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Entry
CA00864                                                            

Classification
Carotenoid Name
α-Ionone;
(E)-α-Ionone;
alpha-Ionone;
(E)-alpha-Ionone
IUPAC name 9,10-dihydro-9-apo-epsilon-caroten-9-one
Formula
C13H20O
Molecular Weight 
192.29 g/mol
Structure   
Mol file
Carotenoid DB Fingerprints 
Biological functions/Properties 
  • Fruit flavor (Ref.476). Floral-woody note, with an additional honey aspect (Ref.490).
  • An aroma component of Asakusa-nori (Ref.623).
  • Number of
    conjugated double bonds 
    2 including one ketone (2 in total)
    Number of
    conjugated multiple bonds 
    2 including one ketone (2 in total)
    Isomers 
  • Constitutional isomer: CA01013, CA01076, CA00803, CA01171, CA01177, CA01164
  • InChI
    InChI=1S/C13H20O/c1-10-6-5-9-13(3,4)12(10)8-7-11(2)14/h6-8,12H,5,9H2,1-4H3/b8-7+
    InChIKey
    UZFLPKAIBPNNCA-BQYQJAHWSA-N
    Canonical SMILES
    CC(=O)/C=C/C1C(=CCCC1(C)C)C
    XLogP
    4.103
    Hydrogen Bond donors
    (Lipinski's definition)
    0
    Hydrogen Bond Acceptors
    (Lipinski's definition)
    1
    LipinskiFailures
    0
    Complexity of molecule
    0.176
    Number of heavy atoms
    14
    TPSA
    (Topological Polar Surface Area) 
    17.070 Å2
    Source organisms
    Medicago truncatula (Ref.554) - Land plant: barrel medic
    Porphyra tenera (Ref.623) - Red alga: Bangiaceae, Asakusa-nori, same as Pyropia tenera
    References
  • Ref.554 : Daniela S. Floss and Michael H. Walter, Plant Signaling & Behavior 4:3, 172-175; March 2009, "Role of carotenoid cleavage dioxygenase 1 (CCD1) in apocarotenoid biogenesis revisited".
  • 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.476 : Yahyaa M1, Bar E, Dubey NK, Meir A, Davidovich-Rikanati R, Hirschberg J, Aly R, Tholl D, Simon PW, Tadmor Y, Lewinsohn E, Ibdah M., J Agric Food Chem. 2013 Dec 18;61(50):12244-52. doi: 10.1021/jf404085k. Epub 2013 Dec 5., "Formation of norisoprenoid flavor compounds in carrot (Daucus carota L.) roots: characterization of a cyclic-specific carotenoid cleavage dioxygenase 1 gene".
  • Ref.490 : Stefano Serra, Molecules 2015, 20, 12817-12840; doi:10.3390/molecules200712817, "Recent Advances in the Synthesis of Carotenoid-Derived Flavours and Fragrances".
  • CAS
    127-41-3
    Links to other DB

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