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Entry
CA01169                                                            

Classification
Carotenoid Name
Megastigma-4,7E,9-trien-3-one
IUPAC name 10-Apo-epsilon-caroten-3-one
Formula
C13H18O
Molecular Weight 
190.274 g/mol
Structure   
Mol file
Carotenoid DB Fingerprints 
Biological functions/Properties 
  • A key flavor compound in wine and tobacco (Ref.624, Ref.623).
  • Number of
    conjugated double bonds 
    4 including one ketone
    Number of
    conjugated multiple bonds 
    4 including one ketone
    Isomers 
    InChI
    InChI=1S/C13H18O/c1-5-6-7-12-10(2)8-11(14)9-13(12,3)4/h5-8,12H,1,9H2,2-4H3/b7-6+
    InChIKey
    YKVWPZJHENXDAJ-VOTSOKGWSA-N
    Canonical SMILES
    C=C/C=C/C1C(=CC(=O)CC1(C)C)C
    XLogP
    3.493
    Hydrogen Bond donors
    (Lipinski's definition)
    0
    Hydrogen Bond Acceptors
    (Lipinski's definition)
    1
    LipinskiFailures
    0
    Complexity of molecule
    0.188
    Number of heavy atoms
    14
    TPSA
    (Topological Polar Surface Area) 
    17.070 Å2
    Source organisms
    Nicotiana tabacum (Ref.623) - Land plant: common tobacco
    Vitis sp. (Ref.623) - Land plant: grapevine
    References
  • Ref.623 : Peter Winterhalter and Russell Rouseff, ”Carotenoid-Derived Aroma Compounds: An Introduction”, ACS Symposium Series; American Chemical Society: Washington, DC, 2001., doi: 10.1021/bk-2002-0802.ch001.
  • Ref.624 : David Slaghenaufi, Marie-Claire Perello, Stéphanie Marchand-Marion, Sophie Temperea, Gilles de Revel, "Quantitative solid phase microextraction – Gas chromatography mass spectrometry analysis of five megastigmatrienone isomers in aged wine", Analytica Chimica Acta, Volume 813, 27 February 2014, Pages 63–69.
  • CAS

    Links to other DB

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