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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      Search similar carotenoids

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

    InChIKey

    Canonical SMILES

    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
    Reaction
  • Substrate: CR00086,  CR00177,  CR00185
  • Product: CR00241
    • Pathway
  • Pathway: CB000055,  CB000105,  CB000106,  CB000056
    • Major carotenoid information
    Major carotenoid in some chlorophytes in nitrogen starvation (Ref.707). Major carotenoid in Anabaena variabilis and Nostoc sp. (Ref.732). Major components found in the gonads of sea cucumbers (Ref.763).
    Minor carotenoid information
    Minor carotenoid in eustigmatophytes, cyanobacteria, and dinoflagellates (Ref.707).
    Source organisms
    Rhizobium lupini (Ref.449) - Alphaproteobacteria: root nodule bacterium (Alphaproteobacteria - Rhizobiaceae)
    Merismopedia punctata (Ref.1) - Cyanobacteria: colony square or rectangular (Cyanobacteria - Merismopediaceae)
    Calothrix parietina (Ref.1) - Cyanobacteria: a hair-forming cyanobacteria rom an upland stream (Cyanobacteria - Rivulariaceae)
    Microcystis aeruginosa (Ref.1) - Cyanobacteria (Cyanobacteria - Microcystaceae)
    Aphanizomenon flos-aquae (Ref.1) - Cyanobacteria (Cyanobacteria - Aphanizomenonaceae)
    Anabaena aerulosa oscillatorioides (Ref.1) - Cyanobacteria (Cyanobacteria - Nostocaceae)
    Anabaena cylindrica (Ref.1, Ref.5) - Cyanobacteria: a nitrogen-fixing filamentous cyanobacterium (Cyanobacteria - Nostocaceae)
    Anabaena flos-aquae (Ref.1, Ref.610) - Cyanobacteria: filamentous cyanobacterium same as Dolichospermum flos-aquae (Cyanobacteria - Aphanizomenonaceae)
    Anabaena variabilis (Ref.1, Ref.5) - Cyanobacteria: filamentous cyanobacterium (Cyanobacteria - Nostocaceae)
    Anabaena variabilis ATCC 29413 (Ref.527) - Cyanobacteria (Cyanobacteria - Nostocaceae)
    Nostoc commune (Ref.1) - Cyanobacteria: star jelly, witch's butter, mare's eggs, fah-tsai and facai, eaten as a salad (Cyanobacteria - Nostocaceae)
    Stigonema ocellatum (Ref.603) - Cyanobacteria: terrestrial cyanobacteria sampled from rock surfaces containing chlorophyll a (Cyanobacteria - Stigonemataceae)
    Stigonema hormoides (Ref.603) - Cyanobacteria: terrestrial cyanobacteria sampled from rock surfaces containing chlorophyll a (Cyanobacteria - Stigonemataceae)
    Scytonema crassum (Ref.603) - Cyanobacteria: terrestrial cyanobacteria sampled from rock surfaces containing chlorophyll a (Cyanobacteria - Scytonemataceae)
    Oscillatoria limosa (Ref.1) - Cyanobacteria (Cyanobacteria - Oscillatoriaceae)
    Oscillatoria tenuis (Ref.1) - Cyanobacteria: hot spring alga (Cyanobacteria - Oscillatoriaceae)
    Phormidium foveolarum (Ref.1) - Cyanobacteria (Cyanobacteria - Oscillatoriaceae)
    Phormidium lucidum (Ref.1) - Cyanobacteria (Cyanobacteria - Oscillatoriaceae)
    Tolypothrix tenuis (Ref.1) - Cyanobacteria: filaments repeated single false branched forming cyanobacteria, yellow-brown colored (Cyanobacteria - Tolypothrichaceae)
    Tetracystis intermidium (Ref.18) - Green alga: Chlamydomonadales (Chlorophyta - Chlamydomonadales)
    Ettlia carotinosa (Ref.16) - Green alga: Chlamydomonadales (Chlorophyta - Chlamydomonadales)
    Protosiphon botryoides (Ref.16, Ref.17) - Green alga: Chlamydomonadales (Chlorophyta - Chlamydomonadales)
    Chlorococcum citriforme (Ref.18) - Green alga: Chlamydomonadales (Chlorophyta - Chlamydomonadales)
    Chlorella zofingiensis (Ref.18) - Green alga: Scenedesmaceae (Chlorophyta - Chromochloridaceae)
    Neochloris wimmeri  - Green alga: Scenedesmaceae (Chlorophyta - Neochloridaceae)
    Scotiellopsis oocystiformis (Ref.16) - Green alga: Scenedesmaceae (Chlorophyta - Scenedesmaceae)
    Chlorella fusca (Ref.18) - Green alga: Scenedesmaceae (Chlorophyta - Scenedesmaceae)
