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1‐Octen‐3‐ol and its relation to other oxidative cleavage products from esters of linoleic acid
Author(s) -
Hoffmann G.
Publication year - 1962
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/bf02637660
Subject(s) - acetal , linoleic acid , cleavage (geology) , chemistry , oxidative cleavage , organic chemistry , stereochemistry , catalysis , fatty acid , biology , paleontology , fracture (geology)
By means of preparative GLC, 1‐octen‐3‐ol and 2‐ trans ‐heptenal could be isolated from mildly oxidized linoleic acid ester and from oils containing this acid (e.g., soybean oil). A hypothesis for the origin of these two substances in natural products is given. The absence of 2‐ trans ‐octenal in the cleavage products from methyl linoleate, its presence in oils and the controversial experimental results obtained by various investigators, seem to be reconcilable by assuming the formation of an acetal. The suggested acetal may, on intermolecular cyclic rearrangement and cleavage, give 1‐octen‐3‐ol.