2873. 3-Dehydroretinal

Nomenclature

CAS number: 472-87-7
3,4-Didehydroretinal; (all-E)-3,7-dimethyl-9-(2,6,6-trimethyl-1,3-cyclohexadien-1-yl)-2,4,6,8-nonatetraenal; all-trans-3,4-dehydroretinal; retinal 2; retinene 2; vitamin A2 aldehyde.
C20H26O; mol wt 282.42.
C 85.06%, H 9.28%, O 5.67%.

Description and references

Carotenoid chromophore of porphyropsin and cyanopsin, q.q.v., which are visual pigments of certain fish, crustaceans and amphibians. May also occur in combination with retinal, q.v., in mixed visual systems. Isoln from retinas of fresh-water fish: G. Wald, Nature 139, 1017 (1937). Recognition as vitamin A2 aldehyde: R. A. Morton, ibid. 153, 69 (1944). Prepn by the oxidation of vitamin A2: G. Wald, Biochim. Biophys. Acta 4, 215 (1950). Synthesis: K. R. Farrar et al., J. Chem. Soc. 1952, 1414; of stereoisomers: U. Schwieter et al., Helv. Chim. Acta 45, 517, 528, 541 (1962); R. S. H. Liu et al., J. Am. Chem. Soc. 99, 8095 (1977). HPLC separation: K. Tsukida et al., J. Chromatogr. 192, 395 (1980); T. Suzuki, M. Makino-Tasaka, Anal. Biochem. 129, 111 (1983). Biological activity: G. Wald, J. Gen. Physiol. 22, 775 (1939); idem, Fed. Proc. 12, 606 (1953). Reviews: G. Wald, Science 162, 230-239 (1968); R. Hubbard et al., Methods Enzymol. 18, 615-653 (1971). Book: The Retinoids Vol. 1-2, M. B. Sporn et al., Eds. (Academic Press, New York, 1984).

Chemical structure

Properties

Orange-red prisms from pentane, mp 77-78°. uv max (ethanol): 401 nm (E1%1cm 1470).

Derivative

11-cis-Isomer.

Nomenclature

CAS number: 41470-05-7

Properties

Oil from petr ether-ether. uv max (ethanol): 393 nm (E1%1cm 882).

Use

As tool in biological energy transduction research.