Myrtillin

Myrtillin

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Names
IUPAC name (2''S'',3''R'',4''S'',5''S'',6''R'')-2-[5,7-dihydroxy-2-(3,4,5-trihydroxyphenyl)chromenylium-3-yl]oxy-6-(hydroxymethyl)oxane-3,4,5-triol chloride
Other names Mirtillin Myrtillin chloride Delphinidin 3-glucoside Delphinidol 3-glucoside Delphinidin 3-O-glucoside Delphinidin 3-monoglucoside Delphinidine 3-monoglucoside Delphinidin-3-glucoside chloride Delphinidin 3-O-beta-D-glucoside
Identifiers
CAS Number	6906-38-3 Y 26770-35-4 N
ChEBI	CHEBI:31463 N
ChemSpider	391783 N
Jmol 3D model	Interactive image
PubChem	165558
InChI InChI=1S/C21H20O12/c22-6-15-17(28)18(29)19(30)21(33-15)32-14-5-9-10(24)3-8(23)4-13(9)31-20(14)7-1-11(25)16(27)12(26)2-7/h1-5,15,17-19,21-22,28-30H,6H2,(H4-,23,24,25,26,27)/p+1/t15-,17-,18+,19-,21-/m1/s1 N Key: XENHPQQLDPAYIJ-PEVLUNPASA-O N
SMILES C1=C(C=C(C(=C1O)O)O)C2=C(C=C3C(=CC(=CC3=[O+]2)O)O)OC4C(C(C(C(O4)CO)O)O)O.[Cl-]
Properties
Chemical formula	C21H21ClO12 C21H21O12+, Cl−
Molar mass	500.83 g/mol (chloride) 465.38 g/mol
Vapor pressure	{{{value}}}
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

Myrtillin is an anthocyanin. It is the 3-glucoside of delphinidin. It can be found in all green plants, most abundantly in blackcurrant, in blueberry or huckleberry leaves and various myrtles, in the roselle plant, in the Centella asiatica plant (Hydrocotyle asiatica) and in the bilberry leaf. It is also present in yeast and oatmeal. The sumac fruits pericarp owes its dark red colour to anthocyanin pigments, of which chrysanthemin, myrtillin and delphinidin have yet been identified.

The various colors, such as red, mauve, purple, violet and blue in, Hydrangea macrophylla are developed from delphinidin 3-glucoside foming complexes with metal ions called metalloanthocyanins.

Health effects

Myrtillin tends to stabilize the blood sugar, which otherwise fluctuates widely, and that it spares insulin.

Metabolism

The enzyme anthocyanin 3-O-glucoside 6''-O-hydroxycinnamoyltransferase produces delphinidin 3-(6-p-coumaroyl)glucoside from delphinidin 3-O-glucoside and p-coumaroyl-CoA in the anthocyanin biosynthesis pathway.