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Mangiferin (MGF) is a natural bioactive polyphenol predominantly isolated from the Mangifera indica (Mango) tree. It has a xanthone glucoside structure and can also be found in other angiosperm plants and herbs. Mangiferin is a yellow powder and is known for its various therapeutic properties.

4773-96-0

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4773-96-0 Usage

Uses

1. Used in Pharmaceutical Applications:
Mangiferin is used as a hepatinica and choleretic agent for the therapy of hepatitis. It exhibits anti-inflammatory, antivirotic, and central nervous system inhibiting functions, as well as immunologic suppression.
2. Used in Respiratory Applications:
Mangiferin has a curative effect on chronic bronchitis, providing relief and support for respiratory health.
3. Used in Oncology:
Mangiferin has cytotoxicity effects on hepatocellular carcinoma cells and may induce apoptosis, making it a potential candidate for cancer treatment.
4. Used in Antioxidant Applications:
Mangiferin possesses antioxidant properties, which can help in delaying aging and promoting overall health.
5. Used in Neurological Applications:
Mangiferin acts as a central nervous system inhibitor, which can be beneficial for various neurological conditions.
6. Used in Immune System Applications:
As an immunostimulant, Mangiferin can help boost the immune system and improve overall immune response.
7. Used in MAO Inhibition:
Mangiferin functions as a monoamine oxidase (MAO) inhibitor, which can be useful in treating certain psychiatric and neurological disorders.

Biochem/physiol Actions

Mangiferin has various pharmacological properties including antioxidant, anti-diabetic, anti-bacterial, cardioprotective, neuroprotective, and immunomodulatory activities. It has also displayed antidiabetic, antihyperlipidemic, and antiatherogenic properties in streptozotocin-induced diabetic rats. MGF exerts chemotherapeutic and chemo-preventative activities. It displays antioxidant, analgesic, and hepatoprotective activity against carbon tetrachloride-induced liver injury. MGF is a known accelerator of gastrointestinal transit (GIT).

Check Digit Verification of cas no

The CAS Registry Mumber 4773-96-0 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 4,7,7 and 3 respectively; the second part has 2 digits, 9 and 6 respectively.
Calculate Digit Verification of CAS Registry Number 4773-96:
(6*4)+(5*7)+(4*7)+(3*3)+(2*9)+(1*6)=120
120 % 10 = 0
So 4773-96-0 is a valid CAS Registry Number.
InChI:InChI=1/C19H18O11/c20-4-11-15(25)17(27)18(28)19(30-11)12-8(23)3-10-13(16(12)26)14(24)5-1-6(21)7(22)2-9(5)29-10/h1-3,11,15,17-23,25-28H,4H2/t11-,15-,17+,18-,19?/m1/s1

4773-96-0 Well-known Company Product Price

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  • Sigma-Aldrich

  • (06279)  Mangiferin  analytical standard

  • 4773-96-0

  • 06279-10MG

  • 1,257.75CNY

  • Detail
  • Sigma-Aldrich

  • (Y0001751)  Mangiferin  European Pharmacopoeia (EP) Reference Standard

  • 4773-96-0

  • Y0001751

  • 1,880.19CNY

  • Detail

4773-96-0SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 19, 2017

Revision Date: Aug 19, 2017

1.Identification

1.1 GHS Product identifier

Product name mangiferin

1.2 Other means of identification

Product number -
Other names Hedysaride

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:4773-96-0 SDS

4773-96-0Synthetic route

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

2-C-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)-6-methoxy-1,3,7-trihydroxyxanthone

mangiferin
4773-96-0

mangiferin

Conditions
ConditionsYield
With boron tribromide In dichloromethane at 0 - 20℃;94%
1,6,7-trihydroxy-2-C-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)-3-O-benzylxanthone

1,6,7-trihydroxy-2-C-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)-3-O-benzylxanthone

mangiferin
4773-96-0

mangiferin

Conditions
ConditionsYield
With 10% palladium hydroxide on charcoal; hydrogen In methanol at 20℃; under 760.051 Torr; for 48h;90%
3-glucosyl-2,3′,4,4′,6-pentahydroxybenzophenone
92631-83-9

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

A

4-β-D-glucopyranosyl-1,3-6,7-tetrahydroxy-9H-xanthen-9-one
24699-16-9

4-β-D-glucopyranosyl-1,3-6,7-tetrahydroxy-9H-xanthen-9-one

B

mangiferin
4773-96-0

mangiferin

Conditions
ConditionsYield
With sodium carbonate; potassium hexacyanoferrate(III) In water for 1.5h; Ambient temperature;A 12 mg
B 7 mg
With sodium carbonate; potassium hexacyanoferrate(III) In water for 1.5h; Product distribution; Ambient temperature;A 12 mg
B 7 mg
6′-O-galloyl-mangiferin
92631-82-8

