Pelargonidin

Pelargonidin
Names

IUPAC name 2-(4-Hydroxyphenyl)chromenylium-3,5,7-triol
Identifiers
CAS Number	134-04-3^Y
3D model (Jmol)	Interactive image
ChEBI	CHEBI:25863^N
ChEMBL	ChEMBL1197905^N
ChemSpider	389676^N
KEGG	C05904^N
PubChem	440832
InChI 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
SMILES C1=CC(=CC=C1C2=C(C=C3C(=CC(=CC3=[O+]2)O)O)O)O
Properties
Chemical formula	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).
N verify (what is ^YN ?)
Infobox references

Pelargonidin is an anthocyanidin, a type of plant pigment. Like all anthocyanins, it is an antioxidant. It produces a characteristic orange color.

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.

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^[1] and chokeberries. It is also found in plums and pomegranates.

It is present in large amounts in kidney beans.^[2]

Glycosides

Pelargonidin 3-glucoside.

Pelargonidin-3-O-glucoside (callistephin) can be found in strawberries.^[3]

Acylated pelargonidin glycosides can be found in red-purple flowers of Ipomoea purpurea.^[4]

External links

Wikimedia Commons has media related to Pelargonidin.

It:Pelargonidin:ChemWiki

References

↑ Mazza, G. (2005). "Compositional and Functional Properties of Saskatoon Berry and Blueberry". International Journal of Fruit Science. 5 (3): 101. doi:10.1300/J492v05n03_10.
↑ Lin, Long-Ze; Harnly, James M.; Pastor-Corrales, Marcial S.; Luthria, Devanand L. (2008). "The polyphenolic profiles of common bean (Phaseolus vulgaris L.)". Food Chemistry. 107: 399. doi:10.1016/j.foodchem.2007.08.038.
↑ Mullen, William; Edwards, Christine A.; Serafini, Mauro; Crozier, Alan (2008). "Bioavailability of Pelargonidin-3-O-glucoside and Its Metabolites in Humans Following the Ingestion of Strawberries with and without Cream". Journal of Agricultural and Food Chemistry. 56 (3): 713–9. doi:10.1021/jf072000p. PMID 18211024.
↑ Saito, N; Tatsuzawa, F; Yokoi, M; Kasahara, K; Iida, S; Shigihara, A; Honda, T (1996). "Acylated pelargonidin glycosides in red-purple flowers of Ipomoea purpurea". Phytochemistry. 43 (6): 1365–70. doi:10.1016/s0031-9422(96)00501-8. PMID 8987912.

Anthocyanidins and their anthocyanin glucosides

3-hydroxyanthocyanidins

3-deoxyanthocyanidins

O-methylated anthocyanidins

Anthocyanins
(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)-beta-D-glucosyl)oxybenzoyl)-beta-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

Misc.

Metalloanthocyanins (Commelinin
Cyanosalvianin
Protocyanin
Protodelphin)
Pyranoanthocyanins
Copigmentation
Anthocyanone A (degradation product of oenin)
Malvone (oxidation product of malvin)

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