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Tulipanin

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(Redirected from Delphinidin-3-O-rutinoside)
Tulipanin
Names
IUPAC name 3′,4′,5,5′,7-Pentahydroxy-3-flavylium
Systematic IUPAC name (4S,4R,4S,4S,4R,7R,7R,7R,7R,7S)-1,1,1,2,2,4,4,4,7,7,7-Undecahydroxy-7-methyl-2λ-3,6-dioxa-2(2,3)-benzopyrana-4(2,6),7(2)-bis(oxana)-1(1)-benzenaheptaphan-2-ylium
Other names Delphinidin-3-rutinoside
Delphinidin 3-O-rutinoside
Delphinidin-3-glucorhamnoside
Identifiers
CAS Number
3D model (JSmol)
ChemSpider
KEGG
PubChem CID
UNII
InChI
  • InChI=1S/C27H30O16/c1-8-18(32)21(35)23(37)26(40-8)39-7-17-20(34)22(36)24(38)27(43-17)42-16-6-11-12(29)4-10(28)5-15(11)41-25(16)9-2-13(30)19(33)14(31)3-9/h2-6,8,17-18,20-24,26-27,32,34-38H,7H2,1H3,(H4-,28,29,30,31,33)/p+1/t8-,17+,18-,20+,21+,22-,23+,24+,26+,27+/m0/s1Key: PLKUTZNSKRWCCA-LTSKFBHWSA-O
SMILES
  • O(C4O(Oc2cc3c(O)cc(O)cc3c2c1cc(O)c(O)c(O)c1)(O)(O)4O)5O((O)(O)5O)C
Properties
Chemical formula C27H31ClO16
C27H31O16
Molar mass 611.52 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). ☒verify (what is  ?) Infobox references
Chemical compound

Tulipanin is an anthocyanin. It is the 3-O-rutinoside of delphinidin. It can be found in Alstroemeria spp., Berberis spp., Cissus sicyoides, Hymenocallis spp., Manihot utilissima, Meliosma tenuis, Musa acuminata, Ophiopogon japonicus, Petunia exserta, Petunia reitzii, blackcurrant (Ribes nigrum), Schismatoglottis concinna, Secale cereale, Solanum betaceum, Thaumatococcus daniellii, Tulipa spp and in eggplants.


References

  1. Harborne, The Handbook of Natural Flavonoids, 2, (1999), 1, Anthocyanins
  2. Tulipanin on kanaya.naist.jp
  3. Structures and Antioxidant Activity of Anthocyanins in Many Accessions of Eggplant and Its Related Species. Keiko Azuma, Akio Ohyama, Katsunari Ippoushi, Takashi Ichiyanagi, Atsuko Takeuchi, Takeo Saito and Hiroyuki Fukuoka, J. Agric. Food Chem., 2008, 56 (21), pp 10154–10159, doi:10.1021/jf801322m


Anthocyanidins and their anthocyanin glucosides
3-Hydroxyanthocyanidins
3-Deoxyanthocyanidins
O-Methylated anthocyanidins
Anthocyanins
(anthocyaninidin glycosides)
Glucosides:

Diglucosides:

Others glycosides:

Acylated anthocyanins
Acetylated anthocyanins
  • Cyanidin 3-O-(6-acetyl)glucoside
  • Delphinidin 3-O-(6-acetyl)glucoside
  • Malvidin 3-O-(6-acetyl)glucoside
  • Petunidin 3-O-(6-acetyl)galactoside
  • Petunidin 3-O-(6-acetyl)glucoside
  • Peonidin 3-O-(6-acetyl)glucoside
  • Coumaroylated anthocyanins
    (cis- and trans-)
    Caffeoylated anthocyanins
    Malonylated anthocyanins
    Acylated anthocyanin diglycosides
    Flavanol-anthocyanin adducts
    Miscellaneous


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