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Entry
CA00998                                                            

Classification
Carotenoid Name
(3R)-3-Hydroxy-β-ionone;
(3R)-3-Hydroxy-beta-ionone;
Apo-9-zeaxanthinone;
(+)-3-Hydroxy-β-ionone
IUPAC name (3R)-9-Apo-3-Hydroxy-beta-caroten-9-one
Formula
C13H20O2
Molecular Weight 
208.29 g/mol
Structure   
Mol file
Carotenoid DB Fingerprints 
Biological functions/Properties 
  • An allelochemical - an endogenous growth inhibitor which may play an important role in the inhibition by light of internode growth of bean seedlings (Ref.613).
  • Number of
    conjugated double bonds 
    3 including one ketone (2 in total)
    Number of
    conjugated multiple bonds 
    3 including one ketone (3 in total)
    Isomers 
    InChI
    InChI=1S/C13H20O2/c1-9-7-11(15)8-13(3,4)12(9)6-5-10(2)14/h5-6,11,15H,7-8H2,1-4H3/b6-5+/t11-/m1/s1
    InChIKey
    HFRZSVYKDDZRQY-MVIFTORASA-N
    Canonical SMILES
    O[C@@H]1CC(=C(C(C1)(C)C)/C=C/C(=O)C)C
    XLogP
    1.565
    Hydrogen Bond donors
    (Lipinski's definition)
    1
    Hydrogen Bond Acceptors
    (Lipinski's definition)
    2
    LipinskiFailures
    0
    Complexity of molecule
    0.171
    Number of heavy atoms
    15
    TPSA
    (Topological Polar Surface Area) 
    37.300 Å2
    Source organisms
    Erythrobacter longus (Ref.364) - Alphaproteobacteria: marine anoxygenic phototroph with BChl a
    Capsicum annuum L. (Ref.380) - Land plant: green pepper
    Chenopodium album (Ref.167) - Land plant: white goosefoot, lamb's-quarters
    References
  • Ref.364 : S. Takaichi, K. Shimada, and J. Ishidsu, Arch Microbiol.(1990) 153:118-122, "Carotenoids from the aerobic photosynthetic bacterium, Erythrobacter longus: β-Carotene and its hydroxyl derivatives".
  • Ref.380 : Maoka, Takashi; Fujiwara, Yasuhiro; Hashimoto, Keiji; Akimoto, Naoshige, Journal of Agricultural and Food Chemistry (2001), 49(3), 1601-1606., "Isolation of a Series of Apocarotenoids from the Fruits of the Red Paprika Capsicum annuum L.".
  • Ref.167 : Della Greca, Marina; Di Marino, Cinzia; Zarrelli, Armando; D'Abrosca, Brigida, Journal of Natural Products, Volume67, Issue9, Pages1492-1495, Journal, 2004, CODEN:JNPRDF ISSN:0163-3864 DOI:10.1021/np049857q, "Isolation and phytotoxicity of apocarotenoids from Chenopodium album".
  • Ref.613 : Kato-Noguchi, H. (1996) An endogenous growth inhibitor, 3- hydroxy-b-ionone. III. Its longitudinal gradients in the first internode of Phaseolus vulgaris. Physiol. Plant. 98, 241–244.
  • CAS
    50281-38-4
    Links to other DB
    KNApSAcK: C00045563

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