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

From Wikipedia, the free encyclopedia

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

IUPAC name 4′,5,7-Trihydroxy-3-{6-O-[(2E)-3-(4-hydroxyphenyl)prop-2-enoyl]-β-D-glucopyranosyloxy}-3′,5′-dimethoxyflavylium
Systematic IUPAC name (4²R,4³S,4⁴R,4⁵R,4⁶S,8E)-1⁴,2⁵,2⁷,4³,4⁴,4⁵,10⁴-Heptahydroxy-1³,1⁵-dimethoxy-7-oxo-2¹λ⁴-3,6-dioxa-2(2,3)-[1]benzopyrana-4(2,6)-oxana-1,10(1)-dibenzenadecaphan-8-en-2¹-ylium
Other names Malvidin 3-O-(6″-p-coumaroyl)glucoside
Identifiers
3D model (JSmol)	Interactive image
ChEBI	CHEBI:192433
ChemSpider	30779237
PubChem CID	71308234
InChI InChI=1S/C32H30O14/c1-41-22-9-16(10-23(42-2)27(22)37)31-24(13-19-20(35)11-18(34)12-21(19)44-31)45-32-30(40)29(39)28(38)25(46-32)14-43-26(36)8-5-15-3-6-17(33)7-4-15/h3-13,25,28-30,32,38-40H,14H2,1-2H3,(H3-,33,34,35,36,37)/p+1/t25-,28-,29+,30-,32-/m1/s1 Key: HXQOVGDXCHFLOP-KWNZYCHBSA-O
SMILES O[C@@H]4[C@@H](O)[C@H](O)[C@@H](OC2=CC=1C(O)=CC(O)=CC=1[O+]=C2C3=CC(OC)=C(O)C(=C3)OC)O[C@H]4COC(=O)/C=C/C5=CC=C(O)C=C5
Properties
Chemical formula	C₃₂H₃₁O₁₄⁺
Molar mass	639.58 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Malvidin-3-O-(6-p-coumaroyl)glucoside is a p-coumaroylated anthocyanin found in grape and wine.^[1] There are two forms with the cis and trans isomers of p-coumaric acid. It is a cation.

References

^ Calvo, D.; Sáenz López, R.; Fernández Zurbano, P.; Tena, M. T. (2004). "Migration order of wine anthocyanins in capillary zone electrophoresis". Analytica Chimica Acta. 524 (1–2): 207–213. Bibcode:2004AcAC..524..207C. doi:10.1016/j.aca.2004.06.023.

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)

Miscellaneous

This article about an aromatic compound is a stub. You can help Wikipedia by expanding it.

Hidden categories: