Delphinidin-3-O-(6-p-coumaroyl)glucoside

Delphinidin-3-O-(6-p-coumaroyl)glucoside
Names

IUPAC name [(2R,3S,4S,5R,6S)-6-[5,7-Dihydroxy-2-(3,4,5-trihydroxyphenyl)chromenylium-3-yl]oxy-3,4,5-trihydroxyoxan-2-yl]methyl (E)-3-(4-hydroxyphenyl)prop-2-enoate
Other names Delphinidin-3-O-p-coumaroyl glucoside
Identifiers
3D model (Jmol)	Interactive image
ChemSpider	26559505
PubChem	15922818
InChI InChI=1S/C30H26O14/c31-15-4-1-13(2-5-15)3-6-24(36)41-12-23-26(38)27(39)28(40)30(44-23)43-22-11-17-18(33)9-16(32)10-21(17)42-29(22)14-7-19(34)25(37)20(35)8-14/h1-11,23,26-28,30,38-40H,12H2,(H5-,31,32,33,34,35,36,37)/p+1/t23-,26-,27+,28-,30-/m1/s1 Key: DHTPVCYNNWQRMN-LHRGPQAGSA-O InChI=1/C30H26O14/c31-15-4-1-13(2-5-15)3-6-24(36)41-12-23-26(38)27(39)28(40)30(44-23)43-22-11-17-18(33)9-16(32)10-21(17)42-29(22)14-7-19(34)25(37)20(35)8-14/h1-11,23,26-28,30,38-40H,12H2,(H5-,31,32,33,34,35,36,37)/p+1/t23-,26-,27+,28-,30-/m1/s1 Key: DHTPVCYNNWQRMN-LEURJHHLBH
SMILES c1cc(ccc1/C=C/C(=O)OC[C@@H]2[C@H]([C@@H]([C@H]([C@@H](O2)Oc3cc4c(cc(cc4[o+]c3c5cc(c(c(c5)O)O)O)O)O)O)O)O)O
Properties
Chemical formula	C₃₀H₂₇O₁₄⁺
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).
Infobox references

Delphinidin 3-O-(6-p-coumaroyl)glucoside is a p-coumaroylated anthocyanin. It can be found in some red Vitis vinifera grape cultivars (like Graciano^[1]) and in red wine.^[2]

References

↑ Vitis vinifera L. cv. Graciano grapes characterized by its anthocyanin proﬁle. V. Núñez, M. Monagas, M.C. Gomez-Cordovés and B. Bartolomé, Postharvest Biology and Technology, 2004, 31, pages 69–79, doi:10.1016/S0925-5214(03)00140-6
↑ Delphinidin 3-(6-p-coumaroyl)glucoside on www.phenol-explorer.eu
↑ Delphinidin 3-(6-p-coumaroyl)glucoside synthesis reaction on www.kegg.jp

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)-beta-D-glucosyl)oxybenzoyl)-beta-D-glucoside)

Malvidin glucoside-ethyl-catechin
Catechin(4α→8)pelargonidin 3-O-β-glucopyranoside
Epicatechin(4α→8)pelargonidin 3-O-β-glucopyranoside
Afzelechin(4α→8)pelargonidin 3-O-β-glucopyranoside
Epiafzelechin(4α→8)pelargonidin 3-O-β-glucopyranoside

Misc.

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