And In Use. Part 2
Whereas during the period described above, aromatic waters were used for medicinal purposes in Europe and more particularly in Germany, in Asia fragrant drugs of vegetable and animal origin, also the ...
-Distilled Oils Known And In Use. Part 3
The distillation of pure volatile oils and the skill to mix them so as to produce agreeably fragrant mixtures, not only stimulated the improvement of methods of preparation, but also their extended us...
-Distilled Oils Known And In Use. Part 4
Glauber's views6) and those of his contemporaries were opposed by Hoffmann. He declared the employment of spiritus salis,') dilute sulphuric acid,8) potash, tartar and alum9) in the distillation of v...
-Distilled Oils Known And In Use. Part 5
3) Caspar Neumann's researches on volatile oils can be found in the second volume of his Chymia medica dogmatico-experimentalis, oder Grundliche mit Experimenten bewiesene Medizinsche Chemie. Publishe...
-Distilled Oils Known And In Use. Part 6
A better knowledge was attained by careful observation. Thus the crystalline deposits formed in some oils upon standing, also the congealing of certain oils at lower temperatures, which had been obser...
-Distilled Oils Known And In Use. Part 7
The first investigation suggested by the new theories that was of positive value, was the elementary analysis of turpentine oil made by Houtton-Labilliardiere.1) He found the ratio of carbon to hydrog...
-Distilled Oils Known And In Use. Part 8
Chemists now became especially interested in the action of hydrogen chloride on various terpenes and in the resulting hydrochlorides, some of which were solid, others liquid; also in the study of terp...
-Distilled Oils Known And In Use. Part 9
Of considerable importance in the further development of the chemistry of volatile oils are the investigations of Berthelot from 1852 to 1863, which involve principally the hydrocarbons contained in t...
-Distilled Oils Known And In Use. Part 10
In the same year, Tilden3) found that the hydrocarbon of turpentine oil combines with nitrosylchloride to form a well crystallizing compound. Together with Stenhouse, he applied this reaction to the t...
-Distilled Oils Known And In Use. Part 11
An important place in Wallach's researches is occupied by the successful efforts to unravel the isomeric complications so prevalent in the terpene group. Thus special investigations dealt with the stu...
-Distilled Oils Known And In Use. Part 12
Shortly after the appearance of Die atherischen Ole by E. Gildemeister and Fr. Hoffmann, a similar work in French was published by Charabot, Dupont and Pillet,11) another in English by E. ). Parry.12)...
-Obtaining Turpentine Oil
The oils obtained by the distillation of the oleoresins of various Abietineae were known to the ancients as cedar oil and later became known as turpentine oil. The oil as well as the resin, the colop...
-American Turpentine Oil
The enormous turpentine industry of the United States had its origin in the large pine forests of North and South Carolina, Georgia, and Alabama. Up to the middle of the last century the products of t...
-French Turpentine Oil
The production of turpentine in southwestern France, from Pinus pinaster, Solander, must have been in progress at a very early period.1) At least this is the inference drawn from petrified trunks of t...
-Turpentine Oil From Venetian (Larch) Turpentine
Larch turpentine was known to the Romans. It is mentioned in the writings of Vitruvius,1) a contemporary of Caesar, also in those of Dioscorides,2) Pliny,8) and Galen. During the middle ages, larch tu...
-Turpentine Oil From Canada Balsam
Canada balsam, which was probably long known to the American Indians and employed by them, is first mentioned in European reports of travel by Marc Lescarbot7) who traveled in Canada during the years ...
-Oil Of Cypress
Oil of cypress was known as early as 1672 (comp. p. 62). In 1892 it was recommended as a remedy against whooping cough by J. M. Bravo9) and since 1894 it has been distilled by Schimmel &Co. on a comme...
-Oil Of Juniper Berries
As Oleum de grant's Juniperi, oil of juniper berries was kept in stock in the Rathsapotheke of Braunschweig in 15212.) Its preparation is described by Valerius Cordus3) in 1546. The oil yield from th...
-Oil Of Savin
Savin was used medicinally and in veterinary practice by the Romans.1) It seems probable that the name Sabina has been derived from the mountainous country of the Sabines lying to the north-east of Ro...
-Lebanon Cedar Oil
According to Herodotus and Diodor the Egyptians used cedar oil in the embalming of the dead. Pliny also mentions an oleum cedrinum and its use in the preservation of dead bodies.1) The method of prepa...
-Andropogon (Cymbopogon) Oils
The aromatic grasses which at the present time yield a number of valuable volatile oils, such as palmarosa oil, ginger-grass oil, citronella oil, lemongrass oil and vetiver oil, have been used on acco...
-Calamus Oil
Both as spice and as medicament, calamus root is mentioned in the writings of antiquity. Thus it is mentioned in the Ayurvedas,3) in the Old Testament4) and in other of the earliest written documents....
-Saffron Oil
In the literature of antiquity saffron is frequently mentioned among the spices, also as medicament and dyestuff.7) During the Arabian period it was cultivated, especially in Persia8) and Spain.9) Its...
-Oil Of Zedoary
During the 6. and 7. centuries, zedoary is mentioned by Aetius, Paulus Aegineta and other writers as coming from India where it had been in use for a long time. In western Europe it became known towar...
-Oil Of Galangal
Galangal appears to have been used in China during antiquity. It is mentioned in the Ayur-Vedas of Susrutas,10) also by Plutarch.11) The Arabian physicians used it for medicinal purposes and thus, no ...
-Oil Of Cardamom
Cardamom, i. e. the capsular fruit of several species of Elettaria and Ammomum, (N. O. Zingiberaceae), indigenous in the islands of the East Indian archipelago, appears, to have been used during antiq...
-Oil Of Paradise Grains
The Grains of Paradise were formerly used extensively as a spice. In the apothecary shops they were known as Grana Paradisi, Semina Cardamom i major is, and as Piper Melegueta. Oil of paradise grains...
-Oil Of Pepper
Pepper is one of the oldest known spices mentioned in Sanskrit and ancient Indian literature. In the 4. century B. C. it is mentioned by Theophrastus.7) Dioscorides,8) and Pliny9) already distinguishe...
-Pepper Oil From Long Pepper
Long pepper was used in antiquity both as spice and as medicament. It is mentioned in a number of mediaeval drug lists.6) Presumably, however, it never was in general use and in recent times it has co...
-Oil Of Cubebs
Apparently cubebs were used as spice in China and in India during antiquity.8) As medicament they appear to have first been used by the Arabians.9) Kurdabah10) of Mesopotamia and Madusi11) of Bagdad, ...
-Oil Of Betel
When and by whom betel oil was first distilled is not known: it is highly probable that the preparation of the oil by Kemp1) in 1885 was not the first. A superficial examination of Siam betel oil in t...
-Oil Of Sweet Birch
Next to turpentine oil, the oils of sassafras, wintergreen and birch bark are among the first oils obtained by distillation in the United States. The similarity in odor and taste of birch bark oil wit...
-Oil Of Hops
As early as the middle ages hops were used for the aromatization of beer, being mentioned in literature since the 8. century.1) For medicinal purposes hops and their glands have been used only in more...
-Oil Of Sandalwood
Because of its peculiar odor sandalwood from Santalum album was highly prized during antiquity in India and China. Of the useful woods it was the most durable because it is avoided by the white ant th...
-Oil Of Ylang Ylang
It is only since the beginning of the sixties of the past century that ylang-ylang oil is being distilled in the island of Luzon, P. I. The first to take up this distillation was F. Steck3) a German a...
-Oils Of Mace And Nutmeg
Older literature contains no definite information pertaining to knowledge of or use made of nutmegs during antiquity. Statements, such as occur in the writings of Plautus, Scribonius Largus, Dioscorid...
-Oil Of Camphor
In China, camphor has been prepared and used in early antiquity. The first documental reference to it is found in the writings of the Arabian prince Imru-l-Kais of the sixth century;4) also in the Kor...
-Oils Of Cassia And Ceylon Cinnamon
The cassia bark of China and the cinnamon bark of the Indian archipelago are among the longest known and used spices. Cassia is mentioned in the earliest herbals and medical treatises of China,4) abou...
