Tulipanin

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[1][2] and in eggplants.[3]

Tulipanin
Names
IUPAC name
3′,4′,5,5′,7-Pentahydroxy-3-[α-L-rhamnopyranosyl-(1→6)-β-D-glucopyranosyloxy]flavylium
Systematic IUPAC name
(42S,43R,44S,45S,46R,72R,73R,74R,75R,76S)-13,14,15,25,27,43,44,45,73,74,75-Undecahydroxy-76-methyl-21λ4-3,6-dioxa-2(2,3)-[1]benzopyrana-4(2,6),7(2)-bis(oxana)-1(1)-benzenaheptaphan-21-ylium
Other names
Delphinidin-3-rutinoside
Delphinidin 3-O-rutinoside
Delphinidin-3-glucorhamnoside
Identifiers
3D model (JSmol)
ChemSpider
KEGG
UNII
  • 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/s1 ☒N
    Key: PLKUTZNSKRWCCA-LTSKFBHWSA-O ☒N
  • O(C[C@H]4O[C@@H](Oc2cc3c(O)cc(O)cc3[o+]c2c1cc(O)c(O)c(O)c1)[C@H](O)[C@@H](O)[C@@H]4O)[C@@H]5O[C@H]([C@H](O)[C@@H](O)[C@H]5O)C
Properties
C27H31ClO16
C27H31O16+
Molar mass 611.52 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references


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



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