2324. β-Citraurin

Nomenclature

CAS number: 650-69-1
3-Hydroxy-8′-apo-β,ψ-carotenal; citraurin.
C30H40O2; mol wt 432.64.
C 83.28%, H 9.32%, O 7.40%.

Description and references

Carotenoid pigment found only in orange peel. Isoln by chromatography: Zechmeister, Tuzson, Ber. 69, 1878 (1936); 70, 1966 (1937). The peels from 100 kilos of oranges yield about 35 mg. Structure: Zechmeister, Tuzson, loc. cit.; Karrer, Solmssen, Helv. Chim. Acta 20, 682 (1937); Karrer et al., ibid. 1020; Zechmeister, v. Cholnoky, Ann. 530, 291 (1937); Karrer et al., Helv. Chim. Acta 21, 445 (1938). Abs config: Bartlett et al., J. Chem. Soc. C 1969, 2527. Synthesis: H. Pfander et al., Helv. Chim. Acta 63, 1377 (1980).

Chemical structure

Properties

Thin orange or yellow-colored plates from benzene + petr ether, mp 147°. Absorption max (benzene): 497, 467 nm. Freely sol in acetone, ethanol, ether, benzene, and carbon disulfide. Sparingly sol in petr ether.