-Oil Of Sassafras
As already mentioned under the oils of sweet birch and wintergreen,8) next to turpentine oil, the oil of sassafras was the first volatile oil distilled in North America. On account of the pleasant aro...
-Oil Of Bayberry
In classical antiquity the laurel, Laurus nobilis, L., was utilized as symbol of victory and fame5) but found no other use than that of a decorative plant. During the middle ages its bark and leaves w...
-Oil Of Spoonwort
During the middle ages spoonwort was regarded as a remedy against scurvy. As such it is mentioned in older treatises on medicine and distillation. It was pictured in Joh. Wier's3) treatise on scrofula...
-Oil Of Mustard
Mustard seed was known during antiquity and was esteemed for one reason or another as becomes evident from the symbolic references made to it in the New Testament.5) It appears to have been utilized f...
-Oil Of Storax
Storax was known as a spice during antiquity and as such is mentioned by Herodotus,9) Theophrastus10) and Dioscorides.11) 1) Journ. f. prakt. Chem. 64 (1855), 504. - Liebig's Annalen 95 (1855), 128. ...
-Oil Of American Storax
Among the drugs from the new world, which received consideration in Europe after the discovery of America, there was an aromatic balsam derived from a tree named Ocosotl which was found in Mexico and ...
-Oil Of Rose
Since the earliest periods the charm and fragrance of the rose have led to its appreciation and use. This is shown by the entire older literature, and of all the flower perfumes that from the rose has...
-Oil Of Rose. Continued
4) See p. 64. 5) See p. 24. 6) Dozy, le Calendrier de Cordoue de I'annee 961. Leyden 1873. 7) Saladini Asculani Compendium aromatariorum. Venetii 1488. fol. 349. 8) L. Langles, Recherches sur la dec...
-Oil Of Bitter Almonds
Almonds were known during antiquity. They are mentioned several times in the Old Testament,2) also by Egyptian and by later Greek and Roman authors. Of the latter Theophrastus,3) Dioscorides,4) Scribo...
-Oil Of Cherry-Laurel
Cherry-laurel (Prunus laurocerasus, L.), appears to have become known in Europe toward the beginning of the 16. century. The aqueous distillate from the leaves has been used medicinally since the firs...
-Oil Of Rose Geranium
The pelargoniums which are indigenous to South Africa and which are now largely cultivated as decorative plants were introduced into Europe in 1690.5) Recluz6) of Lyon in 1819 first obtained a volatil...
-Oil Of Rue
Rue is mentioned in the Bible.1) As medicinal plant useful in the treatment of diseases of the eye, it is mentioned by Dios-corides,2) Pliny, Columella3) and Ovid.4) For like purposes the plant was us...
-Oil Of Buchu Leaves
Buchu leaves indigenous to southern Africa appear to have long been used for medicinal purposes. In 1820 they were introduced into European commerce/) having been brought from Cape Town to London. Sin...
-The Oils Of The Agrumen Fruits
The genus Citrus, belonging to the subfamily Aurantieee of the Rutaceae, is indigenous to Central Asia. The large number of varieties of the citrus fruits, known by the collective term of agrumen frui...
-The Oils Of The Agrumen Fruits. Continued
2) Limones, Citri et alia poma citrina . . . acidi seu pontici saporis quae poma orenges ab indigenis nuncupantur. Bongars, Gesta Dei per Francos. Hanoviae 1611, fol. 1099. 3) For the etymology of th...
-Oil Of Orange Flowers
Oil of orange flowers was known as early as the sixteenth century. Its distillation was described for the first time by Porta.1) About a century later, in the year 1680, it appears to have been made t...
-Oil Of Myrrh
The history of myrrh is inseparable from that of frankincense. Both come from the same countries. From early antiquity on, both have found like application in religious cults. In the commerce of the s...
-Oil Of Frankincense
Like its geographic source, so the history of frankincense coincides very nearly with that of myrrh. However, as a spice gum, it was chewed and for incense purposes it appears to have been used earlie...
-Oil Of Elemi
Statements supposed to pertain to elemi made during the period of the Romans are based largely on surmise.5) In Europe, elemi became known in the course of the 15. century,6) being used as an external...
-Oil Of Lignaloes
Fragrant woods from Mexico and French Guyana have been articles of commerce since the 18. century. They were named aloe wood because at first they were regarded as being identical with the older aloe ...
-Cascarilla Oil
It appears to have been in the first half of the 17. century that cascarilla bark was imported into Europe from the Bahama islands where the Croton Elutaria, Bennett is indigenous.1) The aborigines of...
-Oil Of Mastic
During antiquity mastic was used for fumigation, embalming and as a taste corrective for wine. With other spices used for like purposes, it is frequently mentioned in literature.1) During the middle a...
-Gurjun Balsam Oil
In India, gurjun balsam has been in use for a long time. The attention of Europeans was first directed to gurjun balsam by Franklin1) in 1811 and by Wm. Ainslie2) in 1813. Its source and method of pre...
-Oil Of Ladanum
The ladanum resin, used since antiquity6) as incense and embalming agent, is an exudation of the bush-like plants Cistus creticus, L, C. ladaniferus, L. and other species of the N. O. Cistaceae indige...
-Canella Oil
When first introduced into Europe from the new world, canella bark, from Canella alba, Murray, was regarded as a kind of cinnamon bark. Later is was confounded with other barks, more particularly with...
-Oil Of Cloves
With cinnamon, nutmeg and pepper, cloves belong to the oldest known spices. As such they are mentioned in Chinese, Indian and Sanscrit literature.1) Strange as it seems, they are, however, not referre...
-Oil Of Cajeput
Oil of cajeput appears not to have been brought to Europe until the beginning of the 17. century, when the Dutch took possession of the Moluccas. The first accurate account of the source of this oil w...
-Eucalyptus Oil
The oil of Eucalyptus piperita, Sm., is the oldest oil of eucalyptus leaves, being mentioned as early as 1790.5) In 1853 the botanist Ferdinand von Muller recommended to the Province of Victoria the d...
-Oil Of Coriander
The coriander plant, Coriandrum sativum, L., cultivated in many countries and in nearly all climates, was used as a kitchen spice even before the Christian Era.1) As such, coriander fruit is mentioned...
-Oil Of Cumin
During antiquity both the Roman or mother caraway of the Orient, Cuminum Cyminum, L., and the common caraway were used as spices. In literature, e. g. in the translations of the Bible, both have been ...
-Oil Of Celery Seed
Celery was known at the beginning of the Christian era.1) As a kitchen spice it is recommended in the Capitulare of Charlemagne 812,2) as a medicament by the abbess Hildegard3) in the early part of th...
-Oil Of Caraway
Like other related umbelliferous plants, caraway or Carum Carvi, L., has been cultivated in Europe and Asia since antiquity and used as a kitchen spice.4) With these other umbelliferous plants, and at...
-Oil Of Ajowan
Apparently ajowan3) was first brought to Europe in 1549.1) In 1693 it was used for medical purposes in London.5) In 1773 it is mentioned by Percival6) of England. ...
-Oil Of Anise
Anise is one of the spice plants known to, and used during, antiquity. It is mentioned in the Vedas and in the Bible.7) The cultivation of anise in Egypt and in the Island of Crete is recorded in the ...
-Oil Of Fennel
Fennel was known to the ancient Chinese, Indians and Egyptians who used it principally as kitchen spice. No mention is made of it in the translations of the Bible. It is frequently mentioned, however,...
-Oil Of Lovage
As a kitchen spice, and possibly also for medicinal purposes, lovage was cultivated and used by the Romans.7) Its cultivation north of the Alps was no doubt caused by Charlemagne's Capi-tulare of 812....
-Oil Of Angelica
Angelica appears to have first come into use as a spice plant during the 15. century,1) and was no doubt first used for the preparation of the distilled angelica water, the preparation of which is des...
-Oil Of Asa Fcetida
Asant or asa fcetida was used during antiquity as a spice and as a medicament. As such it is mentioned in Sanskrit and other writings, e. g. in the Susruta (Comp. p. 16). The Egyptians and Hebrews do ...
-Oil Of Galbanum
Oriential people, among them the Israelitis, first used gal-banum in incense offerings and for fumigations.8) It was known to Theophrastus9) and Virgil.10) Dioscorides11) and Pliny12) mention Syria a...
