Pelargonidin

Pelargonidin
Names
	IUPAC name 3,4′,5,7-Tetrahydroxyflavylium
	Systematic IUPAC name 3,5,7-Trihydroxy-2-(4-hydroxyphenyl)-1λ4-benzopyran-4-ylium
Identifiers
CAS Number	134-04-3 ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:25863 ;
ChEMBL	ChEMBL1197905 ;
ChemSpider	389676 ;
KEGG	C05904 ;
PubChem CID	440832;
UNII	DFL6200791 ;
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

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. 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]

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]

References

^ US 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
^ Huihua, Wan; Chao, Yu; Yu, Han; Xuelian, Guo (2019). "Determination of Flavonoids and Carotenoids and Their Contributions to Various Colors of Rose Cultivars (Rosa spp.)". Frontiers in Plant Science. 10: 123. doi:10.3389/fpls.2019.00123. PMC 6379320. PMID 30809238.
^ Mazza, G. (2005). "Compositional and Functional Properties of Saskatoon Berry and Blueberry". International Journal of Fruit Science. 5 (3): 101–120. doi:10.1300/J492v05n03_10. S2CID 85691882.
^ 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 (1): 399–410. doi:10.1016/j.foodchem.2007.08.038. PMC 4276374. PMID 25544796.
^ Levisson, Mark; Patinios, Constantinios; Hein, Sascha; de Groot, Phillip A. (2018). "Engineering de novo anthocyanin production in Saccharomyces cerevisiae". Microbial Cell Factories. 17 (103): 103. doi:10.1186/s12934-018-0951-6. PMC 6029064. PMID 29970082.
^ Li, Wenfeng; Gu, Mengyuan; Gong, Pengling; Wang, Jinxia (2021). "Glycosides changed the stability and antioxidant activity of pelargonidin". Lebensmittel-Wissenschaft & Technologie. 147 (3): 111581. doi:10.1016/j.lwt.2021.111581. S2CID 235531625.
^ Gould, Kevin S. (2009). Anthocyanidins: Biosynthesis, Functions, and Applications. New York: Springer. p. 286. ISBN 978-0-387-77334-6.
^ 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.

External links

[1] US 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] Huihua, Wan; Chao, Yu; Yu, Han; Xuelian, Guo (2019). "Determination of Flavonoids and Carotenoids and Their Contributions to Various Colors of Rose Cultivars (Rosa spp.)". Frontiers in Plant Science. 10: 123. doi:10.3389/fpls.2019.00123. PMC 6379320. PMID 30809238.

[3] Mazza, G. (2005). "Compositional and Functional Properties of Saskatoon Berry and Blueberry". International Journal of Fruit Science. 5 (3): 101–120. doi:10.1300/J492v05n03_10. S2CID 85691882.

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

[5] 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 (1): 399–410. doi:10.1016/j.foodchem.2007.08.038. PMC 4276374. PMID 25544796.

[6] Levisson, Mark; Patinios, Constantinios; Hein, Sascha; de Groot, Phillip A. (2018). "Engineering de novo anthocyanin production in Saccharomyces cerevisiae". Microbial Cell Factories. 17 (103): 103. doi:10.1186/s12934-018-0951-6. PMC 6029064. PMID 29970082.

[7] Li, Wenfeng; Gu, Mengyuan; Gong, Pengling; Wang, Jinxia (2021). "Glycosides changed the stability and antioxidant activity of pelargonidin". Lebensmittel-Wissenschaft & Technologie. 147 (3): 111581. doi:10.1016/j.lwt.2021.111581. S2CID 235531625.

[8] Gould, Kevin S. (2009). Anthocyanidins: Biosynthesis, Functions, and Applications. New York: Springer. p. 286. ISBN 978-0-387-77334-6.

[9] 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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