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Entry
CA00800                                                            

Classification
Carotenoid Name
β-Damascenone;
beta-Damascenone
IUPAC name 10-Apo-7,8,9,10-tetrahydro-8,9-didehydro-beta-caroten-7-one
Formula
C13H18O
Molecular Weight 
190.274 g/mol
Structure   
Mol file
Carotenoid DB Fingerprints 
Biological functions/Properties 
  • Honey-like fruity odor.
  • Contribute to tomato flavor (Ref.393).
  • Number of
    conjugated double bonds 
    4 including one ketone (4 in total)
    Number of
    conjugated multiple bonds 
    4 including one ketone
    Isomers 
    InChI
    InChI=1S/C13H18O/c1-5-7-11(14)12-10(2)8-6-9-13(12,3)4/h5-8H,9H2,1-4H3/b7-5+
    InChIKey
    POIARNZEYGURDG-FNORWQNLSA-N
    Canonical SMILES
    C/C=C/C(=O)C1=C(C)C=CCC1(C)C
    XLogP
    3.407
    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
    Vitis sp. (Ref.155) - Land plant: grapevine
    Coffea arabica (Ref.323) - Land plant: arabica coffee
    Coffea canephora (Ref.323) - Land plant: robusta coffee
    Solanum lycopersicum (Ref.393) - Land plant: Solanaceae: tomato
    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
    References
  • Ref.155 : N. Takatani, K. Nishida, T. Sawabe, T. Maoka, K. Miyashita, M. Hosokawa, Applied Microbiology and Biotechnology (2014), Volume 98, Issue 15, pp 6633-6640, "Identification of a novel carotenoid, 2'-isopentenylsaproxanthin, by Jejuia pallidilutea strain 11shimoA1 and its increased production under alkaline condition".
  • Ref.323 : Andrew J. Simkin, Marcel Kuntz, Helene Moreau, James McCarthy, Plant Physiology and Biochemistry 48 (2010) pp.434-442, "Carotenoid profiling and the expression of carotenoid biosynthetic genes in developing coffee grain".
  • 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.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".
  • CAS
    23726-93-4
    Links to other DB
    KNApSAcK: C00035536

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