Pelargonidin: Difference between revisions

Pelargonidin
Names
	IUPAC name 2-(4-Hydroxyphenyl)chromenylium-3,5,7-triol
Identifiers
CAS Number	134-04-3 ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:25863 ;
ChEMBL	ChEMBL1197905 ;
ChemSpider	389676 ;
KEGG	C05904 ;
PubChem CID	440832;
CompTox Dashboard (EPA)	DTXSID40861793 ;
	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 Key: XVFMGWDSJLBXDZ-UHFFFAOYSA-O ; 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). verify (what is ?) Infobox references

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

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^[2] and chokeberries. It is also found in plums and pomegranates. Pelargonidin gives red radishes their color.^[3]

It is present in large amounts in kidney beans.^[4]

Glycosides

Pelargonidin-3-O-glucoside (callistephin) can be found in strawberries.^[5]

Acylated pelargonidin glycosides can be found in red-purple flowers of Ipomoea purpurea.^[6]

References

^ United States granted 6,767,999, Smirnov, Vitaly; Sidorov, Viktor; Smirnova, Valentina, "Anthocyantin coloring agent and method for the production thereof from organic matter", published Nov 01, 2001, issued July 27, 2004
^ 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.
^ Takeshi Nishio (4 October 2017). Takeshi Nishio, Hiroyasu Kitashiba (ed.). The Radish Genome. Springer. p. 4. ISBN 978-3-319-59253-4.
^ 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.

External links

It:Pelargonidin:ChemWiki

Template:Natural-phenol-stub

[1] United States granted 6,767,999, Smirnov, Vitaly; Sidorov, Viktor; Smirnova, Valentina, "Anthocyantin coloring agent and method for the production thereof from organic matter", published Nov 01, 2001, issued July 27, 2004

[2] 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.

[NishioKitashiba2017-3] Takeshi Nishio (4 October 2017). Takeshi Nishio, Hiroyasu Kitashiba (ed.). The Radish Genome. Springer. p. 4. ISBN 978-3-319-59253-4.

[4] 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.

[5] 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.

[6] 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.

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 === Presence in food ===
-Pelargonidin can be found in berries such as ripe [[Raspberry|raspberries]] and [[Strawberry|strawberries]], as well as [[Blueberry|blueberries]], [[Blackberry|blackberries]], [[Cranberry|cranberries]] but also in [[saskatoon berries]]<ref>{{Cite journal|doi=10.1300/J492v05n03_10|title=Compositional and Functional Properties of Saskatoon Berry and Blueberry|year=2005|last1=Mazza|first1=G.|journal=International Journal of Fruit Science|volume=5|issue=3|pages=101}}</ref> and [[chokeberries]]. It is also found in [[plum]]s and [[pomegranate]]s.
+Pelargonidin can be found in berries such as ripe [[Raspberry|raspberries]] and [[Strawberry|strawberries]], as well as [[Blueberry|blueberries]], [[Blackberry|blackberries]], [[Cranberry|cranberries]] but also in [[saskatoon berries]]<ref>{{Cite journal|doi=10.1300/J492v05n03_10|title=Compositional and Functional Properties of Saskatoon Berry and Blueberry|year=2005|last1=Mazza|first1=G.|journal=International Journal of Fruit Science|volume=5|issue=3|pages=101}}</ref> and [[chokeberries]]. It is also found in [[plum]]s and [[pomegranate]]s. Pelargonidin gives red [[radish|radishes]] their color.<ref name="NishioKitashiba2017">{{cite book|author=Takeshi Nishio|editor=Takeshi Nishio, Hiroyasu Kitashiba|title=The Radish Genome|url=https://books.google.com/books?id=8JQ4DwAAQBAJ&pg=PA70|date=4 October 2017|publisher=Springer|isbn=978-3-319-59253-4|page=4}}</ref>
 It is present in large amounts in [[kidney bean]]s.<ref>{{Cite journal|doi=10.1016/j.foodchem.2007.08.038|title=The polyphenolic profiles of common bean (Phaseolus vulgaris L.)|year=2008|last1=Lin|first1=Long-Ze|last2=Harnly|first2=James M.|last3=Pastor-Corrales|first3=Marcial S.|last4=Luthria|first4=Devanand L.|journal=Food Chemistry|volume=107|pages=399|url=https://naldc.nal.usda.gov/naldc/download.xhtml?id=11587&content=PDF}}</ref>