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Entry
CA00471                                                            

Classification
Carotenoid Name
Canthaxanthin;
Aphanicin;
Chlorellaxanthin
IUPAC name beta,beta-Carotene-4,4'-dione
Formula
C40H52O2
Molecular Weight 
564.816 g/mol
Structure   
Mol file
Carotenoid DB Fingerprints 
Biological functions/Properties 
  • Antioxidant activity - free radical scavenger, potent quenchers of reactive oxygen species (ROS) and nitrogen oxygen species (Ref.415).
  • Anticarcinogenic activity (Ref.415).
  • Immune-enhancing (Ref.415).
  • Cell differentioan and proliferation promoter by upregulating Connexin43 gene (Ref.412).
  • Coloration in cosmetic and food - peach to reddish orange color (Ref.415).
  • Non-provitamin A (Ref.415).;
  • Number of
    conjugated double bonds 
    13 including two ketones (13 in total)
    Number of
    conjugated multiple bonds 
    13 including two ketones (13 in total)
    Isomers 
    InChI
    InChI=1S/C40H52O2/c1-29(17-13-19-31(3)21-23-35-33(5)37(41)25-27-39(35,7)8)15-11-12-16-30(2)18-14-20-32(4)22-24-36-34(6)38(42)26-28-40(36,9)10/h11-24H,25-28H2,1-10H3/b12-11+,17-13+,18-14+,23-21+,24-22+,29-15+,30-16+,31-19+,32-20+
    InChIKey
    FDSDTBUPSURDBL-DKLMTRRASA-N
    Canonical SMILES
    C/C(=C\C=C\C=C(\C=C\C=C(\C=C\C1=C(C)C(=O)CCC1(C)C)/C)/C)/C=C/C=C(/C=C/C1=C(C)C(=O)CCC1(C)C)\C
    XLogP
    10.788
    Hydrogen Bond donors
    (Lipinski's definition)
    0
    Hydrogen Bond Acceptors
    (Lipinski's definition)
    2
    LipinskiFailures
    1
    Complexity of molecule
    0.319
    Number of heavy atoms
    42
    TPSA
    (Topological Polar Surface Area) 
    34.140 Å2
    Source organisms
    Rhizobium lupini (Ref.449) - Alphaproteobacteria: root nodule bacterium
    Oscillatoria tenuis (Ref.1) - Cyanobacteria: hot spring alga
    Oscillatoria limosa (Ref.1) - Cyanobacteria
    Phormidium foveolarum (Ref.1) - Cyanobacteria
    Phormidium lucidum (Ref.1) - Cyanobacteria
    Aphanizomenon flos-aquae (Ref.1) - Cyanobacteria
    Anabaena cylindrica (Ref.1, Ref.5) - Cyanobacteria: a nitrogen-fixing filamentous cyanobacterium
    Anabaena variabilis (Ref.1, Ref.5) - Cyanobacteria: filamentous cyanobacterium
    Anabaena variabilis ATCC 29413 (Ref.527) - Cyanobacteria
    Anabaena flos-aquae (Ref.1, Ref.610) - Cyanobacteria: filamentous cyanobacterium same as Dolichospermum flos-aquae
    Anabaena aerulosa oscillatorioides (Ref.1) - Cyanobacteria
    Stigonema ocellatum (Ref.603) - Cyanobacteria: terrestrial cyanobacteria sampled from rock surfaces containing chlorophyll a
    Stigonema hormoides (Ref.603) - Cyanobacteria: terrestrial cyanobacteria sampled from rock surfaces containing chlorophyll a
    Scytonema crassum (Ref.603) - Cyanobacteria: terrestrial cyanobacteria sampled from rock surfaces containing chlorophyll a
    Nostoc commune (Ref.1) - Cyanobacteria: star jelly, witch's butter, mare's eggs, fah-tsai and facai, eaten as a salad
    Tolypothrix tenuis (Ref.1) - Cyanobacteria: filaments repeated single false branched forming cyanobacteria, yellow-brown colored
    Calothrix parietina (Ref.1) - Cyanobacteria: a hair-forming cyanobacteria rom an upland stream
    Microcystis aeruginosa (Ref.1) - Cyanobacteria
    Merismopedia punctata (Ref.1) - Cyanobacteria: colony square or rectangular
    Neochloris wimmeri  - Green alga: Scenedesmaceae
    Ettlia carotinosa (Ref.16) - Green alga: Chlamydomonadales
    Protosiphon botryoides (Ref.16, Ref.17) - Green alga: Chlamydomonadales
    Scotiellopsis oocystiformis (Ref.16) - Green alga: Scenedesmaceae
    Scenedesmus vacuolatus (Ref.16) - Green alga: Scenedesmaceae
    Chlorella zofingiensis (Ref.16) - Green alga: Scenedesmaceae
