Carotenoids obi
All carotenoids     All organisms   Feedback
Carotenoids DB          Carotenoids DB: CA00799   
[   About  |   Help  |   Search carotenoid entry  |   Search organism entry  |   Search similar carotenoids  |   Predict biological activities of this carotenoid  |   Search possible pathways   ]
Entry
CA00799                                                            

Classification
Carotenoid Name
β-Cyclocitral;
beta-Cyclocitral
IUPAC name 7-Apo-beta-caroten-7-al
Formula
C10H16O
Molecular Weight 
152.228 g/mol
Structure   
Mol file
Carotenoid DB Fingerprints 
Biological functions/Properties 
  • An allelochemical - non enzymatically induced by strong high-light , and induce changes in the expression of a large set of genes that have been identified as singlet oxygen responsive genes (Ref.612).
  • Fruit flavor (Ref.476).
  • An aroma component of Asakusa-nori (Ref.623).
  • Number of
    conjugated double bonds 
    2 including one aldehyde (2 in total)
    Number of
    conjugated multiple bonds 
    2 including one aldehyde (2 in total)
    Isomers 
    InChI
    InChI=1S/C10H16O/c1-8-5-4-6-10(2,3)9(8)7-11/h7H,4-6H2,1-3H3
    InChIKey
    MOQGCGNUWBPGTQ-UHFFFAOYSA-N
    Canonical SMILES
    O=CC1=C(C)CCCC1(C)C
    XLogP
    2.564
    Hydrogen Bond donors
    (Lipinski's definition)
    0
    Hydrogen Bond Acceptors
    (Lipinski's definition)
    1
    LipinskiFailures
    0
    Complexity of molecule
    0.222
    Number of heavy atoms
    11
    TPSA
    (Topological Polar Surface Area) 
    17.070 Å2
    Source organisms
    Microcystis sp. (Ref.146) - Cyanobacteria
    Anabaena spp. (Ref.398) - Terrabacteria group; Cyanobacteria/Melainabacteria group; Cyanobacteria
    Nostoc spp. (Ref.398) - Cyanobacteria
    Spirulina platensis (Ref.398) - Cyanobacteria
    Porphyra tenera (Ref.623); - 
    References
  • Ref.146 : Harada, Ken-ichi; Hasegawa, Masateru; Fukushima, Naoko; Nishizawa, Akito; Fujise, Daiki; Tsuji, Kiyomi, Meijo Daigaku Sogo Kenkyusho Sogo Gakujutsu Kenkyu Ronbunshu (2010), 9, 83-91., "Degradation behavior of β-​carotene during cultivation of cyanobacteria".
  • 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.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.612 : Ramel, F. et al. (2012) Carotenoid oxidation products are stress signals that mediate gene responses to singlet oxygen in plants. Proc. Natl Acad. Sci. U.S.A. 109, 5535–5540.
  • 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".
  • CAS
    432-25-7
    Links to other DB
    KEGG COMPOUND: C20425
    KNApSAcK: C00042278

       Search other references with Google Scholar