6′-O-galloyl-mangiferin

A

3,4,5-trihydroxybenzoic acid
149-91-7

3,4,5-trihydroxybenzoic acid

B

mangiferin
4773-96-0

mangiferin

Conditions
ConditionsYield
In water at 37℃; tannase;
6′-O-acetyl mangiferin

6′-O-acetyl mangiferin

mangiferin
4773-96-0

mangiferin

Conditions
ConditionsYield
With hydrogenchloride In water at 100℃; for 1h; Product distribution; other reagent (2N NaOH); other temp.;
maclurin 3-C-(6''-O-p-hydroxybenzoyl)-β-D-glucoside
92665-82-2

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

mangiferin
4773-96-0

mangiferin

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 20 mg / H2O / 35 °C / hesperidinase
2: 7 mg / K3, Na2CO3 / H2O / 1.5 h / Ambient temperature
View Scheme
maclurin 3-C-(2''-O-p-hydroxybenzoyl-6''-O-galloyl)-β-D-glucoside
92631-85-1

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

mangiferin
4773-96-0

mangiferin

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 40 mg / H2O / 37 °C / hesperidinase
2: 7 mg / K3, Na2CO3 / H2O / 1.5 h / Ambient temperature
View Scheme
maclurin 3-C-(2''-O-galloyl-6''-O-p-hydroxybenzoyl)-β-D-glucoside
92631-84-0

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

mangiferin
4773-96-0

mangiferin

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: H2O / 0.5 h / 37 °C / tannase
2: 20 mg / H2O / 35 °C / hesperidinase
3: 7 mg / K3, Na2CO3 / H2O / 1.5 h / Ambient temperature
View Scheme
C19H18O11*C42H70O35

C19H18O11*C42H70O35

A

mangiferin
4773-96-0

mangiferin

B

β‐cyclodextrin
7585-39-9

β‐cyclodextrin

Conditions
ConditionsYield
In ethanol at 25℃; for 2h; Kinetics; Wavelength;
3-glucosyl-2,3′,4,4′,6-pentahydroxybenzophenone
92631-83-9

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

mangiferin
4773-96-0

mangiferin

Conditions
ConditionsYield
With ethylenediaminetetraacetic acid; NADPH at 30℃; for 2h; Enzymatic reaction;
maclurin
519-34-6

maclurin

4-nitrophenyl-β-D-glucoside
2492-87-7

4-nitrophenyl-β-D-glucoside

mangiferin
4773-96-0

mangiferin

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: UDP; Mangifera indica C-glycosyltransferase / 12 h / Enzymatic reaction
2: NADPH; ethylenediaminetetraacetic acid / 2 h / 30 °C / Enzymatic reaction
View Scheme
UDP-glucose
133-89-1

UDP-glucose

maclurin
519-34-6

maclurin

mangiferin
4773-96-0

mangiferin

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: Mangifera indica C-glycosyltransferase / 12 h / Enzymatic reaction
2: NADPH; ethylenediaminetetraacetic acid / 2 h / 30 °C / Enzymatic reaction
View Scheme
Conditions
ConditionsYield
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
View Scheme
β-D-glucose pentaacetate
604-69-3

β-D-glucose pentaacetate

mangiferin
4773-96-0

mangiferin

Conditions
ConditionsYield
Multi-step reaction with 14 steps
1.1: boron trifluoride diethyl etherate / dichloromethane / 12 h / 20 °C / Inert atmosphere
2.1: sodium methylate / methanol / 1 h / 20 °C / pH 11 - 12
3.1: sodium hydride / N,N-dimethyl-formamide / 12 h / 0 - 20 °C
4.1: N-Bromosuccinimide; water / acetone / 3 h / 20 °C / Darkness
5.1: pyridine / 12 h / 20 °C
6.1: trimethylsilyl trifluoromethanesulfonate / dichloromethane; tetrahydrofuran / 1 h / 0 °C / Inert atmosphere
7.1: trichlorophosphate / 16 h / 20 °C / Inert atmosphere
8.1: n-butyllithium / tetrahydrofuran / 1 h / -40 °C / Inert atmosphere
8.2: 1 h / -40 °C / Inert atmosphere
9.1: manganese(IV) oxide / dichloromethane / 36 h
10.1: toluene-4-sulfonic acid / methanol / 0.5 h / 80 °C
11.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 2 h / 0 °C
12.1: caesium carbonate / methanol / 12 h / 80 °C
13.1: toluene-4-sulfonic acid / methanol / 0.5 h / 80 °C
14.1: 10% palladium hydroxide on charcoal; hydrogen / methanol / 48 h / 20 °C / 760.05 Torr
View Scheme
1-O-acetyl-2,3,4,6-tetra-O-benzyl-D-glucopyranose
80300-30-7

