Cyanidin-3,5-O-diglucoside

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Cyanin
Cyanin.PNG
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 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 220-034-1
KEGG
PubChem CID
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).

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

Contents

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

Related Research Articles

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<span class="mw-page-title-main">Cyanidin</span> Anthocyanidin pigment in flowering plant petals and fruits

Cyanidin is a natural organic compound. It is a particular type of anthocyanidin. It is a pigment found in many red berries including grapes, bilberry, blackberry, blueberry, cherry, chokeberry, cranberry, elderberry, hawthorn, loganberry, açai berry and raspberry. It can also be found in other fruits such as apples and plums, and in red cabbage and red onion. It has a characteristic reddish-purple color, though this can change with pH; solutions of the compound are red at pH < 3, violet at pH 7-8, and blue at pH > 11. In certain fruits, the highest concentrations of cyanidin are found in the seeds and skin. Cyanidin has been found to be a potent sirtuin 6 (SIRT6) activator.

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Cyanin may refer to:

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Antirrhinin is an anthocyanin. It is the 3-rutinoside of cyanidin.

<span class="mw-page-title-main">Chrysanthemin</span> Chemical compound

Chrysanthemin is an anthocyanin. It is the 3-glucoside of cyanidin.

The pyranoanthocyanins are a type of pyranoflavonoids. They are chemical compounds formed in red wines by yeast during fermentation processes or during controlled oxygenation processes during the aging of wine. The different classes of pyranoanthocyanins are carboxypyranoanthocyanins, methylpyranoanthocyanins, pyranoanthocyanin-flavanols, pyranoanthocyanin-phenols, portisins, oxovitisins and pyranoanthocyanin dimers; their general structure includes an additional ring that may have different substituents linked directly at C-10.

<span class="mw-page-title-main">Naturally occurring phenols</span> Group of chemical compounds

In biochemistry, naturally occurring phenols are natural products containing at least one phenol functional group. Phenolic compounds are produced by plants and microorganisms. Organisms sometimes synthesize phenolic compounds in response to ecological pressures such as pathogen and insect attack, UV radiation and wounding. As they are present in food consumed in human diets and in plants used in traditional medicine of several cultures, their role in human health and disease is a subject of research. Some phenols are germicidal and are used in formulating disinfectants.

<i>p</i>-Coumaroylated anthocyanin

p-Coumaroylated anthocyanins are a type of anthocyanins with a p-coumaric acid unit linked with a sugar to an anthocyanidin aglycone. 3-(6-p-Coumaroyl)glucosides are found in grape and wine. Cyanidin-3-O-(di-p-coumarylglucoside)-5-glucoside is found in dark opal basil. Red leaves of Perilla frutescens also accumulate cyanidin 3-(6-O-p-coumaroyl-β-D-glucoside)-5-(6-O-malonyl-β-D-glucoside).

Anthocyanin 5-O-glucosyltransferase is an enzyme that forms anthocyanin 3,5-O-diglucoside from anthocyanin 3-O-glucoside.

<span class="mw-page-title-main">Callistephin</span> Chemical compound

Callistephin is an anthocyanin. It is the 3-O-glucoside of pelargonidin.

<span class="mw-page-title-main">Pelargonin</span> Chemical compound

Pelargonin is an anthocyanin. It is the 3,5-O-diglucoside of pelargonidin.

<span class="mw-page-title-main">Ideain</span> Chemical compound

Ideain, the cyanidin 3-O-galactoside, is an anthocyanin, a type of plant pigment.

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