2-Hydroxysterculate

This type of fatty acid is usually found at low levels (around 1%) in plant oils that contain cyclopropene acids. Cyclopropene acids are characteristic for oils from the Malvalaceae, Stercu-liaceae, Bombaceae, Tiliaceae, and Sapicidaceae families with sterculic acid (9,10-methyleneoctadec-9-enoic acid) and mal-valic acid (8,9-methyleneheptadec-8-enoic acid) as two major compounds. Sterculic acid is more abundant (about 50% of the total fatty acids in Sterculiafoetida oil). 2-Hydroxysterculic acid may also be present in this oil as a possible intermediate in the biosynthesis of malvalic acid (through a-oxidation of sterculic acid). 

Hydroxyoct-2-enal, 457 2-Hydroxyoleic acid, 19 17-Hydroxyoleic acid, 20 Hydroxysphinganine, 32, 519 17-Hydroxystearic acid, 20 2-Hydroxysterculic acid, 17, 53 Hyperlipoproteinemias, 538 Hyphae, 151... 

Hydroxy-12,14-icosadienoic acid, H-00288 2-Hydroxysterculic acid Me ester, in H-00388... 

Hydroxy-9,10-methylene 18 1 (9c) 2-Hydroxysterculate Pachira insignis (20%) Bombacopsis glabra (10%)... 

An acetylenic cyclopropenoid fatty acid, sterculynic acid, is present in the seed lipids of Sterculia alata at a level of about 8% (Jevans and Hopkins, 1968). D-2-Hydroxysterculic acid is found in the seed lipids of Bombacopsis glabra at a level of about 10% (Morris and Hall, 1%7) and, in smaller proportions, in those of various Malvaceae (Bohannon and Kleiman, 1978) (Fig. 2). 

D-2-Hydroxysterculic acid Fig. 2. Structures of less common cyclopropenoid fatty acids. 

Little can be said regarding the biogenesis of sterculynic and D-2-hydrox-ysterculic acids. To the authors knowledge, the biosynthesis of sterculynic acid has not been investigated so far. D-2-Hydroxysterculic acid is consid-... 

Both are responsible for the characteristic color shown by cottonseed oil in the so-called Halphen test. A probable intermediate in the biosynthesis of malvalic from sterculic acid, D-2-hydroxysterculic acid, has been isolated from seed oils (Earle et al., 1964 Morris and Hall, 1967). 

However, the elimination may be achieved in high yield from either cis- or trans-, 2-di-iodo-1,2-dibutylcyclopropanes using one molecular equivalent of butyllithium at low temperature. Since no reaction occurred at the ester group under these conditions, this has been applied in synthesis esters as of sterculic acid, a-hydroxysterculic acid (55)108 and 56, a potential inhibitor of mycolic acid synthesis109 ... 

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