Fucoxanthin

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)
Fucus Fulvestrant Fulvoplumierin Fumagillin Fumaric Acid

Fucoxanthin
Fucoxanthin.svg
Identifiers
CAS number 3351-86-8 YesY
PubChem 5281239
ChemSpider 21864745 N
Jmol-3D images Image 1
Properties
Molecular formula C42H58O6
Molar mass 658.91 g mol−1
 N (verify) (what is: YesY/N?)
Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
Infobox references

Fucoxanthin is a xanthophyll, with formula C42H58O6. It is found as an accessory pigment in the chloroplasts of brown algae and most other heterokonts, giving them a brown or olive-green color. Fucoxanthin absorbs light primarily in the blue-green to yellow-green part of the visible spectrum, peaking at around 510-525 nm by various estimates and absorbing significantly in the range of 450 to 540 nm.

Some metabolic and nutritional studies carried out on rats and mice at Hokkaido University indicate that fucoxanthin promotes fat burning within fat cells in white adipose tissue by increasing the expression of thermogenin.[1] A subsequent double-blind placebo-controlled human study of females with liver disease using supplementation with seaweed extract containing fucoxanthin in combination with pomegranate seed oil [2] showed in an average 4.9 kg (11 lb) weight loss in obese women over a 16-week period.[2]

Another 16-week trial is currently underway that is investigating the effects of a combination supplement of brown seaweed extract (containing fucoxanthin) and pomegranate seed oil. This study is looking at the effects of this supplement on body composition, resting energy expenditure, blood pressure, and serum lipid levels and liver enzyme levels of obese men and women following a hypocaloric diet. A manuscript involving the complete results of this study is still pending.