4281. Fucoxanthin

Nomenclature

CAS number: 3351-86-8
(3S,3′S,5R,5′R,6S,6′R)-3′-(Acetyloxy)-6′,7′-didehydro-5,6-epoxy-5,5′,6,6′,7,8-hexahydro-3,5′-dihydroxy-8-oxo-β,β-carotene; 6′,7′-didehydro-5,6-epoxy-4′,5,5′,6,7,8-hexahydro-3,3′,5′-trihydroxy-8-oxo-α-carotene 3′-acetate; all-trans-fucoxanthin.
C42H58O6; mol wt 658.91.
C 76.56%, H 8.87%, O 14.57%.

Description and references

Carotenoid pigment found in fresh brown algae: Fucus virsoides (Don) J. Ag., Fucaceae. Also found in Zygnema pectinatum (Vauch.) Ag., Zygnemaceae and in Polysiphonia nigrescens (Dillw.) Grev., Rhodomelaceae. Isoln: Karrer et al., Helv. Chim. Acta 14, 628 (1931); Willsttter, Page, Ann. 404, 237 (1914). Structure: Bonnet et al., Chem. Commun. 1966, 515; J. Chem. Soc. C 1969, 429. Abs config: DeVille et al., Chem. Commun. 1969, 1311; K. Bernhard et al., Tetrahedron Lett. 1976, 115.

Chemical structure

Properties

Needles from ether + petr ether, mp 160°. [α]D18 +72.5 ±9° (chloroform). Abs max (chloroform): 492, 457 nm. Abs max (ethanol): 450 nm (E1%1cm 1140), Antia, Can. J. Chem. 43, 302 (1965). Freely sol in ethanol; less sol in carbon disulfide; sparingly sol in ether. Practically insol in petr ether. 1.66 g dissolves in 100 g boiling methanol.