    Chlorella fusca (Ref.18) - Green alga: Scenedesmaceae
    Chlorella zofingiensis (Ref.18) - Green alga: Scenedesmaceae
    Chlorococcum citriforme (Ref.18) - Green alga: Chlamydomonadales
    Muriella decolor (Ref.18) - Green alga: Trebouxiophyceae
    Muriellopsis sp. (Ref.18) - Green alga: Trebouxiophyceae
    Tetracystis intermidium (Ref.18) - Green alga: Chlamydomonadales
    Botryococcus braunii (Ref.19) - Green alga: Trebouxiophyceae
    Nannochloropsis oculata (Ref.27, Ref.28) - Alga: Eustigmatophyceae
    Nannochloropsis salina (Ref.27, Ref.28) - Alga: Eustigmatophyceae
    Nannochloropsis gaditana (Ref.28) - Alga: Eustigmatophyceae
    Pavlova lutheri (Ref.31) - Alga: Haptophyte
    Skeletonema costatum (Ref.36) - Alga: Diatom
    Navicula pelliculosa (Ref.36) - Alga: Diatom
    Euglena gracilis (Ref.38, Ref.8) - Alga: Euglenoid
    Gelliodes callista (Ref.253) - Sea sponge
    Xipholena punicea (Ref.272) - Bird: pompadour cotinga
    Corbicula japonica (Ref.221) - Shellfish: bivalve
    Corbicula sandai (Ref.221) - Shellfish: bivalve
    Corbicula clam (Ref.221) - Shellfish: bivalve
    Solorina crocea (Ref.374) - Fungi: lichen
    Protousnea sp. (Ref.388) - Fungi: lichen
    Fusinus perplexus (Ref.442) - Shellfish: univalve shell
    Oriolus cruentus (Ref.444) - Bird: oriole
    Oriolus traillii (Ref.444) - Bird: maroon oriole
    Euchaeta russelli (Ref.450) - Crustacean: copepod
    Phoenicoparrus andinus (Ref.471) - Bird: Andean flamingo
    Phoenicoparrus jamesi (Ref.471) - Bird: Puna flamingo
    Phoenicoparrus ruber (Ref.471) - Bird: American flamingo
    Paedoclione doliiformis (Ref.635) - gastropods
    References
  • Ref.449 : Kleinig, Hans; Heumann, Wolfram; Meister, Walter; Englert, Gerhard, Helvetica Chimica Acta (1979), 62(8), 2551-7., "Carotenoids of Rhizobia.  I.  New carotenoids from Rhizobium lupini".
  • Ref.1 : S. Hertzberg, S. Liaaen-Jensen, and H. W. Siegelman, Phytochemistry, 1971, Vol. 10, pp. 3121 - 3127 "The carotenois of blue-green algae".
  • Ref.5 : T. W. Goodwin, J. gen. Microbiol. 17, 467-473 (1957), "The nature and distribution of Carotenoids in some Blue-Green Algae".
  • Ref.527 : Shinichi Takaichi, Mari Mochimaru, and Takashi Maoka, Plant Cell Physiol. 47(2): 211–216 (2006), doi:10.1093/pcp/pci236, "Presence of Free Myxol and 4-Hydroxymyxol and Absence of Myxol Glycosides in Anabaena variabilis ATCC 29413, and Proposal of a Biosynthetic Pathway of Carotenoids".
  • Ref.610 : The Biochemistry of the Carotenoids: Volume I Plants, p.237, Springer, ISBN-10: 9400958625, ISBN-13: 978-9400958623.
  • Ref.603 : M Lakatos, W Bilger, B Büdel, Eur. J. Phycol. (2001), 36: 367–375., "Carotenoid composition of terrestrial Cyanobacteria: response to natural light conditions in open rock habitats in Venezuela".
  • Ref.16 : M. Orosa, E. Torres, P. Fidalgo, J. Abalde, Journal of Applied Phycology, October 2000, Volume 12, Issue 3-5, pp 553-556 "Production and analysis of secondary carotenoids in green algae".
  • Ref.17 : H. Kleinig and F. C. Czygan (1969), Z Naturforsch B. 1969 Jul;24(7):927-30. "Lipids of Protosiphon (Chlorophyta) Carotenoids and Carotenoid Esters of five Strains of Protosiphon botryoides Klebs" .
  • Ref.18 : PMID: 10784296 : Del Campo JA1, Moreno J, Rodríguez H, Vargas MA, Rivas J, Guerrero MG., J Biotechnol. 2000 Jan 7;76(1):51-9. "Carotenoid content of chlorophycean microalgae: factors determining Lutein accumulation in Muriellopsis sp. (Chlorophyta).".
  • Ref.19 : Merete Grunga, Pierre Metzger, Synnove Liaaen-jensen, Biochemical Systematics and Ecology, Volume 17, Issue 4, 28 July 1989, Pages 263–269 "Primary and Secondary Carotenoids in Two Races of the Green Alga Botryocossu braunii".