1-O-acetyl-2,3,4,6-tetra-O-benzyl-D-glucopyranose

mangiferin
4773-96-0

mangiferin

Conditions
ConditionsYield
Multi-step reaction with 9 steps
1.1: trimethylsilyl trifluoromethanesulfonate / dichloromethane; tetrahydrofuran / 1 h / 0 °C / Inert atmosphere
2.1: trichlorophosphate / 16 h / 20 °C / Inert atmosphere
3.1: n-butyllithium / tetrahydrofuran / 1 h / -40 °C / Inert atmosphere
3.2: 1 h / -40 °C / Inert atmosphere
4.1: manganese(IV) oxide / dichloromethane / 36 h
5.1: toluene-4-sulfonic acid / methanol / 0.5 h / 80 °C
6.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 2 h / 0 °C
7.1: caesium carbonate / methanol / 12 h / 80 °C
8.1: toluene-4-sulfonic acid / methanol / 0.5 h / 80 °C
9.1: 10% palladium hydroxide on charcoal; hydrogen / methanol / 48 h / 20 °C / 760.05 Torr
View Scheme
1,2,4-Trihydroxybenzene
533-73-3

1,2,4-Trihydroxybenzene

mangiferin
4773-96-0

mangiferin

Conditions
ConditionsYield
Multi-step reaction with 9 steps
1.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 12.5 h / 0 - 20 °C
2.1: N-Bromosuccinimide / N,N-dimethyl-formamide / 12 h / 20 °C
3.1: n-butyllithium / tetrahydrofuran / 1 h / -40 °C / Inert atmosphere
3.2: 1 h / -40 °C / Inert atmosphere
4.1: manganese(IV) oxide / dichloromethane / 36 h
5.1: toluene-4-sulfonic acid / methanol / 0.5 h / 80 °C
6.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 2 h / 0 °C
7.1: caesium carbonate / methanol / 12 h / 80 °C
8.1: toluene-4-sulfonic acid / methanol / 0.5 h / 80 °C
9.1: 10% palladium hydroxide on charcoal; hydrogen / methanol / 48 h / 20 °C / 760.05 Torr
View Scheme
1,2,4-tris(methoxymethoxy)benzene
156862-15-6

1,2,4-tris(methoxymethoxy)benzene

mangiferin
4773-96-0

mangiferin

Conditions
ConditionsYield
Multi-step reaction with 8 steps
1.1: N-Bromosuccinimide / N,N-dimethyl-formamide / 12 h / 20 °C
2.1: n-butyllithium / tetrahydrofuran / 1 h / -40 °C / Inert atmosphere
2.2: 1 h / -40 °C / Inert atmosphere
3.1: manganese(IV) oxide / dichloromethane / 36 h
4.1: toluene-4-sulfonic acid / methanol / 0.5 h / 80 °C
5.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 2 h / 0 °C
6.1: caesium carbonate / methanol / 12 h / 80 °C
7.1: toluene-4-sulfonic acid / methanol / 0.5 h / 80 °C
8.1: 10% palladium hydroxide on charcoal; hydrogen / methanol / 48 h / 20 °C / 760.05 Torr
View Scheme
1-bromo-2,4,5-tris(methoxymethoxy)benzene

1-bromo-2,4,5-tris(methoxymethoxy)benzene

mangiferin
4773-96-0

mangiferin

Conditions
ConditionsYield
Multi-step reaction with 7 steps
1.1: n-butyllithium / tetrahydrofuran / 1 h / -40 °C / Inert atmosphere
1.2: 1 h / -40 °C / Inert atmosphere
2.1: manganese(IV) oxide / dichloromethane / 36 h
3.1: toluene-4-sulfonic acid / methanol / 0.5 h / 80 °C
4.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 2 h / 0 °C
5.1: caesium carbonate / methanol / 12 h / 80 °C
6.1: toluene-4-sulfonic acid / methanol / 0.5 h / 80 °C
7.1: 10% palladium hydroxide on charcoal; hydrogen / methanol / 48 h / 20 °C / 760.05 Torr
View Scheme
1,3,5-tri-O-benzyl-2-C-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)benzene
115130-39-7

