6468. Neovitamin A

Nomenclature

CAS number: 2052-63-3
13-cis-Retinol; 2-cis-vitamin A.
C20H30O; mol wt 286.45.
C 83.86%, H 10.56%, O 5.59%.

Description and references

Naturally occurring, bioactive isomer of vitamin A, q.v. The 13-cis- and all-trans-forms come to equilibrium in solution with ≈33% as 13-cis. Isoln from shark liver oil: C. D. Robeson, J. G. Baxter, J. Am. Chem. Soc. 69, 136 (1947). Synthesis: M. Matsui et al., J. Vitaminol. 4, 178 (1958). Stereoselective synthesis: J. Otera et al., Chem. Lett. 1985, 1883. HPLC determn in food samples: E. Brinkmann et al., J. Chromatogr. A 693, 271 (1995). Review of vitamin A compounds: W. Friedrich in Vitamins (Walter de Gruyter, Berlin, 1988) pp 63-140.

Chemical structure

Properties

Pale yellow needles from ethyl formate, mp 58-60°. uv max: 328 nm (ε 41800).