-Oil Of Gum Ammoniac
The air-hardened gumresin of Dorema ammoniacum, Don. (Peucedanum ammoniacum, H. Baillon) and of several species of Ferula, produced by the puncture of insects, was used during antiquity for incense, f...
-Oil Of Dill
Dill was known during antiquity.1) With other kitchen spices the dill plant is mentioned in Sanskrit literature, and in the Bible.-) Like that of fennel, anise, and caraway, its cultivation was early ...
-Oil Of Wintergreen
The distillation of oil of wintergreen5) was probably begun in the first decades of last century along with that of sassafras bark (p. 129) and birch bark (p. 118) in the states of Pennsylvania, New J...
-Oil Of Rosemary
Rosemary was greatly esteemed by the Greeks and Romans,2) and also by the Arabians.3) Like the laurel, rosemary was employed by the former as a decorative plant in religious rites and in hero cult. In...
-Oils Of Lavender And Spike
Originally the oily distillates from the several species of lavender were all designated spike oil. It was not until the close separieren und absundern mit einem fader/in und dasselbe fleiyssig behal ...
-Oils Of Lavender And Spike. Continued
3) Dioscoridis, De materia medica libri quinque. Editio Kuhn-Sprengel. 1829. Vol. 1, pp. 15, 17, 35, 40, 62, 508, 542. 4) Plinii Naturalis historiae libri XXXVII. 5) Scribonii Largi Compositiones me...
-Oil Of Sage
Sage appears to have been used as a medicinal herb at the time of the Romans8) and was one of the plants recommended by Charlemagne for cultivation.9) In the Destillirbuch by Brun-schwig of 1500 a d...
-Oil Of Balm
On account of its fragrance, balm was cultivated by the Greeks, Romans, and Arabs,11) and during the middle ages in Italy, Germany12) and Scandinavia.13) 1) Brunschwig, Liber de arte destillandi. De ...
-Oil Of Hyssop
In antiquity hyssop was already included among the spice plants.5) The word Ysop, used by Luther in his translation of the Bible, did not apply to hyssop but to Origanum6) The volatile oil thereof w...
-Oil Of Thyme
As a kitchen spice thyme was used during antiquity.7) Theo-phrastus, Dioscorides, Pliny and Columella8) mention thyme and distinguish it from wild thyme or Thymus Serpyllum, whereas the two were not a...
-Mentha Oils
Several mints, the botanical identity of which it may be impossible to establish, were known during antiquity, being used as kitchen spice,5) possibly also as medicament by the Egyptians,6) Hebrews7) ...
-Oil Of Peppermint
Whether or not peppermint was among the mints used during the middle ages can no longer be determined. In the oldest German treatise on distillation the Liber de arte distil/and/6) of the year 1500, t...
-Oil Of European Pennyroyal
European pennyroyal (Ger. Pole/) is derived from Mentha pulegium, L., (Pulegium vulgare, Mill.) or its hybrid varieties, and has been used medicinally since the middle ages3) and possibly earlier.4) T...
-Oil Of Sweet Basil
Oil of sweet basil appears to have been in use during the middle of the 16. century. It is enumerated among the oils of the Frankfurt price ordinance for 1582 and in the Dispensatorium Nor/cum of 1589...
-Oil Of Valerian
During antiquity valerian was known as Phu. It is described in the writings of Dioscorides6) and Pliny. Later it is mentioned as a remedy by Isaac Judaeus1) and Constantinus Africanus,-) who are the f...
-Oil Of Nardostachys Jatamansi
The rhizomes of Nardostachys /atamansi, D. C, (Patrinia Jatamansi, Wallich) and of N grandiflora, D. C, (N. O. Valeri-anacead) which are indigenous to the Himalaya mountains of northern India have an...
-Oil Of Elecampane
Aqueous distillates of elecampane were used medicinally during the middle ages.5) Oleum radicis helenii is first mentioned in the Frankfurt ordinance of 1582. ...
-Oil Of Roman Chamomile
Owing to the similarity of some of the species of Anthemis, Chrysanthemum and Matricaria, it can not longer be determined which were cultivated by the Greeks and Romans and used by them. Nor is it pos...
-Oil Of German Chamomile
The common chamomile, Matricaria Chamomilla, L., was used medicinally by the Greeks and Romans, and is repeatedly referred to in classical literature.3) It was also highly valued during the middle age...
-Oil Of Tansy
The distilled water from the flowers and leaves of tansy was a common remedy during the 16. and 17. centuries.4) The oil is first mentioned in the price ordinance of Frankfurt-on-the-Main for 1582 and...
-Oil Of Wormwood
Wormwood is supposed to have been known to the Egyptians as early as the 16. century B. C.6) In the Old Testament the plant is referred to repeatedly.7) Whether the plant known to the ancients and lat...
-Oil Of Costus Root
Costus root from Saussurea Lappa, Clarke, was known to the Greeks as xooTog. During antiquity it was used as a spice, also in the preparation of a fragrant oil, for purposes of anointmerit,1) similar ...
-IV. History Of The Methods Of Distillation And Of Distilling Apparatus
The literary documents considered in the previous chapter reveal the slow process of evolution leading up to a better understanding of the subject of volatile oils. In like manner, a short historical ...
-Methods Of Distillation And Of Distilling Apparatus. Part 2
As the prototype of a common flask, the figure of an ostrich2) is given (fig. 5); as that of a retort a goose (fig. 6) or a pelican3) (fig. 7). The shape of a bear served for a still (cuc-urbita)4) an...
-Methods Of Distillation And Of Distilling Apparatus. Part 3
Diweil die Geister, so uber sich get He ben werden, vil reyner und subtiler seind, denn in solchem aufsteigen alles, so schwer, irdisch oder flegmatisch ist, nit hinauf kom-men mag. Darumb die Geyster...
-Methods Of Distillation And Of Distilling Apparatus. Part 4
About the middle of the 16. century, Walter Ryff in his treatise on distillation1) describes and illustrates distilling apparatus with condensing tubes which are passed through vessels of cold water. ...
-Methods Of Distillation And Of Distilling Apparatus. Part 5
For the destillatio per descensum on a small scale, glass vessels heated from the side (fig. 30) were also employed, and for some easily distilled substances even the heat of the sun (destillatio sol ...
-Methods Of Distillation And Of Distilling Apparatus. Part 6
1) Valerii Cordi Annotationes in Pedacei Dioscoridis de Materia medica libros quinque. Liber de artificiosis extraction/bus. Liber II. De destillatione oleorum. Anno dei 1540. p. 229. How confused we...
-Methods Of Distillation And Of Distilling Apparatus. Part 7
Fulle einen glasernen Kolben voll mit Cinnamomum oder anderem Holz, Samen, Macis etc. und giesse darauf so viel Spiritus salis,2) dass es das lignum bedecke, setze solchen mit einem alembic in das San...
-Methods Of Distillation And Of Distilling Apparatus. Part 8
One of the better distilling apparatus used for the distillation of volatile oils in the 18. century consisted of a tin or copper body suspended in a water bath, and provided with a Mohren-kopf (fig. ...
-Methods Of Distillation And Of Distilling Apparatus. Part 9
Still another separating vessel has been devised for this same purpose. The bulging flask contracts to a narrow neck, to the middle of which is attached a bill-like tube. The oil mixed with water is ...
-Methods Of Distillation And Of Distilling Apparatus. Part 10
Beginning about the middle of the past century the earlier, simple apparatus took on a different shape in the factories of this larger industry of the volatile oils. The original small distilling appa...
-The Production Of Flower Perfumes By Extraction, Enfleurage, And Maceration
The most common method for the production of volatile oils is that by steam distillation. This method not only produces the best yields and the purest oils, but also enables the operator to attain the...
-A. Extraction With Volatile Solvents
The first to suggest the use of volatile solvents for the extraction of flowers was Robiquet. In a paper2) contributed in 1835 he points out that some plants, such as jonquil, jasmine, heliotrope, and...
-A. Extraction With Volatile Solvents. Continued
2. The systematic extraction of the flowers. The extractors of the mounted extraction batteries are cylindrical vessels, varying in size, but usually of about 500 liter capacity. They contain 3 or 4 l...