1,3,5-tri-O-benzyl-2-C-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)benzene

mangiferin
4773-96-0

mangiferin

Conditions
ConditionsYield
Multi-step reaction with 8 steps
1.1: trichlorophosphate / 16 h / 20 °C / Inert atmosphere
2.1: n-butyllithium / tetrahydrofuran / 1 h / -40 °C / Inert atmosphere
2.2: 1 h / -40 °C / Inert atmosphere
3.1: manganese(IV) oxide / dichloromethane / 36 h
4.1: toluene-4-sulfonic acid / methanol / 0.5 h / 80 °C
5.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 2 h / 0 °C
6.1: caesium carbonate / methanol / 12 h / 80 °C
7.1: toluene-4-sulfonic acid / methanol / 0.5 h / 80 °C
8.1: 10% palladium hydroxide on charcoal; hydrogen / methanol / 48 h / 20 °C / 760.05 Torr
View Scheme
p-tolyl-2,3,4,6-tetra-O-acetyl-1-thio-β-D-glucopyranoside
28244-94-2, 28244-99-7, 86782-41-4, 131488-65-8

p-tolyl-2,3,4,6-tetra-O-acetyl-1-thio-β-D-glucopyranoside

mangiferin
4773-96-0

mangiferin

Conditions
ConditionsYield
Multi-step reaction with 13 steps
1.1: sodium methylate / methanol / 1 h / 20 °C / pH 11 - 12
2.1: sodium hydride / N,N-dimethyl-formamide / 12 h / 0 - 20 °C
3.1: N-Bromosuccinimide; water / acetone / 3 h / 20 °C / Darkness
4.1: pyridine / 12 h / 20 °C
5.1: trimethylsilyl trifluoromethanesulfonate / dichloromethane; tetrahydrofuran / 1 h / 0 °C / Inert atmosphere
6.1: trichlorophosphate / 16 h / 20 °C / Inert atmosphere
7.1: n-butyllithium / tetrahydrofuran / 1 h / -40 °C / Inert atmosphere
7.2: 1 h / -40 °C / Inert atmosphere
8.1: manganese(IV) oxide / dichloromethane / 36 h
9.1: toluene-4-sulfonic acid / methanol / 0.5 h / 80 °C
10.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 2 h / 0 °C
11.1: caesium carbonate / methanol / 12 h / 80 °C
12.1: toluene-4-sulfonic acid / methanol / 0.5 h / 80 °C
13.1: 10% palladium hydroxide on charcoal; hydrogen / methanol / 48 h / 20 °C / 760.05 Torr
View Scheme
2,4,6-tri-O-benzyl-3-C-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)benzaldehyde

2,4,6-tri-O-benzyl-3-C-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)benzaldehyde

mangiferin
4773-96-0

mangiferin

Conditions
ConditionsYield
Multi-step reaction with 7 steps
1.1: n-butyllithium / tetrahydrofuran / 1 h / -40 °C / Inert atmosphere
1.2: 1 h / -40 °C / Inert atmosphere
2.1: manganese(IV) oxide / dichloromethane / 36 h
3.1: toluene-4-sulfonic acid / methanol / 0.5 h / 80 °C
4.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 2 h / 0 °C
5.1: caesium carbonate / methanol / 12 h / 80 °C
6.1: toluene-4-sulfonic acid / methanol / 0.5 h / 80 °C
7.1: 10% palladium hydroxide on charcoal; hydrogen / methanol / 48 h / 20 °C / 760.05 Torr
View Scheme
C74H76O15

C74H76O15

mangiferin
4773-96-0

mangiferin

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1: manganese(IV) oxide / dichloromethane / 36 h
2: toluene-4-sulfonic acid / methanol / 0.5 h / 80 °C
3: N-ethyl-N,N-diisopropylamine / dichloromethane / 2 h / 0 °C
4: caesium carbonate / methanol / 12 h / 80 °C
5: toluene-4-sulfonic acid / methanol / 0.5 h / 80 °C
6: 10% palladium hydroxide on charcoal; hydrogen / methanol / 48 h / 20 °C / 760.05 Torr
View Scheme
2,4,6-tribenzyloxy-3-C-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)-2′,4′,5′-tris(methoxymethoxy)benzophenone

2,4,6-tribenzyloxy-3-C-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)-2′,4′,5′-tris(methoxymethoxy)benzophenone

mangiferin
4773-96-0

mangiferin

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: toluene-4-sulfonic acid / methanol / 0.5 h / 80 °C
2: N-ethyl-N,N-diisopropylamine / dichloromethane / 2 h / 0 °C
3: caesium carbonate / methanol / 12 h / 80 °C
4: toluene-4-sulfonic acid / methanol / 0.5 h / 80 °C
5: 10% palladium hydroxide on charcoal; hydrogen / methanol / 48 h / 20 °C / 760.05 Torr
View Scheme
2,4,6-tribenzyloxy-3-C-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)-2′,4′,5′-trihydroxybenzophenone

