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Entry
CA00803                                                            

Classification
Carotenoid Name
β-Ionone;
beta-Ionone
IUPAC name 9-Apo-beta-caroten-9-one
Formula
C13H20O
Molecular Weight 
192.29 g/mol
Structure   
Mol file
Carotenoid DB Fingerprints 
Biological functions/Properties 
  • Non enzymatically induced by strong high-light (Ref.614).
  • Fruit flavor (Ref.476), flavor of white-fleshed nectarines (Ref.623), typical floral-woody note (Ref.490).;Contribute to tomato flavor (Ref.393).
  • An aroma component of Asakusa-nori (Ref.623).
  • Number of
    conjugated double bonds 
    3 including one ketone (3 in total)
    Number of
    conjugated multiple bonds 
    3 including one ketone
    Isomers 
  • Constitutional isomer: CA01013, CA01076, CA01171, CA01177, CA00864, CA01164
  • InChI
    InChI=1S/C13H20O/c1-10-6-5-9-13(3,4)12(10)8-7-11(2)14/h7-8H,5-6,9H2,1-4H3/b8-7+
    InChIKey
    PSQYTAPXSHCGMF-BQYQJAHWSA-N
    Canonical SMILES
    CC(=O)/C=C/C1=C(C)CCCC1(C)C
    XLogP
    3.650
    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
    Anabaena spp. (Ref.398) - Terrabacteria group; Cyanobacteria/Melainabacteria group; Cyanobacteria
    Nostoc sp. PCC 7120 (Ref.550) - Cyanobacteria: same as Anabaena sp. PCC 7120
    Nostoc spp. (Ref.398) - Cyanobacteria
    Spirulina platensis (Ref.398) - Cyanobacteria
    Rosa damascena (Ref.479) - Land plant: Rosaceae: Damask rose, same as Rosa damascena Mill
    Rosa centifolia L. (Ref.479) - Land plant: Rosaceae: Rose de Mai, Burgundy rose
    Coffea arabica (Ref.324) - Land plant: arabica coffee
    Coffea canephora (Ref.324) - Land plant: robusta coffee
    Solanum lycopersicum (Ref.393, Ref.395) - Land plant: Solanaceae: tomato
    Cucumis melo (Ref.396) - Land plant: orange-fleshed muskmelon "honeydew"
    Laurus nobilis L. (Ref.397) - 
    Porphyra tenera (Ref.623) - Red alga: Bangiaceae, Asakusa-nori, same as Pyropia tenera
    References
  • Ref.398 : Ivan Milovanovic, Aleksandra Mišan, Jelica Simeunovic, Dajana KovaI, Dubravka Jambrec, and Anamarija Mandic, Hindawi Publishing Corporation, Journal of Chemistry, Volume 2015, Article ID 969542, 6 pages, http://dx.doi.org/10.1155/2015/969542, "Determination of Volatile Organic Compounds in Selected Strains of Cyanobacteria".
  • Ref.550 : Erin K. Marasco, Kimleng Vay, and Claudia Schmidt-Dannert, THE JOURNAL OF BIOLOGICAL CHEMISTRY VOL. 281, NO. 42, pp. 31583–31593, October 20, 2006, "Identification of Carotenoid Cleavage Dioxygenases from Nostoc sp. PCC 7120 with Different Cleavage Activities".
  • Ref.479 : Rosana Álvarez, Belen Vaz, Hinrich Gronemeyer, and Ángel R. de Lera, Chem Rev. 2014 Jan 8;114(1):1-125. doi: 10.1021/cr400126u. Epub 2013 Nov 22., PMID: 24266866, "Functions, Therapeutic Applications, and Synthesis of Retinoids and Carotenoids".
  • Ref.324 : Andreas Degenhardta, Martin Preinigerb, Frank Ullrich, Developments in Food Science, Volume 43, 2006, Pages 379–382, "Carotenoids as flavour precursors in coffee".
  • Ref.393 : Jonathan T Vogel, Denise M Tieman, Charles A Sims, Asli Z Odabasi, David G Clark, and Harry J Klee, J Sci Food Agric. 2010 Oct;90(13):2233-40. doi: 10.1002/jsfa.4076., "Carotenoid content impacts flavor acceptability in tomato (Solanum lycopersicum).".
  • Ref.395 : Andrew J. Simkin, Steven H. Schwartz, Michele Auldridge, Mark G. Taylor, and Harry J. Klee, The Plant Journal (2004) 40, 882–892, doi: 10.1111/j.1365-313X.2004.02263.x, "The tomato carotenoid cleavage dioxygenase 1 genes contribute to the formation of the flavor volatiles b-ionone, pseudoionone, and geranylacetone".
  • Ref.396 : Ibdah M, Azulay Y, Portnoy V, Wasserman B, Bar E, Meir A, Burger Y, Hirschberg J, Schaffer AA, Katzir N, Tadmor Y, Lewinsohn E., Phytochemistry. 2006 Aug;67(15):1579-89. Epub 2006 Mar 23., "Functional characterization of CmCCD1, a carotenoid cleavage dioxygenase from melon.".
  • Ref.397 : Yahyaa, Mosaab; Berim, Anna; Isaacson, Tal; Marzouk, Sally; Bar, Einat; Davidovich-Rikanati, Rachel; Lewinsohn, Efraim; Ibdah, Mwafaq, ournal of Agricultural and Food Chemistry (2015), 63(37), 8275-8282., "Isolation and Functional Characterization of Carotenoid Cleavage Dioxygenase-1 from Laurus nobilis L. (Bay Laurel) Fruits".
  • 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.614 : Hou, X., Rivers, J., León, P., McQuinn, R.P., Pogson, B.J., 2016. Synthesis and Function of Apocarotenoid Signals in Plants. Trends Plant Sci. xx, 1–12. doi:10.1016/j.tplants.2016.06.001.
  • 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
    79-77-6
    Links to other DB
    KEGG COMPOUND: C12287
    KNApSAcK: C00029816

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