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) checkY
3D model (JSmol)
  • Interactive image
ChEBI
  • CHEBI:31985
ChemSpider
  • 391784
KEGG
  • C12139 checkY
PubChem CID
  • 443651
UNII
  • AA9G36JBHT (chloride) checkY
CompTox Dashboard (EPA)
  • DTXSID40990158 Edit this at Wikidata
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
  • 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
 C
22H
23O+
12
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
Chemical compound

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

See also

References

  1. ^ Petunidin 3-O-glucoside on www.phenol-explorer.eu Archived 2013-02-13 at archive.today
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Anthocyanidins and their anthocyanin glucosides
3-Hydroxyanthocyanidins3-DeoxyanthocyanidinsO-Methylated anthocyanidinsAnthocyanins
(anthocyaninidin glycosides)
Glucosides:
  • Callistephin (Pelargonidin 3-O-glucoside)
  • Chrysanthemin (Cyanidin 3-O-glucoside)
  • Myrtillin (Delphinidin 3-O-glucoside)
  • Oenin (Malvidin 3-O-glucoside)
  • Peonidin 3-O-glucoside
  • Petunidin 3-O-glucoside
  • Pulchellidin 3-glucoside

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:

  • Antirrhinin (Cyanidin 3-O-rutinoside)
  • Ideain (Cyanidin 3-O-galactoside)
  • Delphinidin 3-O-rhamnoside
  • Petunidin 3-O-arabinoside
  • Petunidin 3-O-galactoside
  • Petunidin 3-O-rhamnoside
  • Petunidin 3-O-rutinoside
  • Primulin (Malvidin 3-O-galactoside)
  • Pulchellidin 3-rhamnoside
  • Tulipanin (Delphinidin 3-O-rutinoside)
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)
    Flavanol-anthocyanin adducts
    • 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
    Miscellaneous
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