    Scenedesmus vacuolatus (Ref.16) - Green alga: Scenedesmaceae (Chlorophyta - Scenedesmaceae)
    Muriellopsis sp. (Ref.18) - Green alga: Trebouxiophyceae (Chlorophyta - Oocystaceae)
    Botryococcus braunii (Ref.19) - Green alga: Trebouxiophyceae (Chlorophyta - Botryococcaceae)
    Muriella decolor (Ref.18) - Green alga: Trebouxiophyceae (Chlorophyta - Trebouxiophyceaeincertae sedis)
    Euglena gracilis (Ref.38, Ref.8) - Alga: Euglena (Euglenida - Euglenaceae)
    Pavlova lutheri (Ref.31) - Alga: Haptophyte ((Haptophyceae) - Pavlovaceae)
    Navicula pelliculosa (Ref.36) - Alga: Diatom (Bacillariophyta - Naviculaceae)
    Skeletonema costatum (Ref.36) - Alga: Diatom (Bacillariophyta - Skeletonemataceae)
    Nannochloropsis oculata (Ref.27, Ref.28) - Alga: Eustigmatophyceae ((Eustigmatophyceae) - Monodopsidaceae)
    Nannochloropsis salina (Ref.27, Ref.28) - Alga: Eustigmatophyceae ((Eustigmatophyceae) - Monodopsidaceae)
    Nannochloropsis gaditana (Ref.28) - Alga: Eustigmatophyceae ((Eustigmatophyceae) - Monodopsidaceae)
    Protousnea sp. (Ref.388) - Fungi: lichen (Ascomycota - Lecanorineae)
    Solorina crocea (Ref.374) - Fungi: lichen (Ascomycota - Peltigeraceae)
    Euchaeta russelli (Ref.450) - Crustacean: copepod (Arthropoda - Euchaetidae)
    Corbicula clams (Ref.221) - Shellfish: bivalve (Mollusca - Corbiculidae)
    Corbicula japonica (Ref.221) - Shellfish: bivalve (Mollusca - Corbiculidae)
    Corbicula sandai (Ref.221) - Shellfish: bivalve (Mollusca - Corbiculidae)
    Fusinus perplexus (Ref.442) - Shellfish: univalve shell (Mollusca - Fasciolariidae)
    Paedoclione doliiformis (Ref.635) - gastropods (Mollusca - Clionidae)
    Gelliodes callista (Ref.253) - Sea sponge (Porifera - Niphatiidae)
    Plesiocolochirus minutus (Ref.763) - sea cucumber (Echinodermata - Cucumariidae)
    Gymnogobius castaneus (Ref.772) - Bony fish: Rosary goby, small goby（4～6 cm body length）that inhabits the middle stretches of rivers, lakes, and lagoons in North Eastern Japan. Its tail fin is bright orange in color. (Chordata - Gobiidae)
    Xipholena punicea (Ref.272) - Bird: pompadour cotinga (Chordata - Cotingidae)
    Phoenicoparrus andinus (Ref.471) - Bird: Andean flamingo (Chordata - Phoenicopteridae)
    Phoenicoparrus jamesi (Ref.471) - Bird: Puna flamingo (Chordata - Phoenicopteridae)
    Phoenicoparrus ruber (Ref.471) - Bird: American flamingo (Chordata - Phoenicopteridae)
    Oriolus cruentus (Ref.444) - Bird: oriole (Chordata - Corvidae)
    Oriolus traillii (Ref.444) - Bird: maroon oriole (Chordata - Corvidae)
    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.763: Takashi Maoka, Syu Nakachi, Ryouhei Kobayashi, Miho Mori, Yoshikazu Sakagami, / Tetrahedron Letters 56 (2015) 5954–5955, http://dx.doi.org/10.1016/j.tetlet.2015.09.060, “A new carotenoid, 9Z,9'Z-tetrahydroastaxanthin, from the sea cucumber Plesiocolochirus minutus”.
  • Ref.772: Takashi Maoka, J. Oleo Sci. 67, (10) 1259-1263 (2018), “New Acetylenic Carotenoid 6’-Epimonadoxanthin from the Rosary Goby Gymnogobius castaneus”, doi: 10.5650/jos.ess18153.
  • 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".
  • Ref.707: Suzanne Roy et al., Phytoplankton Pigments Characterization, Chemotaxonomy and Applications in Oceanography, October 2011, Cambridge University Press, pp 665-674, "Part VII - Data sheets aiding identification of phytoplankton carotenoids and chlorophylls", available at http://www.cambridge.org/gb/files/2013/6697/5826/Data_sheets_part_3_Xanthophylls.pdf, ISBN: 9781107000667.
  • Ref.732: S. Takaichia and M. Mochimaru, Cell. Mol. Life Sci. 64 (2007) 2607 – 2619, "Carotenoids and carotenogenesis in cyanobacteria: unique ketocarotenoids and carotenoid glycosides", DOI 10.1007/s00018-007-7190-z.
    • CAS
    514-78-3
    Links to other DB
    KEGG COMPOUND: C08583
    KNApSAcK: C00000922
    LipidBank: VCA0040
    ProCarDB: C1924

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