Cyanin
Names
IUPAC name
3,5-Bis(β-D -glucopyranosyloxy)-3′,4′,7-trihydroxyflavylium
Systematic IUPAC name
2-(3,4-Dihydroxyphenyl)-7-hydroxy-3,5-bis{[(2S ,3R ,4S ,5S ,6R )-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1λ4 -benzopyran-1-ylium
Other names
Cyanidin 3,5-O -diglucoside
Identifiers
1417221
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.018.214
EC Number
KEGG
UNII
InChI=1S/C27H30O16/c28-7-17-19(33)21(35)23(37)26(42-17)40-15-5-10(30)4-14-11(15)6-16(25(39-14)9-1-2-12(31)13(32)3-9)41-27-24(38)22(36)20(34)18(8-29)43-27/h1-6,17-24,26-29,33-38H,7-8H2,(H2-,30,31,32)/p+1/t17-,18-,19-,20-,21+,22+,23-,24-,26-,27-/m1/s1
Key: RDFLLVCQYHQOBU-ZOTFFYTFSA-O
c1cc(c(cc1c2c(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)O
Properties
C27 H31 O16
Molar mass
611.52 g/mol (chloride 647 g/mol)
Except where otherwise noted, data are given for materials in their
standard state (at 25 °C [77 °F], 100 kPa).
Chemical compound
Cyanidin-3,5-O -diglucoside , also known as cyanin , is an anthocyanin . It is the 3,5-O -diglucoside of cyanidin .
Natural occurrences
Cyanin can be found in species of the genus Rhaponticum [1]
In food
Cyanin can be found in red wine as well as pomegranate juice according to a study done by Graça Miguel, Susana Dandlen, Dulce Antunes, Alcinda Neves, and Denise Martins in the winter of 2004. Pomegranate juice extracted through centrifugal seed separation has higher amounts of cyanidin-3,5-O -diglucoside than juice extracted by squeezing fruit halves with an electric lemon squeezer .[2]
Anthocyanidins and their anthocyanin glucosides
3-Hydroxyanthocyanidins 3-Deoxyanthocyanidins O -Methylated anthocyanidinsAnthocyanins 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 anthocyaninscis - 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
