2589. Crocetin

Nomenclature

CAS number: 27876-94-4
8,8′-Diapo-ψ,ψ-carotenedioic acid; trans-crocetin.
C20H24O4; mol wt 328.40.
C 73.15%, H 7.37%, O 19.49%.

Description and references

Carotenoid-dicarboxylic acid isolated from Crocus sativus L.; C. albiflorus var. neapolitanus Hort.; C. luteus Lam., Iridaceae. Extraction procedure and structure: Jucker, Karrer, Carotinoide (Basel, 1948) p 282.

Chemical structure

Properties

Brick-red rhombs from acetic anhydride, mp 285°. Absorption max (pyridine): 464, 436, 411 nm. Sol in pyridine, in very dil NaOH solns. Very sparingly sol in water, and in the usual organic solvents except pyridine and similar organic bases. Forms a solid dipyridyl salt.

Derivative

Dimethyl ester.
C22H28O4; mol wt 356.46.
C 74.13%, H 7.92%, O 17.95%.

Properties

Brick-red elongated leaflets, mp 222.5°. Total synthesis: Buchta, Andree, Naturwissenschaften 46, 74 (1959).

Derivative

Di-gentiobiose ester.

Nomenclature

CAS number: 42553-65-1
Crocin.
C44H64O24; mol wt 976.96.
C 54.09%, H 6.60%, O 39.30%.

Description and references

One of the yellow-red pigments of saffron. Isoln and structure: Karrer, Salomon, Helv. Chim. Acta 10, 397 (1927); 11, 513, 711 (1928); Karrer et al., ibid. 12, 985 (1929); 13, 392 (1930); Kuhn, Winterstein, Ber. 67, 344 (1934); Reichstein, Angew. Chem. 74, 887 (1962).

Properties

Hydrated brownish-red needles from methanol, mp 186° (effervescence). Absorption max (methanol): 464, 434 nm. Freely sol in hot water giving an orange-colored soln. Sparingly sol in abs alcohol, ether, other organic solvents.