Mangiferin

Base Information

• Chemical Name: Mangiferin
• CAS No.: 4773-96-0
• Deprecated CAS: 99331-60-9
• Molecular Formula: C19H18O11
• Molecular Weight: 422.345
• Hs Code.: 29389090
• European Community (EC) Number: 624-757-7
• UNII: 1M84LD0UMD
• ChEMBL ID: CHEMBL464825
• DSSTox Substance ID: DTXSID60197263
• Metabolomics Workbench ID: 53275
• Nikkaji Number: J15.735J
• Wikidata: Q1074417
• Wikipedia: Mangiferin
• Mol file: 4773-96-0.mol

Synonyms:2-beta-D-glucopyranosyl-1,3,6,7-tetrahydroxy-9H-xanthen-9-one;9H-xanthen-9-one, 2-beta-D-glucopyranosyl-1,3,6,7-tetrahydroxy-;alpizarin;chinonin;mangiferin

Chemical Property of Mangiferin

Chemical Property:

• Appearance/Colour: Light yellow powder
• Vapor Pressure: 3.67E-30mmHg at 25°C
• Melting Point: 269-270°C
• Refractive Index: 1.788
• Boiling Point: 842.7 °C at 760 mmHg
• PKA: 6.09±0.20(Predicted)
• Flash Point: 303.6 °C
• PSA: 201.28000
• Density: 1.843 g/cm³
• LogP: -0.71650
• Storage Temp.: 2-8°C
• Solubility.: DMSO (Slightly, Sonicated), Methanol (Slightly), Pyridine (Slightly, Heated)
• XLogP3: -0.4
• Hydrogen Bond Donor Count: 8
• Hydrogen Bond Acceptor Count: 11
• Rotatable Bond Count: 2
• Exact Mass: 422.08491139
• Heavy Atom Count: 30
• Complexity: 646

Purity/Quality:

99% ^*data from raw suppliers

Mangiferin ^*data from reagent suppliers

Safty Information:

• Pictogram(s): T+,N
• Hazard Codes: T+,Xi,Xn
• Statements: 28-36/37/38-22
• Safety Statements: 22-28-36/37-45-36-26-24/25

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1=C2C(=CC(=C1O)O)OC3=C(C2=O)C(=C(C(=C3)O)C4C(C(C(C(O4)CO)O)O)O)O
• Isomeric SMILES: C1=C2C(=CC(=C1O)O)OC3=C(C2=O)C(=C(C(=C3)O)[C@H]4[C@@H]([C@H]([C@@H]([C@H](O4)CO)O)O)O)O
• Uses: MAO inhibitor, immunostimulant Mangiferin is a xanthonoid, a chemical compound found in mangoes and in Anemarrhena asphodeloides rhizomes. Mangiferin has effect of hepatinica and choleretic, and is used to therapy hepatitis. Mangif erin is an anti-inflammatory, antivirotic, central nervous system inhibit function and immunologic suppression. Mangiferin has curative effect on chronic bronchitis. Mangiferin has cytotoxicity effec t on hepatocellular carcinoma ce1l, and may induce apoptosis. Mangiferin has the effect of antioxidation and delaying caducity. Mangiferin is a xanthonoid, a chemical compound found in mangoes and in Anemarrhena asphodeloides rhizomes. Mangiferin has effect of hepatinica and choleretic, and is used to therapy hepatitis. Mangiferin is an anti-inflammatory, antivirotic, central nervous system inhibit function and immunologic suppression. Mangiferin has curative effect on chronic bronchitis. Mangiferin has cytotoxicity effect on hepatocellularcarcinoma ce1l, and may induce apoptosis. Mangiferin has the effect of antioxidation and delaying caducity.

