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Entry
CA00608                                                            

Classification
Carotenoid Name
Loroxanthin
IUPAC name (3R,3'R,6'R)-beta,epsilon-Carotene-3,19,3'-triol
Formula
C40H56O3
Molecular Weight 
584.848 g/mol
Structure   
Mol file
Carotenoid DB Fingerprints 
Biological functions/Properties 
  • Not an active antenna pigment but instead participates in the loroxanthin/lutein interconversion (Ref.626)
  • Number of
    conjugated double bonds 
    10
    Number of
    conjugated multiple bonds 
    10
    Isomers 
    InChI
    InChI=1S/C40H56O3/c1-29(16-12-17-31(3)20-22-37-32(4)24-35(42)26-39(37,6)7)14-10-11-15-30(2)18-13-19-34(28-41)21-23-38-33(5)25-36(43)27-40(38,8)9/h10-24,35-37,41-43H,25-28H2,1-9H3/b11-10+,16-12+,18-13+,22-20+,23-21+,29-14+,30-15+,31-17+,34-19-/t35-,36+,37-/m0/s1
    InChIKey
    ODGGKCNQKSEQNL-CWBMHJDKSA-N
    Canonical SMILES
    OC/C(=C\C=C\C(=C\C=C\C=C(\C=C\C=C(\C=C\[C@H]1C(=C[C@@H](CC1(C)C)O)C)/C)/C)\C)/C=C/C1=C(C)C[C@H](CC1(C)C)O
    XLogP
    9.402
    Hydrogen Bond donors
    (Lipinski's definition)
    3
    Hydrogen Bond Acceptors
    (Lipinski's definition)
    3
    LipinskiFailures
    2
    Complexity of molecule
    0.303
    Number of heavy atoms
    43
    TPSA
    (Topological Polar Surface Area) 
    60.690 Å2
    Source organisms
    Chlamydomonas reinhardtii (Ref.12, Ref.13, Ref.14) - Green alga: Chlamydomonadales, unicellular green alga
    Botryococcus braunii (Ref.19) - Green alga: Trebouxiophyceae
    Chlorella vulgaris (Ref.23) - Green alga: Trebouxiophyceae
    Aegagrophila linnaei (Ref.24) - Green alga: Ulvophyceae
    Basicladia sp. (Ref.24) - Green alga: Ulvophyceae
    Chaetomorpha okamurae (Ref.24) - Green alga: Ulvophyceae
    Cladophora conchopheria (Ref.24) - Green alga: Ulvophyceae
    Cladophora horii (Ref.24) - Green alga: Ulvophyceae
    Cladophora kosterae (Ref.24) - Green alga: Ulvophyceae
    Cladophora ohkuboana (Ref.24) - Green alga: Ulvophyceae
    Pithophora sp. (Ref.24) - Green alga: Ulvophyceae
    Wittrockiella lyallii (Ref.24) - Green alga: Ulvophyceae
    Wittrockiella paradoxa (Ref.24) - Green alga: Ulvophyceae
    Cladophoropsis fasciculatus (Ref.24) - Green alga: Ulvophyceae
    Chaetomorpha crassa (Ref.24) - Green alga: Ulvophyceae
    Cladophora albida (Ref.24) - Green alga: Ulvophyceae
    Cladophora glomerata (Ref.24) - Green alga: Ulvophyceae
    Cladophora japonica (Ref.24) - Green alga: Ulvophyceae
    Cladophora ohkuboana (Ref.24) - Green alga: Ulvophyceae
    Cladophora pellucida (Ref.24) - Green alga: Ulvophyceae
    Cladophora sericea (Ref.24) - Green alga: Ulvophyceae
    Cladophora vagabunda (Ref.24) - Green alga: Ulvophyceae
    Rhizoclonium grande (Ref.24) - Green alga: Ulvophyceae
    Euglena sanguinea (Ref.43) - Alga: Euglenoid
    Tetraselmis chui (Ref.48) - Green alga: Chlorodendraceae
    Tetraselmis marina (Ref.48) - Green alga: Chlorodendraceae
    Tetraselmis rubens (Ref.48) - Green alga: Chlorodendraceae
    Tetraselmis subcordiformis (Ref.48) - Green alga: Chlorodendraceae
    Tetraselmis suecica (Ref.48) - Green alga: Chlorodendraceae
    Tetraselmis tetrathele (Ref.48) - Green alga: Chlorodendraceae
    Pyramimonas parkeae (Ref.48) - Green alga: Prasinophyte
    Botryococcus braunii Kawaguchi-1 (Ref.231) - Green alga: Trebouxiophyceae
    Corbicula sandai (Ref.221) - Shellfish: bivalve
    Corbicula clam (Ref.221) - Shellfish: bivalve
    Protousnea sp. (Ref.388) - Fungi: lichen
    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.19 : Merete Grunga, Pierre Metzger, Synnove Liaaen-jensen, Biochemical Systematics and Ecology, Volume 17, Issue 4, 28 July 1989, Pages 263–269 "Primary and Secondary Carotenoids in Two Races of the Green Alga Botryocossu braunii".
