Myrtillin

Names
IUPAC name (2S,3R,4S,5S,6R)-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-β-D-glucoside
Identifiers
CAS Number	6906-38-3 Y
3D model (JSmol)	Interactive image
ChEBI	CHEBI:31463 N
ChemSpider	391783 N
KEGG	C12138 Y
PubChem CID	165558
UNII	474A9U89JS Y
CompTox Dashboard (EPA)	DTXSID901028800
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
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 black beans, blackcurrant, blueberry, huckleberry, bilberry leaves^[1][2] and in various myrtles, roselle plants, and Centella asiatica plant.^{[citation needed]} It is also present in yeast and oatmeal.^{[citation needed]} The sumac fruit's pericarp owes its dark red colour to anthocyanin pigments, of which chrysanthemin, myrtillin and delphinidin have yet been identified.^{[3][unreliable source?]}

The various colors, such as red, mauve, purple, violet, and blue in Hydrangea macrophylla are developed from myrtillin complexes with metal ions called metalloanthocyanins.^[4]

Metabolism

The enzyme anthocyanin 3-O-glucoside 6''-O-hydroxycinnamoyltransferase produces delphinidin 3-(6-p-coumaroyl)glucoside from myrtillin and p-coumaroyl-CoA in the anthocyanin biosynthesis pathway.^[5]

References