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Fatty acids, Part 30 The formation of 1,4-epoxides from two series of trihydroxystearic acids by acid-catalysed cyclisation

Authors
Journal
Chemistry and Physics of Lipids
0009-3084
Publisher
Elsevier
Publication Date
Volume
7
Issue
4
Identifiers
DOI: 10.1016/0009-3084(71)90006-5
Disciplines
  • Chemistry

Abstract

Abstract Ricinoleic acid can give four diastereoisomeric 9,10,12-trihydroxystearic acids. Each of these, when treated with acidic methanol, gives, mainly or entirely, one isomer of methyl 9,12-epoxy-10-hydroxystearate from which the corresponding 10-methoxy and 10-oxo esters are prepared. Structural identification is based mainly on mass spectroscopy. 9-Hydroxyoctadec- cis-12-enoic acid gives a similar series of 9,12,13-trihydroxystearic acids which yield 9,12-epoxy-13-hydroxy (methoxy, oxo)stearates. The mechanism and stereochemistry of the cyclisation reaction are discussed.

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