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3681-99-0

Basic Information
CAS No.: 3681-99-0
Name: Puerarin
Article Data: 6
Cas Database
Molecular Structure:
Molecular Structure of 3681-99-0 (Puerarin)
Formula: C21H20O9
Molecular Weight: 416.384
Synonyms: 7-hydroxy-3-(4-hydroxyphenyl)-8-[(2S,3S,4R,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]chromen-4-one;Hexitol, 1,5-anhydro-1-C-[7-hydroxy-3-(4-hydroxyphenyl)-4-oxo-4H-1-benzopyran-8-yl]-;Pneranin;NPI 031G;4H-1-Benzopyran-4-one, 8-beta-D-glucopyranosyl-7-hydroxy-3-(4-hydroxyphenyl)- (9CI);8-beta-D-Glucopyranosyl-7-hydroxy-3-(4-hydroxyphenyl)-4H-1-benzopyran-4-one;Sanguinarine citrate;Puerarin 99% (UV);Puerariae P.E.;Pueraria lobata;Pueraria P.E;
EINECS: 609-296-1
Density: 1.642 g/cm3
Melting Point: 187-189 °C
Boiling Point: 791.2 °C at 760 mmHg
Flash Point: 281.5 °C
Solubility: Soluble in DMSO or DMF. Slightly soluble in water or ethanol
Appearance: Yellow brown Fine Powder
Hazard Symbols: FlammableF,CorrosiveC
Risk Codes: 11-34
Safety: 22-24/25-45-36/37/39-26-16
Transport Information: N/A
PSA: 160.82000
LogP: 0.38610
Synthetic route

7-hydroxy-4'-methoxy-8-C-(2,3,4,6-tetra-O-benzyl-β-D-glucocopyranosyl)isoflavone

3681-99-0

puerarin

Conditions
ConditionsYield
Stage #1: 7-hydroxy-4'-methoxy-8-C-(2,3,4,6-tetra-O-benzyl-β-D-glucocopyranosyl)isoflavone With boron tribromide In dichloromethane at -78℃; for 0.5h; Inert atmosphere;
Stage #2: With methanol In dichloromethane at 0℃; for 0.0833333h; Inert atmosphere;
95%
1029605-74-0

6-[7-hydroxy-3-(4-hydroxy-phenyl)-4-oxo-4H-chromen-8-yl]-3,4,5-tris-trimethyl-silanyloxy-tetrahydro-pyran-2-carbaldehyde

3681-99-0

puerarin

Conditions
ConditionsYield
Stage #1: 6-[7-hydroxy-3-(4-hydroxy-phenyl)-4-oxo-4H-chromen-8-yl]-3,4,5-tris-trimethyl-silanyloxy-tetrahydro-pyran-2-carbaldehyde With sodium tetrahydroborate In tetrahydrofuran; ethanol at 0℃; for 0.166667h;
Stage #2: With hydrogenchloride In tetrahydrofuran; ethanol at 0 - 20℃; for 0.25h; Further stages.;
75%
1242241-66-2

4',7-di-O-benzyldaidzein 8-C-β-D-(2,3,4,6-tetra-O-benzylglucoside)

3681-99-0

puerarin

Conditions
ConditionsYield
With boron tribromide In dichloromethane at -78 - 20℃; Inert atmosphere;71%
69655-50-1

4',7-di-O-methyl-puerarin

A

3681-99-0

puerarin

B

7-O-methylpuerarin

Conditions
ConditionsYield
With trimethylsilyl iodide In acetonitrile for 120h; Heating;A 35%
B 39%
147899-32-9

Malonic acid mono-{(2R,3S,4R,5R,6S)-3,4,5-trihydroxy-6-[7-hydroxy-3-(4-hydroxy-phenyl)-4-oxo-4H-chromen-8-yl]-tetrahydro-pyran-2-ylmethyl} ester

3681-99-0

puerarin

Conditions
ConditionsYield
With sodium hydroxide; water Ambient temperature;
69667-95-4

Acetic acid (2S,3S,4R,5R,6R)-4,5-diacetoxy-2-{2-acetoxy-6-methoxy-3-[(E)-3-(4-methoxy-phenyl)-acryloyl]-phenyl}-6-acetoxymethyl-tetrahydro-pyran-3-yl ester

3681-99-0

puerarin

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: Tl(NO3)3; trimethyl orthoformate / methanol
1.2: 84 percent / aq. HCl / methanol / Heating
2.1: 35 percent / Me3SiI / acetonitrile / 120 h / Heating
View Scheme

8-C-β-glucofuranosyl-7,4'-dihydroxyisoflavone

A

8-C-α-glucofuranosyl-7,4'-dihydroxyisoflavone

B

3681-99-0

puerarin

Conditions
ConditionsYield
With hydrogenchloride; water In methanol for 1h; Reflux;

4-(4-methoxyphenethyl)-6-tert-butyl-2-C-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)-1,3-dihydroxybenzene

3681-99-0

puerarin

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1.1: sodium dithionite; trifluoroacetic acid / 11 h / 20 °C
2.1: acetic acid; 2,3-dicyano-5,6-dichloro-p-benzoquinone / water / 14 h / 20 °C
3.1: trichlorophosphate / 0.25 h / 10 °C
3.2: 6 h / 70 °C
4.1: boron tribromide / dichloromethane / 0.5 h / -78 °C / Inert atmosphere
4.2: 0.08 h / 0 °C / Inert atmosphere
View Scheme

4-(4-methoxyphenethyl)-6-tert-butylbenzene-1,3-diol

3681-99-0

puerarin

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1.1: trimethylsilyl trifluoromethanesulfonate / dichloromethane / 12 h / 0 - 20 °C / Inert atmosphere; Molecular sieve
2.1: sodium dithionite; trifluoroacetic acid / 11 h / 20 °C
3.1: acetic acid; 2,3-dicyano-5,6-dichloro-p-benzoquinone / water / 14 h / 20 °C
4.1: trichlorophosphate / 0.25 h / 10 °C
4.2: 6 h / 70 °C
5.1: boron tribromide / dichloromethane / 0.5 h / -78 °C / Inert atmosphere
5.2: 0.08 h / 0 °C / Inert atmosphere
View Scheme
339276-14-1

2,3,4,6-tetra-O-benzyl-D-glucopyranosyl 1-(N-phenyl)-2,2,2-trifluoroacetimidate

3681-99-0

puerarin

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1.1: trimethylsilyl trifluoromethanesulfonate / dichloromethane / 12 h / 0 - 20 °C / Inert atmosphere; Molecular sieve
2.1: sodium dithionite; trifluoroacetic acid / 11 h / 20 °C
3.1: acetic acid; 2,3-dicyano-5,6-dichloro-p-benzoquinone / water / 14 h / 20 °C
4.1: trichlorophosphate / 0.25 h / 10 °C
4.2: 6 h / 70 °C
5.1: boron tribromide / dichloromethane / 0.5 h / -78 °C / Inert atmosphere
5.2: 0.08 h / 0 °C / Inert atmosphere
View Scheme
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    3681-99-0

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Chemistry

MF: C21H20O10
MW: 432.38
mp  187-189°C

Toxicity Data With Reference

RTECS  UO5216000

Safety Profile

Hazard Codes  F,C
Risk Statements  11-34
Safety Statements  22-24/25-45-36/37/39-26-16
WGK Germany  3
F  10
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