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Carotenoid


DATA No : VCA0051 INFORMANT : Masayoshi Ito

NAME : (3R,3'R)-7,8,7',8'-Tetradehydro-b,b-carotene-3,3'-diol

COMMON NAME: Alloxanthin/ Tetradehydrozeaxanthin / (Cynthiaxanthin)/ (Pectenoxanthin)
SYMBOL:
FORMULA: C40H52O2 MOL.WT (average) : 564.840


Download ChemDraw structure data
BIOLOGICAL ACTIVITY
Inhibitotory effect on Epstein-Barr virus activation (anti-tumor promotion) (Ref. 0217)
PHYSICAL AND CHEMICAL PROPERTIES
MELTING POINT:186degC (Ref. 0145)

BOILING POINT:

REFRACTIVE INDEX:

OPTICAL ROTATION:

DENSITY:

SOLUBILITY:
SPECTRAL DATA
UV SPECTRA:lmax (nm): hexane 480, 451 (Ref. 0145); ethanol 481, 452 (Ref. 0145); benzene (e) 492, 462 (131,000) (Ref. 0145); methanol
[Spectrum 1152]

IR SPECTRA:nmax(KBr)/cm-1: 3350, 2170vw, 1560, 1450, 1050, 1020, 960, 950

NMR SPECTRA:1H-NMR d(CDCl3): 1.14, 1.19 (1-gem-Me), 1.90 (5-Me), 1.99 (9-Me), 1.94 (13-Me), 1.94 (13'-Me), 1.99 (9'-Me), 1.90 (5'-Me), 1.19, 1.14 (1'-gem-Me), 1.50 (2H, s), 2.29 (4H, d, J 7) (Ref. 0145)
13C-NMR d(CDCl3): 36.9 (1,1'C), 46.7 (2,2'C), 64.8 (3,3'C), 41.5 (4,4'C), 137.2 (5,5'C), 124.3 (6,6'C), 89.1 (7,7'C), 98.8 (8,8'C), 119.1 (9,9'C), 138.0 (10,10'C), 124.3 (11,11'C), 135.2 (12,12'C), 136.4 (13,13'C), 133.4 (14,14'C), 130.3 (15,15'C), 24.8 and 30.5 (1,1'-gem-Me), 22.4 (5,5'-Me), 18.0 (9,9'-Me), 12.7 (13,13'-Me) (Ref. 0061)

MASS SPECTRA:m/z: 564 (10, M), 549 (1), 546 (<0.5, M-18), 528 (<0.5, M-18-18), 472 (4, M-92), 457 (1), 406 (3), 105 (12), 92 (75), 91 (100) (Ref. 0145)

OTHER SPECTRA:CD in EPA: De 210 (-7.0), 280 (-3.0), 325 (-1.8), 492 (0) (Ref. 0426)
255 (0), 290 (-2), 350 (+0.5) (Ref. 0518)
CHROMATOGRAM DATA

SOURCE
Cynthia roretzi (Sea squirt) (Ref. 0493)
Halocynthia roretzi (Sea suirt) (Ref. 0401/0402)
Mytilus edulis (Shell fish) (Ref. 0426)
Mytilus corusucus (Ref. 0427)
Patinopecten yessoensis (Scallop) (Ref. 0494)
Pecten maximus (Scallop) (Ref. 0496)
Scapharca broughtonii (Shell fish) (Ref. 0495)
Marine Shell Fishes (Ref. 0430)
Asterina pectinifera, Asterias amurensis (Starfish) (Ref. 0423)
Carassius auratus (gold fish) (integuments) (Ref. 0470)
Oncorhynchus masou macrostomus, Salmo gairdneri (trout) (Ref. 0473)
CHEMICAL SYNTHESIS
The Wittig reaction between the C10-dialdehyde and an excess of the 3-acetoxy-7,8-didehydro-C10-phosphonium salt in the presence of KOH in propan-2-ol at -30degC leads to the racemic all-E alloxanthin and its 9Z isomer. (Ref. 0145)
METABOLISM

GENETIC INFORMATION

NOTE

REFERENCES
[0061]
AUTHOR:Moss,G.P.
TITLE:Carbon-13 NMR spectra of carotenoids
JOURNAL:Pure Appl. Chem.
VOL:2047 PAGE : 97 -102 (1976)
[TOP]

[0145]
AUTHOR:Davies,A.,Khare,A.,Mallams,A.K.,Massy-Westropp,R.A.,Moss,G.P., and Weedon,B.C.L.
TITLE:Carotenoids and Related Compounds. Part 38. Synthesis of (3RS,3'RS)-Alloxanthin and Other Acetylenes
JOURNAL:J. Chem. Soc., Perkin Trans. 1
VOL: PAGE : 2147 -2157 (1984)
[TOP]