2,4,6-tribenzyloxy-3-C-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)-2′,4′,5′-trihydroxybenzophenone

mangiferin
4773-96-0

mangiferin

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: N-ethyl-N,N-diisopropylamine / dichloromethane / 2 h / 0 °C
2: caesium carbonate / methanol / 12 h / 80 °C
3: toluene-4-sulfonic acid / methanol / 0.5 h / 80 °C
4: 10% palladium hydroxide on charcoal; hydrogen / methanol / 48 h / 20 °C / 760.05 Torr
View Scheme
2,4,6-tribenzyloxy-3-C-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)-2′-hydroxy-4′,5′-bis(methoxymethoxy)benzophenone

2,4,6-tribenzyloxy-3-C-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)-2′-hydroxy-4′,5′-bis(methoxymethoxy)benzophenone

mangiferin
4773-96-0

mangiferin

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: caesium carbonate / methanol / 12 h / 80 °C
2: toluene-4-sulfonic acid / methanol / 0.5 h / 80 °C
3: 10% palladium hydroxide on charcoal; hydrogen / methanol / 48 h / 20 °C / 760.05 Torr
View Scheme
1,3-di-O-benzyl-2-C-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)-6,7-di-O-methoxymethylxanthone

1,3-di-O-benzyl-2-C-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)-6,7-di-O-methoxymethylxanthone

mangiferin
4773-96-0

mangiferin

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: toluene-4-sulfonic acid / methanol / 0.5 h / 80 °C
2: 10% palladium hydroxide on charcoal; hydrogen / methanol / 48 h / 20 °C / 760.05 Torr
View Scheme
p-methylphenyl 1-thio-β-D-glucopyranoside
1152-39-2

p-methylphenyl 1-thio-β-D-glucopyranoside

mangiferin
4773-96-0

mangiferin

Conditions
ConditionsYield
Multi-step reaction with 12 steps
1.1: sodium hydride / N,N-dimethyl-formamide / 12 h / 0 - 20 °C
2.1: N-Bromosuccinimide; water / acetone / 3 h / 20 °C / Darkness
3.1: pyridine / 12 h / 20 °C
4.1: trimethylsilyl trifluoromethanesulfonate / dichloromethane; tetrahydrofuran / 1 h / 0 °C / Inert atmosphere
5.1: trichlorophosphate / 16 h / 20 °C / Inert atmosphere
6.1: n-butyllithium / tetrahydrofuran / 1 h / -40 °C / Inert atmosphere
6.2: 1 h / -40 °C / Inert atmosphere
7.1: manganese(IV) oxide / dichloromethane / 36 h
8.1: toluene-4-sulfonic acid / methanol / 0.5 h / 80 °C
9.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 2 h / 0 °C
10.1: caesium carbonate / methanol / 12 h / 80 °C
11.1: toluene-4-sulfonic acid / methanol / 0.5 h / 80 °C
12.1: 10% palladium hydroxide on charcoal; hydrogen / methanol / 48 h / 20 °C / 760.05 Torr
View Scheme
p-methylphenyl 2,3,4,6-tetra-O-benzyl-thio-β-D-glucopyranoside
131531-76-5

p-methylphenyl 2,3,4,6-tetra-O-benzyl-thio-β-D-glucopyranoside

mangiferin
4773-96-0

mangiferin

Conditions
ConditionsYield
Multi-step reaction with 11 steps
1.1: N-Bromosuccinimide; water / acetone / 3 h / 20 °C / Darkness
2.1: pyridine / 12 h / 20 °C
3.1: trimethylsilyl trifluoromethanesulfonate / dichloromethane; tetrahydrofuran / 1 h / 0 °C / Inert atmosphere
4.1: trichlorophosphate / 16 h / 20 °C / Inert atmosphere
5.1: n-butyllithium / tetrahydrofuran / 1 h / -40 °C / Inert atmosphere
5.2: 1 h / -40 °C / Inert atmosphere
6.1: manganese(IV) oxide / dichloromethane / 36 h
7.1: toluene-4-sulfonic acid / methanol / 0.5 h / 80 °C
8.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 2 h / 0 °C
9.1: caesium carbonate / methanol / 12 h / 80 °C
10.1: toluene-4-sulfonic acid / methanol / 0.5 h / 80 °C
11.1: 10% palladium hydroxide on charcoal; hydrogen / methanol / 48 h / 20 °C / 760.05 Torr
View Scheme
acetic anhydride
108-24-7

acetic anhydride

mangiferin
4773-96-0

mangiferin

2-β-D-tetraacetoxyglucopyranosyl-1,6,7-triacetoxy-3-hydroxy-9H-xanthen-9-one

2-β-D-tetraacetoxyglucopyranosyl-1,6,7-triacetoxy-3-hydroxy-9H-xanthen-9-one

Conditions
ConditionsYield
With sodium acetate; acetic acid at 120℃; for 3.5h;93.6%
mangiferin
4773-96-0

