The best grades of sandal wood are used in India, more particularly in Kanara, for artistic carving, especially of idols, cupboards, tables, canes, chests, etc. In religious rites, especially as incense, the wood plays an important role. Most of the wood, however, is used for distillation.
Production. Formerly the distillation of sandal wood played a more important role in India than it does at present. Up to 1860 it was carried on in Mysore. At present the distillation is still conducted along the west coast of India, in South Kanara, more particularly in the Udipi district. But even here the old industry is constantly dwindling.
According to Mr. Werner Reinhardt of the firm of Gebr. Volkart, who has himself visited the distilleries1), the industry in southern India is located principally north east of Karkul as far as the river Ghat. The distilling apparatus consists of a spherical earthenware vessel provided with a circular opening. It is 21/2 ft. high and about 67* ft. in circumference. There is no head. When charged, the still is closed with an earthenware cover, into the center of which is fastened a bent copper tube about 51/2 ft. in length. The tube ends in a copper receiver placed in a porous earthenware vessel which is filled with water. For the purpose of distillation the wood is cut up into chips and a charge of 50 lbs. placed into the still. Water is then added and the distillation of a single charge is continued uninterruptedly day and night for an entire month. The condensed water of the receiver is returned to the still about 15 times. The yield of oil is recorded as follows: for roots . . . about 4,34 °/» „ Jugpokals . „ 3,47 °/o „ Ain Chiltas „ 2,60 °/o.
The oil enters commerce in part via Udipi, in part via Mangalore. Of the two, the latter place is more important. According to local statements, the exports for 1909 from this port are said to have reached the value of Rs. 150000 (?). No doubt, this figure also includes Mysore oil which found its way to Mangalore. Practically all the oil is taken to Bombay by steamer, thence it is re-exported to the Persian gulf and to China.
. It is evident that with such a primitive method of distillation no really good sandal wood oils can be obtained. Owing to the prolonged distillation, decomposition products are inevitable. These interfere with the quality of the oil, exerting an unfavorable influence on both color and odor. The anomaly of the Indian oils is also shown by their constants. (See below.)
Sandal wood oil is also distilled in the northern parts of India, namely in Kanouj (Kanauj)2), a city in Oudh (Audh) between Cawnpur and Allahabad. In Lucknow and jaunpur, where the distillation was formerly carried on, it has been discontinued. Kanouj is the center of the ancient perfume industry of India where the several attars, i. e. floral perfumes, were prepared with sandal wood oil as base.
1) Report of Schimmel & Co. October 1910, 114.
2) Comp. Watt, Commercial products of India, London 1908, p. 977.
Fig. 32. Sandal wood tree (Santalum album, L)
Because of the more perfect comminution, and also because of improved stills, larger yields are obtained in Europe than by the primitive methods employed in India. As much as 6 p. c. and more of oil are obtained, the light color and agreeable odor of which are in striking contrast with the Indian distillates as they are contaminated with empyreumatic products.
Composition. More than 90 p. c. of the sandal wood oil consists of santalol, a mixture of two isomeric alcohols to which the oil owes its medicinal virtues. The other constituents play a minor role. They are of interest, however, because they are genetically related to the principal components.
1. Isovaleric aldehyde, together with other aldehydes that boil between 50 and 130°, is found in the first portions that distil over. The presence of isovaleric aldehyde was established by means of its thiosemicarbazone1), melting at 49 to 53°, which had been obtained from the aldehyde isolated from fraction 90 to 95° by means of its bisulphite addition product.
2. Santene, C9H14. This hydrocarbon is remarkable as the next lower homologue of the terpenes. (Comp. vol. I, p. 289). It was discovered in the oil by F. Muller2). A very pure santene, obtained through fractionation by Schimmel & Co.1), had the following properties: b. p. 140 to 141° (770 mm.), d15o 0,869, aD - 0°16', nD20o1,46436.
3. Hydrocarbon C11H18 (Nortricycloeksantalane?). This hydrocarbon, found by Schimmel & Co.3) in the first fractions of the oil after having been distilled over sodium, had the following properties: d15o 0,9133; d20o 0,9092; aD - 23°55'; nD20o1,47860; mol. refr. found 46,74, computed for C11H18 46,40, for C11H18/1=48,11. The elementary analysis yielded results agreeing with the formula for a homoterpene C11 H18. This hydrocarbon, of which sufficient quantities of solid derivatives have not yet been obtained, is permanent toward permanganate at ordinary temperatures and apparently identical with Semmler's nortricycloeksantalane. In connection with his work on the constitution of the santalols of the eksantal series, this investigator1) had obtained a hydrocarbon, named nortricycloeksantalene, by splitting off carbon dioxide from tricycloeksantalic acid, to which he assigned the formula C10H16 because of the method of formation. The more recent investigations of Semmler2), however, have revealed that tricycloeksantalic acid contains twelve carbon atoms, hence the nortricycloeksantalane must be C11H18 with which formula Semmler's analyses agree.
1) Report of Schimmel & Co. October 1910, 118.
2) Arch, der Pharm. 238 (1900), 366.
3) Report of Schimmel & Co October 1910, 121.
4. Santenone, C11H14O. In the lowest fraction of sandal wood oil F. Muller3) had found a ketone, the semicarbazone of which melted at 224°. According to Schimmel & Co.4) this ketone is identical with the a-norcamphor obtained by Semmler5) from teresantalic acid and with the santenone obtained by Aschan") from santene. The ketone obtained from sandal wood oil by fractional distillation has an odor reminding one of camphor and cineol. It has the following properties: m. p. 48 to 52°; b. p. 193 to 195°; [a]D - 4° 40' in 18,9 p. c. alcoholic solution. It forms a liquid oxime which boils at 110 to 113° (6 mm.).
5. Santenone alcohol (a-norisoborneol). The fractions freed from santenone contain an alcohol which can be isolated by the aid of phthalic acid anhydride7). There results a liquid acid phthalate, the sparingly soluble silver salt of which melts at 230°.