Technology Process of Mangiferin

There total 29 articles about Mangiferin 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: 94.0%

2-C-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)-6-methoxy-1,3,7-trihydroxyxanthone (1239694-50-8) → mangiferin (4773-96-0)

Guidance literature:

With boron tribromide; In dichloromethane; at 0 - 20 ℃;

DOI:10.1021/jo100776q

Reference yield: 90.0%

1,6,7-trihydroxy-2-C-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)-3-O-benzylxanthone → mangiferin (4773-96-0)

Guidance literature:

With 10% palladium hydroxide on charcoal; hydrogen; In methanol; at 20 ℃; for 48h; under 760.051 Torr;

DOI:10.1039/c6ob01622g

Reference yield:

2,3,4,6-Tetra-O-benzyl-D-glucopyranose (4291-69-4,6386-24-9,6564-72-3,59531-24-7,69257-52-9,78184-89-1,78609-16-2,78609-17-3,78609-18-4,96553-53-6,104111-61-7,131347-08-5,4132-28-9) → mangiferin (4773-96-0)

Guidance literature:

Multi-step reaction with 10 steps

1.1: pyridine / 12 h / 20 °C

2.1: trimethylsilyl trifluoromethanesulfonate / dichloromethane; tetrahydrofuran / 1 h / 0 °C / Inert atmosphere

3.1: trichlorophosphate / 16 h / 20 °C / Inert atmosphere

4.1: n-butyllithium / tetrahydrofuran / 1 h / -40 °C / Inert atmosphere

4.2: 1 h / -40 °C / Inert atmosphere

5.1: manganese(IV) oxide / dichloromethane / 36 h

6.1: toluene-4-sulfonic acid / methanol / 0.5 h / 80 °C

7.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 2 h / 0 °C

8.1: caesium carbonate / methanol / 12 h / 80 °C

9.1: toluene-4-sulfonic acid / methanol / 0.5 h / 80 °C

10.1: 10% palladium hydroxide on charcoal; hydrogen / methanol / 48 h / 20 °C / 760.05 Torr

With pyridine; manganese(IV) oxide; n-butyllithium; trimethylsilyl trifluoromethanesulfonate; 10% palladium hydroxide on charcoal; hydrogen; caesium carbonate; toluene-4-sulfonic acid; N-ethyl-N,N-diisopropylamine; trichlorophosphate; In tetrahydrofuran; methanol; dichloromethane; 3.1: |Vilsmeier-Haack Formylation;

DOI:10.1039/c6ob01622g

upstream raw materials:

3-glucosyl-2,3′,4,4′,6-pentahydroxybenzophenone

mangiferin-6’-O-gallate

maclurin 3-C-(6''-O-p-hydroxybenzoyl)-β-D-glucoside

maclurin 3-C-(2''-O-p-hydroxybenzoyl-6''-O-galloyl)-β-D-glucoside

Downstream raw materials:

1,3,6-tri-O-benzyl-2-C-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-7-O-acetylxanthone

1,3,6-tri-O-benzyl-2-C-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-7-hydroxyxantone

1,6,7-trihydroxy-3-methoxylxanthone-2-C-β-D-glucopyranoside

norathyriol

Refernces

• 1、 Ferreira, Fabricia Da Rocha,Da Silva, Emanuella Gomes,De Leo, Lucila P. Méndez,Calvo, Ernesto J.,Bento, Edson De Souza,Goulart, Marília Oliveira Fonseca,De Abreu, Fabiane Caxico. "Electrochemical investigations into host-guest interactions of a natural antioxidant compound with β-cyclodextrin". . p. 797 - 803. Retrieved 2010.
• 2、 Chen, Dawei,Chen, Ridao,Wang, Ruishan,Li, Jianhua,Xie, Kebo,Bian, Chuancai,Sun, Lili,Zhang, Xiaolin,Liu, Jimei,Yang, Lin,Ye, Fei,Yu, Xiaoming,Dai, Jungui. "Probing the catalytic promiscuity of a regio- and stereospecific C-glycosyltransferase from Mangifera indica". . p. 12678 - 12682. Retrieved 2015/10/28.