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UV‐Autoxidized linolenic acid in high yield for cancer study
Author(s) -
Baker N.,
Wilson L.
Publication year - 1974
Publication title -
lipids
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.601
H-Index - 120
eISSN - 1558-9307
pISSN - 0024-4201
DOI - 10.1007/bf02533112
Subject(s) - autoxidation , chemistry , azelaic acid , hydrogen peroxide , ether , organic chemistry , linolenic acid , petroleum ether , chromatography , peroxide , thiobarbituric acid , nuclear chemistry , linoleic acid , extraction (chemistry) , fatty acid , antioxidant , lipid peroxidation
Abstract Aqueous emulsions of linolenic acid were exposed repeatedly to UV light in an oxygen atmosphere. After each exposure, a dense, yellow liquid formed which was insoluble in petroleum ether, poorly soluble in water, but highly soluble in ethyl ether. After 5 cyclic 90 min exposures, linolenic acid was almost quantitatively converted to autoxidation products which had the following properties: average mol wt, 510; 2‐thiobarbituric acid‐reactive (pink derivative); peroxidase‐reactive; peroxide no., 1100 meq/kg; hydrogen no., 404 mg/mmole H 2 ; C, 61%; H, 9.0%; and O, 30%. Only trace amounts of free aldehydes were present. After treatment with BF 3 ‐methanol, the major, volatile products found were methyl acetal‐esters of azelaic semialdehyde and azelaic acid. These products did not vary qualitatively from one UV exposure to another as shown by gas liquid chromatographic analyses. Ca. 90% of the autoxidized material did not appear on gas liquid chromatography even after methylation. Our technique allows the rapid preparation of high yields of autoxidized linolenic acid sufficient to study chemical properties and anticancer activities of the autoxidation products.