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Carotenoid


DATA No : VCA0042 INFORMANT : Masayoshi Ito

NAME : (3'S)-3'-Hydroxy-4',5'-didehydro-4,5'-retro-b,b-caroten-3-one

COMMON NAME: Eschscholtzxanthone
SYMBOL:
FORMULA: C42H52O2 MOL.WT (average) : 588.861


Download ChemDraw structure data
BIOLOGICAL ACTIVITY
Antioxidative activity (Ref. 0460)
PHYSICAL AND CHEMICAL PROPERTIES
MELTING POINT:

BOILING POINT:

REFRACTIVE INDEX:

OPTICAL ROTATION:

DENSITY:

SOLUBILITY:
SPECTRAL DATA
UV SPECTRA:lmax (nm): ether 480 (Ref. 0460)

IR SPECTRA:nmax(KBr)/cm-1: 3400 (OH), 1660 (conj. C=O), 973, 950 (retro type olefin) (Ref. 0450)

NMR SPECTRA:1H-NMR d(300 MHz, CDCl3): 1.25 (3H, s, 16'-Me), 1.39(6H, s, 16',17'-Me), 1.45 (3H, s, 17'-Me), 1.51 (1H, dd J 12, 8, 2'ax-H), 1.81 (1H, dd J 12, 5, 2'eq-H), 1.95 (3H, d J1.5, 18'-Me), 1.97 (6H, s, 19', 20'-Me), 2.00 (3H, s, 20'-Me), 2.03 (3H, s, 19'-Me), 2.159 (3H, d J 1, 18-Me), 2.40 (2H, s, 2-H), 4.35 (1H, m, H-3'), 5.94 (1H, br.s, 4-H), 6.26-6.91 (14H, olefinic H) (Ref. 0460)

MASS SPECTRA:m/z: 564 (M, 18%), 546 (20%), 532 (8%), 454 (6%), 119 (100%), 107 (76%), 91(78%) (Ref. 0460)

OTHER SPECTRA:CD data in ether solution: De 232 (+4.0), 240 (0), 272 (+5.7), 285(0), 318(-7.2), 345 (0), 390 (+5.0) (Ref. 0460)
CHROMATOGRAM DATA

SOURCE
Taxus caspidata (berries) (Ref. 0460)
CHEMICAL SYNTHESIS

METABOLISM
Taxus caspidata: Eschscholtzxanthin a_right eschscholtzxanthone a_right rhodoxanthin(Ref. 0460>
GENETIC INFORMATION

NOTE

REFERENCES
[0450]
AUTHOR:Märki-Fischer,E., and Eugster,C.H.
TITLE:Eine weitere, diesmal erfolgreiche Suche nach 3'-Epilutein in Pflanzen
JOURNAL:Helv. Chim. Acta
VOL:73 PAGE : 1205 -1209 (1990)
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[0460]
AUTHOR:Maoka,T.,Ito,Y.,Fujiwara,Y., and Hashimoto,K.
TITLE:Structures and Antioxidative Activity of retro Carotenoids from the Berries of the Japanese Yew, Taxus cuspidata
JOURNAL:J. Jap. Oil Chem. Soc.
VOL:45 PAGE : 641 -646 (1996)
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Last updated June 19, 2007. Copyright © 1989-2007 Japanese Conference on the Biochemistry of Lipids (JCBL). All rights reserved.