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Entry
CA00419                                                            
Classification
Carotenoid Name
Luteoxanthin
IUPAC name (3S,5R,6S,3'S,5'R,8'RS)-5,6:5',8'-Diepoxy-5,6,5',8'-tetrahyrdro-beta,beta-carotene-3,3'-diol
Formula
C40H56O4
Molecular Weight 
600.848 g/mol
Structure      Search similar carotenoids

Mol file
Carotenoid DB Fingerprints 
Biological functions/Properties 
  • Antimicrobial activity - anti-H. pylori (Ref.492).
    • Number of
    conjugated double bonds 
    8
    Number of
    conjugated multiple bonds 
    8
    Isomers 
    InChI

    InChIKey

    Canonical SMILES

    XLogP
    7.710
    Hydrogen Bond donors
    (Lipinski's definition)
    2
    Hydrogen Bond Acceptors
    (Lipinski's definition)
    4
    LipinskiFailures
    1
    Complexity of molecule
    0.320
    Number of heavy atoms
    44
    TPSA
    (Topological Polar Surface Area) 
    62.220 Å2
    Reaction
    Pathway
    Major carotenoid information

    Minor carotenoid information

    Source organisms
    Chlamydomonas reinhardtii (Ref.12, Ref.13, Ref.14) - Green alga: Chlamydomonadales, unicellular green alga (Chlorophyta - Chlamydomonadaceae)
    Ascophyllum nodosum (Ref.53) - Brown alga: Fucaceae ((Phaeophyceae) - Fucaceae)
    Fucus serratus (Ref.53) - Brown alga: Fucaceae ((Phaeophyceae) - Fucaceae)
    Fucus vesiculosus (Ref.53) - Brown alga: Fucaceae ((Phaeophyceae) - Fucaceae)
    Pelvetia canaliculata (Ref.53) - Brown alga: Fucaceae ((Phaeophyceae) - Fucaceae)
    Laminaria saccharina (Ref.53) - Brown alga: Laminariaceae ((Phaeophyceae) - Laminariaceae)
    Laminaria digitata (Ref.53) - Brown alga: Laminariaceae ((Phaeophyceae) - Laminariaceae)
    Nannochloropsis oculata (Ref.27, Ref.28) - Alga: Eustigmatophyceae ((Eustigmatophyceae) - Monodopsidaceae)
    Nannochloropsis salina (Ref.27, Ref.28) - Alga: Eustigmatophyceae ((Eustigmatophyceae) - Monodopsidaceae)
    Capsicum annuum var. longum  - Land plant: red spice paprika (Streptophyta - Solanaceae)
    Malus domestica (Ref.492) - Land plant: Rosaceae: peel and flesh of apple fruits (Streptophyta - Rosaceae)
    Mangifera indica (Ref.284) - Land plant: mango (Streptophyta - Anacardiaceae)
    Citrus reticulata (Ref.292) - Land plant: mandarin orange, tangerine (Streptophyta - Rutaceae)
    Citrus sinensis L. Osbeck (Ref.373) - Land plant: orange (Streptophyta - Rutaceae)
    Curcurbita maxima  - Land plant: pumpkin (Streptophyta - Cucurbitaceae)
    References
  • Ref.12: N.I. Krinsky and R. P. Levine, Plant Physiol. Jul 1964; 39(4): 680–687. "Carotenoids of Wild Type and Mutant Strains of the Green Alga, Chlamydomonas reinhardi".
  • Ref.13: PMID: 1190948: Francis GW, Strand LP, Lien T, Knutsen G., Arch Microbiol. 1975 Aug 28;104(3):249-54. "Variations in the Carotenoid Content of Chlamydomonas reinhardii throughout the Cell cycle".
  • Ref.14: S. Tkaichi, and M. Mimuro, Plant Cell Physiol. 39(9): 968-977 (1998) "Distribution and Geometric Isomerism of Neoxanthin in Oxygenic Phototrophs: 9'-Cis, a Sole Molecular Form".
  • Ref.27: N. J. Antial, and J.Y. Cheng, British Phycological Journal, Volume 17, Issue 1, 1982 "The Keto carotenoids of two marine cocoid members of the eustimaphyceae" DOI:10.1080/00071618200650061 .
  • Ref.28: Luis M. Lubián, Olimpio Montero, Ignacio Moreno-Garrido, I. Emma Huertas, Cristina Sobrino, Manuel González-del Valle, Griselda Parés, Journal of Applied Phycology, October 2000, Volume 12, Issue 3-5, pp 249-255 "Nannochloropsis (Eustigmatophyceae) as source of commercially valuable pigments".
  • Ref.53: G. Nybraaten, and S. L. Jensen, Acta Chem. Scand. Ser. B, 28,(1974), 485, "Algal Carotenoids. XII. * Chemical Reactions of Carotenoids with 2-Hydroxylated beta-Rings".
  • Ref.284: Adriana Z. Mercadante ,Délia B. Rodriguez-Amaya, George Britton, J. Agric. Food Chem., 1997, 45 (1), pp 120–123, "HPLC and Mass Spectrometric Analysis of Carotenoids from Mango".
  • 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.373: Kudritskaya, S. E.; Fishman, G. M.; Zagorodskaya, L. M., Subtropicheskie Kul'tury (1977), (5-6), 154-8., "Identification of orange peel (Citrus sinensis Osb.) carotenoids".
  • Ref.492: Péter Molnár, József Deli, Toru Tanaka,Yoshiyuki Kann, Satoru Tani, Nóra Gyémánt, Joseph Molnár ,and Masami Kawase, Phytotherapy Research, Volume 24, Issue 5, pages 644–648, May 2010, “Carotenoids with anti-Helicobacter pylori activity from Golden deliciousapple”.
    • CAS
    1912-50-1
    Links to other DB
    MassBank: CA000075

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