Petunidin

From Wikipedia, the free encyclopedia

Petunidin

IUPAC name 2-(3,4-dihydroxy-5-methoxyphenyl)-3,5,7-trihydroxychromenylium
Other names Petunidine; Petunidin chloride; Petunidol; Myrtillidin
Identifiers
CAS number	1429-30-7^N
PubChem	441774
ChemSpider	390371^Y
Jmol-3D images	{{#if:Oc1cc(cc(OC)c1O)c3[o+]c2cc(O)cc(O)c2cc3O\|Image 1
SMILES Oc1cc(cc(OC)c1O)c3[o+]c2cc(O)cc(O)c2cc3O
InChI InChI=1S/C16H12O7/c1-22-14-3-7(2-11(19)15(14)21)16-12(20)6-9-10(18)4-8(17)5-13(9)23-16/h2-6H,1H3,(H4-,17,18,19,20,21)/p+1^Y Key: AFOLOMGWVXKIQL-UHFFFAOYSA-O^Y InChI=1/C16H12O7/c1-22-14-3-7(2-11(19)15(14)21)16-12(20)6-9-10(18)4-8(17)5-13(9)23-16/h2-6H,1H3,(H4-,17,18,19,20,21)/p+1 Key: AFOLOMGWVXKIQL-IKLDFBCSAS
Properties
Molecular formula	C₁₆H₁₃O₇⁺ (Cl^-)
Molar mass	317.27 g/mol
N (verify) (what is: Y/N?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
Infobox references

Petunidin (Pt) is an O-methylated anthocyanidin. It is a natural organic compound and a particular type of anthocyanidin. It is a dark-red or purple water-soluble pigment found in many redberries including chokeberries (Aronia sp), Saskatoon berries (Amelanchier alnifolia) or different species of grape (for instance Vitis vinifera, or muscadine, Vitis rotundifolia), and also part of the pigments responsible for the petal colors in many flowers. The name of the molecule itself is derived from the word Petunia.

Biosynthesis

Petunidin could form in the exocarp of fruits from delphinidin, with an anthocyanin flavonoid O-methyltransferase (Catechol-O-methyl transferase) catalyzing the B-ring methylation and S-Adenosyl-L-methyl-3H methionine being the methyl group donor.

Glycosides

Glycoside forms of petunidin are present in grape.^[1] These include :

petunidine-3-O-glucoside
Petunidin-3-O-(6-p-coumaroyl) glucoside
Petunidin-3-O-(6-p-acetyl) glucoside
Petunidin-3-O-galactoside
Petunidin-3-rutinoside

The bark of Commiphora angolensis contains petunidin-3-rhamnoglucoside.^[2]

Uses

Petunidin is referred as E165f, E163 and following numbers corresponding to anthocyanins in the food coloring E number list.

References

↑ http://www.food-info.net/uk/colour/anthocyanin.htm
↑ Chemical study of bark from Commiphora angolensis Engl. Cardoso Do Vale, J., Bol Escola Farm Univ Coimbra Edicao Cient, 1962, volume 3, page 128 (abstract)

v t e Anthocyanidins and their anthocyanin glucosides

3-hydroxyanthocyanidins	5-Desoxy-peonidin Aurantinidin Cyanidin 6-Hydroxycyanidin Delphinidin Fisetinidin Guibourtinidin Pelargonidin Robinetinidin

3-deoxyanthocyanidins	Apigeninidin Columnidin Diosmetinidin Gesneridin Luteolinidin Tricetinidin

O-methylated anthocyanidins	5-Desoxy-malvidin Capensinidin Europinidin Hirsutidin Malvidin Peonidin Petunidin Pulchellidin Rosinidin

Anthocyanins	Antirrhinin (Cyanidin-3-O-rutinoside) Callistephin (Pelargonidin 3-O-glucoside) Chrysanthemin (Cyanidin-3-O-glucoside) Malvin (Malvidin 3,5-diglucoside) Myrtillin (Delphinidin-3-O-glucoside) Oenin (Malvidin-3-O-glucoside) Peonidin-3-O-glucoside Petunidin 3,5-O-diglucoside Petunidin 3-O-arabinoside Petunidin 3-O-galactoside Petunidin-3-O-glucoside Petunidin 3-O-rhamnoside Petunidin-3-O-rutinoside Primulin (Malvidin-3-O-galactoside) Pulchellidin 3-glucoside Pulchellidin 3-rhamnoside Tulipanin (Delphinidin 3-O-rutinoside)

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 Cyanidin-3-O-(di-p-coumarylglucoside)-5-glucoside Delphinidin-3-O-(6-p-coumaroyl)glucoside Malvidin-3-O-(6-p-coumaroyl)glucoside Petanin (petunidin 3-[6-O-(4-O-E-p-coumaroyl-O-α-l-rhamnopyranosyl)-β-d-glucopyranoside]-5-O-β-d-glucopyranoside) 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 Gentiodelphin (delphinidin 3-O-glucosyl-5-O-(6-O-caffeoyl-glucosyl)-3′-O-(6-O-caffeoyl-glucoside))

p-hydroxybenzoylated anthocyanins	Violdelphin

Flavanol-anthocyanin adducts	Malvidin glucoside-ethyl-catechin

Misc.	Metalloanthocyanins (Commelinin Cyanosalvianin Protocyanin Protodelphin) Pyranoanthocyanins Copigmentation

This article is issued from Wikipedia. The text is available under the Creative Commons Attribution/Share Alike; additional terms may apply for the media files.

Petunidin

Biosynthesis

Glycosides

Uses

See also

References