Cyanidin-3,5-O-diglucoside

Cyanidin-3,5-O-diglucoside, also known as cyanin, is an anthocyanin. It is the 3,5-O-diglucoside of cyanidin.

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
3D model (JSmol)
1417221
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.018.214
EC Number
  • 220-034-1
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
C27H31O16
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).
Infobox references

Natural occurrences

Cyanin can be found in species of the genus Rhaponticum (Asteraceae).[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]

See also

References
  1. Vereskovskii, V. V.; Chekalinskaya, I. I. (July 1978). "Chrysanthemin and cyanin in species of the genus Rhaponticum". Chemistry of Natural Compounds. 14 (4): 450–451. doi:10.1007/bf00565267. S2CID 4817423.
  2. 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. doi:10.3390/molecules17021571. PMC 6268338. PMID 22314380.

Cyanidin-3,5-O-diglucoside at Phenol-Explorer.eu

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