-Description Of Garmier's Apparatus For The Extraction Of Flowers
Figures 58 to 60 illustrate an apparatus constructed by Gamier1) for the extraction of flowers. It consists of a stationary outer cylinder, (figs. 58 and 59) which at 2 is provided with a manhole that...
-B. Extraction With Non-Volatile Solvents
1. Without the aid of heat: absorption or enfleurage a froid. The absorption method, known as enfleurage, applied to those flowers which continue to produce volatile oil even after they have been rem...
-Pneumatic Method
In the course of time a number of so called improvements of the enfleurage process have been tried, however, with but little or no success. Best known of these is the pneumatic method of A. Piver.2)...
-Natural And Artificial Perfumes
The volatile oils are widely distributed in the vegetable kingdom, more particularly among the phanerogams. However, volatile oils have also been isolated from several of the cryptogams. In most case...
-Natural And Artificial Perfumes. Continued
When exposed to low temperatures, a number of oils deposit one or more of their constituents in crystalline form. Some oils, like rose oil, contain crystals even at ordinary temperature, others, like ...
-A. Aliphatic Hydrocarbons
The lowest member of the limit series of hydrocarbons CnH2n + 2 which has been found in volatile oils is the normal heptane, C7H16 (b. p. 98,5 to 99; d15o 0,6880). In addition to minimal amounts...
-Ocimene
This aliphatic terpene is isomeric with myrcene. It differs from the latter, presumably, in the position of the double bonds. It was discovered by van Romburgh in the oil of Ocimum Basili-cum. Possibl...
-B. Aromatic Hydrocarbons
From the oil of the mammoth fir, Sequoia gigantea, Lunge and Steinkauler 1) obtained a hydrocarbon C13H10 which they named sequoiene. It consists of laminar crystals, with a reddish fluorescence, that...
-C. Alicyclic Hydrocarbons
The principal hydrocarbons occurring in volatile oils are alicyclic. The composition of by far the greater number is represented by the formula C10H16, hence they belong to that class of the terpenes ...
-C. Alicyclic Hydrocarbons. Part 2
VI. Synthesis with the aid of Grignards reaction. VII. Ring-formation accompanied by dehydration. a) from aliphatic terpene alcohols: Linalool -- Dipentene3) and Terpinene3) Geraniol -...
-C. Alicyclic Hydrocarbons. Part 3
/-rt-Pinene has been found in coriander oil, lemon oil, cumin oil, American peppermint oil, and oil of Levant wormseed. a-Pinene has frequently been found in other oils, but its optical rotation has ...
-C. Alicyclic Hydrocarbons. Part 4
In the presence of water and oxygen, pinene yields pinol hydrate (sobrerol) C10H18O2, which is at times found in old turpentine oils as a crystalline deposit. The active modifications of pinol hydrate...
-C. Alicyclic Hydrocarbons. Part 5
As the nitrosochlorides of different terpenes show very similar melting points and besides decompose very readily, they are less suitable for characterization than the nitrolamines, which are very sta...
-Sabinene
This hydrocarbon, which resembles ,B-pinene in some respects, has thus far been found in the oils of savin, Ceylon cardamom, marjoran and pilea. The following constants have been recorded: B. p. 16...
-Camphene
Although camphene is the only solid hydrocarbon C10H16 which occurs in Nature, its isolation in a crystalline state from volatile oils has been accomplished but rarely. In this form /-camphene has b...
-Fenchene
A positive proof for the occurrence of fenchene in volatile oils has not yet been brought. The inference of its presence in terpene fractions boiling about 160 has been drawn from the formation o...
-Isofenchene
The Isofenchene obtained by Bertram and Helle6) from Isofenchyl alcohol was recognized byWallach7) as D-d-fenchene. 1) Wallach, Liebig's Annalen 300 (1898), 313. 2) Wallach, Ibidem 302 (1898), 376....
-Limonene
Limonene is a very widely distributed terpene. It is found in volatile oils, not only in the dextrogyrate and laevogyrate modifications, but also in the racemic modification, which is called dipente...
-Dipentene
The optically inactive form of limonene, the dipentene, has been found frequently in nature, though not as commonly as limonene. It must also be born in mind that the dipentene identified may have b...
-Terpinolene
Thus far this terpene has been obtained by synthetical means only, although Clover1) claims to have found it in a Manila elemi oil, observing at the same time a gradual inversion into dipentene. Rec...
-Terpinene
Until very recently our knowledge of the occurrence of te-pinene was very limited. Besides the dihalogen addition product, also yielded by other terpenes, the addition product of nitrous acid was th...
-Phellandrene
and Phellandrene belongs to those hydrocarbons C10H16 that are widely distributed. In nature it occurs in several modifications. According to Wallach1), phellandrene is defined as a hydrocarbon ...
-Sesquiterpenes
In addition to the terpenes C10H16, the higher boiling fractions of many volatile oils, viz., those between 250 and 280, contain hydrocarbons corresponding to the formula C15H24 which have been n...
-Aliphatic Sesquiterpenes
To this group there possibly belongs the light sesquiterpene which was isolated by Schimmel & Co.1) from Ceylon citronella oil and which possesses the following properties: B. p. under atmospheric ...
-Monocyclic Sesquiterpenes. Bisabolene
Bisabolene was first found by Tucholka2) in Bisabol myrrh oil. The same name was given later to sesquiterpenes which had originally been known by other designations, but which had been found to be ide...
-Zingiberene
This sesquiterpene, first found by Tresh2) in ginger oil, was later examined by v.Soden and Rojahn,3) also bySchreinerand Kremers.4) The last mentioned investigators ascertained the following constant...
-Cadinene
The best known representative of this subgroup as of the group of the sesquiterpenes in general is the cadinene, which is widely distributed and which occurs in both optical modifications. 1) Berl. B...
-Caryophyllene
A second well characterized hydrocarbon, which belongs to the bicyclic group of sesquiterpenes, is the caryophyllene. However, it is not as common as cadinene. Up to the present time it has been found...
-Selinene
While investigating the highest boiling fractions of celery seed oil, Ciamician and Silber3) found a sesquiterpene which, however, they did not further characterize. When this sesquiterpene was later ...
-Humulene
This sesquiterpene, which was first discovered by Piccard, and which up to the present time has been found only in oil of hops and oil of poplar buds, closely resembles caryophyllene. Thus far the att...
-Santalene
In addition to the two santalols, East Indian sandalwood oil contains two sesquiterpenes, a- and B-santalene, so named by Guerbet.1) a-Santalene shows the following properties: B. p. 252 to 252,5...
-Caparrapene
Caparrapene is a sesquiterpene which has been obtained by Tapia5) by the action of dehydrating agents on caparrapiol, a sesquiterpene alcohol occurring in the volatile oil from caparrapi-balsam. The h...
-Guajene
Upon dehydrating guajol, a new sesquiterpene alcohol isolated by Schimmel & Co.1) from guajac wood oil, with zinc chloride, Wallach and Tuttle2) obtained a new sesquiterpene the properties of which di...
-Cedrene
The term cedrene was originally applied to a sesquiterpene obtained by the dehydration of cedrol.2) Upon finding a similar sesquiterpene in oil of cedar, this likewise was designated cedrene. In as mu...
-Cloven e
Upon dehydration with zinc chloride or phosphorus pent-oxide of the caryophyllene alcohol, obtained by hydration of the the hydrocarbon, Wallach1) secured the clovene, a sesquiterpene thus far not fou...
-Heerabolene
A sesquiterpene, probably tricyclic, has been found in Heer-abol myrrh oil by O. v. Friedrichs3) and designated heerabolene by him. B. p. 130 to 136 (16 mm.); d20o0,943; aD1412'; nD20o1,512...
-Heveene
This sesquiterpene is obtained, together with isoprene and dipentene, upon the destructive distillation of caoutchouc or gutta percha.4) Thus, 5 ko. of para caoutchouc5) yield about 1) Liebig's Annal...
-Aliphatic Alcohols
Of the monatomic alcohols of the saturated or methane series but few representatives have thus far been found in volatile oils. In the free state they are found but rarely and then only the lower homo...
-Linalool
or Linalool, the licareol of Barbier, which is more or less widely distributed and which occurs in both optical modifications, constitutes the bulk of lignaloe oil. The Mexican lignaloe oils cont...
