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Epoxidierung von Kohlenstoff‐Kohlenstoff‐Doppelbindungen in Terpenen durch Linolsäurehydroperoxide
Author(s) -
Meyer Werner,
Spiteller Gerhard
Publication year - 1993
Publication title -
liebigs annalen der chemie
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 0170-2041
DOI - 10.1002/jlac.1993199301204
Subject(s) - chemistry , epoxide , terpene , linoleic acid , double bond , squalene , regioselectivity , yield (engineering) , organic chemistry , fatty acid , catalysis , metallurgy , materials science
Epoxidation of Carbon‐Carbon Double Bonds in Terpenes by Linoleic Acid Hydroperoxides Epoxidation of CC double bonds in terpenes is achieved by reaction with linoleic acid hydroperoxides (LOOH) exemplified with caryophyllene ( 3 ), methyl farnesoate ( 5 ) and squalene ( 8 ). Linoleic acid (9 S )‐hydroperoxide was obtained by reaction of linoleic acid ( 1 ) with lipoxygenase present in tomato homogenisate. When 18 O 2 ‐labeled (9 S )‐LOOH ( 2 ) was used 18 O was found in the terpene epoxide. While 3 is converted under physiological conditions regioselectively in high yiled into its 4,5‐epoxide 4 , the yield of epoxidized products from long‐chain molecules, e.g. squalene ( 8 ), decreases strongly and no regioselectivity was observed.