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Carotenoid


DATA No : VCA0053 INFORMANT : Masayoshi Ito

NAME : (3S,5R,6S,3'S,5'R,6'R)-5,6-Epoxy-3,3',5'-trihydroxy-6',7'-didehydro-5,6,7,8,5',6'-hexahydro-b,b-caroten-8-one

COMMON NAME: Fucoxanthinol
SYMBOL:
FORMULA: C40H56O5 MOL.WT (average) : 616.870


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BIOLOGICAL ACTIVITY
Inhibitotory effect on Epstein-Barr virus activation (anti-tumor promotion) (Ref. 0217)
PHYSICAL AND CHEMICAL PROPERTIES
MELTING POINT:

BOILING POINT:

REFRACTIVE INDEX:

OPTICAL ROTATION:

DENSITY:

SOLUBILITY:
SPECTRAL DATA
UV SPECTRA:lmax (nm): acetone (420), 445, (465) (Ref. 0148)

IR SPECTRA:nmax(KBr)/cm-1: 3248s (OH), 3031-2734s (CH), 1929w (C=C=C), 1726w, 1650m (conj. C=O), 1606s, 1530w, 1385s (gem Me), 1294w, 1270w, 1149m, 1123m, 1071m, 1052m, 965w (trans CH=CH) (Ref. 0148)

NMR SPECTRA:1H-NMR d(CDCl3): 0.9631, 1.035 (1-gem-Me), 3.82 (3-H), 1.79 (4ax-H), 2.30 (4eq-H), 1.220 (5-Me), 2.60, 3.66 (7-H2), 1.943 (9-Me), 7.15 (10-H), 6.58 (11-H), 6.67 (12-H), 1.990 (13-Me), 6.41 (14-H), 6.64 (15-H), 6.75 (15'-H), 6.27 (14'-H), 1.990 (13'-Me), 6.35 (12'-H), 6.61 (11'-H), 6.12 (10'-H), 1.810 (9'-Me), 6.03 (8'-H), 1.336 (5'-Me), 4.32 (3'-H), 1.351, 1.070 (1'-gem-Me) (Ref. 0148) (Ref. 1309)

MASS SPECTRA:

OTHER SPECTRA:
CHROMATOGRAM DATA
TLC [Kieselgel 60 (Merck Art. 7731)]: acetone-hexane 3:7, Rf = 0.08; acetone-hexane 1:1, Rf = 0.20 (Ref. 0148)
SOURCE
Tapes philippinarum (Clam) (Ref. 0403)
Psammechinus miliaris (sea-urchin) (Ref. 0500)
Algae (Ref. 0409)
CHEMICAL SYNTHESIS

METABOLISM
Fucoxanthin - Fucoxanthinol in Psammechinus miliaris (sea-urchin) (Ref. 0500)
In lying hens, fucoxanthin in Fucus serratus (brown algae) is metabolized to fucoxanthinol, and then fucoxanthinol 3'-sulphate and paracentrone (Ref. 1309).
GENETIC INFORMATION

NOTE

REFERENCES
[0148]
AUTHOR:Haugan,A.J.,Englert,G., and Liaaen-Jensen,S.
TITLE:Algal Carotenoids 50. Alkali Lability of Fucoxanthin - Reactions and Products
JOURNAL:Acta. Chem. Scand.
VOL:46 PAGE : 614 -624 (1992)
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[0217]
AUTHOR:Tsushima, M., Maoka, T., Katsuyama, M., Kozuka, M., Matsuno, T., Tokuda, H., Nishino, H., and Iwashima, A.
TITLE:Inhibitory effect of natural carotenoids on Epstein-Barr virus activation activity of a tumor promoter in Raji cells. A screening study for anti-tumor promoters PubMed ID:7742789
JOURNAL:Biol Pharm Bull.
VOL:18 PAGE : 227-233 (1995)
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[0403]
AUTHOR:Matsuno,T.,Maoka,T.,Shiba,K., and Ookubo,M.
TITLE:Isolation of fucoxanthinol from short-necked clam Tapes philippinarum [Asari in Japanese]
JOURNAL:Bull. Jap. Soc. Sci. Fish.
VOL:52 PAGE : 167 -167 (1986)
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[0409]
AUTHOR:Goodwin T. W. (1980) The biochemistry of the carotenoids, Volume I, Plants, Chapman and Hall, London and New York
TITLE:
JOURNAL:
VOL: PAGE : - ()
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[0500]
AUTHOR:Hallenstvet,M.,Pyberg,E., and Liaaen-Jensen,S.
TITLE:Animal carotenoids - XIV Carotenoids of Psammechinus miliaris (sea-urchin)
JOURNAL:Comp. Biochem. Physiol.
VOL:60 PAGE : 173 -175 (1978)
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[1309]
AUTHOR:Strand, A., Herstad, O., Liaaen-Jensen, S.
TITLE:Animal carotenids: 33. Fucoxanthin metabolites in egg yolks of laying hens
JOURNAL:Comp. Biochem. Physiol.
VOL:119 PAGE : 963 -974 (1998)
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Last updated June 19, 2007. Copyright © 1989-2007 Japanese Conference on the Biochemistry of Lipids (JCBL). All rights reserved.