3-Dehydroretinal
Title: 3-Dehydroretinal
CAS Registry Number: 472-87-7
CAS Name: 3,4-Didehydroretinal
Additional Names: (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
Molecular Formula: C20H26O
Molecular Weight: 282.42
Percent Composition: C 85.06%, H 9.28%, O 5.67%
Literature 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).
Properties: Orange-red prisms from pentane, mp 77-78°. uv max (ethanol): 401 nm (E1%1cm 1470).
Melting point: mp 77-78°
Absorption maximum: uv max (ethanol): 401 nm (E1%1cm 1470)
 
Derivative Type: 11-cis-Isomer
CAS Registry Number: 41470-05-7
Properties: Oil from petr ether-ether. uv max (ethanol): 393 nm (E1%1cm 882).
Absorption maximum: uv max (ethanol): 393 nm (E1%1cm 882)
 
Use: As tool in biological energy transduction research.

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