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Carotenoid


DATA No : VCA0064 INFORMANT : Masayoshi Ito

NAME : 3,3',8'-Trihydroxy-7,8-didehydro-b,k-carotene-4,6'-dione

COMMON NAME: 4-Oxomytiloxanthin
SYMBOL:
FORMULA: C40H52O5 MOL.WT (average) : 612.838


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BIOLOGICAL ACTIVITY

PHYSICAL AND CHEMICAL PROPERTIES
MELTING POINT:

BOILING POINT:

REFRACTIVE INDEX:

OPTICAL ROTATION:

DENSITY:

SOLUBILITY:
SPECTRAL DATA
UV SPECTRA:lmax (nm): hexane/isopropyl ethanoate/acetone (76:17:7, v/v) 447, 473, 502 (Ref. 0420)

IR SPECTRA:

NMR SPECTRA:1H-NMR d(400 MHz, CDCl3): 0.852 (3H, s 16'-Me), 1.191 (3H, s 17'-Me), 1.311 (3H, s, 16-Me), 1.351 (3H, s 18'-Me), 1.355 (3H, s, 17-Me), 1.55 (1H, dd, J 14.3, 3, 4'-Hb), 1.72 (1H, dd, J 13.5, 4.5, 2'-Hb), 1.80 (1H, t, J 13, 2-Hax), 1.990 (3H, s, 19'-Me), 1.984 (3H, s, 20-Me), 2.004 (3H, s, 20'-Me), 2.052 (3H, s, 19-Me), 2.027 (3H, s, 18-Me), 2.09 (1H, dd, J 13.5, 7.5, 2'-Ha), 2.22 (1H, dd, J 12.8, 5.5, 2-Heq), 2.88 (1H, dd, J 14.3, 8.5, 4'-Ha), 4.33 (1H, ddd, J 14, 6, 1.8, 3-H), 4.53 (1H, m, 3'-H), 5.862 (1H, s, 7'-H), 6.34-7.24 olefinic H (Ref. 0420)

MASS SPECTRA:m/z: 612(1, M), 594 (1, M-H2O), 576 (1, M-2H2O), 413 (2), 383 (2), 83 (64), 41 (100) (Ref. 0420)

OTHER SPECTRA:
CHROMATOGRAM DATA
HPLC (columun: Sherisorb S 5-CN, detection : 450nm, mobile phase: hexana/isopropyl ethanoate/2-propanol/N-ethyldiisopropylamine 82.4:17:0.5:0.1 (v/v), flow rate : 1 mL/min. 7,8,7',8'-tetradehydroastaxanthin tR=798 sec, 7,8-didehydroastaxanthin tR=914 sec, astaxanthin tR=1042 sec, 4-oxomytiloxanthin tR=1712 sec) (Ref. 0420)
SOURCE
Asterias rubens (Starfish) (Ref. 0420)
CHEMICAL SYNTHESIS

METABOLISM
Mytiloxanthin - 4-oxomytiloxanthin in Asterias rubens (Starfish) (Ref. 0420)
GENETIC INFORMATION

NOTE

REFERENCES
[0420]
AUTHOR:Bernhard,K.,Englert,G.,Meister,W.Vecchi,M.,Renstrom,B., and Liaaen-Jensen,S.
TITLE:Carotenoids of the carotenoprotein asteriarubin. Optical purity of asterinic acid
JOURNAL:Helv. Chim. Acta
VOL:65 PAGE : 2224 -2229 (1982)
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Last updated June 19, 2007. Copyright © 1989-2007 Japanese Conference on the Biochemistry of Lipids (JCBL). All rights reserved.