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Entry
CA01074                                                            

Classification
Carotenoid Name
Ditaxanthin
IUPAC name Methyl-3,6-epoxy-5-hydroxy-4,5-dihydro-8'-apo-epsilon,psi-caroten-8'-oate
Formula
C31H42O4
Molecular Weight 
478.646 g/mol
Structure   
Mol file
Carotenoid DB Fingerprints 
Biological functions/Properties 
  • Antioxidant activity comparable to astaxanthin (Ref.477).
  • Antiradical activity (Ref.477).
  • Orange color - absorption maxima at 227, 280, 322, 396, 418, and 459nm (Ref.477).
  • Number of
    conjugated double bonds 
    9 including carboxylic acid methyl ester (9 in total)
    Number of
    conjugated multiple bonds 
    9 including carboxylic acid methyl ester (9 in total)
    Isomers 
    InChI
    InChI=1S/C31H42O4/c1-23(13-9-10-14-24(2)17-12-18-26(4)28(32)34-8)15-11-16-25(3)19-20-31-29(5,6)21-27(35-31)22-30(31,7)33/h9-20,27,33H,21-22H2,1-8H3/b10-9+,15-11+,17-12+,20-19+,23-13+,24-14+,25-16+,26-18+/t27-,30-,31+/m0/s1
    InChIKey
    LTYWXDKNOZKXJR-UXMQVZHISA-N
    Canonical SMILES
    COC(=O)/C(=C/C=C/C(=C/C=C/C=C(/C=C/C=C(/C=C/[C@@]12O[C@H](CC1(C)C)C[C@]2(C)O)\C)\C)/C)/C
    XLogP
    7.039
    Hydrogen Bond donors
    (Lipinski's definition)
    1
    Hydrogen Bond Acceptors
    (Lipinski's definition)
    4
    LipinskiFailures
    1
    Complexity of molecule
    0.091
    Number of heavy atoms
    35
    TPSA
    (Topological Polar Surface Area) 
    55.760 Å2
    Source organisms
    Ditaxis heterantha (Ref.477) - Land plant: azafrán, azafrancillo
    References
  • Ref.477 : Marıa D. Mendez-Robles, Herry H. Permady, Marıa E. Jaramillo-Flores, Eugenia C. Lugo-Cervantes, Anaberta Cardador-Martınez, Alejandro A. Canales-Aguirre, Fernando Lopez-Dellamary, Carlos M. Cerda-Garcı´a-Rojas, and Joaquın Tamariz, J. Nat. Prod. 2006, 69, 1140-1144, "C-26 and C-30 Apocarotenoids from Seeds of Ditaxis heterantha with Antioxidant Activity and Protection against DNA Oxidative Damage".
  • CAS

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