Carotenoids obi
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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      Search similar carotenoids

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 
  • Constitutional isomer: CA00801, CA01170, CA01169, CA00802
    • InChI

    InChIKey

    Canonical SMILES

    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
    Reaction
    Pathway
  • Pathway: CB000124
    • Major carotenoid information

    Minor carotenoid information

    Source organisms
    Solanum lycopersicum (Ref.393) - Land plant: Solanaceae: tomato, same as Lycopersicon esculentum (Streptophyta - Solanaceae)
    Coffea canephora (Ref.323) - Land plant: robusta coffee (Streptophyta - Rubiaceae)
    Coffea arabica (Ref.323) - Land plant: arabica coffee (Streptophyta - Rubiaceae)
    Vitis sp. (Ref.155) - Land plant: grapevine (Streptophyta - Vitaceae)
    Rosa damascena (Ref.479) - Land plant: Rosaceae: Damask rose (Streptophyta - Rosaceae)
    Rosa centifolia L. (Ref.479) - Land plant: Rosaceae: Rose de Mai, Burgundy rose (Streptophyta - Rosaceae)
    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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