-Geraniol
Isomeric with linalool is geraniol C10H18O which is distinguished from the former by its optical inactivity, higher boiling point and higher specific gravity. It is the lemonol of Barbier and Bouv...
-Geraniol. Continued
In the cold geraniol is scarcely acted upon by alkalies. When heated with concentrated alcoholic potassa to 150, there is formed, according to Barbier,9) a tertiary alcohol C9H180 while carbon di...
-Nerol
This alcohol which is stereoisomeric with geraniol was found in 1902 in neroli oil3) in which it occurs principally as acetate. Furthermore, nerol has been found in the oils of petitgrain, rose, Mexic...
-Citronellol
or (The rhodinol of Barbier?) Citronellol, C10H20O, was first obtained by Dodge3) by the reduction of citronellal from citronella oil. The citronellol thus prepared like the aldehyde from which it...
-Citronellol. Continued
Pure citronellol is a colorless oil with an agreable, rose-like odor, but finer than that of geraniol. According to its method of formation it reveals slight variations in its physical properties. Wal...
-Benzyl alcohol. C6H5CH2OH
This alcohol, which is of importance because of its application in perfumery, has been found as such in the oils of tuberose, ylang-ylang, jasmin, cloves and of cassie flowers (Acacia Farnesiana and A...
-Phenylethyl Alcohol
C6 H5 CH2 CH2 OH. Phenylethyl alcohol, which is used in the preparation of artificial volatile oils, has been observed as constituent of the leaf oil of Pinus halepensis, of oil of ro...
-Phenylpropyl Alcohol
. C6 H6 CH2 CH2 CH2 OH. As cinnamic acid ester, normal phenylpropyl alcohol has been found in several resins and balsams, e. g. in Sumatra benzoes, in Oriental and American st...
-Cinnamic Alcohol. C6H5CH:CHCH2OH
Cinnamic alcohol, formerly also designated styrone, is found in volatile oils, not as such, but as ester. As acetate it occurs in cassia oil; as cinnamate (styracin) in storax, also in the oils of hya...
-Dihydrocuminic alcohol
This alcohol, the constitution of which has not yet been definitely determined, was recently found in the laboratory of Schimmel & Co.,2) to occur free and as ester, also in both optical modifications...
-A-Terpineol
By the action of dilute sulphuric acid on terpin hydrate (see p. 384) the liquid terpineol of commerce results. This, however, is not a chemical unit, but a mixture of isomeric compounds C10H18O, am...
-A-Terpineol. Continued
Inactive modifications Active modifications Melting point 35 37 to 38 Nitrosochloride 112 to 113 107 108 Nitrolpipe...
-B-Terpineol
As already mentioned under a-terpineol, B-terpineol results together with a-terpineol when terpin hydrate is acted upon by dilute acids. Thus far B-terpineol has not been found in volatile oils. Sch...
-Y-Terpineol
y-Terpineol has not yet been found in nature. v. Baeyer3) obtained it by reducing tribrom-l,4,8-terpane, which in time he had obtained by brominating dipentene dihydrobromide. It also results when ...
-Terpinenol-1
This alcohol also has not yet been found in volatile oils. Of interest is its occurrence in the first fraction of commercial liquid terpineol.1) Synthetically it was prepared by Wallach2) from v-iso...
-Terpinenol-4
This alcohol which in its general characteristics closely resembles a-terpineol, is derived from terpinene. It has been discovered only recently. In nature it has been found in the oils of juniper, ...
-Terpinhydrate
From the theoretical and historical points of view, terpin-hydrate is an important compound. But technically also it is of importance as the material from which terpineol is made. (Comp. p. 375.) It...
-Dihydrocarveol
Dihydrocarveol, C10H18O, has only recently been found in caraway oil.1) Artificially prepared it has been known for a longer period. Thus it has been prepared from carvone by reduction with sodium a...
-Isopulegol
Isopulegol, C10H18O, has not yet been found in volatile oils. It results from citronellal when this is treated with acids. The observation made by Schimmel & Co.3) viz., when the oil of Barosma pulc...
-Menthol
Menthol (peppermint camphor), C10H20O, is found in the peppermint oils of which the laevogyrate menthol constitutes the principal constituent. The oil of Hyptis suaveolens also consists in large par...
-Sabinol
Sabinol, C10H16O, is contained in oil of savin partly free, partly as acetate. Presumably it also occurs in oil of cypress. The constants of sabinol from oil of savin are as follows: B. p. 210 to ...
-Pinocarveol
This dicyclic alcohol, the constitution of which is probably correctly expressed by the above formula, occurs in all probability in the last fractions of the oil of Eucalyptus Globulus.1) Artificial...
-Myrtenol
Myrtenol, C10H16O, is the name applied by v. Soden and Elze3) to an alcohol which they found, mostly as acetic ester, in oil of myrtle. Its acid phthalic ester melts at 116 from which the alco...
-Borneol
As such borneol, C10H18O, is found in both optically active modifications, as ester mostly in the laevogyrate modification. Borneo camphor from Dryobanalops Camphora is (d-borneol, Ngai camphor (or ...
-Isoborneol
This alcohol which results together with borneol upon reduction of camphor, and which, according to the latest views, is regarded as stereoisomeric with borneol, can also be obtained upon hydration of...
-Thujyl alcohol
Thujyl alcohol (tanacetyl alcohol), C10H18O, occurs in oil of wormwood, in part as such, in part as esters of acetic, valeric and possibly also of palmitic acids. Artificially it was obtained by Semm...
-Fenchyl alcohol
Fenchyl alcohol, to which Semmler has assigned the above formula, has thus far been found but once in a volatile oil,8) namely in the oil obtained by steam distillation from the stumps of the yellow...
-Aliphatic Sesquiterpene Alcohols
Nerolidol, C15H260, has been found in the high-boiling fractions of orange blossom oil. B. p. 276 to 277, 128 to 129 (6 mm.); d0,880; aD + 1332/.1) While it itself possesses but a fai...
-Dicyclic Sesquiterpene Alcohols
Santalols, C16H240. The principal component of East Indian sandalwood oil (from Santalum album) is a mixture of two primary unsaturated alcohols, which have been designated a- and B-santalol. The form...
-Tricyclic Sesquiterpene Alcohols
Cedrol (cedar camphor, cypress camphor), C15H260, has been found in oils of cedarwood (Juniperus virginiana), Juni-perus chinensis (?), cypress and Origanum smyrnaeum (?) as the dextrogyrate modificat...
-Aliphatic Aldehydes
Aside from the aldehydes citral and citronellal, which are to be mentioned later in this chapter and which occur rather frequently, the aliphatic aldehydes constitute only minor constituents of the vo...
-Citral
or Citral1) is the only aliphatic aldehyde of the formula C10H16O that has thus far been isolated from volatile oils. It is also known as geranial, because of its close relation to geraniol, being ...
-Citral. Continued
The labile citral dihydrodisulphonate of sodium results likewise when an aqueous solution of sodium sulphite is shaken with citral: C9H16CHO + 2Na2S03 + 2H20 = C9H17(S03Na)2CHO +2NaOH. In as much ...
-Citronellal
or The second aliphatic terpene aldehyde with ten carbon atoms that is found in volatile oils is the citronellal, C10H18O. It occurs occasionally as companion to citral, of which it is the dihydro-...
-Citronellal. Continued
Another method of separation is based on the property of the citronellal to combine only with a concentrated solution of sodium sulphite and sodium bicarbonate, whereas citral also combines with dilut...
-Benzaldehyde
Benzaldehyde occurs rather frequently in volatile oils. Its existence in these oils is due to the presence, in parts of plants, of certain glucosides which, upon hydrolysis, yield benzaldehyde, hydr...
-Cuminic aldehyde
Cuminic aldehyde (p-isopropyl benzaldehyde, cuminol) has been observed repeatedly in volatile oils. It is the principal constituent of oil of cumin and has also been found in the oils of boldo leave...
-Phenylacetic aldehyde
Although this aldehyde has not yet been found in a volatile oil, it may be mentioned here since it finds application in perfumery on account of its hyacinth-like odor. It can be prepared in one of s...
