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:

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-hydroxyxantone

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

norathyriol

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

Refernces

Synthesis of new glycosylated flavonoids with inhibitory activity on cell growth

10.3390/molecules23051093

The research focuses on the synthesis and biological evaluation of new glycosylated flavonoids and xanthones with inhibitory activity on cell growth. The study involves the synthesis of four flavonoids (compounds 5, 6, 9, and 10) and one xanthone (compound 7) containing acetoglycoside moieties. Key chemicals used in the synthesis include rutin, diosmin, mangiferin, and 3,4-dihydroxyflavone as starting materials. Acetic anhydride and microwave irradiation were employed for acetylation, while 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide was used as the glucose donor for glycosylation. The synthesized compounds were evaluated for their in vitro cell growth inhibitory activity against six human tumor cell lines, including A375-C5, MCF-7, NCI-H460, U251, U373, and U87MG. The results showed that compound 10 exhibited the most potent inhibitory activity across all tested cell lines, with GI50 values < 8 μM and notable selectivity for cancer cells. The study highlights the importance of both acetylation and glycosylation in enhancing the biological activity of these compounds, providing insights for future development of more effective antitumor agents.

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