Pelargonin

Pelargonin
Chemical structure of 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
CAS Number
  • 17334-58-6 checkY
3D model (JSmol)
  • Interactive image
ChEBI
  • CHEBI:133365 checkY
ChemSpider
  • 390369
ECHA InfoCard 100.037.584 Edit this at Wikidata
KEGG
  • C08725 checkY
PubChem CID
  • 441772
UNII
  • 4OJV6238UJ checkY
CompTox Dashboard (EPA)
  • DTXSID00938359 Edit this at Wikidata
InChI
  • 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
Chemical formula
 C27H31O15+
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).
Infobox references
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

  1. ^ 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.
  2. ^ Saunders Currey, Geoffrey (1922). "The Colouring Matter of the Scarlet Pelargonium". J. Chem. Soc., Trans. 121: 319–323. doi:10.1039/CT9222100319.
  3. ^ 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.
  4. ^ 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

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Anthocyanidins and their anthocyanin glucosides
3-Hydroxyanthocyanidins3-DeoxyanthocyanidinsO-Methylated anthocyanidinsAnthocyanins
(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)-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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