Apocarotenoic acids

Wang, X. D., R. M. Russell, C. Liu et al. 1996. Beta-oxidation in rabbit liver in vitro and in the perfused ferret liver contributes to retinoic acid biosynthesis from beta-apocarotenoic acids. J Biol Chem 271 (43) 26490-26498. 

Figure 9-2 Structural Formulas of Some Provitamins A. (A) P-carotene, and (B) apocarotenal (R = CHO) and apocarotenoic acid ester (R = COOC2H5).

The alkylation/elimination methodology is also applicable to synthesis of carotenoids. The basic strategies for the apo-8 -p-carotenoids [ 12] and for p,p-carotene (3) [ 13] are depicted in Schemes 10 and 11. Vitamin A acetate (10) was reacted with sodium /7-phenoxybenzene-sulphinate to give the sulphone 31. The reaction of 31 with the bromo compounds 32 and 33, respectively gave the apocarotenoic acid ester 34 and the corresponding aldehyde 482. 

Azafrin (504), a well known C2 -apocarotenoic acid, possesses the (5R,6R)-5,6-dihydroxy-... 

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