Cyanidin

Cyanidin is a natural organic compound. It is a particular type of anthocyanidin (glycoside version called anthocyanins). 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.

Cyanidin
Names
IUPAC name
3,3′,4′,5,7-Pentahydroxyflavylium
Systematic IUPAC name
2-(3,4-Dihydroxyphenyl)-3,5,7-trihydroxy-1λ4-benzopyran-1-ylium
Other names
Cyanidine
2-(3,4-Dihydroxyphenyl)chromenylium-3,5,7-triol
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
E number E163a (colours)
KEGG
PubChem CID
UNII
  • InChI=1S/C15H10O6/c16-8-4-11(18)9-6-13(20)15(21-14(9)5-8)7-1-2-10(17)12(19)3-7/h1-6H,(H4-,16,17,18,19,20)/p+1 Y
    Key: VEVZSMAEJFVWIL-UHFFFAOYSA-O Y
  • InChI=1/C15H10O6/c16-8-4-11(18)9-6-13(20)15(21-14(9)5-8)7-1-2-10(17)12(19)3-7/h1-6H,(H4-,16,17,18,19,20)/p+1
    Key: VEVZSMAEJFVWIL-IKLDFBCSAG
SMILES
  • C1=CC(=C(C=C1C2=C(C=C3C(=CC(=CC3=[O+]2)O)O)O)O)O
  • Oc1ccc(cc1O)c3[o+]c2cc(O)cc(O)c2cc3O
Properties
C15H11O6+
Molar mass 287.24 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N verify (what is YN ?)
Infobox references
Cyanidin (pH indicator)
below pH 3 above pH 11
3 ⇌ 11
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