Carotenoids obi
All carotenoids     All organisms   Feedback
Carotenoids DB          Carotenoids DB: CA00739   
[   About  |   Help  |   Search carotenoid entry  |   Search organism entry  |   Search similar carotenoids  |   Predict biological activities of this carotenoid  |   Search possible pathways   ]
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   
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±3 (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
    InChI=1S/C40H56O3/c1-29(17-13-19-31(3)21-23-36-33(5)25-34(41)26-38(36,6)7)15-11-12-16-30(2)18-14-20-32(4)22-24-37(43)40(10)28-35(42)27-39(40,8)9/h11-24,34-35,41-42H,25-28H2,1-10H3/b12-11+,17-13+,18-14+,23-21+,24-22+,29-15+,30-16+,31-19+,32-20+/t34-,35+,40+/m1/s1
    InChIKey
    VYIRVAXUEZSDNC-RDJLEWNRSA-N
    Canonical SMILES
    C/C(=C\C=C\C=C(\C=C\C=C(\C=C\C1=C(C)C[C@H](CC1(C)C)O)/C)/C)/C=C/C=C(/C=C/C(=O)[C@]1(C)C[C@H](CC1(C)C)O)\C
    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
    Source organisms
    Gallus gallus (Ref.219) - Bird: chicken
    Capsicum annuum (Ref.447) - Land plant: red pepper
    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 " .
  • CAS
    465-42-9
    Links to other DB
    KEGG COMPOUND: C08584
    KNApSAcK: C00003763
    LipidBank: VCA0045
    MassBank: CA000015

       Search other references with Google Scholar