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Fatty acid allene oxides II. Formation of two macrolactones from 12,13(S)-epoxy-9(Z),11-octadecadienoic acid

✍ Scribed by Mats Hamberg

Book ID: 103039524
Publisher: Elsevier Science
Year: 1988
Tongue: English
Weight: 764 KB
Volume: 46
Category: Article
ISSN: 0009-3084
DOI: 10.1016/0009-3084(88)90037-0

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✦ Synopsis

An unstable fatty acid allene oxide, 12,13(S)-epoxy-Y(Z).1 I-octadecadienoic acid. was recently identified as the product formed from 13(S)-hydroperoxy-9(Z), I I(E)-octadecadienoic acid in the presence of corn (Zra rnu~s L.) hydroperoxide dehydrase (M. Hamberg ( 19X7) Biochim. Biophys. Acta 920, 7684). The present paper is concerned with the spontaneous decomposition of 12,13(S)-epoxy-9(Z). I I -octadecadienoic acid in acetonitrile solution. Two major products were isolated and characterized, i.e. macrolactones 12-keto-V(Z)-octadecen-I I-olide and I2-keto-9(Z)-octadecen-l3-olide.

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