Product Name

  • Name

    Puerarin

  • EINECS 609-296-1
  • CAS No. 3681-99-0
  • Article Data6
  • CAS DataBase
  • Density 1.642 g/cm3
  • Solubility Soluble in DMSO or DMF. Slightly soluble in water or ethanol
  • Melting Point 187-189 °C
  • Formula C21H20O9
  • Boiling Point 791.2 °C at 760 mmHg
  • Molecular Weight 416.384
  • Flash Point 281.5 °C
  • Transport Information
  • Appearance Yellow brown Fine Powder
  • Safety 22-24/25-45-36/37/39-26-16
  • Risk Codes 11-34
  • Molecular Structure Molecular Structure of 3681-99-0 (Puerarin)
  • Hazard Symbols FlammableF,CorrosiveC
  • 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;
  • 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

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

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

puerarin
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%
4',7-di-O-benzyldaidzein 8-C-β-D-(2,3,4,6-tetra-O-benzylglucoside)
1242241-66-2

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

puerarin
3681-99-0

puerarin

Conditions
ConditionsYield
With boron tribromide In dichloromethane at -78 - 20℃; Inert atmosphere;71%
4',7-di-O-methyl-puerarin
69655-50-1

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

A

puerarin
3681-99-0

puerarin

B

7-O-methylpuerarin

7-O-methylpuerarin

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

puerarin
3681-99-0

puerarin

Conditions
ConditionsYield
With sodium hydroxide; water Ambient temperature;
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
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

puerarin
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

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

A

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

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

B

puerarin
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

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

puerarin
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

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

puerarin
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
2,3,4,6-tetra-O-benzyl-D-glucopyranosyl 1-(N-phenyl)-2,2,2-trifluoroacetimidate
339276-14-1

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

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

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

puerarin
3681-99-0

puerarin

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: acetic acid; 2,3-dicyano-5,6-dichloro-p-benzoquinone / water / 14 h / 20 °C
2.1: trichlorophosphate / 0.25 h / 10 °C
2.2: 6 h / 70 °C
3.1: boron tribromide / dichloromethane / 0.5 h / -78 °C / Inert atmosphere
3.2: 0.08 h / 0 °C / Inert atmosphere
View Scheme
puerarin
3681-99-0

puerarin

C21H24O8

C21H24O8

Conditions
ConditionsYield
With hydrogen; palladium(II) hydroxide In methanol at 20℃; for 4h;95%
6-bromo-hexanoic acid ethyl ester
25542-62-5

6-bromo-hexanoic acid ethyl ester

puerarin
3681-99-0

puerarin

7-O-[5-(ethoxycarbonyl)pentyl]puerarin

7-O-[5-(ethoxycarbonyl)pentyl]puerarin

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide at 80℃; for 6h; Williamson synthesis;91.14%
diethyl sulfate
64-67-5

diethyl sulfate

puerarin
3681-99-0

puerarin

4',7-diethylpuerarin

4',7-diethylpuerarin

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide at 0 - 20℃; for 4h;91%
puerarin
3681-99-0

puerarin

N-Trimethylsilylacetamide
13435-12-6

N-Trimethylsilylacetamide

7-hydroxy-3-(4-trimethylsilanyloxy-phenyl)-8-(3,4,5-tris-trimethylsilanyloxy-6-trimethylsilanyloxy-methyl-tetrahydro-pyran-2-yl)-chromen-4-one
1029605-66-0

7-hydroxy-3-(4-trimethylsilanyloxy-phenyl)-8-(3,4,5-tris-trimethylsilanyloxy-6-trimethylsilanyloxy-methyl-tetrahydro-pyran-2-yl)-chromen-4-one

