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Entry
CA00825                                                            

Classification
Carotenoid Name
β-Apo-8'-carotenal;
beta-Apo-8'-carotenal;
4,4'-Diapotorulen-4'-al
IUPAC name 8'-Apo-beta-caroten-8'-al
Formula
C30H40O
Molecular Weight 
416.62 g/mol
Structure   
Mol file
Carotenoid DB Fingerprints 
Biological functions/Properties 
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: CA00011, CA00789
  • InChI
    InChI=1S/C30H40O/c1-24(13-8-9-14-25(2)16-11-18-27(4)23-31)15-10-17-26(3)20-21-29-28(5)19-12-22-30(29,6)7/h8-11,13-18,20-21,23H,12,19,22H2,1-7H3/b9-8+,15-10+,16-11+,21-20+,24-13+,25-14+,26-17+,27-18+
    InChIKey
    DFMMVLFMMAQXHZ-DOKBYWHISA-N
    Canonical SMILES
    O=C/C(=C/C=C/C(=C/C=C/C=C(/C=C/C=C(/C=C/C1=C(C)CCCC1(C)C)\C)\C)/C)/C
    XLogP
    9.684
    Hydrogen Bond donors
    (Lipinski's definition)
    0
    Hydrogen Bond Acceptors
    (Lipinski's definition)
    1
    LipinskiFailures
    1
    Complexity of molecule
    0.085
    Number of heavy atoms
    31
    TPSA
    (Topological Polar Surface Area) 
    17.070 Å2
    Source organisms
    Nostoc sp. PCC 7120 (Ref.72, Ref.550, Ref.560) - Cyanobacteria: same as Anabaena sp. PCC 7120
    Microcystis sp. (Ref.146) - Cyanobacteria
    Chromatiaceae spp. (Ref.148) - purple sulfur bacteria
    Novosphingobium aromaticivorans (Ref.166) - Alphaproteobacteria: Sphingomonadaceae
    Gallus gallus (Ref.219) - Bird: chicken
    Averrhoa carambola (Ref.281) - Land plant: starfruit
    Cucumis melo Inodorus Group (Ref.392) - Land plant: orange-fleshed muskmelon "honeydew"
    Mycobacterium tuberculosis (Ref.557) - Actinobacteria
    References
  • Ref.72 : Heo, Jinsol; Kim, Se Hyeuk; Lee, Pyung Cheon, Applied and Environmental Microbiology (2013), 79(11), 3336-3345., "New insight into the cleavage reaction of Nostoc sp. strain PCC 7120 carotenoid cleavage dioxygenase in natural and nonnatural carotenoids".
  • Ref.550 : Erin K. Marasco, Kimleng Vay, and Claudia Schmidt-Dannert, THE JOURNAL OF BIOLOGICAL CHEMISTRY VOL. 281, NO. 42, pp. 31583–31593, October 20, 2006, "Identification of Carotenoid Cleavage Dioxygenases from Nostoc sp. PCC 7120 with Different Cleavage Activities".
  • 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.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.148 : Schaeffer, Philippe; Adam, Pierre; Wehrung, Patrick; Albrecht, Pierre, Tetrahedron Letters (1997), 38(48), 8413-8416., "Novel aromatic carotenoid derivatives from sulfur photosynthetic bacteria in sediments".
  • Ref.166 : YS Kim, ES Seo, DK Oh - Biotechnology letters, October 2012, Volume 34, Issue 10, pp 1851-1856, "Characterization of an apo-carotenoid 13, 14-dioxygenase from Novosphingobium aromaticivorans that converts β-apo-8′-carotenal to β-apo-13-carotenone".
  • Ref.219 : Brulc, Lucka; Simonovska, Breda; Vovk, Irena; Glavnik, Vesna, Journal of Chromatography A (2013), 1318, 134-141. "Determination of egg yolk xanthophylls by isocratic high-performance liquid chromatography".
  • Ref.281 : Jeana Gross, Raphael Ikan, Gert Eckhardt, Phytochemistry, Volume 22, Issue 6, 1983, Pages 1479-1481, "Carotenoids of the fruit of Averrhoa carambola".
  • Ref.392 : Fleshman, Matthew K.; Lester, Gene E.; Riedl, Ken M.; Kopec, Rachel E.; Narayanasamy, Sureshbabu; Curley, Robert W.; Schwartz, Steven J.; Harrison, Earl H., Journal of Agricultural and Food Chemistry (2011), 59(9), 4448-4454., "Carotene and Novel Apocarotenoid Concentrations in Orange-Fleshed Cucumis melo Melons: Determinations of β-Carotene Bioaccessibility and Bioavailability".
  • Ref.557 : Daniel Scherzinger, Erdmann Scheffer, Cornelia Bar, Hansgeorg Ernst and Salim Al-Babili, FEBS J. 2010 Nov;277(22):4662-73. doi: 10.1111/j.1742-4658.2010.07873.x. Epub 2010 Oct 4."The Mycobacterium tuberculosis ORF Rv0654 encodes a carotenoid oxygenase mediating central and excentric cleavage of conventional and aromatic carotenoids" .
  • CAS
    1107-26-2, 71869-13-1
    Links to other DB
    ProCarDB: C0244

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