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Carotenoid


DATA No : VCA0049 INFORMANT : Masayoshi Ito

NAME : (3S,3'S)-3,3'-dihydroxy-7,8-Didehydro-b,b-carotene-4,4'-dione

COMMON NAME: 7,8-Didehydroastaxanthin
SYMBOL:
FORMULA: C40H50O4 MOL.WT (average) : 594.823


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BIOLOGICAL ACTIVITY

PHYSICAL AND CHEMICAL PROPERTIES
MELTING POINT:211-212degC (Ref. 0143)

BOILING POINT:

REFRACTIVE INDEX:

OPTICAL ROTATION:

DENSITY:

SOLUBILITY:
SPECTRAL DATA
UV SPECTRA:lmax (nm) (e): benzene 300sh (16,466), 330 (16,481), 493 (102,913) (Ref. 0143); pyridine 324 (20,175), 496 (109,336), 520sh (96,320) (Ref. 0143); CS2 480sh (83,718), 507 (103,546), 540sh (81,515) (Ref. 0143)

IR SPECTRA:nmax(KBr)/cm-1: 3506m (OH), 2160m (acetylene), 1664s (conj. C=O), 1564m (conj. C=C), 1374m, 1365m (gem. dimethyl), 1079s (OH), 970s (trans CH=CH) (Ref. 0143)

NMR SPECTRA:1H-NMR d(400 MHz, CDCl3): 1,211, 1.323 (16',17'-Me), 1.312, 1.356 (16,17-Me), 1.801 (t, J 13.4, 2ax-H), 1.811 (t, J 13.4, 2'ax-H), 1.945 (18'-Me), 1.976 (20-Me), 1.999 (20'-Me), 2.003 (19'-Me), 2.026 (8-Me), 2.047 19-Me), 2.16 (dd, J 12.6, 5.6, 2'eq-H), 2.22 (dd, J 12.6, 5.5, 2eq-H), 3.610 (d, J 1.6, 3-OH), 3.682 (d, J 1.8, 3'-OH), 4.30-4.36 (2H, m, 3'ax, 3ax-H), 6.222 (d, J 16, 7'-H), 6.28-6.70 (11H, 10',14,14',8',12,12',11,10,11',15,15'-H) (Ref. 0143)
13C-NMR d(67.892 MHz, CDCl3): 12.59 (19'Me), 12.74, 12.85 (20,20'-Me), 13.99 (18'-Me), 14.33 (18-Me), 17.60 (19-Me), 26.15, 30.74 (16',17'-Me), 26.18, 31.04 (16,17-Me), 36.63 (1C), 36.80 (1'C), 44.20 (2C), 45.47 (2'C), 69.21, 69.32 (3,3'C), 88.01, 110.99 (7,8C), 117.43 (9C), 123.41, 123.77, 124.86, 126.87, 130.52, 131.27, 133.60, 133.72, 134.73, 134.95, 135.14, 136.32, 137.13, 138.99, 139.65, 140.62, 142.30 (9',11,11',15,15',5,5',14,14',13,13',10,10',12,12',8',7'C), 147.71 (6C), 162.18 (6'C), 199.28 (4C) (Ref. 0143)

MASS SPECTRA:m/z: 594 (65, M), 592 (26), 578 (18), 576 (19), 203 (93), 119 (67), 105 (70), 91 (100) (Ref. 0143)

OTHER SPECTRA:CD: De 372 (+4.02), 317 (-14.13), 300sh (-11.3), 275 (+3.78), 263sh (+1.0), 247 (-3.35), 224 (+4.10) (Ref. 0143)
CHROMATOGRAM DATA
TLC [Kieselgel F254 (Merck); CH2Cl2-ether 4:1) Rf = 0.20 (Ref. 0143)
HPLC (column: Spherisorb S 5-CN 0.31times50 cm, eluent: hexane/isopropyl ethanoate/2-propanol/N-ethyldiisopropylamine, 82.4:17:0.5:0.1, flow rate: 1 ml/min)
[Chromatogram 0021] --- di-(-)-camphanate tR = 1168 sec [all-E-(3R,3'S)], 1406 sec [all-E-(3S,3'S)] (Ref. 0420)
HPLC (column: Sperisorb S 5-CN 0.31times50 cm, eluent: hexane/isopropyl ethanoate/2-propanol/N-ethyldiiopropylamine 82.4:17:0.5:0.1, flow: 1.0 ml/min) Retention time: 914 sec (Ref. 0420)
SOURCE
Asterias rubens (Starfish) (Ref. 0420)
Asterina pectinifera, Asterias amurensis (Starfish) (Ref. 0423)
Watasenia scintilans, Sepia modokai, Sepia officinales (cuttlefish) (Ref. 0424)
Octopus vulgaris, Octopus ocellatus, Octopus minor (octopus) (Ref. 0424)
Salmo salar, Oncorhynchus sp. (Salmon) (Ref. 0419)
Paralithodes brevipes (crab) (Ref. 0469)
CHEMICAL SYNTHESIS
Wittig condensation between (3S)-3-hydroxy-4-oxo-C15-phosphonium salt and (3S)-3-Hydroxy-7,8-didehydro-4-oxo-12'-apo-b-carotenal provided 7,8-didehydroastaxanthin. (Ref. 0143)
METABOLISM
Doatoxanthin a_right 7,8-didehydroastaxanthin Asterias rubens (Starfish) (Ref. 0420)
Diatoxanthin a_right 4,4'-dihydroxydiatoxanthin a_right 4-keto-4'-hydroxydiatoxanthin a_right 7,8-didehydroastaxanthin in Asterina pectinifera, Asterias amurensis (Starfish) (Ref. 0423)
GENETIC INFORMATION

NOTE

REFERENCES
[0143]
AUTHOR:Bernhard,K., Kienzle,F., Mayer,H., and Müller, R.K.
TITLE:Synthesis of optically active natural carotenoids and structurally related compounds. VIII. Synthesis of (3S,3'S)-7,8,7',8'-tetradehydroastaxanthin and (3S,3'S)-7,8-didehydroastaxanthin (asterinic acid)
JOURNAL:Helv. Chim. Acta
VOL:63 PAGE : 1473 -1490 (1980)
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[0419]
AUTHOR:Schiedt,K.,Leuenberger,F.J., and Vecchi,M.
TITLE:Natural Occurrences of enantiomeric and meso-astaxanthin 5, Ex Wild salmon (Salmo salar and Oncorynchus)
JOURNAL:Helv. Chim. Acta
VOL:64 PAGE : 449 -457 (1981)
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[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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[0423]
AUTHOR:Maoka,T.,Tsushima,M., and Matsuno,T.
TITLE:New acetylenic carotenoids from the starfishes Asterina pectinifera and Asterias amurensis
JOURNAL:Comp. Biochem. Physiol.
VOL:93 PAGE : 829 -834 (1989)
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[0424]
AUTHOR:Maoka,T.,Yokoi,S., and Matsuno,T.
TITLE:Comparative biochemical studies of carotenoids in nine species of cephalopoda
JOURNAL:Comp. Biochem. Physiol.
VOL:92 PAGE : 247 -250 (1989)
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[0469]
AUTHOR:Matsuno,T., and Maoka,T.
TITLE:The Carotenoids of Crab Paralithodes brevipes (Hanasakigani in Japanese)
JOURNAL:Nippon Suisan Gakkaishi
VOL:54 PAGE : 1437 -1442 (1988)
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Last updated June 19, 2007. Copyright © 1989-2007 Japanese Conference on the Biochemistry of Lipids (JCBL). All rights reserved.