Title: Fucoxanthin
CAS Registry Number: 3351-86-8
CAS Name: (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-b,b-carotene
Additional Names: 6¢,7¢-didehydro-5,6-epoxy-4¢,5,5¢,6,7,8-hexahydro-3,3¢,5¢-trihydroxy-8-oxo-a-carotene 3¢-acetate; all-trans-fucoxanthin
Molecular Formula: C42H58O6
Molecular Weight: 658.91
Percent Composition: C 76.56%, H 8.87%, O 14.57%
Literature 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); Willstätter, 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.
Properties: Needles from ether + petr ether, mp 160°. [a]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.
Melting point: mp 160°
Optical Rotation: [a]D18 +72.5 ±9° (chloroform)
Absorption maximum: Abs max (chloroform): 492, 457 nm; Abs max (ethanol): 450 nm (E1%1cm 1140), Antia, Can. J. Chem. 43, 302 (1965) |