View source for Myrtillin

{{chembox
| Verifiedfields = changed
| Watchedfields = changed
| verifiedrevid = 440231978
| Name = Myrtillin
| ImageFile = Mirtillin.svg
| ImageSize = 300px
| IUPACName = (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
| OtherNames = {{bulletedlist|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-<small>D</small>-glucoside}}
|Section1={{Chembox Identifiers
| CASNo_Ref = {{cascite|correct|CAS}}
| CASNo = 6906-38-3
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = 474A9U89JS
| KEGG_Ref = {{keggcite|correct|kegg}}
| KEGG = C12138
| PubChem = 165558
| ChEBI_Ref = {{ebicite|changed|EBI}}
| ChEBI = 31463
| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}}
| ChemSpiderID = 391783
| 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-]
| StdInChI_Ref = {{stdinchicite|changed|chemspider}}
| StdInChI = 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
| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}}
| StdInChIKey = XENHPQQLDPAYIJ-PEVLUNPASA-O
}}
|Section2={{Chembox Properties
| Formula = C<sub>21</sub>H<sub>21</sub>ClO<sub>12</sub><br>C<sub>21</sub>H<sub>21</sub>O<sub>12</sub><sup>+</sup>, Cl<sup>−</sup>
| MolarMass = 500.83 g/mol (chloride)<br>465.38 g/mol
| Appearance =
| Density =
| MeltingPt =
| BoilingPt =
| Solubility =
}}
|Section3={{Chembox Hazards
| MainHazards =
| FlashPt =
| AutoignitionPt =
}}
}}
'''Myrtillin''' is an [[anthocyanin]]. It is the 3-[[glucoside]] of [[delphinidin]]. It can be found in all green plants, most abundantly in [[Black turtle bean|black beans]], [[blackcurrant]], [[blueberry]], [[huckleberry]], [[bilberry]] leaves<ref>[http://www.florahealth.com/flora/home/USA/HealthInformation/Encyclopedias/BilberryLeaf.htm Bilberry Leaf on florahealth.com] {{webarchive |url=https://web.archive.org/web/20090205123323/http://www.florahealth.com/flora/home/USA/HealthInformation/Encyclopedias/BilberryLeaf.htm |date=February 5, 2009 }}</ref><ref>Yang W, Kortesniemi M, Ma X, Zheng J, Yang B. Enzymatic acylation of blackcurrant (Ribes nigrum) anthocyanins and evaluation of lipophilic properties and antioxidant capacity of derivatives. ''Food Chem''. 2019 May 30;281:189-196. {{doi|10.1016/j.foodchem.2018.12.111}} {{PMID|30658747}}</ref> and in various [[Myrtle (plant)|myrtle]]s, [[Roselle (plant)|roselle plant]]s, and ''[[Centella asiatica]]'' plant.{{cn|date=October 2016}} It is also present in [[yeast]] and [[oatmeal]].{{cn|date=October 2016}} The [[sumac]] fruit's pericarp owes its dark red colour to anthocyanin pigments, of which chrysanthemin, myrtillin and delphinidin have yet been identified.<ref>[https://web.archive.org/web/20090819181412/http://www.spicesworld.net/sumac.php Sumac on spicesworld.net] </ref>{{Unreliable source?|date=October 2016}}
The various colors, such as red, mauve, purple, violet, and blue in ''[[Hydrangea macrophylla]]'' are developed from myrtillin complexes with metal ions called [[metalloanthocyanin]]s.<ref>{{cite journal |vauthors=Yoshida K, Mori M, Kondo T |title=Blue flower color development by anthocyanins: from chemical structure to cell physiology |journal=Nat. Prod. Rep. |volume=26 |issue=7 |pages=884–915 |year=2009 |pmid=19554240 |doi=10.1039/b800165k }}</ref>
== 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.<ref>{{cite web|url=http://www.kegg.jp/dbget-bin/www_bget?rn:R07929 |title=Delphinidin 3-(6-p-coumaroyl)glucoside synthesis reaction on www.kegg.jp |publisher=Kegg.jp |date= |accessdate=2013-04-09}}</ref>
== References ==
{{Reflist}}
{{Anthocyanins}}
[[Category:Anthocyanidins]]
[[Category:Flavonoid glucosides]]