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Entry
CA00739                                                            

Classification
Carotenoid Name
Capsanthin
IUPAC name (3R,3'S,5'R)-3,3'-Dihydroxy-beta,kappa-caroten-6'-one
Formula
C40H56O3
Molecular Weight 
584.848 g/mol
Structure      Search similar carotenoids

Mol file
Carotenoid DB Fingerprints 
Biological functions/Properties 
  • An antioxidant - 107 times stronger singlet oxygen quenching ability than that of α-tocopherol - SOAC value: 107 (Ref.616, Ref.597, Ref.598, Ref.599).
  • Anticarcinogenic activity (Ref.414).
  • Orange red-food coloring, and flavouring (Ref.468).
  • Non-provitamin A (Ref.466).
  • Number of
    conjugated double bonds 
    11 including one ketone (11 in total)
    Number of
    conjugated multiple bonds 
    11 including one ketone (11 in total)
    Isomers 
    InChI

    InChIKey

    Canonical SMILES

    XLogP
    9.892
    Hydrogen Bond donors
    (Lipinski's definition)
    2
    Hydrogen Bond Acceptors
    (Lipinski's definition)
    3
    LipinskiFailures
    2
    Complexity of molecule
    0.303
    Number of heavy atoms
    43
    TPSA
    (Topological Polar Surface Area) 
    57.530 Å2
    Reaction
  • Substrate: CR00160,  CR00409,  CR00411,  CR00414,  CR00415,  CR00417,  CR00419,  CR00422,  CR00423,  CR00425,  CR00427
  • Product: CR00384
  • Pathway
  • Pathway: CB000069
  • Major carotenoid information
    Main carotenoid in red paprika (Ref.715).
    Minor carotenoid information

    Source organisms
    Capsicum annuum (Ref.447) - Land plant: red pepper (Streptophyta - Solanaceae)
    Gallus gallus (Ref.219) - Bird: chicken (Chordata - Phasianidae)
    References
  • Ref.219: Brulc, Lucka; Simonovska, Breda; Vovk, Irena; Glavnik, Vesna, Journal of Chromatography A (2013), 1318, 134-141. "Determination of egg yolk xanthophylls by isocratic high-performance liquid chromatography".
  • Ref.447: Cholnoky, L.; Szabolcs, J., Acta Chimica Academiae Scientiarum Hungaricae (1960), 22, 117-19., "Structure of the coloring matter of paprika".
  • 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.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.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.468: Gerard P. Moss, Herbert Baxter, J.B. Harborne, Gerald P. Moss, CRC Press; 1 edition (February 15, 1993), ISBN-10: 0850667364, ISBN-13: 978-0850667363, "Phytochemical Dictionary: A Handbook of Bioactive Compounds from Plants".
  • Ref.466: Torsten Bohn, Current Nutrition & Food Science, 2008, 4, 240-258, "Bioavailability of Non-Provitamin A Carotenoids " .
  • Ref.715: Ji-Sun Kim, Tae-Youl Ha, Suna Kim, Sun-Joon Lee, Jiyun Ahn, Journal of Functional Foods, Volume 31, April 2017, Pages 131-140, "Red paprika (Capsicum annuum L.) and its main carotenoid capsanthin ameliorate impaired lipid metabolism in the liver and adipose tissue of high-fat diet-induced obese mice", https://doi.org/10.1016/j.jff.2017.01.044.
  • CAS
    465-42-9
    Links to other DB
    KEGG COMPOUND: C08584
    KNApSAcK: C00003763
    LipidBank: VCA0045
    MassBank: CA000015

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