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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      Search similar carotenoids

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 
  • Constitutional isomer: CA00804, CA01107, CA01111, CA01165, CA01117, CA01134, CA01173
    • InChI

    InChIKey

    Canonical SMILES

    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
    Reaction
  • Product: CR00085,  CR00092,  CR00409
    • Pathway
    Major carotenoid information

    Minor carotenoid information

    Source organisms
    Erythrobacter longus (Ref.364) - Alphaproteobacteria: marine anoxygenic phototroph with BChl a (Alphaproteobacteria - Erythrobacteraceae)
    Capsicum annuum L. (Ref.380) - Land plant: green pepper (Streptophyta - Solanaceae)
    Lycium chinense (Ref.692) - Land plant: goji berry, Chinese boxthorn, Chinese wolfberry, kuko, gou qi, same as Lycium chinense Mill., 1768 (Streptophyta - Solanaceae)
    Chenopodium album (Ref.167) - Land plant: white goosefoot, lamb's-quarters (Streptophyta - Amaranthaceae)
    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.692: Olivier Potterat, Planta Med 2010; 76: 7–19, "Goji (Lycium barbarum and L. chinense): Phytochemistry, Pharmacology and Safety in the Perspective of Traditional Uses and Recent Popularity", DOI http://dx.doi.org/10.1055/s-0029-1186218 .
  • 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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