Carotenoids obi
All carotenoids     All organisms   Feedback
Carotenoids DB          Carotenoids DB: CA00519   
[   About  |   Help  |   Search carotenoid entry  |   Search organism entry  |   Search similar carotenoids  |   Predict biological activities of this carotenoid  |   Search possible pathways   ]

Carotenoid Name
IUPAC name (3S,5R,6S,3'S,5'R,6'R)-5,6-Epoxy-3'-ethanoyloxy-3,5'-dihydroxy-6',7'-didehydro-5,6,7,8,5',6'-hexahydro-beta,beta-caroten-8-one
Molecular Weight 
658.884 g/mol
Structure      Search similar carotenoids

Mol file
Carotenoid DB Fingerprints 
Biological functions/Properties 
  • Photosynthetic pigment - Coulomb coupling as a mechanism for carotenoid to Chl A energy transfer (Ref.501).
  • Antiproliferative, and chemopreventive activity (Ref.493).
  • Anticarcinogenic activity - induces apoptosis in various cancer cell (Ref.414, Ref.493).
  • Anti-inflammatory activity (Ref.512, Ref.513).
  • Antioxidant activity as an electron donor (Ref.415).
  • Free-radical quencher (Ref.453).
  • Anti-obese property (Ref.417, Ref.453).
  • Antidiabetes agent (Ref.511).
  • Brown/Orange color (Ref.415).
  • Non-provitamin A (Ref.415).
  • Photoprotective activity - protective effect of UV-B induced cell damage (Ref.496).
  • Number of
    conjugated double bonds 
    9 including one ketone (9 in total)
    Number of
    conjugated multiple bonds 
    9 including one ketone (9 in total)
  • Constitutional isomer: CA00518
  • InChI
    Canonical SMILES
    Hydrogen Bond donors
    (Lipinski's definition)
    Hydrogen Bond Acceptors
    (Lipinski's definition)
    Complexity of molecule
    Number of heavy atoms
    (Topological Polar Surface Area) 
    96.360 Å2
    Source organisms
    Pelagococcus subviridis (Ref.29) - Alga: Pelagophyceae
    Ochromonas sp. (Ref.30) - Golden alga: Chrysophyceae
    Poterioochromonas malhamensis (Ref.30) - Golden alga: Synurophyceae
    Olisthodiscus luteus (Ref.30) - Alga: unclassified stramenopiles
    Synura petersenii (Ref.30) - Golden alga: Synurophyceae
    Chromulina ochromonoides (Ref.30) - Golden alga: Chrysophyceae
    Sarcinochrysis marina Getler (Ref.30) - Alga: Pelagophyceae
    Hymenomonas carterae (Ref.31) - Alga: Haptophyte
    Isochrysis galbana (Ref.31) - Alga: Haptophyte
    Pavlova lutheri (Ref.31) - Alga: Haptophyte
    Pavlova sp. (NEP)  - Alga: Haptophyte
    Phaeocystis sp. (Ref.31) - Alga: Haptophyte
    Prymnesium parvum (Ref.31) - Alga: Haptophyte
    Chattonella japonica (Ref.35) - Alga: Raphidophyceae
    Fibrocapsa japonica (Ref.35) - Alga: Raphidophyceae
    Skeletonema costatum (Ref.36) - Alga: Diatom
    Skeletonema menzelii (Ref.36) - Alga: Diatom
    Thalassiosira eccentrica (Ref.36) - Alga: Diatom
    Thalassiosira oceanica (Ref.36) - Alga: Diatom
    Thalassiosira pseudonana (Ref.36) - Alga: Diatom
    Thalassiosira rotula (Ref.36) - Alga: Diatom
    Grammatophora oceanica (Ref.36) - Alga: Diatom
    Navicula pelliculosa (Ref.36) - Alga: Diatom
    Nitzschia sp. (Ref.36) - Alga: Diatom
    Phaeodactylum tricornutum (Ref.36) - Alga: Diatom
    Fucus serratus (Ref.53) - Brown alga: Fucaceae
    Fucus vesiculosus (Ref.53) - Brown alga: Fucaceae
    Pelvetia canaliculata (Ref.53) - Brown alga: Fucaceae
    Ascophyllum nodosum (Ref.53) - Brown alga: Fucaceae
    Laminaria saccharina (Ref.53) - Brown alga: Laminariaceae
    Gelliodes callista (Ref.253) - Sea sponge
    Corbicula japonica (Ref.221) - Shellfish: bivalve
    Corbicula sandai (Ref.221) - Shellfish: bivalve
    Corbicula clam (Ref.221) - Shellfish: bivalve
    Solorina crocea (Ref.374) - Fungi: lichen
    Echinoidea sp. (Ref.375) - Sea urchin
    Limacina helicina (Ref.635) - gastropods
  • Ref.29 : T.Bjoernland, S. Liaaen-Jensen, and J. Throndsen, Phytochemistry, Vol. 28, No. 12, pp. 3347-3353, 1989; "Carotenoids of the marine chrysophyte Pelagococcus subviridis".
  • Ref.30 : N. W. Withers, A. Fiksdahl, R.C. Tuttle, and S. Liaaen-Jense, Comp. Biochem. Physiol. Vol. 68B, pp. 345 to 349, 1979, "Carotenoids of the Chrysophyceae".
  • Ref.31 : R. Berger, and S. Liaaen-Jensen, Biochemical Systematics and Ecology, 1977, Vol. 5, pp.71-75 "Carotenoids of Prymnesiophyceae (Haptophyceae)* ".