-Cinnamic aldehyde
Cinnamic aldehyde occurs in Ceylon cinnamon oil, in cinnamon leaf oil, cinnamon root oil, Japanese cinnamon oil, oil of myrrh, oil of cassia and oil of patchouli. Artificially it is obtained by the...
-Salicylic Aldehyde
Salicylic aldehyde (ohydroxybenzaldehyde) has been found in the oils of Spiraea (S. Ulmaria, S. Filipendula, S. digitata, S. lobata), in the leaves of Homalium tomentosum, in Cordia asperrima (?), a...
-Anisic Aldehyde
Anisic aldehyde (p-methoxy benzaldehyde), also known as aubepine, results upon oxidation of anethol. Hence it is found in old, anethol-containing oils, such as anise oil, staranise oil and fennel oi...
-P-Methoxycinnamic Aldehyde
p-Methoxycinnamicaldehyde (p-cumaric aldehyde methyl ether) has been found in esdragon oil by Daufresne.1) Its constants are: B. p. 170 (14 mm.); d0o 1,137. The semicarbazone melts at 222o the...
-Vanillin
Vanillin, the methyl ether of protocatechuic aldehyde, occurs widely distributed in the Vegetable Kingdom but mostly in very small amounts. Moreover, in the living plant it does not appear to occur ...
-Heliotropin
Heliotropin, also known as piperonal, is the methylene ether of protocatechuic aldehyde. It has been observed but once in a volatile oil and then only in minimal amount, namely in the oil from the f...
-Furfurol
Its presence in volatile oils is possibly due to the united action of heat and acid on the cell-membrane and other carbo-hydrates of the crude materials subjected to distillation in the presence of ...
-Alicyclic (Hydroaromatic) Aldehydes
So far as occurrence in volatile oils is concerned, this group of aldehydes is much less important than the others already considered. ...
-Phellandral
Phellandral, to which in all probability the above formula may be assigned, is found in small amounts in the oil of water-fennel. B. p. 89 (5 mm.); d15o0,9445; aD - 3630'; nD20o1,4911.1) W...
-Aliphatic Ketones
Of the aliphatic ketones only a few are found in volatile oils. They are mostly methyl ketones which can be isolated by means of their acid sulphite addition products. The lower members are water-solu...
-Methyl heptenone
Of greater interest than the saturated ketones already enumerated, is the unsaturated methyl heptenone, C8H140. It occurs as constituent of several volatile oils and has been obtained as decompositi...
-Aromatic Ketones
As constituents of volatile oils, these ketones play but a minor role. The following may here be mentioned. o-Hydroxyacetophenone, CH3COC6H4OH, and possibly its methyl ether, are contained in the oil...
-Carvone
The dextrogyrate modification of carvone, C10H14O, occurs to the extent of from 50 to 60 p. c. in caraway oil, also in dill oil in much the same amount. /-Carvone is not as common and has been found...
-Pulegone
Pulegone, a ketone C10H16O, has thus far been found in labiate oils only. In these it frequently occurs in large amounts, occasionally together with menthol and menthone. European pennyroyal oil con...
-Isopulegone
This ketone, which has thus far not been found in volatile oils, may receive brief mention at least. As described on p. 446, it can be prepared by way of the oxime from pulegone. It can also be obta...
-Dihydrocarvone
It is only recently that this ketone has been found in caraway oil by the chemists of Schimmel & Co.1) Artificially it is obtained by the oxidation of dihydrocarveol with chromic acid in glacial ac...
-Menthone
Both optical modifications of menthone, C10H18O, are found in nature. d-Menthone has been found in the oil of Barosma pulchellum and in American pennyroyal oil from Hedeoma pulegioides; /-menthone i...
-Camphor
d-Camphor, known also as Japanese or Laurus camphor in order to distinguish it from borneo camphor (d-borneol), is obtained on a large scale together with camphor oil by the distillation of the wood o...
-Fenchone
Fenchone is a ketone C10H16O which closely resembles camphor but is liquid at ordinary temperature. In volatile oils both optically active modifications occur. d-Fenchone has been found in fennel oi...
-Thujone
Thujone, C10H16O, occurs in two physically isomeric forms, namely as lasvogyrate a-thujone and as dextrogyrate B-thujone (the tanacetone of Semmler). These two modifications are not optical antipode...
-Ionone
A-Ionone. B-Ionone This violet perfume of the formula C13H20O, the presence ) which in nature has not yet been definitely established, was first obtained synthetically in 1893 by Tiemann and Kru...
-Pseudoionone
The inversion of pseudoionone to ionone may be brought about more particularly by concentrated sulphuric acid, phosphoric acid, formic acid, and oxalic acid, also by dilute mineral acids and solutions...
-Irone
Irone, C13H20O, has thus far been found only in orris oil, the German Veilchenwurzelol (from Iris florentina, I. pallida, I. germanica). Tiemann and Kriiger1) were the first tho isolate it from or...
-Phenols And Phenol Ethers
The phenols and their ethers occur frequently in volatile oils. On account of the practical importance which many have acquired, they are prepared on a large scale. Thus thymol finds application on ac...
-Thymol
Thymol (isopropyl-m-cresol), C10H14O, is frequently accompanied by carvacrol. In addition to p-cymene and terpenes, it constitutes the larger part of ajowan oil. It occurs also in the oils of Ocimum...
-Carvacrol
Carvacrol (isopropyl-o-cresol), C10H14O, occurs principally in labiate oils. Thus far its presence has been demonstrated in camphor oil, schinus oil, the oils of Monarda punctata (?), M. fistulosa, ...
-Chavicol
Chavicol (p-allylphenol), C9H10O, occurs in some of the betel leaf oils, also in oil of bay, and possesses strongly antiseptic properties. It is a colorless liquid that boils at about 237. Acc...
-Methylchavicol
Methylchavicol (estragol, isoanethol, p-allylanisol), C10H12O, was first found in anise bark oil, later also in staranise oil, 1) Berl. Berichte 23 (1890), 862. Japanese staranise oil, kobuschi oi...
-Anethol
Anethol (p-propenylanisol), C10H12O, is the principal constituent of anise and staranise oils and is an important constituent of fennel oil. Its presence in the oil of Osmorrhiza longistylis and in ...
-Thymohydroquinone
Thymohydroquinone, C10H14O2, has been found in the oil of Callitris quadrivalvis, Algerian fennel oil (?) and in the oil of Monarda fistulosa. Artificially it is obtained by the reduction of thymoqu...
-Allylpyrocatechin
The presence of allylpyrocatechin, C9H10O2, in Javanese betel leaf oil was demonstrated by Schimmel & Co.1) Previously this phenol had not been known to exist in the vegetable kingdom, neither had i...
-Betelphenol
Betelphenol2) (allylguaiacol), C10H12O2, has thus far been found only in betel oil, from which it can be isolated in the usual manner by shaking it out with caustic soda solution. It is a strongly r...
-Eugenol
Eugenol, C10H12O2, an isomer of position to betelphenol is found widely distributed, especially among the Myrtaceae and Lauraceae. In largest amount it is found in oil of cloves and oil of clove ste...
-Aceteugenol
In addition to eugenol, oil of cloves, but not oil of clove stems, contains some aceteugenol, CH3COOC6H3.CgH6.OCH3. This compound can be freed from eugenol by treating it with dilute alkali in the col...
-Methyleugenol
Eugenol is frequently accompanied by its methyl ether, the methyleugenol (allylveratrol), C11h14O2. It occurs in citronella oil, Japanese calamus oil, matico oil (?), betel oil, Canada snake-root oi...
-Isoeugenol
When eugenol in heated with an excess of solid potassa,4) or in amyl alcoholic solution,5) or when eugenol potassium is heated to about 200 6) with exclusion of air, it is converted into the is...
-Methylteoeugenol
Thus far methylIsoeugenol has been found only in the oil from Asarum arifolium. Artificially it is obtained by the methy-lation of isoeugenol and by the inversion of methyleugenol. The following pro...
-Safrol
Safrol, C10H10O2, is the principal constituent of oil of sassafras. It is also contained in appreciable amount in camphor oil from which it is obtained technologically. In addition it has been found...
