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Entry
CA00502                                                            

Classification
Carotenoid Name
(3S,3'S)-Astaxanthin
IUPAC name (3S,3'S)-3,3'-Dihydroxy-beta,beta-carotene-4,4'-dione
Formula
C40H52O4
Molecular Weight 
596.816 g/mol
Structure   
Mol file
Carotenoid DB Fingerprints 
Biological functions/Properties 
  • Strong antioxidant activity - free radical scavenger, potent quenchers of reactive oxygen species (ROS) and nitrogen oxygen species, strong singlet quenching ability - 111 times stronger than that of α-tocopherol - SOAC value: 111±2 (Ref.616, Ref.413, Ref.415, Ref.597, Ref.598, Ref.599).
  • Anti-inflammatory (Ref.413).
  • Immune response enhancement (Ref.473).
  • Anticarcinogenic activity (Ref.414).
  • Antidiabetes agent (Ref.415).
  • Strong coloring agent - deep red (Ref.413, 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/C40H52O4/c1-27(17-13-19-29(3)21-23-33-31(5)37(43)35(41)25-39(33,7)8)15-11-12-16-28(2)18-14-20-30(4)22-24-34-32(6)38(44)36(42)26-40(34,9)10/h11-24,35-36,41-42H,25-26H2,1-10H3/b12-11+,17-13+,18-14+,23-21+,24-22+,27-15+,28-16+,29-19+,30-20+/t35-,36-/m0/s1
    InChIKey
    MQZIGYBFDRPAKN-UWFIBFSHSA-N
    Canonical SMILES
    C/C(=C\C=C\C=C(\C=C\C=C(\C=C\C1=C(C)C(=O)[C@H](CC1(C)C)O)/C)/C)/C=C/C=C(/C=C/C1=C(C)C(=O)[C@H](CC1(C)C)O)\C
    XLogP
    9.696
    Hydrogen Bond donors
    (Lipinski's definition)
    2
    Hydrogen Bond Acceptors
    (Lipinski's definition)
    4
    LipinskiFailures
    1
    Complexity of molecule
    0.312
    Number of heavy atoms
    44
    TPSA
    (Topological Polar Surface Area) 
    74.600 Å2
    Source organisms
    Haematococcus pluvialis (Ref.313, Ref.516) - Green alga: Chlamydomonadales
    Neochloris wimmeri (Ref.313) - Green alga: Scenedesmaceae
    Protosiphon botryoides (Ref.313) - Green alga: Chlamydomonadales
    Scotiellopsis oocystiformis (Ref.313) - 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, Ref.313) - Green alga: Scenedesmaceae
    Chlorella zofingiensis (Ref.16, Ref.313) - Green alga: Scenedesmaceae
    Chlorella fusca (Ref.18) - Green alga: Scenedesmaceae
    Chlorella zofingiensis (Ref.18, Ref.313) - Green alga: Scenedesmaceae
    Chlorococcum citriforme (Ref.18) - Green alga: Chlamydomonadales
    Coelastrum proboscideum (Ref.18) - Green alga: Scenedesmaceae
    Muriella aurantiaca (Ref.18) - Green alga: Scenedesmaceae
    Muriellopsis sp. (Ref.18) - Green alga: Trebouxiophyceae
    Tetracystis sp. (Ref.18) - Green alga: Chlamydomonadales
    Nannochloropsis oculata (Ref.27, Ref.28) - Alga: Eustigmatophyceae
    Nannochloropsis salina (Ref.27, Ref.28) - Alga: Eustigmatophyceae
    Nannochloropsis gaditana (Ref.28) - Alga: Eustigmatophyceae
    Glenodinium sp. (Ref.33) - Alga: Dinoflagellate
    Tovellia sanguinea (Ref.34) - Alga: Dinoflagellate
    Euglena rubida mainx (Ref.42) - Alga: Euglenoid
    Pycnococcus provasolii (Ref.46) - Green alga: Prasinophyte
    Gelliodes callista (Ref.253) - Sea sponge
    Adonis aestivalis (Ref.271) - Land plant: adonis flower
