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Entry
CA00593                                                            

Classification
Carotenoid Name
α-Cryptoxanthin;
alpha-Cryptoxanthin
IUPAC name (3'R,6'R)-beta,epsilon-Caroten-3'-ol
Formula
C40H56O
Molecular Weight 
552.848 g/mol
Structure   
Mol file
Carotenoid DB Fingerprints 
Biological functions/Properties 
  • Yellow food coloring (Ref.468).
  • Number of
    conjugated double bonds 
    10
    Number of
    conjugated multiple bonds 
    10
    Isomers 
    InChI
    InChI=1S/C40H56O/c1-30(18-13-20-32(3)23-25-37-34(5)22-15-27-39(37,7)8)16-11-12-17-31(2)19-14-21-33(4)24-26-38-35(6)28-36(41)29-40(38,9)10/h11-14,16-21,23-26,28,36,38,41H,15,22,27,29H2,1-10H3/b12-11+,18-13+,19-14+,25-23+,26-24+,30-16+,31-17+,32-20+,33-21+/t36-,38?/m0/s1
    InChIKey
    ORAKUVXRZWMARG-DWADUKLPSA-N
    Canonical SMILES
    C/C(=C\C=C\C=C(\C=C\C=C(\C=C\C1=C(C)CCCC1(C)C)/C)/C)/C=C/C=C(/C=C/C1C(=C[C@@H](CC1(C)C)O)C)\C
    XLogP
    13.368
    Hydrogen Bond donors
    (Lipinski's definition)
    1
    Hydrogen Bond Acceptors
    (Lipinski's definition)
    1
    LipinskiFailures
    1
    Complexity of molecule
    0.309
    Number of heavy atoms
    41
    TPSA
    (Topological Polar Surface Area) 
    20.230 Å2
    Source organisms
    Ceramium rubrum (Ref.9) - Red alga: Ceramiales
    Carica papaya (Ref.126) - Land plant: papaya
    Capsicum annuum var. lycopersiciforme flavum (Ref.283) - Land plant: yellow paprika
    Citrus reticulata (Ref.292) - Land plant: mandarin orange, tangerine
    Rosa gallica officinalis (Ref.378) - Land plant: Rosaceae: French rose
    Protousnea sp. (Ref.388) - Fungi: lichen
    References
  • Ref.9 : T. Bjoernland and M. Aguilar-Martinez, Phytochemistry, 1976, Vol.15 pp.291-296, "Carotenoids in red algae".
  • Ref.126 : Barreto, Gisela P. M.; Fabi, Joao P.; De Rosso, Veridiana V.; Cordenunsi, Beatriz R.; Lajolo, Franco M.; do Nascimento, Joao R. O.; Mercadante, Adriana Z., Journal of Food Composition and Analysis (2011), 24(4-5), 620-624., "Influence of ethylene on carotenoid biosynthesis during papaya postharvesting ripening".
  • Ref.283 : Zoltan Matus, Jozsef Deli, Jozsef Szabolcs, J. Agric. Food Chem., 1991, 39 (11), pp 1907–1914, "Carotenoid composition of yellow pepper during ripening: isolation of .beta.-cryptoxanthin 5,6-epoxide".
  • Ref.292 : Thomas Wingerath ,Wilhelm Stahl ,Dieter Kirsch, Raimund Kaufmann, and Helmut Sies, J. Agric. Food Chem., 1996, 44 (8), pp 2006–2013, DOI: 10.1021/jf960057y, "Fruit Juice Carotenol Fatty Acid Esters and Carotenoids As Identified by Matrix-Assisted Laser Desorption Ionization (MALDI) Mass Spectrometry".
  • Ref.378 : Maerki-Fischer, Edith; Eugster, Conrad Hans, Helvetica Chimica Acta (1990), 73(5), 1205-9., "Rose pigments. Part 11. New sources of 3'-epilutein in plants".
  • Ref.388 : B. Czeczuga, E. Czeczuga-Semeniuk, S. Calvelo, and S. Liberatore, Journal of Botanical Taxonomy and Geobotany, Volume 116, Issue 3-4, pages 195–200, August 2005, "Carotenoids in representatives of the Protousnea (Parmeliaceae), endemic genus from South America".
  • Ref.468 : Gerard P. Moss, Herbert Baxter, J.B. Harborne, Gerald P. Moss, CRC Press; 1 edition (February 15, 1993), ISBN-10: 0850667364, ISBN-13: 978-0850667363, "Phytochemical Dictionary: A Handbook of Bioactive Compounds from Plants".
  • CAS
    24480-38-4
    Links to other DB
    KEGG COMPOUND: C15981
    KNApSAcK: C00003770
    LipidBank: VCA1159

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