3,4-Didehydroretinoic acid

An unsaturated derivative of retinoic acid, 3,4-didehydroretinoic acid (Fig. 7.10), has been demonstrated by Eichele and Thaller to be an important signaling molecule in a model system of limb development, the chick limb bud assay (42). 3,4-Didehydroretinoic acid is derived from 3,4-didehydroretinol, which is... 

Thaller, C. and Eichele, G. (1990) Isolation of 3,4-didehydroretinoic acid, a novel morphogenetic signal in the chick wing bud. Nature 345, 815-819. 

Creech idaft J, Kimelman D, Juchau MR (1995) Xenopus laevis A Model System for the Study of Retinoid Metabolism 2. Embryonic metabolism of all-rran5-3,4-didehydroretinol to all-tran5-3,4-didehydroretinoic acid. Drug Metab Dispos 23 83-89... 

Finally, it is important to remember that this assay does not measure tRA alone because several retinoids are equally efficient at activating the RARs, including didehydroretinoic acid and 9-cis. Therefore, what one measures here is the combined concentration of the retinoic acids. 

The 7,8-didehydro C,s aldehyde (415) served as a starting material from which, via the phosphonium salt (416), both (all- )-7,8-didehydroretinoic acid (417) (Attenburrow et al., 1952) and (13Z)-7,8-didehydroretinoic acid (418) were prepared (Baumann et al., 1979 Paust et al., 1980a). 

The epoxidation of methyl 3,4-didehydroretinoate (72) at the double bond with monoperphthalic acid to give the ester (73) has been reported (Barua... 

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