Idaein

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Idaein
Structure of ideain chloride
Names
IUPAC name
(2S,4S,5R)-2-[2-(3,4-dihydroxyphenyl)-5,7-dihydroxychromenylium-3-yl]oxy-6-(hydroxymethyl)oxane-3,4,5-triol;chloride
Other names
Ideain, cyanidin 3-O-galactoside, Cy3Gal
Identifiers
3D model (JSmol)
ChemSpider
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KEGG
UNII
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  • InChI=1S/C21H20O11.ClH/c22-7-16-17(27)18(28)19(29)21(32-16)31-15-6-10-12(25)4-9(23)5-14(10)30-20(15)8-1-2-11(24)13(26)3-8;/h1-6,16-19,21-22,27-29H,7H2,(H3-,23,24,25,26);1H/t16?,17-,18-,19?,21+;/m0./s1
    Key: YTMNONATNXDQJF-DJBUQWCWSA-N
  • C1=CC(=C(C=C1C2=C(C=C3C(=CC(=CC3=[O+]2)O)O)OC4C(C(C(C(O4)CO)O)O)O)O)O.[Cl-]
Properties
C21H21ClO11 (chloride), C21H21O11+ (cation)
Molar mass 484.83 g/mol (chloride), 449.38 g/mol (cation)
UV-vis (λmax) 528 nm (in methanol)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Idaein, also known as ideain, cyanidin 3-O-galactoside, or Cy3Gal, is a type of anthocyanin, a class of plant pigment compounds.

Natural occurrences

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Idaein is the main anthocyanin compound in lingonberries (Vaccinium vitis-idaea),[1][2] and the name of the compound is derived from the Latin name of the plant.[1][3] It is also present as one of the many anthocyanins compounds found in bilberries (Vaccinium myrtillus)[4] and cranberries (Vaccinium macrocarpon).[5]

Idaein is the main anthocyanin in red-skinned or red-fleshed (for example Weirouge[6] or Surprise) apple varieties.[7][8][9] It is also found in Chinese hawthorn fruits (Crataegus spp.).[10] It is also the pigment in the copper beech (cultivar of Fagus sylvatica), that was identified in 1932.[11]

Quintinia serrata, the tawheowheo, a species of evergreen trees endemic to New Zealand, has different patterns of anthocyanins (cyanidin 3-O-glucoside and cyanidin 3-O-galactoside) in its leaves to protect the shade-adapted chloroplasts from direct sunlight.[12]

References

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