-Isosafrol
When boiled with alcoholic potassa, safrol is changed to isosafrol. 1) Observations made in the laboratory of Schimmel & Co. 2) Recueil des trav. chim. des P.-B. 4 (1885), 32; Berl. Berichte 23 (1...
-Asarone
Asarone (4-propenyl-l,2,5-trimethoxybenzene), C12H1603, is a constituent of Asarum oil. It has been found in the oils of calamus, matico and Asarum arifolium. If present in larger amounts, it separa...
-Elemicin
Elemicin (4-allyl-l,2,6-trimethoxy benzene), C12H1603, constitutes the principal constituent of Manila elemi oil, in which it was discovered by Semmler1) who also gave it its name. It is found in fr...
-Myristicin
Thus far myristicin (4-allyl-6-methoxy-l,2-methylenedihydroxy benzene),1) C11H1203, has been found only in the oils of nutmeg and mace, also in French parsley oil. It is characterized by the followi...
-Apiol
Apiol (4-allyl-3,6-dimethoxy-l,2-methylenedihydroxy benzene), C12H1404, is a constituent of parsley seed oil and of Venezuelan camphorwood oil and matico oil from which it congeals upon cooling. Api...
-Dillapiol
Dillapiol occurs in matico oil, in East Indian, Japanese, and Spanish dill oils, also in the oil of Crithmum maritimum. It is a viscid, oily liquid, which boils at 285 under ordinary pressure a...
-Allyltetramethoxybenzene
From a French oil of parsley Thorns4) isolated a substance C18H1804, which he recognized as a phenol ether characterized by the above formula, and for which he records the following constants: M. p...
-Diosphenol
Diosphenol (buchu camphor), C10H16O2, is a constituent of the oil of buchu leaves, in which it was first found by Fliickiger.1) Since then it has been subjected to investigation repeatedly. Its chem...
-B-Naphthol Ether
The methyl and ethyl ethers of B-naphthol are both used extensively for perfuming cheaper grades of soap. In commerce these ethers are known as nerolin. The methyl ether is sometimes differentiated ...
-Acids
The aqueous distillate obtained as a byproduct in the preparation of volatile oils occasionally contains free fatty acids such as acetic, propionic, butyric or valeric acids. Like the methyl and ethyl...
-Esters
Esters occur in most volatile oils and are frequently of essential import so far as the fragrance of these oils is concerned. On account of their mostly pleasant odor they play an important role in pe...
-Methyl Benzoate. C6H5COOCH3
The methyl ester of benzoic acid, also known as oil of Niobe, occurs in ylang-ylang oil and probably also in the oils of cloves and of tuberose. It is a colorless, optically inactive liquid, of a stro...
-Methyl Cinnamate. C6H5CH:CHCOOCH3
The only oils in which this ester has been found are those from the rootstock and leaves of Alpinia malaccensis and from the seeds of wartara. At ordinary temperature methyl benzoate is a solid posse...
-Methyl Salicylate
Methyl salicylate (salicylic acid methyl ester, artificial oil of wintergreen) is one of the most important perfumes and is also highly esteemed on account of its antiseptic properties. It has been ...
-Ethyl Acetate. CH3COOC2H5
The presence of ethyl acetate (acetic ether) in volatile oils has not yet been demonstrated. However, an observation by Goppert1) is on record, according to which the flowers of Magnolia fuscata, more...
-Ethyl Benzoate. C6H5COOC2H5
Thus far ethyl benzoate has not been found in nature. Its odor resembles that of the methyl ester, but is somewhat milder. Its constants are: 1) Liebig's Annalen 111 (1859), 127. B. p. 211,2 (7...
-Ethyl Salicylate
Salicylic acid ethyl ester is of interest only in so far as it finds application in perfumery. In volatile oils it has not yet been found. It is a colorless liquid, the odor of which is more faint ...
-Ethyl cinnamate. C6H5CH:CHCOOC2H5
Cinnamic acid ethyl ester is one of the more rarely occurring constituents of volatile oils. Its occurrence is restricted to the oils of kaempferia and storax. Artificially it is obtained by passing h...
-Amyl Salicylate
While not a constituent of volatile oils, salicylic acid amyl ester, also known as orchidee, trefle or trefol, finds extensive application in perfumery and may, therefore, be mentioned. It is a col...
-Linalyl Acetate. CH3COOC10H17
Linalyl acetate, the most valuable and characteristic constituent of the oils of bergamot and lavender, is rather widely distributed. In addition to the above mentioned two oils, it has been found in ...
-Geranyl Formate. HCOOC10H17
This ester, which has not yet been observed in nature, is formed even upon standing of a solution of geraniol in crystallized formic acid,3) better still upon the addition of a small amount of a miner...
-Geranyl Acetate. CH3COOC10H17
Like linalyl acetate, geranyl acetate occurs rather commonly in volatile oils. It is the principal constituent of the oil of Darwinia fascicularis, and has also been found in the oils of the needles o...
-Citronellyl Formate. HCOOC10H19
The formic ester of citronellol has thus far not been found in volatile oils. It is readily formed by boiling citronellol with twice its volume of strong formic acid/) also by setting aside for severa...
-Citronellyl Acetate
CH3COOC10H19 Citronellyl acetate is probably a constituent of citronella oil and oil of geranium, but its presence in either oil has not yet been definitely established. Artificially it can readily b...
-Benzyl Acetate. CH3COOCH2C6H5
Benzyl acetate is the principal constituent of the oil of jasmine flowers and of gardenia oil. It is also contained in ylang-ylang oil and in hyacinth oil. Artificially this ester can be obtained in a...
-Benzyl Benzoate. C8H5COOCH2C6H5
This ester is an essential constituent of cinnamein or Peru balsam oil. It likewise occurs in the oils of tuberose, ylang-ylang and tolu balsam. According to Claisen,5) benzyl benzoate can be prepare...
-Benzyl Cinnamate. C6H5CH:CHCOOCH2C6H5
Cinnamic acid benzyl ester, C16H1402, has been found in the oils of storax, tolu balsam and Peru balsam. According to Grimaux,2) it can be obtained artificially by boiling sodium cinna mate, alcohol a...
-Cinnamyl Cinnamate
C6 H5 CH : CH COOCH2 CH : CH C6 H6. The cinnamyl ester of cinnamic acid, also known as styracin, C18H1602, is found in storax, also in the oils of hyacinth (?), xanthorrhoea resin, P...
-Terpinyl Formate. HCOOC10H17
Terpinyl formate possibly occurs in Ceylon cardamom oil, but its presence therein has not yet been definitely established. Artificially, the ester has been obtained by Lafont3) who allowed two parts o...
-Terpinyl Acetate. CH3COOC10H17
The acetate of terpineol has been found only occasionally in volatile oils: the dextrogyrate ester in cypress oil and the oil of Malabar cardamom, the inactive in oil of cajeput. It possibly, occurs a...
-Bornyl Formate. HCOOC10H17
Bornyl formate occurs in valerian oil and possibly in the oil of Achillea nobilis. It results upon the interaction of borneol on formic acid in the presence of some mineral acid.1) It is a colorless l...
-Bornyl Acetate. CH8COOC10H17
This ester, which is a characteristic constituent of many coniferous oils, also occurs in several other oils. The dextrogyrate acetate occurs in the needle oil of Callitris glauca, the lasvogyrate ace...
-Bornyl Isovalerate. C4H9COOC10H17
Bornyl Isovalerate occurs in oil of valerian and in kesso root oil. In the latter it is found in the lagvogyrate modification. Artificially it is obtained by the esterification of borneol with isovale...
-Menthyl Acetate. CH3COOC10H19
Menthyl acetate, a liquid having a peppermint-like odor, has thus far been observed only in oil of peppermint. It can readily be obtained by boiling menthol with acetic acid anhydride and some sodium ...
-Lactones
Lactones also have been found in volatile oils. Some of them, like sedanolid, coumarin, and hydrocoumarin are characterized by a strong odor. Alantolactone and the lactone C10H16O2 from peppermint oil...
-Coumarin
Coumarin (o-hydroxycinnamic acid anhydride), C9H602, the odoriferous principle of the Waldmeister (Asperula odorata), is widely distributed in the vegetable kingdom. It was first observed in the t...
