Petunidin

Summary

Petunidin (Pt), like Europinidin and Malvidin, is derived from Delphinidin and is an O-methylated anthocyanidin of the 3-hydroxy type. It is a natural organic compound, a dark-red or purple water-soluble pigment found in many red berries 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. This pigment gives the Indigo Rose tomatoes the majority of their deep purple color when the fruits are exposed to sunlight.[1] The name of the molecule itself is derived from the word Petunia.

Petunidin
Names
IUPAC name
3,3′,4′,5,7-Pentahydroxy-5′-methoxyflavylium
Systematic IUPAC name
2-(3,4-Dihydroxy-5-methoxyphenyl)-3,5,7-trihydroxy-1λ4-benzopyran-1-ylium
Other names
Petunidine; Petunidin chloride;
Petunidol; Myrtillidin
Identifiers
  • 1429-30-7 checkY
3D model (JSmol)
  • Interactive image
ChEBI
  • CHEBI:75318 ☒N
ChemSpider
  • 390371 checkY
ECHA InfoCard 100.014.409 Edit this at Wikidata
KEGG
  • C08727 checkY
  • 441774
UNII
  • WRK4Q8K2D8 checkY
  • DTXSID90931677 Edit this at Wikidata
  • 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 checkY
    Key: AFOLOMGWVXKIQL-UHFFFAOYSA-O checkY
  • 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
  • Oc1cc2c(O)cc(O)cc2[o+]c1c3cc(O)c(O)c(OC)c3
Properties
C16H13O7+ (Cl)
Molar mass 317.27 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

Biosynthesis edit

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 edit

Glycoside forms of petunidin are present in grape.[2] These include :

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

Uses edit

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

See also edit

References edit

  1. ^ "The Purple Tomato FAQ". 2 May 2012.
  2. ^ "Food-Info.net : Anthocyanins and anthocyanidins".
  3. ^ 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)