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Entry
CA00321                                                            

Classification
Carotenoid Name
2-Hydroxy-β-carotene;
2-Hydroxy-beta-carotene;
β-caroten-2-ol
IUPAC name (2R)-beta,beta-Caroten-2-ol
Formula
C40H56O
Molecular Weight 
552.848 g/mol
Structure   
Mol file
Carotenoid DB Fingerprints 
Biological functions/Properties 
Number of
conjugated double bonds 
11
Number of
conjugated multiple bonds 
11
Isomers 
InChI
InChI=1S/C40H56O/c1-30(18-13-20-32(3)23-26-36-34(5)22-15-29-39(36,7)8)16-11-12-17-31(2)19-14-21-33(4)24-27-37-35(6)25-28-38(41)40(37,9)10/h11-14,16-21,23-24,26-27,38,41H,15,22,25,28-29H2,1-10H3/b12-11+,18-13+,19-14+,26-23+,27-24+,30-16+,31-17+,32-20+,33-21+/t38-/m1/s1
InChIKey
KOTBWDXNYNTNIY-FLCXWBGESA-N
Canonical SMILES
C/C(=C\C=C\C=C(\C=C\C=C(\C=C\C1=C(C)CC[C@H](C1(C)C)O)/C)/C)/C=C/C=C(/C=C/C1=C(C)CCCC1(C)C)\C
XLogP
12.227
Hydrogen Bond donors
(Lipinski's definition)
1
Hydrogen Bond Acceptors
(Lipinski's definition)
1
LipinskiFailures
1
Complexity of molecule
0.309
Number of heavy atoms
41
TPSA
(Topological Polar Surface Area) 
20.230 Å2
Source organisms
Epicoccum nigrum  - Fungi: fungus, a plant pathogen
Extatosoma tiaratum (Ref.308, Ref.22) - Insect: giant prickly stick insect
Cerura vinula (Ref.22) - Insect: moth
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
    39668-21-8
    Links to other DB
    KNApSAcK: C00022831

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