Myrtillin

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 ; 26770-35-4 ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:31463 ;
ChemSpider	391783 ;
PubChem CID	165558;
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 Key: XENHPQQLDPAYIJ-PEVLUNPASA-O ;
	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). verify (what is ?) 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, blueberry, huckleberry, bilberry leaves^[1]^{[unreliable source?]} and in various myrtles, roselle plants, and Centella asiatica plant.^{[citation needed]} It is also present in yeast and oatmeal.^{[citation needed]} The sumac fruits pericarp owes its dark red colour to anthocyanin pigments, of which chrysanthemin, myrtillin and delphinidin have yet been identified.^[2]^{[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.^[3]

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.^[4]

References

^ Bilberry Leaf on florahealth.com Archived February 5, 2009, at the Wayback Machine
^ Sumac on spicesworld.net
^ Yoshida K, Mori M, Kondo T (2009). "Blue flower color development by anthocyanins: from chemical structure to cell physiology". Nat. Prod. Rep. 26 (7): 884–915. doi:10.1039/b800165k. PMID 19554240.
^ "Delphinidin 3-(6-p-coumaroyl)glucoside synthesis reaction on www.kegg.jp". Kegg.jp. Retrieved 2013-04-09.

[1] Bilberry Leaf on florahealth.com Archived February 5, 2009, at the Wayback Machine

[2] Sumac on spicesworld.net

[3] Yoshida K, Mori M, Kondo T (2009). "Blue flower color development by anthocyanins: from chemical structure to cell physiology". Nat. Prod. Rep. 26 (7): 884–915. doi:10.1039/b800165k. PMID 19554240.

[4] "Delphinidin 3-(6-p-coumaroyl)glucoside synthesis reaction on www.kegg.jp". Kegg.jp. Retrieved 2013-04-09.

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