Pelargonin
Pelargonin
Names
IUPAC name
7-Hydroxy-2-(4-hydroxyphenyl)-3,5-bis{[(2S ,3R ,4S ,5S ,6R )-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1λ4 -benzopyran-1-ylium
Other names
Pelargonidin 3,5-di-β-D -glucoside
Identifiers
ChEBI
ChemSpider
ECHA InfoCard
100.037.584
KEGG
UNII
InChI=1S/C27H30O15/c28-8-17-19(32)21(34)23(36)26(41-17)39-15-6-12(31)5-14-13(15)7-16(25(38-14)10-1-3-11(30)4-2-10)40-27-24(37)22(35)20(33)18(9-29)42-27/h1-7,17-24,26-29,32-37H,8-9H2,(H-,30,31)/p+1/t17-,18-,19-,20-,21+,22+,23-,24-,26-,27-/m1/s1
Key: SLCKJKWFULXZBD-ZOTFFYTFSA-O
InChI=1/C27H30O15/c28-8-17-19(32)21(34)23(36)26(41-17)39-15-6-12(31)5-14-13(15)7-16(25(38-14)10-1-3-11(30)4-2-10)40-27-24(37)22(35)20(33)18(9-29)42-27/h1-7,17-24,26-29,32-37H,8-9H2,(H-,30,31)/p+1/t17-,18-,19-,20-,21+,22+,23-,24-,26-,27-/m1/s1
Key: SLCKJKWFULXZBD-OJOSBQBKBL
c1cc(ccc1c2c(cc3c([o+]2)cc(cc3O[C@H]4[C@@H]([C@H]([C@@H]([C@H](O4)CO)O)O)O)O)O[C@H]5[C@@H]([C@H]([C@@H]([C@H](O5)CO)O)O)O)O
Properties
C27 H31 O15 +
Molar mass
595.53 g/mol
Except where otherwise noted, data are given for materials in their
standard state (at 25 °C [77 °F], 100 kPa).
Chemical compound
Pelargonin is an anthocyanin . It is the 3,5-O -diglucoside of pelargonidin .
Natural occurrences
Pelargonin is a pigment, found in barberries ,[1] the petals of the scarlet pelargonium flower[2] pomegranates ,[3] and red wine .[4]
See also
References
^ Duke, James (1992). "Berberis vulgaris (Berberidaceae), United States Department of Agriculture, National Agricultural Library: Dr. Duke's Phytochemical and Ethnobotanical Databases" . phytochem.nal.usda.gov .
^ Saunders Currey, Geoffrey (1922). "The Colouring Matter of the Scarlet Pelargonium" . J. Chem. Soc., Trans . 121 : 319–323. doi :10.1039/CT9222100319 .
^ Gil, M.I.; Cherif, J.; Ayed, N.; Artes, F.; Tomasbarberan, F.A. (1995). "Influence of Cultivar, Maturity Stage and Geographical Location on the Juice Pigmentation of Tunisian Pomegranates". Zeitschrift für Lebensmittel-Untersuchung und Forschung . 201 (4): 361–364. doi :10.1007/BF01192733 . S2CID 95566626 .
^ He, Fei; Liang, Na-Na; Mu, Lin; Pan, Qiu-Hong; Wang, Jun; Reeves, Michael J.; Duan, Chang-Qing (February 2012). "Anthocyanins and Their Variation in Red Wines I. Monomeric Anthocyanins and Their Color Expression" . Molecules . 17 (2): 1571–1601. CiteSeerX 10.1.1.399.2775 . doi :10.3390/molecules17021571 . PMC 6268338 . PMID 22314380 .
External links
3-Hydroxyanthocyanidins 3-Deoxyanthocyanidins O -Methylated anthocyanidinsAnthocyanins (anthocyaninidin glycosides)Glucosides:
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 -) 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)-β-D -glucosyl)oxybenzoyl)-β-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
Miscellaneous
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