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Carotenoid


DATA No : VCA0015 INFORMANT : Masayoshi Ito

NAME : (3S,3'R)-3-(b-D-Glucopyranosyloxy)-3'-hydroxy-b,b-caroten-4-one

COMMON NAME: Adonixanthin 3-glucoside/ Adonixanthin 3-b-D-glucoside
SYMBOL:
FORMULA: C46H64O8 MOL.WT (average) : 744.996


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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): benzene 476 (Ref. 0085)

IR SPECTRA:

NMR SPECTRA:1H-NMR d(CDCl3): 2.04 (m, 2-H), 2.15 (dd, J 14, 6, 2-H), 4.40 (dd, J 14, 6, 3-H), 1.23 and 1.35 (s, 1-gem-Me), 1.91 (s, 5-Me), 1.48 (t, J 12, 2'-H), 1.77 (ddd, J 12, 4, 2, 2'-H), 4.00 (m, 3'-H), 2.05 (m, 4'-H), 2.39 (ddd, J 17, 6, 2, 4'-H), 1.08 (s, 1'-gem-Me), 1.74 (s, 5'-Me), 1.98-2.00 (s, 19,19',20,20'-Me), 6.10-6.70 (14H, m, olefinic-H), 4.57 (d, J 8, 1''-H), 3.45 (dd, J 9, 8, 2''-H), 3.61 (m, 3''-H), 3.61 (m, 4''-H), 3.41 (m, 5''-H), 3.83 and 3.93 (m, 6''-H2) (Ref. 0085)

MASS SPECTRA:HRFABMS m/z: 745.4689 [M+H]+ (Ref. 0085)

OTHER SPECTRA:CD data: De 234 (-14.2), 260 (+17.4), 301 (-21.4) (Ref. 0085)
CHROMATOGRAM DATA
HPLC (columun: TSK gel ODS-80Ts (Tosoh) 0.46times15 cm, eluent and flow: 1.0 ml/min, H2O-MeOH 5:95 for 5 min, then 5 min-linear gradient MeOH-THF 7:3) tR = 4.84 min
[Chromatogram 0012] (Ref. 0085)
SOURCE
Marine bacterium ---Agrobacterium aurantiacum (Rhizobiaceae; present name, Paracoccus sp. N81106) (Ref. 0085)
CHEMICAL SYNTHESIS

METABOLISM

GENETIC INFORMATION

NOTE

REFERENCES
[0085]
AUTHOR:Yokoyama,A.,Adachi,K., and Shizuri,Y.
TITLE:New Carotenoid Glucosides, Astaxanthin Glucoside and Adonixanthin Glucoside, Isolation from the Astaxanthin-Producing Marine Bacterium Agrobacterium aurantiacum
JOURNAL:J. Nat. Prod.
VOL:58 PAGE : 1929 -1933 (1995)
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Last updated June 19, 2007. Copyright © 1989-2007 Japanese Conference on the Biochemistry of Lipids (JCBL). All rights reserved.