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  • High Quality 99% 9H-Xanthen-9-one, 2-b-D-glucopyranosyl-1,3,6,7-tetrahydroxy- 4773-96-0 ISO Producer

    Cas No: 4773-96-0

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4773-96-0 Usage

Chemical Properties

Yellow powder

Uses

Different sources of media describe the Uses of 4773-96-0 differently. You can refer to the following data:
1. MAO inhibitor, immunostimulant
2. 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.
3. 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.

Definition

ChEBI: A C-glycosyl compound consisting of 1,3,6,7-tetrahydroxyxanthen-9-one having a beta-D-glucosyl residue at the 6-position.

General Description

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

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

-

Markham,K.,Wallace,J.

, p. 415 (1980)

-

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.

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.

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