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Entry
CA01065                                                            

Classification
Carotenoid Name
Safranal
IUPAC name 3,4-didehydro-7-apo-beta-caroten-7-al
Formula
C10H14O
Molecular Weight 
150.212 g/mol
Structure   
Mol file
Carotenoid DB Fingerprints 
Biological functions/Properties 
  • An antioxidant - high radical scavenging activity. (Ref.456)
  • Anticarcinogenic activity (Ref.457).
  • Antitussive activity (Ref.458).
  • Iodoform or hay-like fragrance (Ref.458).
  • An aroma component of Asakusa-nori (Ref.623).
  • Number of
    conjugated double bonds 
    3 including one aldehyde (3 in total)
    Number of
    conjugated multiple bonds 
    3 including one aldehyde (3 in total)
    Isomers 
    InChI
    InChI=1S/C10H14O/c1-8-5-4-6-10(2,3)9(8)7-11/h4-5,7H,6H2,1-3H3
    InChIKey
    SGAWOGXMMPSZPB-UHFFFAOYSA-N
    Canonical SMILES
    O=CC1=C(C)C=CCC1(C)C
    XLogP
    2.450
    Hydrogen Bond donors
    (Lipinski's definition)
    0
    Hydrogen Bond Acceptors
    (Lipinski's definition)
    1
    LipinskiFailures
    0
    Complexity of molecule
    0.240
    Number of heavy atoms
    11
    TPSA
    (Topological Polar Surface Area) 
    17.070 Å2
    Source organisms
    Crocus sativus (Ref.454, Ref.455) - Land plant: saffron crocus
    Porphyra tenera (Ref.623) - Red alga: Bangiaceae, Asakusa-nori, same as Pyropia tenera
    References
  • Ref.454 : Sarah Frusciantea,b, Gianfranco Direttoa, Mark Brunoc, Paola Ferrantea, Marco Pietrellaa, Alfonso Prado-Cabrerod, Angela Rubio-Moragae, Peter Beyerc, Lourdes Gomez-Gomeze, Salim Al-Babilic,d, and Giovanni Giulianoa, PNAS, August 19, 2014, pp.12246–12251, vol. 111, no. 33, "Novel carotenoid cleavage dioxygenase catalyzes the first dedicated step in saffron crocin biosynthesis".
  • Ref.455 : H. Pfander, and H. Schurternberger, Phytochemistry, vol.21, No.5, pp.1039-1042, 1982, "Biosynthesis of C20-carotenoids in Crocus sativus".
  • 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.456 : A. N. Assimopoulou, Z. Sinakos, and V. P. Papageorgiou, Phytotherapy Research, Volume 19, Issue 11, pages 997–1000, November 2005, "Radical scavenging activity of Crocus sativus L. extract and its bioactive constituents".
  • Ref.457 : Julio Escribanoa, Gonzalo-Luis Alonsob, Miguel Coca-Pradosc, José-Antonio Fernández, Cancer Letters, Volume 100, Issues 1–2, 27 February 1996, Pages 23–30, "Crovin, safranal, and picrocrocin from saffron (Crocus sativus L.) inhibit the growth of human cancer cell in vitro".
  • Ref.458 : R. Srivastava, H. Ahmed, R. K. Dixit, Dharamveer, and S. A. Saraf, Pharmacogn Rev. 2010 Jul-Dec; 4(8): 200–208., doi: 10.4103/0973-7847.70919, "Crocus sativus L.: A comprehensive review".
  • CAS

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