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Cyclic Fatty Acids: Qualitative And Quantitative Analysis

G. Dobson
Published 1998 · Chemistry

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Cyclic fatty acids can be classified into those that are naturally occurring and those that are formed in vegetable oils during heating. The former include cyclopropane, cyclopropene and cyclopentenyl acids. C17 (structure la, Fig. 5.1) and C19 (structure Ib) cyclopropane acids are common in many bacteria, for example Lactobacilli and enterobacteria, and mycolic (2-alkyl-3-hydroxy) acids (structure II), with up to about 90 carbons and one or two cyclopropane rings, occur in mycobacteria (Christie, 1970; Minnikin, 1978). Recently, several acids with up to 26 carbons, one or two cyclopropane rings and a double bond in the Δ5 position were identified in an invertebrate from a deep-water lake (Rezanka and Dembitsky, 1994). C18 (structure Ic) and C19 (structure Id) cyclopropane acids occur in varying amounts in the seed oils of some species of a few plant families including Malvaceae and Sterculiaceae (Christie, 1970; Sebedio and Grandgirard, 1989). The cyclopropene counterparts (structures IIIa and IIIb) are more widespread in these families, and cyclopentenyl acids (structures IV a-c) are present in the seed oils of the family Flacourtiaceae, notably the genus Hydnocarpus (Sebedio and Grandgirard, 1989). Fatty acids with six-membered (structure Va; Hippchen, Roell and Poralla, 1981) and, unusually, seven-membered (structure Vb; Poralla and Koenig, 1983) rings have been characterized from the thermoacidophilic bacterium, Bacillus acidocaldarius.
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