Conditions
ConditionsYield
at 175℃; for 0.25h;86%
1-iodo-1-propyne
624-66-8

1-iodo-1-propyne

puerarin
3681-99-0

puerarin

methyl iodide
74-88-4

methyl iodide

4'-n-propyl-7-methylpuerarin

4'-n-propyl-7-methylpuerarin

Conditions
ConditionsYield
Stage #1: 1-iodo-1-propyne; puerarin With potassium carbonate In N,N-dimethyl-formamide at 0 - 20℃; for 4h;
Stage #2: methyl iodide In N,N-dimethyl-formamide at 20℃; for 12h;		85%
...Expand
puerarin
3681-99-0

puerarin

3-(2,4-dihydroxy-3-C-β-D-glucosylphenyl)-4-(4-dihydroxyphenyl)-1H-pyrazole

3-(2,4-dihydroxy-3-C-β-D-glucosylphenyl)-4-(4-dihydroxyphenyl)-1H-pyrazole

Conditions
ConditionsYield
With hydrazine hydrate In ethanol at 90℃;82%
phosphonic acid diethyl ester
762-04-9

phosphonic acid diethyl ester

puerarin
3681-99-0

puerarin

C25H29O12P

C25H29O12P

Conditions
ConditionsYield
With triethylamine In methanol; tetrachloromethane at 20℃; Atherton-Todd reaction;75%
chloroacetyl chloride
79-04-9

chloroacetyl chloride

puerarin
3681-99-0

puerarin

C23H21ClO10

C23H21ClO10

Conditions
ConditionsYield
With pyridine In chloroform at 0 - 28℃; for 22h; Temperature;72.4%
benzaldehyde
100-52-7

benzaldehyde

puerarin
3681-99-0

puerarin

4'',6''-O-benzylidenepuerarin
934696-18-1

4'',6''-O-benzylidenepuerarin

Conditions
ConditionsYield
With zinc(II) chloride at 20℃; for 3h;70%
With toluene-4-sulfonic acid In acetone at 0 - 20℃;48%
bis(N-pyrrolidinyl)methane
7309-47-9

bis(N-pyrrolidinyl)methane

puerarin
3681-99-0

puerarin

C26H29NO9

C26H29NO9

Conditions
ConditionsYield
With pyridine; hydrogenchloride In methanol; water at 120℃; for 5h; Reagent/catalyst;70%
2-(4-bromobutyl)isoindoline-1,3-dione
5394-18-3

2-(4-bromobutyl)isoindoline-1,3-dione

puerarin
3681-99-0

puerarin

2-{4-[3-(4-Hydroxy-phenyl)-4-oxo-8-((2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yl)-4H-chromen-7-yloxy]-butyl}-isoindole-1,3-dione

2-{4-[3-(4-Hydroxy-phenyl)-4-oxo-8-((2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yl)-4H-chromen-7-yloxy]-butyl}-isoindole-1,3-dione

Conditions
ConditionsYield
With potassium hydroxide In acetone for 72h; Williamson synthesis; Heating;69%
pivaloyl chloride
3282-30-2

pivaloyl chloride

puerarin
3681-99-0

puerarin

7-O-pivalyl puerarin
934696-09-0

7-O-pivalyl puerarin

Conditions
ConditionsYield
With potassium carbonate In acetone at 20℃;69%
bis-(diethylamino)methane
102-53-4

bis-(diethylamino)methane

puerarin
3681-99-0

puerarin

3',5'-methylene-diethylamine-puerarin

3',5'-methylene-diethylamine-puerarin

Conditions
ConditionsYield
With pyridine; hydrogenchloride In methanol; water at 80℃; for 6h; Reagent/catalyst;67%
diisopropyl hydrogenphosphonate
1809-20-7

diisopropyl hydrogenphosphonate

puerarin
3681-99-0

puerarin

C27H33O12P

C27H33O12P

Conditions
ConditionsYield
With triethylamine In methanol; tetrachloromethane at 20℃; Atherton-Todd reaction;66.7%
bis(N-pyrrolidinyl)methane
7309-47-9

bis(N-pyrrolidinyl)methane

puerarin
3681-99-0

puerarin

3'-methylene-morpholine-puerarin

3'-methylene-morpholine-puerarin

Conditions
ConditionsYield
With pyridine; hydrogenchloride In methanol; water at 100℃; for 8h; Reagent/catalyst;65%
bis-(dimethylamino)methane
51-80-9

bis-(dimethylamino)methane

puerarin
3681-99-0

puerarin

3'-methylene-dimethylamine-puerarin

3'-methylene-dimethylamine-puerarin

Conditions
ConditionsYield
With pyridine; hydrogenchloride In methanol; water at 60℃; for 4h; Reagent/catalyst;65%
puerarin
3681-99-0

puerarin

C21H17(2)H3O9

C21H17(2)H3O9

Conditions
ConditionsYield
Stage #1: puerarin With [D]-sodium hydroxide; platinum on activated charcoal; water-d2 at 130℃; for 8h; Inert atmosphere;
Stage #2: With formic acid at 130℃; for 1h; Inert atmosphere;		65%
succinic acid anhydride
108-30-5

succinic acid anhydride

puerarin
3681-99-0

puerarin

C25H23O12(1-)*Na(1+)