mangiferin

mangiferin calcium

mangiferin calcium

Conditions
ConditionsYield
With calcium hydroxide In dimethyl sulfoxide; glycerol Product distribution / selectivity;90.4%
With potassium hydrogencarbonate In ethanol; water Product distribution / selectivity;82.1%
mangiferin
4773-96-0

mangiferin

mangiferin-3-monosodium
929635-04-1

mangiferin-3-monosodium

Conditions
ConditionsYield
With sodium carbonate In ethanol; water Product distribution / selectivity;81.7%
mangiferin
4773-96-0

mangiferin

mangiferin-3-monopotassium
1158716-92-7

mangiferin-3-monopotassium

Conditions
ConditionsYield
With sodium hydrogencarbonate In ethanol; water Product distribution / selectivity;78.1%
acetic anhydride
108-24-7

acetic anhydride

mangiferin
4773-96-0

mangiferin

1,3,6,7-tetra-O-acetyl-2-C-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)xanthone
4706-56-3

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

Conditions
ConditionsYield
With iodine at 130℃; for 0.25h; Microwave irradiation;78%
With pyridine at 20℃; for 36h;
mangiferin
4773-96-0

mangiferin

mangiferin-6-O-calcium salt

mangiferin-6-O-calcium salt

Conditions
ConditionsYield
Stage #1: mangiferin With sodium hydrogencarbonate In water; dimethyl sulfoxide at 85℃;
Stage #2: With calcium chloride In water; dimethyl sulfoxide at 20℃; Reagent/catalyst;
74.5%
mangiferin
4773-96-0

mangiferin

mangiferin-6-O-potassium salt

mangiferin-6-O-potassium salt

Conditions
ConditionsYield
With potassium carbonate In water; dimethyl sulfoxide at 60℃; Temperature;60.2%
mangiferin
4773-96-0

mangiferin

mangiferin-6-O-sodium salt

mangiferin-6-O-sodium salt

Conditions
ConditionsYield
With sodium hydrogencarbonate In water; dimethyl sulfoxide at 85℃; Temperature; Reagent/catalyst;50.5%
copper(II) nitrate trihydrate

copper(II) nitrate trihydrate

water
7732-18-5

water

mangiferin
4773-96-0

mangiferin

C19H20CuO13*5H2O

C19H20CuO13*5H2O

Conditions
ConditionsYield
With triethylamine In ethanol at 65℃; for 5h; pH=7.5;46%
mangiferin
4773-96-0

mangiferin

norathyriol
3542-72-1

norathyriol

Conditions
ConditionsYield
With hydrogen iodide; phenol for 7h; Heating;43%
With hydrogenchloride; recorcinol In water for 6h; Reagent/catalyst; Reflux;
With hydrogenchloride; recorcinol In water at 150℃; for 6h; Reagent/catalyst; Green chemistry;
zinc(II) nitrate hexahydrate

zinc(II) nitrate hexahydrate

water
7732-18-5

water

mangiferin
4773-96-0

mangiferin

C19H20O13Zn*4H2O

C19H20O13Zn*4H2O

Conditions
ConditionsYield
With triethylamine In methanol; ethanol at 65℃; for 6h; pH=7.5;40%
cinnamoyl chloride
102-92-1

cinnamoyl chloride

mangiferin
4773-96-0

mangiferin

2-β-D-glucopyranosyl-7-cinnamoyloxy-1,3,6-trihydroxy-9H-xanthen-9-one

2-β-D-glucopyranosyl-7-cinnamoyloxy-1,3,6-trihydroxy-9H-xanthen-9-one

Conditions
ConditionsYield
With pyridine at 20℃; for 20h;
dimethyl sulfate
77-78-1

dimethyl sulfate

mangiferin
4773-96-0

mangiferin

2-β-D-tetrahydroxyglucopyranosyl-3,6,7-trimethoxy-1-hydroxy-9H-xanthen-9-one

2-β-D-tetrahydroxyglucopyranosyl-3,6,7-trimethoxy-1-hydroxy-9H-xanthen-9-one

Conditions
ConditionsYield
With potassium carbonate In acetone at 20℃; for 168h;
Cinnamoyl chloride
102-92-1

Cinnamoyl chloride

mangiferin
4773-96-0

mangiferin

2-β-D-glucopyranosyl-1,3,6,7-tetrahydroxy-9H-xanthen-9-one

2-β-D-glucopyranosyl-1,3,6,7-tetrahydroxy-9H-xanthen-9-one

Conditions
ConditionsYield
With pyridine at 20℃; for 20h;
Cinnamoyl chloride
102-92-1

