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Pelargonidin

Red anthocyanidin pigment found in certain flowers and fruits From Wikipedia, the free encyclopedia

Pelargonidin

Pelargonidin is an anthocyanidin, a type of plant pigment producing a characteristic orange color used in food and industrial dyes.[1]

Quick Facts Names, Identifiers ...
Pelargonidin
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Names
IUPAC name
3,4′,5,7-Tetrahydroxyflavylium
Systematic IUPAC name
3,5,7-Trihydroxy-2-(4-hydroxyphenyl)-1λ4-benzopyran-4-ylium
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
KEGG
UNII
  • InChI=1S/C15H10O5/c16-9-3-1-8(2-4-9)15-13(19)7-11-12(18)5-10(17)6-14(11)20-15/h1-7H,(H3-,16,17,18,19)/p+1 N
    Key: XVFMGWDSJLBXDZ-UHFFFAOYSA-O N
  • InChI=1/C15H10O5/c16-9-3-1-8(2-4-9)15-13(19)7-11-12(18)5-10(17)6-14(11)20-15/h1-7H,(H3-,16,17,18,19)/p+1
    Key: XVFMGWDSJLBXDZ-IKLDFBCSAF
  • C1=CC(=CC=C1C2=C(C=C3C(=CC(=CC3=[O+]2)O)O)O)O
Properties
C15H11O5+
Molar mass 271.24 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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Natural occurrences

Presence in flowers

Pelargonidin can be found in red geraniums (Geraniaceae). It is the predominant pigment causing the red coloration in the spathes of Philodendron (Araceae). The orange-coloured flowers of blue pimpernel (Anagallis monelli, Myrsinaceae) have a higher concentration of pelargonidin pigment. Red and Pink Roses (Rosa) obtain their color from this phytochemical. [2]

Presence in food

Pelargonidin can be found in berries such as ripe raspberries and strawberries, as well as blueberries, blackberries, cranberries but also in saskatoon berries[3] and chokeberries. It is also found in plums and pomegranates. Pelargonidin gives red radishes their color.[4]

It is present in large amounts in kidney beans.[5]

Glycosides

In many plant systems, Pelargonidin can be added to a glucose molecule to form Pelargonidin 3-glucoside (callistephin). This is done by the 3GT, anthocyanin 3-O-glucosyltransferase gene. [6]

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Pelargonidin 3-glucoside.

However this glucosidation reduces its antioxidant activity,[7] and changes the wavelength of max light absorbance from 520 nm to 516 nm. [8]

Acylated pelargonidin glycosides can be found in red-purple flowers of Ipomoea purpurea.[9]

See also

References

External links

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