Charles F. Krewson

Vernonia anthelmintica (L.) Willd. trivernolin, 1,3-divernolin and vernolic (Epoxyoleic) acid from the seed oil

The epoxy fatty acid components isolated from the seed oil ofV. anthelmintica, Indian ironweed, where the seed had been allowed to undergo lipolysis after grinding, were trivernolin, 1,3-divernolin, and vernolic acid. By inactivation of the hydrolytic enzyme system present in the seed, oil containing more than 50% trivernolin may be obtained. This species has potentialities as a replacement crop for those now in surplus; its seed contains 20 to 26% of an oil rich in epoxyoleic (vernolic) acid combined as glycerides amounting to 70 to 75%.

Buckwheat leaf meal fat. II. Composition of the fatty acids

SummaryThe composition of fatty acids of the saponified fat of buckwheat leaf meal was investigated. The mixed fatty acids amounted to 49.6% of the composition of the fat. The chief organic acids found were: linolenic, 15.1%; oleic, 13.1%; linoleic, 8.5%; and palmitic, 8.0%. Less than 1% each of such acids as formic, lactic, stearic, arachidic, hexacosanoic, and octacosanoic, and only traces of acetic, lignoceric, and tricontanoic (or higher) acids were found. The so-called “insoluble acids” of the saponified fat, less the unsaponifiable matter, contained 28.5% (18.5% based on the original fat) of material identified as red pigment and probably a mixture of chlorophyll degradation compounds, chiefly phylloerythrin.

Buckwheat leaf meal fat. I. Its physical and chemical characteristics and the constituents of the water-soluble and unsaponifiable fractions of the saponified fat

SummaryThe leaf meal fat of the Japanese buckwheat plant has been prepared, and its physical and chemical characteristics have been determined. Spectrophotometric analysis of the fat of this variety indicates that in composition it is similar to the fat of the Tartary variety, the one now preferably used for manufacture of rutin. The large quantity of unsaponifiable matter is unusual. This fraction contains carotene, xanthophylls, phytol, β-sitosterol, and an eicosanol.Also of interest is the presence in the fat of significant quantities of lecithin when isopropanol is used for extraction. The water-soluble acidic constituents of the saponified fat consist of the organic acids formic, acetic, and lactic, and the inorganic acids phosphoric, nitric, sulfuric, and hydrochloric. Ammonia was present in the alcohol distillate collected after saponification, and glycerol was identified in the water-soluble acid fraction. Quantitative values are given for formic and lactic acids and for ammonia.

Vernonia anthelmintica (L.) Willd. enzyme studies conversion of epoxyoleic acid to (+)-threo-12,13-dihydroxyoleic acid

Vernonia anthelmintica (L.) Willd. seed was found to contain enzymes that were active only after the seed was ground. By deactivation of the enzymes, an oil rich in trivernolin (the triglyceride of epoxyoleic acid) was produced, and pure trivernolin was isolated. Acceleration of the enzyme activity altered the composition of the oil as evidenced by changes in free fatty acid content, iodine values, and oxirane oxygen (epoxy) content. Investigation showed that these changes were due, at least partially, to the conversion of epoxyoleic acid to (+)-threo-12,13-dihydroxyoleic acid, which was isolated in pure form. Pure (−)-threo-12,13-dihydroxyoleic acid was prepared by acetolysis ofV. anthelmintica seed oil. Neither of these isomers had been obtained previously from mature,V. anthelmintica seed.