Upon extraction of the flowers of Cheiranthus Cheiri, L. (Ger. Goldlack, family Cruciferae) with low boiling solvents, Kummert-E.3) obtained a dark colored extract of salve-like consistence. When treated with strong alcohol, the extract was freed of wax and vegetable fats and subsequently distilled with water-vapor. The yield of oil thus obtained amounted to 0,06 p. a;
1) Arch, der Pharm. 245 (1907), 657. 2) Liebig's Annalen 392 (1912), 1. 3) Chem. Ztg. 35 (1911), 667.
When distilled in a vacuum of 3 mm., only a small amount of oil came over below 40°. The odor of these substances, presumably mustard oils1), was very disagreeable. With semicar-bazide the higher boiling fractions yielded a mixture of semicar-bazones that was decomposed with oxalic acid. The product thus obtained had an odor reminding one of hawthorn (Ger.Weiss-dorri) and violet, thus indicating possibly the presence of anisic aldehyde and irone.
When the oil that had been deprived of aldehydes and ketones was treated with phthalic acid anhydride, nerol (m. p. of the diphenyl urethane 50°), geraniol (m. p. of the diphenyl-urethane 82°) and benzyl alcohol (m. p. of the acid phthalic ester 106°) were shown to be present. Linalool (m. p. of phenyl-urethane 65°) is also present in the oil. After the removal of traces of phenols (possibly p-cresol) and lactones (possibly cumarin-like compounds) Kummert found the following acids in the saponification liquid: acetic acid, salicylic acid (m. p. 156°) and anthranilic acid (m. p. 145°).
The highest fractions had a decided odor of indol. To the ethereal solution, prepared with three volumes of ether, sulphuric acid was added. The precipitate resulting was decomposed with warm soda solution. Thus Kummert isolated the methyl ester of anthranilic acid. The bases freed from ether were then dissolved in petroleum ether. The addition of picric acid to this solution caused the precipitation of a red picrate which, when decomposed with soda solution, yielded indol (m. p. 52°), also a small amount of bases that had the odor of pyridine.