7411. Picrocrocin

Nomenclature

CAS number: 138-55-6
(4R)-4-(β-d-Glucopyranosyloxy)-2,6,6-trimethyl-1-cyclohexene-1-carboxaldehyde; saffron-bitter.
C16H26O7; mol wt 330.37.
C 58.17%, H 7.93%, O 33.90%.

Description and references

From stigmas of Crocus sativus L., Iridaceae. Isoln: Kayser, Ber. 17, 2228 (1884). Structure: Kuhn, Winterstein, Ber. 67, 344 (1934). Exerts sex-determining influences in the plant organism: Kuhn, Angew. Chem. 53, 1 (1940). Its moieties are glucose and safranal, q.q.v. Abs config: Buchecker, Eugster, Helv. Chim. Acta 56, 1121 (1973). Synthesis: H. Mayer, J.-M. Santer, Helv. Chim. Acta 63, 1463 (1980).

Chemical structure

Properties

Crystals, mp 154-156°. [α]D20 -58° (c = 0.6). Bitter taste. Alkali unstable. Sol in water, alcohol; slightly sol in chloroform, ether. Practically insol in petr ether, benzene.