    Xipholena punicea (Ref.272) - Bird: pompadour cotinga
    Lophelia pertusa (Ref.314) - Stony coral
    Paragorgia arborea (Ref.314) - Bubblegum coral
    Primnoa resedaeformis (Ref.314) - Soft coral
    Xanthophyllomyces dendrorhous (Ref.315) - Fungi: red yeast
    Protousnea sp. (Ref.388) - Fungi: lichen
    Rhacophorus bipunctatus (Ref.421) - Himalaya flying frog
    Salvelinus alpinus (Ref.440) - Bony fish: arctic char
    Oriolus cruentus (Ref.444) - Bird: oriole
    Euchaeta russelli (Ref.450) - Crustacean: copepod
    Temora turbinata (Ref.450) - Crustacean: copepod
    Centropages furcatus (Ref.450) - Crustacean: copepod
    Undinula vulgaris (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
    Carassius auratus (Ref.365) - Bony fish: gold fish
    Fusinus perplexus (Ref.442) - Shellfish: univalve shell
    Clione limacina (Ref.635) - gastropods
    Paedoclione doliiformis (Ref.635) - gastropods
    References
  • Ref.313 : M. Orosa, J.F. Valero, C. Herrero and J. Abalde, Biotechnology Letters, July 2001, Volume 23, Issue 13, pp 1079-1085, "Comparison of the accumulation of astaxanthin in Haematococcus pluvialis and other green microalgae under Nstarvation and high light conditions".
  • Ref.516 : Synnøve Liaaen-Jensen, Britta Renstrøm, Gunner Borch, Olav M. Skulberg, Phytochemistry 20(11):2561-2564 · December 1981, "Optical purity of (3S, 3'S)-Astaxanthin from Haematococcus pluvialis".
  • 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.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.33 : J. E. Joansen, W. A. Svec, and S. Liaaen-Jensen, Phytochemistry, 1974, Vol.13 pp.2261-2271, "Carotenoids of the Dinophyceae".
  • Ref.34 : R. Frassanito G. Flaim, I. Mancini, G. Guella, Biochemical Systematics and Ecology 34 (2006) pp.843-853, "High production of unexpected carotenoids in Dinophyceae. Astaxanthin esters from freshwater dinoflagellate Tovellia sanguinea".
  • Ref.42 : B.Czeczuga, Comp. Biochem. Physiol., 1974, Vol. 48B, pp. 349-354, "Carotenoids in Euglena rubida mainx".
  • Ref.46 : E. S. Egeland, R. R. L. Guillard, and S. Liaaen-Jensen, Phytochemistry, Vol. 44, No. 6, pp.1087-1097, 1997, "Additional carotenoid prototype representatices and general chemosystematic evaluation of carotenoids in prasinophyceae (chlorophyta)".
  • Ref.253 : Tanaka, Yoshito; Inoue, Tsuyoshi, Nippon Suisan Gakkaishi (1987), 53(7), 1271-3., "new aldehydic carotenoid gelliodesxanthin from sea sponge Gelliodes callista".
  • Ref.271 : Kazuko Ida, Kazumori Masamoto, Takashi Maoka, Yasuhiro Fujiwara, Satomi Takeda, Emiko Hasegawa, Journal of Plant Research, September 1995, Volume 108, Issue 3, pp 369-376, "The leaves of the common box,Buxus sempervirens (Buxaceae), become red as the level of a red carotenoid, anhydroeschscholtzxanthin, increases".
  • 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.314 : Anette C. Elde, Ragnhild Pettersen, Per Bruheim, Johanna Järnegren, and Geir Johnsen, Mar. Drugs 2012, 10, 1400-1411; doi:10.3390/md10061400, "Pigmentation and Spectral Absorbance Signatures in Deep-Water Corals from the Trondheimsfjord, Norway".
