Myrtillin

Base Information

• Chemical Name: Myrtillin
• CAS No.: 6906-38-3
• Deprecated CAS: 1329-23-3,100432-93-7
• Molecular Formula: C₂₁H₂₁O₁₂*Cl
• Molecular Weight: 500.844
• European Community (EC) Number: 805-222-9
• UNII: 474A9U89JS
• DSSTox Substance ID: DTXSID901028800
• Wikipedia: Myrtillin
• Wikidata: Q945655
• Mol file: 6906-38-3.mol

Synonyms:delphinidin 3-O-beta-D-glucopyranoside;delphinidin 3-O-beta-glucoside;delphinidin 3-O-glucopyranoside;delphinidin-3-glucoside;myrtillin

Chemical Property of Myrtillin

Chemical Property:

• PSA: 213.67000
• LogP: -2.90840
• Storage Temp.: ?20°C
• Hydrogen Bond Donor Count: 9
• Hydrogen Bond Acceptor Count: 12
• Rotatable Bond Count: 4
• Exact Mass: 500.0721538
• Heavy Atom Count: 34
• Complexity: 641

Purity/Quality:

99%, ^*data from raw suppliers

Delphinidin 3-glucoside chloride ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=C(C=C(C(=C1O)O)O)C2=[O+]C3=CC(=CC(=C3C=C2OC4C(C(C(C(O4)CO)O)O)O)O)O.[Cl-]
• Isomeric SMILES: C1=C(C=C(C(=C1O)O)O)C2=[O+]C3=CC(=CC(=C3C=C2O[C@H]4[C@@H]([C@H]([C@@H]([C@H](O4)CO)O)O)O)O)O.[Cl-]
• Uses: A metabolite of Delphinidin. A constituent of blue honeysuckle Myrtillin is a natural anthocyanin found in plants. It is the 3-glucoside of delphinidin. Anthocyanins, including myrtillin, are potent antioxidants. A metabolite of Delphinidin. A constituent of blue honeysuckle as to novel source for phenolic antioxidants. Antimicrobial.

Technology Process of Myrtillin

There total 2 articles about Myrtillin which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

C29H29O16(1+)*Cl(1-) → myrtillin (6906-38-3,26770-35-4,68852-84-6)

Guidance literature:

C₂₉H₂₉O₁₆⁽¹⁺⁾*Cl^(1-); With methanol; sodium hydroxide; water; Acidic conditions;

With hydrogenchloride;

Reference yield:

2-formyl-3,5-dihydroxyphenyl benzoate (32292-78-7) → myrtillin (6906-38-3,26770-35-4,68852-84-6)

Guidance literature:

With ethyl acetate; Einleiten von Chlorwasserstoff, Behandlung des Reaktionsprodukts mit Bariumhydroxid in Methanol und anschliessend Umsetzung mit Pikrinsaeure;

DOI:10.1039/jr9340001039

Reference yield: 4.3%

myrtillin (6906-38-3,26770-35-4,68852-84-6) + castalagin (24312-00-3) → 1-deoxyvescalagin-(1β→8)-myrtillin (1487430-09-0) + 1-deoxyvescalagin-(1β→6)-myrtillin (1496637-18-3)

Guidance literature:

With trifluoroacetic acid; In tetrahydrofuran; at 60 ℃; for 24h; regioselective reaction;

DOI:10.1021/jf4033188

upstream raw materials:

2-formyl-3,5-dihydroxyphenyl benzoate

Downstream raw materials:

3,4,5-trihydroxybenzoic acid

2,4,6-trihydroxybenzaldehyde

C₂₂H₂₃O₁₂⁽¹⁺⁾

C₂₇H₂₉O₁₈⁽¹⁺⁾

Refernces