Tulipanin

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
CAS Number	58285-26-0^Y
3D model (JSmol)	Interactive image
ChemSpider	4590910^N
KEGG	C16315
PubChem CID	5492231
UNII	6I4SV29842^Y
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/s1^N Key: PLKUTZNSKRWCCA-LTSKFBHWSA-O^N
SMILES 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
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 [77 °F], 100 kPa). N verify (what is ^YN ?) 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^[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

O-Methylated anthocyanidins

Anthocyanins
(anthocyaninidin glycosides)

Glucosides:

Diglucosides:

Cyanin (Cyanidin 3,5-O-diglucoside)
Delphin (Delphinidin 3,5-O-diglucoside)
Malvin (Malvidin 3,5-diglucoside)
Pelargonin (Pelargonidin 3,5-O-diglucoside)
Peonin (Peonidin 3,5-O-diglucoside)
Petunin (Petunidin 3,5-O-diglucoside)

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-)	Cyanidin 3-O-(6-p-coumaroyl)glucoside Delphinidin 3-O-(6-p-coumaroyl)glucoside Malvidin 3-O-(6-p-coumaroyl)glucoside Petunidin 3-O-(6-p-coumaroyl)glucoside Peonidin 3-O-(6-p-coumaroyl)glucoside
Caffeoylated anthocyanins	Malvidin 3-O-(6-p-caffeoyl)glucoside Peonidin 3-O-(6-p-caffeoyl)glucoside
Malonylated anthocyanins	Malonylmalvin (malvidin 3-(6″-malonylglucoside)-5-glucoside)
Acylated anthocyanin diglycosides	Cyanidin 3-O-(di-p-coumarylglucoside)-5-glucoside Gentiodelphin (delphinidin 3-''O''-glucosyl-5-''O''-(6-''O''-caffeoyl-glucosyl)-3′-''O''-(6-''O''-caffeoyl-glucoside)) Nasunin (Delphinidin 3-(p-coumaroylrutinoside)-5-glucoside) Petanin (petunidin 3-[6-O-(4-O-(E)-p-coumaroyl-O-α-l-rhamnopyranosyl)-β-D-glucopyranoside]-5-O-β-D-glucopyranoside) Violdelphin (Delphinidin 3-rutinoside-7-O-(6-O-(4-(6-O-(4-hydroxybenzoyl)-β-D-glucosyl)oxybenzoyl)-β-D-glucoside)