  • Ref.315 : Zhong-Ce Hu, Yu-Guo Zheng*, Zhao Wang and Yin-Chu Shen, Food Technol. Biotechnol. 45 (2) 209–212 (2007), ISSN 1330-9862, "Production of Astaxanthin by Xanthophyllomyces dendrorhous ZJUT46 with Fed-Batch Fermentation in 2.0 M3 Fermentor".
  • 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.421 : Pinky Baruah and Goswami UC., Journal of Research in Biology, pp.114-118, 2012, Vol.2, No.2, "Characterization of carotenoid pigments in amphibian, Rhacophorous bipunctatus".
  • Ref.440 : B. Bjerkeng, B. Hatlen, M. Jobling, Comparative Biochemistry and Physiology Part B: Biochemistry and Molecular Biology Volume 125, Issue 3, March 2000, Pages 395–404 "Astaxanthin and its metabolites idoxanthin and crustaxanthin in flesh, skin, and gonads of sexually immature and maturing Arctic charr (Salvelinus alpinus (L.))".
  • 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.365 : Masahiro Ohkubo, Miyuki Tsushima, Takashi Maoka, Takao Matsuno, Comparative Biochemistry and Physiology Part B: Biochemistry and Molecular Biology, Volume 124, Issue 3, November 1999, Pages 333–340, "Carotenoids and their metabolism in the goldfish Carassius auratus (Hibuna)".
  • 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.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.616 : Takahashi S., Iwasaki-Kino Y., and Terao J., and Mukai K., FOOD COMPOSITION AND ADDITIVES, Journal of AOAC International Vol. 99, no.1, 2016 pp.193-197, "Development of Singlet Oxygen Absorption Capacity (SOAC) Assay Method Using a Microplate Reader".
  • Ref.413 : Martin Guerin, Mark E Huntley, Miguel Olaizola, Trends in Biotechnology Volume 21, Issue 5, May 2003, Pages 210–216, "Haematococcus astaxanthin: applications for human health and nutrition".
  • Ref.415 : Takuji Tanaka, Masahito Shnimizu, and Hisataka Moriwaki, Molecules 2012, 17, 3202-3242; doi:10.3390/molecules17033202, "Cancer Chemoprevention by Carotenoids".
  • Ref.597 : Kazuo MUKAI, Aya OUCHI, Oleoscience, Vol. 13 (2013) No. 8 p. 371-378, "Antioxidant Activity of Foods Development of Singlet Oxygen Absorption Capacity (SOAC) Assay Method".
  • Ref.598 : Ouchi, A., Aizawa, K., Iwasaki, Y., Inakuma, T., Terao, J., Nagaoka, S., Mukai, K., 2010. Kinetic study of the quenching reaction of singlet oxygen by carotenoids and food extracts in solution. Development of a singlet oxygen absorption capacity (SOAC) assay method. J. Agric. Food Chem. 58, 9967–78. doi:10.1021/jf101947a.
  • Ref.599 : Aizawa, K., Iwasaki, Y., Ouchi, A., Inakuma, T., Nagaoka, S., Terao, J., Mukai, K., 2011. Development of singlet oxygen absorption capacity (SOAC) assay method. 2. Measurements of the SOAC values for carotenoids and food extracts. J. Agric. Food Chem. 59, 3717–29. doi:10.1021/jf104955a .
  • Ref.473 : H. Jyonouchi, S. Sun, Y. Tomita, M. D. Gross, J Nutr. 1995 Oct;125(10):2483-92., "Astaxanthin, a Carotenoid without Vitamin A Activity, Augments Antibody Responses in Cultures Including T-helper Cell Clones and Suboptimal Doses of Antigen".
  • 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.".
  • CAS
    472-61-7
    Links to other DB
    KEGG COMPOUND: C08580
    KNApSAcK: C00000918
    LipidBank: VCA0002
    MassBank: CA000004
    ProCarDB: C1942

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