C25H23O12(1-)*Na(1+)

Conditions
ConditionsYield
With dmap In dichloromethane for 24h; Reflux;63.3%
acetyl chloride
75-36-5

acetyl chloride

puerarin
3681-99-0

puerarin

7-O-acetyl puerarin
934696-10-3

7-O-acetyl puerarin

Conditions
ConditionsYield
With potassium carbonate In acetone at 20℃;63%
C6H13ClN2O

C6H13ClN2O

puerarin
3681-99-0

puerarin

C27H32N2O10

C27H32N2O10

Conditions
ConditionsYield
With sodium hydrogencarbonate In dichloromethane at 10℃; for 24h;62%
diisobutyl phosphite
1189-24-8

diisobutyl phosphite

puerarin
3681-99-0

puerarin

C29H37O12P

C29H37O12P

Conditions
ConditionsYield
With triethylamine In methanol; tetrachloromethane at 20℃; Atherton-Todd reaction;61.7%
O-[(α-D-mannopyranosyl)-(1->6)-(α-D-mannopyranosyl)-(1->3)-β-D-mannopyranosyl]-(1->4)-(1,2-dideoxy-α-D-glucopyrano)-[2,1-d]-2-methyloxazoline
861695-58-1

O-[(α-D-mannopyranosyl)-(1->6)-(α-D-mannopyranosyl)-(1->3)-β-D-mannopyranosyl]-(1->4)-(1,2-dideoxy-α-D-glucopyrano)-[2,1-d]-2-methyloxazoline

puerarin
3681-99-0

puerarin

C47H63NO29
1093135-90-0

C47H63NO29

Conditions
ConditionsYield
With endo-β-N-acetylglucosaminidase from Arthrobactor protophormiae In dimethyl sulfoxide at 23℃; for 2h; pH=7.0; aq. phosphate buffer; Enzymatic reaction;60%
2-Methoxypropene
116-11-0

2-Methoxypropene

puerarin
3681-99-0

puerarin

C24H24O9
934696-19-2

C24H24O9

Conditions
ConditionsYield
With toluene-4-sulfonic acid In acetone at 0 - 20℃;59%
di-n-propyl phosphonate
1809-21-8

di-n-propyl phosphonate

puerarin
3681-99-0

puerarin

C27H33O12P

C27H33O12P

Conditions
ConditionsYield
With triethylamine In methanol; tetrachloromethane at 20℃; Atherton-Todd reaction;58.3%
di(N-piperidinyl)methane
880-09-1

di(N-piperidinyl)methane

puerarin
3681-99-0

puerarin

3'-methylene-hexahydropyridine-puerarin

3'-methylene-hexahydropyridine-puerarin

Conditions
ConditionsYield
With pyridine; hydrogenchloride In methanol; water at 80℃; for 8h; Reagent/catalyst;56%
dibutyl hydrogen phosphite
1809-19-4

dibutyl hydrogen phosphite

puerarin
3681-99-0

puerarin

C29H37O12P

C29H37O12P

Conditions
ConditionsYield
With triethylamine In methanol; tetrachloromethane at 20℃; Atherton-Todd reaction;53.3%
methyl chloroformate
79-22-1

methyl chloroformate

puerarin
3681-99-0

puerarin

10-O-methoxyformyl puerarin
934696-16-9

10-O-methoxyformyl puerarin

Conditions
ConditionsYield
With potassium carbonate In acetone at 20℃;53%

Puerarin Chemical Properties

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

Puerarin Toxicity Data With Reference

RTECS  UO5216000

Puerarin 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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