Cinnamoyl chloride

mangiferin
4773-96-0

mangiferin

2-β-D-tetracinnamoylglucopyranosyl-7-cynnamoyloxy-1,3,6-trihydroxy-9H-xanthen-9-one

2-β-D-tetracinnamoylglucopyranosyl-7-cynnamoyloxy-1,3,6-trihydroxy-9H-xanthen-9-one

Conditions
ConditionsYield
With pyridine at 20℃; for 600h;
mangiferin
4773-96-0

mangiferin

1,3,6,7-tetrahydroxyxanthone acetate
2054-37-7

1,3,6,7-tetrahydroxyxanthone acetate

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 43 percent / phenol, hydroiodic acid (d= 1.7) / 7 h / Heating
2: pyridine / 24 h
View Scheme
potassium carbonate
584-08-7

potassium carbonate

mangiferin
4773-96-0

mangiferin

A

mangiferin-3-monopotassium
1158716-92-7

mangiferin-3-monopotassium

B

mangiferin-7-monopotassium
1158716-92-7

mangiferin-7-monopotassium

Conditions
ConditionsYield
In methanol; water Product distribution / selectivity;
sodium hydrogencarbonate
144-55-8

sodium hydrogencarbonate

mangiferin
4773-96-0

mangiferin

A

mangiferin-3-monosodium
929635-04-1

mangiferin-3-monosodium

B

mangiferin-7-monosodium
929635-04-1

mangiferin-7-monosodium

Conditions
ConditionsYield
In ethanol; water Product distribution / selectivity;
sodium carbonate
497-19-8

sodium carbonate

mangiferin
4773-96-0

mangiferin

A

mangiferin-3-monosodium
929635-04-1

mangiferin-3-monosodium

B

mangiferin-7-monosodium
929635-04-1

mangiferin-7-monosodium

Conditions
ConditionsYield
In ethanol; water Product distribution / selectivity;
calcium hydroxide

calcium hydroxide

mangiferin
4773-96-0

mangiferin

mangiferin calcium

mangiferin calcium

Conditions
ConditionsYield
In dimethyl sulfoxide; glycerol Product distribution / selectivity;

4773-96-0Relevant articles and documents

Electrochemical investigations into host-guest interactions of a natural antioxidant compound with β-cyclodextrin

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

, p. 797 - 803 (2010)

The electrochemical behavior of mangiferin (MGN), a natural antioxidant compound, is examined using cyclic and differential pulse voltammetry in a protic medium on a glassy carbon electrode. The voltammograms exhibit a single irreversible pH-dependent anodic wave with current controlled by adsorption. Complexes of MGN with β-cyclodextrin (β-CD) were prepared and their formation was confirmed by UV-vis spectroscopy and electrochemical experiments, using a self-assembled monolayer of cyclodextrin on a gold electrode. The association constant of MGN:β-CD complexes was estimated by the Benesi-Hildebrand method, based on the spectrophotometric quantification of free β-CD and by the direct method using cyclic voltammetry and the Langmuir isotherm. PM IRRAS experiments corroborated the inclusion process based on the observation of the corresponding peaks in the spectra of the samples. MGN was quantified using a simple electrochemical method based on a β-CD incorporated carbon nanotube (CNT)-modified electrode (β-CDCNT). The presence of β-CD led to a 10-fold lower detection limit than that obtained with a CNT-modified electrode.

Total synthesis of mangiferin, homomangiferin, and neomangiferin

Wei, Xiong,Liang, Danlin,Wang, Qing,Meng, Xiangbao,Li, Zhongjun

, p. 8821 - 8831 (2016/10/03)

Total synthesis of mangiferin, homomangiferin, and neomangiferin, three C-glycosyl xanthone natural products with a wide spectrum of pharmacological effects, has been achieved starting from 2,3,4,6-tetra-O-benzyl-α/β-d-glucopyranose. The key steps involve a stereoselective Lewis acid promoted C-glycosylation of protected phloroglucinol with tetrabenzylglucopyranosyl acetate and a highly regioselective base-induced cyclization for the construction of the core xanthone skeleton.

