Anacardic acid 8 monoene

However, on account of the unavailability of the corresponding aldehyde, anacardic acid (8Z)-monoene Fig (2)-2 and Fig (2)-3, the (8Z,llZ)-diene were obtained by the alkylation route as described in [2],... 

The isomer of Fig (2)-2, anacardic acid 8(E)-monoene has been synthesised by a Xrans elimination reaction as depicted in Scheme 2 [234], which also depicts the route used for the (Z)- isomer, ginkgolic acid. [235],... 

Constituents of natural cashew nutshell liquid (Anacardium occidentale) are active inhibitors of a-glucosidase, invertase and aldose reductase. The saturated, monoene, diene and triene anacardic acid constituents were the most potent inhibitors compared with commercially structurally-related compounds which showed a negligible activity [283]. 

Regiospecific hydroperoxidation of (15 2)-anacardic acid has been effected with soy bean lipogenase to form 2-hydroxy-6-[12-hydroperoxy-(8Z,10E)-pentadecadienyl]-benzoic acid [288] but the (15 l)-monoene exhibited inhibitory action, (IC50, 50pM) [289]. Related work on the inhibitory properties of anacardic acids towards soybean 5-lipogenase and ovine prostaglandin endoperoxide synthase has been carried out [39], These authors reported that 8Z-(15 l)-anacardic acid and the 10Z-(15 1)-... 

Alkylation routes have been used for the monoenes in this group. Thus, ethyl 2-methoxy-6-methylbenzoate as the carbanion (formed from lithium di-isopropylamide) has been alkylated with (Z) 1-bromotetradec-7-ene in the presence of hexamethylphosphoric triamide. Demethylation with lithium t-butytthiolate yielded (15 1)-anacardic acid (ref. 114). A more activated benzyl group having an adjacent sulphur atom was used for a synthesis of the 10(Z)-isomer of ginkgolic acid in the following way (ref. 8). 

Long-chain alkylphenols have been investigated extensively (33) by both adsorption and reversed-phase partition methods (34). The cashew phenols (from Anacardium occidentale) comprise cardanol (1), cardol (2), 2-methylcardol (3), and anacardic acid (4), each existing as a mixture of the saturated, 8 -monoene, 8 ,11 -diene, and 8 ,1 l ,14 -trieneconstituents. In ammoniated solvent [light petroleum-diethyl ether-ammonia (60 40 2)] the acidic compound anacardic acid remained practically on the baseline, whereas in an acidic solvent [light petroleum-diethyl ether-formic acid (70 30 1)] it migrated toward the solvent front as an intramolecularly bonded substance. In natural cashew nut shell liquid the phenols and their unsaturated constituents have the values 0.20 (cardol). 

Anacardic 8(Z)-monoene (ginkgolic acid) has been synthesised from... 

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