  • Ref.35 : A.Fiksdahl, N. Withers, R. R. L. Guillard, and S. Liaaen-Jensen, Comp. Biochem. Physiol. Vol. 78B, No. 1, pp. 265-271, 1984, "Carotenoids of the Raphidophyceae - a chemosystematic contribution ".
  • Ref.36 : F. Pennington, R. R. L. Guillard and S. Liaaen-Jensen, Biochemical Systematics and Ecology, Vol.16, No.7/8, pp. 589-592, 1988, "Carotenoid Distribution Patterns in Bacillariophyceae (Diatoms)".
  • Ref.53 : G. Nybraaten, and S. L. Jensen, Acta Chem. Scand. Ser. B, 28,(1974), 485, "Algal Carotenoids. XII. * Chemical Reactions of Carotenoids with 2-Hydroxylated beta-Rings".
  • Ref.253 : Tanaka, Yoshito; Inoue, Tsuyoshi, Nippon Suisan Gakkaishi (1987), 53(7), 1271-3., "new aldehydic carotenoid gelliodesxanthin from sea sponge Gelliodes callista".
  • Ref.221 : Maoka, Takashi; Fujiwara, Yasuhiro; Hashimoto, Keiji; Akimoto, Naoshige, Journal of Agricultural and Food Chemistry (2005), 53(21), 8357-8364. "Carotenoids in Three Species of Corbicula Clams, Corbicula japonica, Corbicula sandai, and Corbicula sp. (Chinese Freshwater Corbicula Clam)".
  • Ref.374 : Czeczuga, Bazyli; Olech, Maria, Phyton (Horn, Austria) (1990), 30(2), 235-45., "Investigations on carotenoids in lichens.  XXV.  Studies of carotenoids in lichens from Spitsbergen".
  • Ref.375 : Galasko, Gail; Hora, J.; Toube, T. P.; Weedon, B. C. L.; Andre, D.; Barbier, M.; Lederer, E.; Villanueva, V. R., Journal of the Chemical Society [Section] C:  Organic (1969), (9), 1264-5., "Carotenoids and related compounds.  XXII.  Allenic carotenoids in sea urchins".
  • Ref.501 : A.P. Shreve, J.K. Trautman, T.G. Owens, A.C. Albrecht, Chemical Physics, Volume 154, Issue 1, 15 June 1991, Pages 171-178, "A femtosecond study of electronic state dynamics of fucoxanthin and implications for photosynthetic carotenoid-to-chlorophyll energy transfer mechanisms".
  • Ref.493 : Anne-Laure Gagez, Valérie Thiery, Virginie Pasquet, Jean-Paul Cadoret, and Laurent Picot, Current Bioactive Compounds 2012, 8, 000-000, "Epoxycarotenoids and Cancer. Review".
  • Ref.414 : Nishino H, Murakosh M, Ii T, Takemura M, Kuchide M, Kanazawa M, Mou XY, Wada S, Masuda M, Ohsaka Y, Yogosawa S, Satomi Y, Jinno K., Cancer Metastasis Rev. 2002;21(3-4):257-64., "Carotenoids in cancer chemoprevention.".
  • Ref.512 : K.-N. Kim, S.-J. Heo, W.-J. Yoon et al., “Fucoxanthin inhibits the inflammatory response by suppressing the activation of NF-𝜅B and MAPKs in lipopolysaccharide-induced RAW 264.7 macrophages,” European Journal of Pharmacology, vol. 649, no.1–3, pp. 369–375, 2010.
  • Ref.513 : S. Sakai, T. Sugawara, K. Matsubara, and T. Hirata, “Inhibitory effect of carotenoids on the degranulation of mast cells via suppression of antigen-induced aggregation of high affinity IgE receptors,” The Journal of Biological Chemistry, vol. 284, no. 41, pp. 28172–28179, 2009..
  • Ref.415 : Takuji Tanaka, Masahito Shnimizu, and Hisataka Moriwaki, Molecules 2012, 17, 3202-3242; doi:10.3390/molecules17033202, "Cancer Chemoprevention by Carotenoids".
  • Ref.453 : Graziano Riccioni, Nicolantonio D’Orazio, Sara Franceschelli, and Lorenza Speranza, Marine Drugs 2011, 9(7), 1166-1175; doi:10.3390/md9071166, "Marine Carotenoids and Cardiovascular Risk Markers".
  • Ref.417 : Woo MN, Jeon SM, Shin YC, Lee MK, Kang MA, Choi MS., Mol Nutr Food Res. 2009 Dec;53(12):1603-11. doi: 10.1002/mnfr.200900079., "Anti-obese property of fucoxanthin is partly mediated by altering lipid-regulating enzymes and uncoupling proteins of visceral adipose tissue in mice.".
  • Ref.511 : H. Maeda, M. Hosokawa, T. Sashima, K. Murakami-Funayama,and K. Miyashita, “Anti-obesity and anti-diabetic effects of fucoxanthin on diet-induced obesity conditions in a murine model,” Molecular Medicine Reports, vol. 2, no. 6, pp. 897–902,2009..
  • Ref.496 : Soo-Jin Heoa, You-Jin Jeon, Journal of Photochemistry and Photobiology B: Biology, Volume 95, Issue 2, 4 May 2009, Pages 101–107, "Protective effect of fucoxanthin isolated from Sargassum siliquastrum on UV-B induced cell damage".
  • CAS
    Links to other DB
    KNApSAcK: C00003773
    LipidBank: VCA0003
    MassBank: CA000057

       Search other references with Google Scholar