  • Ref.27 : N. J. Antial, and J.Y. Cheng, British Phycological Journal, Volume 17, Issue 1, 1982 "The Keto carotenoids of two marine cocoid members of the eustimaphyceae" DOI:10.1080/00071618200650061 .
  • Ref.28 : Luis M. Lubián, Olimpio Montero, Ignacio Moreno-Garrido, I. Emma Huertas, Cristina Sobrino, Manuel González-del Valle, Griselda Parés, Journal of Applied Phycology, October 2000, Volume 12, Issue 3-5, pp 249-255 "Nannochloropsis (Eustigmatophyceae) as source of commercially valuable pigments".
  • Ref.31 : R. Berger, and S. Liaaen-Jensen, Biochemical Systematics and Ecology, 1977, Vol. 5, pp.71-75 "Carotenoids of Prymnesiophyceae (Haptophyceae)* ".
  • 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.38 : D. V. Heelis, W. Kernick, G. O. Philips, and K. Davies, Arch. Microbiol. 121, 207-211 (1979), "Separation and Identification of the Carotenoid Pigments of Stigmata Isolated from Light Grown Cells of Euglena gracilis Strain Z".
  • Ref.8 : L. Schlueter, T. L. Lauridsen, G. Krogh, and Joergensen, Freshwater Biology, 2006, 51, 1474-1485 " Identification and quantification of phytoplankton groups in lakes using new pigment ratios – a comparison between pigment analysis by HPLC and microscopy".
  • Ref.253 : Tanaka, Yoshito; Inoue, Tsuyoshi, Nippon Suisan Gakkaishi (1987), 53(7), 1271-3., "new aldehydic carotenoid gelliodesxanthin from sea sponge Gelliodes callista".
  • Ref.272 : Amy M. LaFountain, Shanti Kaligotla, Shannon Cawley, Ken M. Riedl, Steven J. Schwartz, Harry A. Frank, and Richard O. Prum, Arch Biochem Biophys. 2010 Dec 1; 504(1): 10.1016/j.abb.2010.08.006., doi: 10.1016/j.abb.2010.08.006, "Novel methoxy-carotenoids from the burgundy-colored plumage of the Pompadour Cotinga Xipholena punicea".
  • 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.388 : B. Czeczuga, E. Czeczuga-Semeniuk, S. Calvelo, and S. Liberatore, Journal of Botanical Taxonomy and Geobotany, Volume 116, Issue 3-4, pages 195–200, August 2005, "Carotenoids in representatives of the Protousnea (Parmeliaceae), endemic genus from South America".
  • Ref.442 : Kiyoshi Katagiri, Takashi Maoka, Takao Matsuno, COMPARATIVE BIOCHEMISTRY AND PHYSIOLOGY. B, COMPARATIVE BIOCHEMISTRY, 84(4):473-476 · JANUARY 1986, "Carotenoids of shell fishes-VIII. Comparative biochemical studies of carotenoids in three species of spindleshell, Fusinus perplexus, F.p. ferrugineus and F. forceps".
  • Ref.444 : LaFountain, Amy M.; Frank, Harry A.; Prum, Richard O., Archives of Biochemistry and Biophysics (2013), 539(2), 126-132., "Carotenoids from the crimson and maroon plumages of Old World orioles (Oriolidae)".
  • Ref.450 : Bandaranayake, Wickramasinghe M.; Gentien, Patrick, Comparative Biochemistry and Physiology, Part B:  Biochemistry & Molecular Biology (1982), 72B(3), 409-14., "Carotenoids of Temora turbinata, Centropages furcatus, Undinula vulgaris, and Euchaeta russelli".
  • Ref.471 : Denis L Fox, Thomas S Hopkins, Comparative Biochemistry and Physiology, Volume 17, Issue 3, March 1966, Pages 841–856, "Comparative metabolic fractionation of carotenoids in three flamingo species".
  • Ref.635 : Takashi Maoka, Takashi Kuwahara, and Masanao Narita, Mar. Drugs 2014, 12, 1460-1470, "Carotenoids of Sea Angels Clione limacina and Paedoclione doliiformis from the Perspective of the Food Chain", doi:10.3390/md12031460.
  • Ref.415 : Takuji Tanaka, Masahito Shnimizu, and Hisataka Moriwaki, Molecules 2012, 17, 3202-3242; doi:10.3390/molecules17033202, "Cancer Chemoprevention by Carotenoids".
  • Ref.412 : Li-Xin Zhang, Robert V. Cooney, and John S. Bertram, CANCER RESEARCH 52, 5707-5712, October 15, 1992, "Carotenoids Up-Regulate Connexin43 Gene Expression Independent of Their Provitamin A or Antioxidant Properties1".
  • CAS
    514-78-3
    Links to other DB
    KEGG COMPOUND: C08583
    KNApSAcK: C00000922
    LipidBank: VCA0040
    ProCarDB: C1924

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