Probing the catalytic promiscuity of a regio- and stereospecific C-glycosyltransferase from Mangifera indica

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

, p. 12678 - 12682 (2015/10/28)

The catalytic promiscuity of the novel benzophenone C-glycosyltransferase, MiCGT, which is involved in the biosynthesis of mangiferin from Mangifera indica, was explored. MiCGT exhibited a robust capability to regio- and stereospecific C-glycosylation of 35 structurally diverse druglike scaffolds and simple phenolics with UDP-glucose, and also formed O- and N-glycosides. Moreover, MiCGT was able to generate C-xylosides with UDP-xylose. The OGT-reversibility of MiCGT was also exploited to generate C-glucosides with simple sugar donor. Three aryl-C-glycosides exhibited potent SGLT2 inhibitory activities with IC50 values of 2.6×, 7.6×, and 7.6×10-7-M, respectively. These findings demonstrate for the first time the significant potential of an enzymatic approach to diversification through C-glycosidation of bioactive natural and unnatural products in drug discovery. C-glycodiversification: MiCGT, as the first benzophenone C-glycosyltransferase (CGT) from Mangifera indica, showed robust regio- and stereospecific C-glycosylation activity for 35 structurally diverse acceptors with UDP-glucose or xylose. The aryl-C-glycoside 1 exhibited potent antidiabetic activity toward SGLT2.

Synthesis of mangiferin, isomangiferin, and homomangiferin

Wu, Zhongtao,Wei, Guo,Lian, Gaoyan,Yu, Biao

supporting information; experimental part, p. 5725 - 5728 (2010/10/03)

Mangiferin, isomangiferin, and homomangiferin, the xanthone C-glycosides with a wide spectrum of pharmacological effects, were synthesized concisely, featuring a C-glycosylation of a xanthene derivative with perbenzylglucopyranosyl N-phenyltrifluoroacetimidate.

Process for preparing mangiferin

-

, (2008/06/13)

A process for preparing mangiferin from plants of the genus of Hedysarum (Hedysarum alpinum L., Hedysarum flavescens Rgl. et Schmalh) comprising extraction of xanthone glycosides from the aerial portion of the plants by means of a mixture acetone-water at a volume ratio of the mixture components of 1:0.5-2 respectively; the resulting extract is evaporated, the evaporated extract is filtered. To the filtered evaporated extract sulphuric acid is added to a pH of from 2 to 4, heated at reflux and filtered. The thus-prepared extract is treated with a non-polar organic solvent with the formation of two layers, wherefrom the upper aqueous layer contains xanthone glycosides. This upper layer is treated with butanol with the formation of two layers, wherefrom the upper layer comprises a solution of xanthone glycosides in butanol. This upper butanolic layer is evaporated. The precipitated mangiferin is separated and recrystallized.

Tannins and Related Compounds. XXI. Isolation and Characterization of Galloyl and p-Hydroxybenzoyl Esters of Benzophenone and Xanthone C-glucosides from Mangifera indica L.

Tanaka, Takashi,Sueyasu, Tokiko,Nonaka, Gen-ichiro,Nishioka, Itsuo

, p. 2676 - 2686 (2007/10/02)

Six new galloyl and p-hydroxybenzoyl esters (2-7) of benzophenone C-glucosides have been isolated, together with a new benzophenone C-glucoside (1), from the leaves of Mangifera indica L. (Anacardiaceae).On the basis of chemical and spectroscopic evidence, the structures of these compounds have been established as maclurin 3-C-β-D-glucoside (1), maclurin 3-C-(6''-O-p-hydroxybenzoyl)-β-D-glucoside (2), maclurin 3-C-(2''-O-galloyl-6''-O-p-hydroxybenzoyl)-β-D-glucoside (3), maclurin 3-C-(2''-O-p-hydroxybenzoyl-6''-O-galloyl)-β-D-glucoside (4), maclurin 3-C-(2'',3'',6''-tri-O-galloyl)-β-D-glucoside (5), iriflophenone 3-C(2'',6''-di-O-galloyl)-β-D-glucoside (6) and iriflophenone 3-C-(2'',3'',6''-tri-O-galloyl)-β-D-glucoside (7). (-)-Epicatechin 3-O-gallate (9), mangiferin (10), isomangiferin (11) and a new xanthone C-glucoside gallate, mangiferin 6'-O-gallate (8), have also been isolated and their structures have been similarly characterized.Furthermore, the above plant source contained polygalloylglucoses which were characterized on the basis of chemical and high performance liquid chromatographic analyses as a mixture of penta- to undecagalloylglucoses based on a 1,2,3,4,6-penta-O-galloyl-β-D-glucose core.Maclurin 3-C-glucoside (1) has been transformed enzymatically to mangiferin (10) and isomangiferin (11), and it has become clear that 1 is a key intermediate in the biosynthesis of 10 and 11. Keywords - Mangifera indica; Anacardiaceae; galloyl maclurin 3-C-glucoside p-hydroxybenzoate; galloyl iriflopenone 3-C-glucoside; galloyl mangiferin; benzophenone C-glucoside; biosynthesys; mangiferin; isomangiferin; galloylglucose

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