Petunidin-3-O-glucoside

Petunidin-3-O-glucoside
Names

IUPAC name (2S,3R,4S,5S,6R)-2-[2-(3,4-dihydroxy-5-methoxyphenyl)-5,7-dihydroxychromenylium-3-yl]oxy-6-(hydroxymethyl)oxane-3,4,5-triol
Other names Petunidin-3-glucoside Petunidin 3-O-glucoside Petunidin 3-O-β-glucopyranoside
Identifiers
CAS Number	6988-81-4 (chloride)
3D model (Jmol)	Interactive image
ChEBI	CHEBI:31985
ChemSpider	391784
PubChem	443651
InChI InChI=1S/C22H22O12/c1-31-14-3-8(2-12(26)17(14)27)21-15(6-10-11(25)4-9(24)5-13(10)32-21)33-22-20(30)19(29)18(28)16(7-23)34-22/h2-6,16,18-20,22-23,28-30H,7H2,1H3,(H3-,24,25,26,27)/p+1/t16-,18-,19+,20-,22-/m1/s1 Key: CCQDWIRWKWIUKK-QKYBYQKWSA-O
SMILES COC1=CC(=CC(=C1O)O)C2=C(C=C3C(=CC(=CC3=[O+]2)O)O)OC4C(C(C(C(O4)CO)O)O)O
Properties
Chemical formula	C₂₂H₂₃O₁₂⁺ C₂₂H₂₃O₁₂Cl (chloride)
Molar mass	479.41 g/mol, 514.86 g/mol (chloride)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Petunidin-3-O-glucoside is anthocyanin. It is found in fruits and berries, in red Vitis vinifera grapes and red wine.^[1]

References

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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