-Alantolactone
The commercial helenin,5) also known as alant camphor, is chemically alantolactone and is the principal constituent of the oil of elecampane root (from Inula Helenium). Kallen6) originally regarde...
-Oxides
Oxides have been found in volatile oils in isolated cases only, those of the aliphatic series having not yet been observed. Of synthetic products, however, several are known. Of special importance is ...
-Cineol
Cineol (eucalyptol), C10H18O, is very widely distributed. It is the principal constituent of the oil of Eucalyptus Globulus, of cajeput oil, niaouli oil and of the oil of wormseed. In varying amount...
-Nitrogen- And Sulphur-Containing Compounds
Compounds containing nitrogen or sulphur are frequently obtained during the distillation of such parts of plants which are rich in albuminous substances (protoplasm) or similar bodies, e. g. during th...
-Hydrocyanic Acid
The principal representative of the nitriles is that of formic acid, viz., hydrogen cyanide, HCN. It is formed during the production of the oils of bitter almond and cherry laurel, but also occurs in ...
-Nitrobenzene. C6H5N02
This compound, also known as oil of mirbane, which is prepared in large quantities, principally for the dye stuff industry, is also used in perfumery as a cheap substitute for oil of bitter almonds. T...
-Artificial Musk
Natural musk owes its odor to a ketone, muscone, which is contained in the natural product to the extent of from 0,5 to 2/o. As to its chemical composition only this much is known that either the...
-Indol
Indol has long been known to occur in the animal organism as a product of intestinal digestion. It has also been produced artificially for some time, but it is only recently that its occurrence in t...
-Skatol
Skatol, B-methylindol, has thus far been found in civet and in the wood of Celtis reticulosa, also in a wood1) obtained from German East Africa. It crystallizes in white laminae which melt at 95...
-Sulphides
Sulphuretted hydrogen, H2S, is frequently observed during the distillation of seeds, e. g. anise and particularly of caraway. Small amounts of carbon disulphide, CS2, are contained in the oil of black...
-Mustard Oils
The esters of isothiocyanic acid, characterized by their penetrating odor, and commonly known as mustard oils, constitute a special group of sulphur compounds. Their typical representative is the comm...
-Teothiocyanallyl
CSNCH2CH:CH2. Isothiocyanallyl, allyl mustard oil or commonly mustard oil, constitutes the bulk of the volatile oil of mustard. It has also been obtained from the following plants: Alliaria officinal...
-The Examination Of Volatile Oils
As the various oils are fully described in the second vol. of this treatise, it will be expedient, in order to avoid repetition, to discuss briefly in a special chapter the general methods used in the...
-Determination Of The Physical Properties Specific Gravity
On account of its ready determination the specific gravity is the most frequently taken and, therefore, the best known property of the volatile oils. Even concerning the rare and little investigated o...
-Optical Rotation
The optical rotation is such a characteristic property of most of the volatile oils that its determination should never be omitted in an examination. Especially adapted for this purpose is the half-sh...
-Refraction
The determination of the index of refraction nD has been recommended repeatedly for the examination of the volatile oils. As is well known, certain relations exist between chemical constitution and re...
-Congealing Point
With certain oils, especially anise, star anise, fennel and rue oils, the congealing point affords a good means for judging the quality. With the first three oils a high congealing point shows a large...
-Behavior On Boiling And Fractional Distillation
Inasmuch as the volatile oils are mixtures of substances with different boiling points, it is improper to speak, as is so often done, of the boiling point of a volatile oil. It is more correct to spea...
-Solubility
The volatile oils are readily soluble in the ordinary solvents, such as alcohol, ether, chloroform, benzene, acetic ether, carbon disulphide, etc. Mention of this general property is not made in the d...
-Chemical Methods Of Testing
The rational examination of a volatile oil in a chemical manner is possible only if its composition or at least its main constituents are known. The chemical investigation must be directed as much as ...
-Saponification
Through scientific investigation it has been established that many volatile oils contain ester-like compounds, the components of which, on the one hand are alcohols, usually of the composition C10H18O...
-Acetylation
Many volatile oils contain as important constituents alcohols varying in composition, for instance, borneol, geraniol, terpineol, linalool, thujylalcohol, menthol, citronellol and santalol. For the qu...
-Acetylation. Continued
The reaction between alcohol and acetic acid anhydride is quantitative in the case of borneol, isoborneol, geraniol,1) menthol2) and santalol, hence enables an accurate determination of these substanc...
-Formylation
As has already been pointed out under citronellol (p. 365), this alcohol is converted into the formate when boiled with formic acid, whereas other terpene alcohols, such as geraniol and linalool, are ...
-Determination Of Aldehydes And Ketones
Although attempts have been made repeatedly to work out a general method for the determination of aldehydes and ketones, this problem has not yet been solved in a satisfactory manner. Failure has been...
-Determination Of Aldehydes And Ketones. Part 2
Closely related to the bisulphite method is the Sulphite method, which is based on the observation that certain aldehydes and ketones react with neutral sodium sulphite to form water soluble compounds...
-Determination Of Aldehydes And Ketones. Part 3
1) Zeitschr. Untersuch. der Nahrungs- u. Genubmittel 6 (1903), 817. Comp. also Report of Schimmel & Co. April 1904, 19. 2) Report of Schimmel & Co. April 1904, 21. 3) As to the method of preparation...
-Phenol Determination
For the determination of phenols the method of shaking out with dilute sodium hydroxide solution has proven satisfactory. 1) Pharm. Rundsch. (Mew York) 12 (1894), 162; Arch, der Pharm. 282 (1894), 65...
-Phenol Determination. Continued
This method, which determines only free phenols, is appliciable only for such oils that are free from alcohols, aldehydes and ketones, to those oils that are mixtures of phenols and terpenes.1) On acc...
-Methyl Number
A number of volatile oils contain as important constituents methyl and ethyl ethers of phenols and acids, the alkyl groups of which can be determined according to Zeisel's method.1) Bene-dikt and Grus...
-Cineol Determination
In addition to fractional distillation, several methods for the assay of cineol have been recommended. They all depend on the capacity of cineol to form addition products with certain other compounds....
-Hydrocyanic Acid Assay
The qualitative test for hydrogen cyanide has already been referred to on p. 533. Quantitatively it is best determined gravimetrically: About 1 g. of oil is accurately weighed and dissolved in 10 to 2...
-Mustard Oil Assay
Mustard oil can be assayed by weighing it as thiosinamine, or better by double decomposition with ammoniacal silver nitrate solution. In this case also thiosinamine is first obtained as intermediate p...
-Test For Chlorine
The test for chlorinated products is an important one in the examination of bitter almond oil, cherry laurel oil and a number of chemical preparations. In the case of the two oils mentioned, the test ...
-Turpentine Oil
Turpentine oil may be considered as the adulterant most often used. Very often it can be recognized by its characteristic odor, especially in those oils which contain no pinene, as this is the main co...
-Cedar Wood, Copaiba And Gurjun Balsam Oils
On account of their cheapness and faint odor, these three oils belong to the most favored and the most dangerous of adulterants. They may, however, be detected without difficulty in most cases by mean...
-Alcohol
The addition of alcohol to a volatile oil always results in a lowering of the specific gravity. When an oil containing alcohol is dropped into water, the drops do not remain clear and transparent, as ...
-Fatty Oil
The volatile oils adulterated with fatty oil leave a permanent fatty stain when evaporated on paper. With high boiling and difficultly volatile oils, however, similar residues are left, which may give...
-Mineral Oil, Petroleum
Mineral oil, paraffin oil, kerosene, petroleum and petroleum fractions are insoluble in alcohol and can therefore be detected without difficulty in volatile oils; besides, they are often easily recogn...
-Chloroform
This body, which has been found occasionally in volatile oils (for instance, in cognac oil), can be isolated by distillation on a water bath and identified by the Isonitrile reaction. This consists in...
-Additions To Increase The Ester Content
The valuation of such oils as bergamot and lavender according to their ester content has led to the occasional adulteration of such oils with cheaper esters or organic acids for the purpose of increas...
-Tables
Table I for Calculating the Percentage Content of Alcohols of the Formulas C10H18O, C10H20O, C15H240 and C15H260 from the Saponification Values before and after Acetylation, also the Percentage Conten...









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