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Structure Database (LMSD)

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Common Name

fucoxanthin

Systematic Name

(3S,5R,6S,3'S,5'R,6'R)-3,5'-dihydroxy-8-oxo-6',7'-didehydro-5,6-epoxy-5,6,7,8,5',6'-hexahydro-β,β-caroten-3'-yl acetate

Synonyms

(3'S,5'R,6'R)-3'-acetoxy-5,6-epoxy-3,5'-dihydroxy-6',7'-didehydro-5,6,7,8,5',6'-hexahydro-beta,beta-caroten-8-one
(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-beta,beta-carotene
Fucoxanthin

LM ID

LMPR01070300

Formula

C₄₂H₅₈O₆

Exact Mass

Calculate m/z

658.42334

Status

Curated

Show lipids differing only in stereochemistry/bond geometry

Classification

Biological Context

Fucoxanthin is a carotenoid that occurs naturally in certain algae. It significantly reduces abdominal white adipose tissue (WAT) in mice and rats when included in their diet.¹ Fucoxanthin increases the amount of mitochondrial uncoupling protein 1 (UCP1), a fatty acid-stimulated protein involved in respiration and thermogenesis in WAT of mice and rats.¹ In KK-Ay mice, which are used to model obese type 2 diabetics with hyperinsulinemia, fucoxanthin reduces WAT gain and also decreases blood glucose and plasma insulin levels.^1,2

This information has been provided by Cayman Chemical

References

1. Maeda, H., Hosokawa, M., Sashima, T., et al. Fucoxanthin from edible seaweed, Undaria pinnatifida, shows antiobesity effect through UCP1 expression in white adipose tissues. Biochem. Biophys. Res. Commun. 332(2), 392-397 (2005).

2. Chen, J.K., Chen, J., Imig, J.D., et al. Identification of novel endogenous cytochrome p450 arachidonate metabolites with high affinity for cannabinoid receptors. J. Biol. Chem. 283(36), 24514-24524 (2008).

Cayman Chemical

String Representations

InChiKey (Click to copy)

SJWWTRQNNRNTPU-XJUZQKKNSA-N

InChi (Click to copy)

InChI=1S/C42H58O6/c1-29(18-14-19-31(3)22-23-37-38(6,7)26-35(47-33(5)43)27-40(37,10)46)16-12-13-17-30(2)20-15-21-32(4)36(45)28-42-39(8,9)24-34(44)25-41(42,11)48-42/h12-22,34-35,44,46H,24-28H2,1-11H3/b13-12+,18-14+,20-15+,29-16+,30-17+,31-19+,32-21+/t23-,34-,35-,40+,41+,42-/m0/s1

SMILES (Click to copy)

C(C(=O)/C(/C)=C/C=C/C(/C)=C/C=C/C=C(\C)/C=C/C=C(/C([H])=[C@@]=C1[C@@](O)(C)C[C@@H](OC(=O)C)CC1(C)C)\C)[C@]12C(C)(C)C[C@H](O)C[C@@]1(C)O2