Carotenoids obi
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Entry
CA01026                                                            
Classification
Carotenoid Name
Tobiraxanthin A2
IUPAC name (3S,3'S)-3,3'-dihydroxy-5,6,5',6'-diseco-beta,beta-carotene-5,6,5',6'-tetraone-3-myristate-3'-laurate
Formula
C66H104O8
Molecular Weight 
1025.492 g/mol
Structure      Search similar carotenoids

Mol file
Carotenoid DB Fingerprints 
Biological functions/Properties 
  • Tobiraxanthin A shows strong activity to quench singlet oxygen induced by sunlight, and the red color of the seed acts as an attractant for birds to eat seeds to disperse them. (Ref.779)
    • Number of
    conjugated double bonds 
    11 including two ketones (11 in total)
    Number of
    conjugated multiple bonds 
    11 including two ketones (11 in total)
    Isomers 
    InChI

    InChIKey

    Canonical SMILES

    XLogP
    19.802
    Hydrogen Bond donors
    (Lipinski's definition)
    0
    Hydrogen Bond Acceptors
    (Lipinski's definition)
    8
    LipinskiFailures
    2
    Complexity of molecule
    0.000
    Number of heavy atoms
    74
    TPSA
    (Topological Polar Surface Area) 
    120.880 Å2
    Reaction
  • Product: CR00462
    • Pathway
    Major carotenoid information

    Minor carotenoid information

    Source organisms
    Pittosporum tobira (Ref.403, Ref.404, Ref.405) - Land plant (Streptophyta - Pittosporaceae)
    References
  • Ref.403: Maoka, Takashi; Hashimoto, Keiji; Manabe, Kiyoshi; Fujiwara, Yasuhiro, Tennen Yuki Kagobutsu Toronkai Koen Yoshishu (1997), 39th, 487-492., "Structures of novel red carotenoids, tobiraxanthins from the seeds of Pittosporum tobira".
  • Ref.404: Fujiwara, Yasuhiro; Hashimoto, Keiji; Manabe, Kiyoshi; Maoka, Takashi, Tetrahedron Letters (2002), 43(24), 4385-4388., "Structures of tobiraxanthins A1, A2, A3, B, C and D, new carotenoids from the seeds of Pittosporum tobira".
  • Ref.405: Maoka, Takashi; Fujiwara, Yasuhiro; Hashimoto, Keiji; Akimoto, Naoshige, Phytochemistry (Elsevier) (2006), 67(19), 2120-2125., "5-Hydroxy-seco-carotenoids from Pittosporum tobira".
  • Ref.779: Takashi Maoka, Journal of Natural Medicines ISSN 1340-3443 Volume 74 Number 1 J Nat Med (2020) 74:1-16, “Carotenoids as natural functional pigments”, DOI 10.1007/s11418-019-01364-x.
    • CAS
    229314-57-2
    Links to other DB

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