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Entry
CA00472                                                            

Classification
Carotenoid Name
2-Keto-2'-hydroxy-β-carotene;
2-Keto-2'-hydroxy-beta-carotene
IUPAC name 2'-Hydroxy-beta,beta-caroten-2-one
Formula
C40H54O2
Molecular Weight 
566.832 g/mol
Structure      Search similar carotenoids

Mol file
Carotenoid DB Fingerprints 
Biological functions/Properties 
Number of
conjugated double bonds 
11
Number of
conjugated multiple bonds 
11
Isomers 
InChI
InChI=1S/C40H54O2/c1-29(17-13-19-31(3)21-25-35-33(5)23-27-37(41)39(35,7)8)15-11-12-16-30(2)18-14-20-32(4)22-26-36-34(6)24-28-38(42)40(36,9)10/h11-22,25-26,37,41H,23-24,27-28H2,1-10H3/b12-11+,17-13+,18-14+,25-21+,26-22+,29-15+,30-16+,31-19+,32-20+
InChIKey
AOPBWKXNULORDB-RIRRTMASSA-N
Canonical SMILES
C/C(=C\C=C\C=C(\C=C\C=C(\C=C\C1=C(C)CCC(=O)C1(C)C)/C)/C)/C=C/C=C(/C=C/C1=C(C)CCC(C1(C)C)O)\C
XLogP
9.930
Hydrogen Bond donors
(Lipinski's definition)
1
Hydrogen Bond Acceptors
(Lipinski's definition)
2
LipinskiFailures
1
Complexity of molecule
0.312
Number of heavy atoms
42
TPSA
(Topological Polar Surface Area) 
37.300 Å2
Source organisms
Extatosoma tiaratum (Ref.308, Ref.22) - Insect: giant prickly stick insect
References
  • Ref.308 : Kayser, Hartmut, Zeitschrift fuer Naturforschung, C:  Journal of Biosciences (1981), 36C(9-10), 755-64., "Carotenoids in the stick insect, Ectatosoma tiaratum.  Isolation of β,ε-carotene-2-ol and β,ε-carotene-2-one".
  • Ref.22 : H. Kayser, K. Aareskjold, G. Borch, S. Liaaen-Jensen, Inct Biochem. Insect Biochemistry, Volume 14, Issue 1, 1984, Pages 51–54, "Partly racemized 2-hydroxy-beta-type carotenoids from the insects Cerura vinula and Ectatosoma tiaratum".
  • CAS
    63596-37-2
    Links to other DB
    KNApSAcK: C00022974

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