[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)
[TOP]

[0401]
AUTHOR:Ookubo,M., and Matsuno,T.,
TITLE:Carotenoids of sea squirts - II. Comparative biochemical studies of carotenoids in sea squirts
JOURNAL:Comp. Biochem. Physiol.
VOL:81 PAGE : 137 -141 (1985)
[TOP]

[0402]
AUTHOR:Matsuno,T. and Ookubo,M.
TITLE:A new carotenoid, halocynthiaxanthin from the sea squirt, Halocynthia roretzi
JOURNAL:Tetrahedron Lett.
VOL:22 PAGE : 4659 -4660 (1981)
[TOP]

[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)
[TOP]

[0426]
AUTHOR:Hertzberg,S.,Partali,V., and Liaaen-Jensen,S.
TITLE:Animal carotenoids. 32. Carotenoids of Mytilus edulis (Edible mussel)
JOURNAL:Acta Chem. Scand.
VOL:42 PAGE : 495 -503 (1988)
[TOP]

[0427]
AUTHOR:Matsuno,T., and Maoka,T.
TITLE:Isolation of a new carotenoid, 3,4,3'-trihydroxy-7',8'-didehydro-b-carotene-3,4,3'-triol from dea mussels
JOURNAL:Bull. Jap. Soc. Sci. Fish.
VOL:47 PAGE : 377 -384 (1981)
[TOP]

[0430]
AUTHOR:Fujita,T.,Satake,M.,Hikichi,S.,Takeda,M.,Shimeno,S.,Kuwabara,H.,Miki,W.,Yamaguchi,K., and Konosu,S.
TITLE:Pigmentation of cultured yellowtail with krill oil
JOURNAL:Bull. Jap. Soc. Sci. Fish.
VOL:49 PAGE : 1595 -1600 (1983)
[TOP]

[0470]
AUTHOR:Matsuno,T., and Matsutaka,M.
TITLE:Carotenoids of Four Species of Crucian Carp and Two Varieties of Goldfish
JOURNAL:Bull. Jap. Soc. Sci. Fish.
VOL:47 PAGE : 85 -88 (1981)
[TOP]

[0473]
AUTHOR:Matsuno,T.,Nagata.,S.,Katsuyama,M.,Matsutaka,H.,Maoka,M., and Akita,T.
TITLE:Comparative Biochemical Studies of Carotenoids in Fishes - XVIII Carotenoids of Cultured Fishes, Japanese Char, Brook Trout, Lake Trout, Masu Trout, Red-Spotted Masu Ttout, Rainbow Trout and Brown Trout
JOURNAL:Bull. Jap. Soc. Sci. Fish.
VOL:46 PAGE : 473 -478 (1980)
[TOP]

[0493]
AUTHOR:Tsuchiya,T., and Suzuki,Y.
TITLE:Biochemical studies of the ascidian, Cynthia roreti V. DRASHE IV. Carotenoids in test.
JOURNAL:Tohoku J. Agr. Res.
VOL:10 PAGE : 397 -405 (1960)
[TOP]

[0494]
AUTHOR:Matsuno,T.,Hiraoka,K., and Maoka,T.
TITLE:Carotenoids in the Gonad of Scallop
JOURNAL:Bull. Jap. Soc. Sci. Fish.
VOL:47 PAGE : 385 -390 (1981)
[TOP]

[0495]
AUTHOR:Matsuno,T., and Maoka,T.,
TITLE:Isolation of Diatoxanthin, Pectenoxanthin, Pectenolone and a New Carotenoid, 3,4,3'-trihydroxy-7',8'-didehydro-b-carotene from Arkshell and related Three Species of Bivalves
JOURNAL:Bull. Jap. Soc. Sci. Fish.
VOL:47 PAGE : 495 -499 (1981)
[TOP]

[0496]
AUTHOR:Campbell,S.A.,Mallams,A.K.,Waight,E.S.,Weedon,B.C.L.,Barbier,M.,Lederer,E., and Salaque,A.
TITLE:Pectenoxanthin, cynthiaxanthin, and a new acetylenic carotenoid pectenolone
JOURNAL:Chem. Comm.
VOL: PAGE : 941 -942 (1967)
[TOP]

[0518]
AUTHOR:Maoka,T., and Matsuno,T.
TITLE:Isolation and Structural Elucidation of Three New Acetylenic Carotenoids from the Japanese Sea Mussel Mytilus coruscus
JOURNAL:Bull. Jap. Soc. Sci. Fish.
VOL:54 PAGE : 1443 -1447 (1988)
[TOP]

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