  • Ref.23 : Märki-Fischer, E., Bütikofer, P.-A., Buchecker, R., and Eugster, C.H. Helv. Chim. Acta, 66 PAGE : 1175 -1182 (1983) "Absolute configuration of loroxanthin (=(3R,3'R,6'R)-b,e-carotene-3,19,3'-triol)".
  • Ref.24 : Y. Yoshii, I,. Wakana, K. Miriya, S. Arai, K. Ueda, and I. Inouye, J. Phycol. 40, 1170-1177 (2004) "Carotenoid comositions of Cladophora Balls (Aegagropila linnaei) and some members of the Cladophorales (Ulvophyceae, Chlorophyta): their taxonomic and evolutionary implication".
  • Ref.43 : Merte grung et.al, S. Liaaen-Jensen, Biochemical Systematics and Ecology, Vol. 21, No. 8, pp. 757-763, 1993 "Algal Carotenoids52*; Secondary carotenoids of Algae 3; Carotenoids in natural bloom of Euglena sanguinea".
  • Ref.48 : Jose L. Carrido, Francisco Rodriguez, and Mannuel Zapata J. Phycol. 15, 366-374 (2009) "Occurrence of Loroxanthin, Loroxanthin decenoate, and Loroxanthin dodecenoate in Tetraselmis species (Prasinophyceae, Chlorophyta)".
  • Ref.231 : Agrawal, Poonam; Laddha, Kirti; Tiwari, Ashok, Agrawal, Poonam; Laddha, Kirti; Tiwari, Ashok., "Isolation and HPLC method development of azafrin from Alectra parasitica var. chitrakutensis".
  • Ref.221 : Maoka, Takashi; Fujiwara, Yasuhiro; Hashimoto, Keiji; Akimoto, Naoshige, Journal of Agricultural and Food Chemistry (2005), 53(21), 8357-8364. "Carotenoids in Three Species of Corbicula Clams, Corbicula japonica, Corbicula sandai, and Corbicula sp. (Chinese Freshwater Corbicula Clam)".
  • 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.626 : Yukie Yoshii, Takeaki Hanyuda, Isamu Wakana, Kazuyuki Miyaji, Shogo Arai, Kunihiko Ueda, and Isao Inouye, J. Phycol. 40, 1170–1177 (2004), DOI: 10.1111/j.1529-8817.2004.03210.x, "CAROTENOID COMPOSITIONS OF CLADOPHORA BALLS (AEGAGROPILA LINNAEI) AND SOME MEMBERS OF THE CLADOPHORALES (ULVOPHYCEAE, CHLOROPHYTA): THEIR TAXONOMIC AND EVOLUTIONARY IMPLICATION1".
  • CAS
    27637-71-4
    Links to other DB
    KNApSAcK: C00022916
    LipidBank: VCA1074

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