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

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]

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 (JSmol)	Interactive image
ChemSpider	26559505
PubChem CID	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	C 30H 27O^+ 14
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

It is formed by the enzyme anthocyanin 3-O-glucoside 6″-O-hydroxycinnamoyltransferase from delphinidin 3-O-glucoside and p-coumaroyl-CoA in the anthocyanin biosynthesis pathway.[3]

See also

• Phenolic compounds in wine

References

1. Núñez, V.; Monagas, M.; Gomez Cordovés, M. C.; Bartolomé, B. (2004). "Vitis vinifera L. cv. Graciano grapes characterized by its anthocyanin profile". Postharvest Biology and Technology. 31: 69–79. doi:10.1016/S0925-5214(03)00140-6.
2. "Delphinidin 3-(6-p-coumaroyl)glucoside on www.phenol-explorer.eu". Archived from the original on 2011-12-30. Retrieved 2012-02-21.
3. Delphinidin 3-(6-p-coumaroyl)glucoside synthesis reaction on www.kegg.jp