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Tulipanin
Names
IUPAC name
3′,4′,5,5′,7-Pentahydroxy-3-[α-L -rhamnopyranosyl-(1→6)-β-D -glucopyranosyloxy]flavylium
Systematic IUPAC name
(42 S ,43 R ,44 S ,45 S ,46 R ,72 R ,73 R ,74 R ,75 R ,76 S )-13 ,14 ,15 ,25 ,27 ,43 ,44 ,45 ,73 ,74 ,75 -Undecahydroxy-76 -methyl-21 λ4 -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
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
C27 H31 ClO16 C27 H31 O16 +
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).
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
[1]
[2] and in
eggplants .
[3]
References
^ Harborne, The Handbook of Natural Flavonoids, 2, (1999), 1, Anthocyanins
^
Tulipanin on kanaya.naist.jp
^ 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
3-Hydroxyanthocyanidins
3-Deoxyanthocyanidins O -Methylated anthocyanidins
Anthocyanins (anthocyaninidin glycosides) Glucosides:
Diglucosides:
Others glycosides:
Acylated anthocyanins
Acetylated anthocyanins Coumaroylated anthocyanins (cis - and trans -) Caffeoylated anthocyanins Malonylated anthocyanins Acylated anthocyanin diglycosides
Flavanol-anthocyanin adducts Miscellaneous