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Entry
CA00832                                                            

Classification
Carotenoid Name
β-Citraurin;
beta-Citraurin;
Apo-8'-zeaxanthinal;
(3R)-3-Hydroxy-β-apo-8'-carotenal
IUPAC name (3R)-3-Hydroxy-8'-apo-beta-caroten-8'-al
Formula
C30H40O2
Molecular Weight 
432.62 g/mol
Structure   
Mol file
Carotenoid DB Fingerprints 
Biological functions/Properties 
  • Orange-reddish color of oranges and mandarins' peels (Ref.475).
  • Number of
    conjugated double bonds 
    10 including one aldehyde (10 in total)
    Number of
    conjugated multiple bonds 
    10 including one aldehyde (10 in total)
    Isomers 
  • Constitutional isomer: CA01126, CA00015, CA00880, CA00853
  • InChI
    InChI=1S/C30H40O2/c1-23(12-8-9-13-24(2)15-11-17-26(4)22-31)14-10-16-25(3)18-19-29-27(5)20-28(32)21-30(29,6)7/h8-19,22,28,32H,20-21H2,1-7H3/b9-8+,14-10+,15-11+,19-18+,23-12+,24-13+,25-16+,26-17+/t28-/m1/s1
    InChIKey
    AVPAEFHIEZLSLZ-QCPGYTKSSA-N
    Canonical SMILES
    O=C/C(=C/C=C/C(=C/C=C/C=C(/C=C/C=C(/C=C/C1=C(C)C[C@H](CC1(C)C)O)\C)\C)/C)/C
    XLogP
    7.599
    Hydrogen Bond donors
    (Lipinski's definition)
    1
    Hydrogen Bond Acceptors
    (Lipinski's definition)
    2
    LipinskiFailures
    1
    Complexity of molecule
    0.083
    Number of heavy atoms
    32
    TPSA
    (Topological Polar Surface Area) 
    37.300 Å2
    Source organisms
    Nostoc sp. PCC 7120 (Ref.560) - Cyanobacteria: same as Anabaena sp. PCC 7120
    Crocus sativus (Ref.145) - Land plant: saffron crocus
    Citrus unshiu: Yamashitabeni-wase (Ref.149) - Land plant: mandarin orange
    Citrus sinensis L. Osbeck (Ref.150,  - Land plant: orange
    Citrus reticulata Blanco (Ref.151) - Land plant: mandarin orange
    Citrus reticulata x Citrus paradisi (Ref.151) - Land plant: mandarin orange
    Aplysia kurodai (Ref.227) - Kuroda's sea hare
    Capsicum annuum L. (Ref.380) - Land plant: green pepper
    References
  • Ref.560 : Scherzinger D, Ruch S, Kloer DP, Wilde A, Al-Babili S., Biochem J. 2006 Sep 15;398(3):361-9., PMID: 16759173 PMCID: PMC1559462 DOI: 10.1042/BJ20060592, "Retinal is formed from apo-carotenoids in Nostoc sp. PCC7120: in vitro characterization of an apo-carotenoid oxygenase.".
  • Ref.145 : Frusciante, Sarah; Diretto, Gianfranco; Bruno, Mark; Ferrante, Paola; Pietrella, Marco; Prado-Cabrero, Alfonso; Rubio-Moraga, Angela; Beyer, Peter; Gomez-Gomez, Lourdes; Al-Babili, Salim; et al, Proceedings of the National Academy of Sciences of the United States of America (2014), 111(33), 12246-12251., "Novel carotenoid cleavage dioxygenase catalyzes the first dedicated step in saffron crocin biosynthesis".
  • Ref.149 : Ma, Gang; Zhang, Lancui; Matsuta, Asami; Matsutani, Kazuki; Yamawaki, Kazuki; Yahata, Masaki; Wahyudi, Anung; Motohashi, Reiko; Kato, Masaya, Plant Physiology (2013), 163(2), 682-695., "Enzymatic formation of β-​citraurin from β-​cryptoxanthin and zeaxanthin by carotenoid cleavage dioxygenase4 in the flavedo of citrus fruit".
  • Ref.150 : Carmona, Lourdes; Zacarias, Lorenzo; Rodrigo, Maria J., Postharvest Biology and Technology (2012), 74, 108-117., "Stimulation of coloration and carotenoid biosynthesis during postharvest storage of 'Navelina' orange fruit at 12 °C".
  • Ref.152 : Alquezar, Berta; Rodrigo, Maria J.; Zacarias, Lorenzo, Phytochemistry (Elsevier) (2008), 69(10), 1997-2007., "Regulation of carotenoid biosynthesis during fruit maturation in the red-​fleshed orange mutant Cara Cara".
  • Ref.151 : Xu, Juan; Liu, Baozhen; Liu, Xi; Gao, Huijun; Deng, Xiuxin, Acta Physiologiae Plantarum (2011), 33(3), 745-753., "Carotenoids synthesized in citrus callus of different genotypes".
  • Ref.227 : Yamashita, Eiji; Matsuno, Takao, Comparative Biochemistry and Physiology, Part B:  Biochemistry & Molecular Biology (1990), 96B(3), 465-70., "A new apocarotenoid from the sea hare Aplysia kurodai".
  • Ref.380 : Maoka, Takashi; Fujiwara, Yasuhiro; Hashimoto, Keiji; Akimoto, Naoshige, Journal of Agricultural and Food Chemistry (2001), 49(3), 1601-1606., "Isolation of a Series of Apocarotenoids from the Fruits of the Red Paprika Capsicum annuum L.".
  • Ref.475 : Rodrigo MJ, Alquézar B, Alós E, Medina V, Carmona L, Bruno M, Al-Babili S, Zacarías L., J Exp Bot. 2013 Nov;64(14):4461-78. doi: 10.1093/jxb/ert260. Epub 2013 Sep 4., "A novel carotenoid cleavage activity involved in the biosynthesis of Citrus fruit-specific apocarotenoid pigments.".
  • CAS
    650-69-1
    Links to other DB
    KNApSAcK: C00000891
    MassBank: CA000010

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