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Epoxy acid in seed oils of Malvaceae and preparation of (+) threo ‐12,13‐Dihydroxyoleic acid
Author(s) -
Hopkins C. Y.,
Chisholm Mary J.
Publication year - 1960
Publication title -
journal of the american oil chemists' society
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.512
H-Index - 117
eISSN - 1558-9331
pISSN - 0003-021X
DOI - 10.1007/bf02632100
Subject(s) - malvaceae , yield (engineering) , epoxy , chemistry , fatty acid , organic chemistry , botany , biology , materials science , metallurgy
Seed oils of six species of Malvaceae , representing four genera, were found to contain cis ‐12,13‐epoxyoleic acid in amounts estimated at 1,5–7% of the total fatty acids. Acetolysis of the oils gave the corresponding dihydroxyoleic acid, which was shown to be predominantly a dextro ‐rotatory form of threo ‐12,13‐dihydroxyoleic acid. It was obtained optically pure, and its structure was confirmed by orthodox methods. The hydrogenation product, (+)‐ threo ‐12,13‐dihydroxystearic acid, was also obtained optically pure and characterized. The best yield of dihydroxyoleic acid was obtained from the seed oil of Malope trifida . Samples of oil from four other species of Malvaeae had a very low or negligible content of epoxy acid.