Berberine supplier | CasNO.2086-83-1

Name
Berberine
EINECS 218-229-1
CAS No. 2086-83-1
Article Data11
CAS DataBase
Density 1.2976 (rough estimate)
Solubility SOLUBLE IN COLD WATER
Melting Point 204-206 °C (dec.)
Formula C₂₀H₁₈NO₄
Boiling Point 486.8°C (rough estimate)
Molecular Weight 336.367
Flash Point
Transport Information UN 1544
Appearance Yellow
Safety
Risk Codes
Molecular Structure
Hazard Symbols
Synonyms Berbinium,7,8,13,13a-tetradehydro-9,10-dimethoxy-2,3-(methylenedioxy)- (8CI);Umbellatine(6CI);Berbericine;Berberin;Majarine;Thalsine;Umbellatin;5,6-Dihydro-9,10-dimethoxybenzo[g]-1,3-benzodioxolo[5,6-a]quinolizinium;
PSA 40.80000
LogP 3.09630

Synthetic route

: 94272-86-3
C21H19NO6

: 2086-83-1
berberine

Conditions

Conditions	Yield
With sodium cyanoborohydride In methanol	96%

: 29074-38-2
canadine

: 2086-83-1
berberine

Conditions

Conditions	Yield
With iodine In ethanol at 20℃;	90%
Multi-step reaction with 2 steps 1.1: 81 percent / mCPBA / CHCl3 / 20 °C 2.1: TFAA / CH2Cl2 / -30 - 20 °C 2.2: NaOAc / CH2Cl2; H2O / 0.5 h / 20 °C View Scheme
With (S)-tetrahydroprotoberberine oxidase; tris hydrochloride at 37℃; for 2h; pH=8.8; Enzymatic reaction;

: 2-{6-[(7,8-dimethoxyisoquinolin-3-yl)]benzo[d][1,3]-dioxol-5-yl}ethanol

: 2086-83-1
berberine

Conditions

Conditions	Yield
With methanesulfonyl chloride; triethylamine In dichloromethane at 20℃; for 6h;	88%

: 151-50-8
potassium cyanide

: 75821-49-7
(+/-)-trans-canadine N-oxide

A: 2086-83-1
berberine

: (8S,14S)-(+/-)-8-cyanocanadine

Conditions

Conditions	Yield
Stage #1: (+/-)-trans-canadine N-oxide With trifluoroacetic anhydride In dichloromethane at -30 - 20℃; Elimination; Polonovski-Potier reaction; Stage #2: potassium cyanide With sodium acetate In dichloromethane; water at 20℃; for 0.5h; Addition; tautomerization; aromatization;	A n/a B 29%

...Expand

: 29074-38-2
canadine

A: 549-21-3
oxyberberine

B: 2086-83-1
berberine

C: 64939-64-6, 66408-44-4
3-<3,4-dihydro-1-oxo-6,7-(methylenedioxy)-2H-isoquinolin-2-yl>-4,5-dimethoxy-1(3H)-isobenzofuranone

Conditions

Conditions	Yield
With iodosylbenzene; tetra-(n-butyl)ammonium iodide In water; acetonitrile at 50℃; for 18h;	A 6% B 15% C 25%

...Expand

: 29074-38-2
canadine

A: 2086-83-1
berberine

B H2O2, H2O: H2O2, H2O

Conditions

Conditions	Yield
With (S)-protoberberine oxidase; oxygen Equilibrium constant; enzyme activity for the substrate;

: 113975-46-5
9,10-dimethoxy-5,6,7,8-tetrahydro-2H-1,3-dioxolano[4,5-g]isoquinolino[3,2-a]isoquinoline-8-carbonitrile

: 2086-83-1
berberine

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1.1: NaBH4 2.1: 81 percent / mCPBA / CHCl3 / 20 °C 3.1: TFAA / CH2Cl2 / -30 - 20 °C 3.2: NaOAc / CH2Cl2; H2O / 0.5 h / 20 °C View Scheme

: 633-65-8
berberine chloride

: 2086-83-1
berberine

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1.1: NaBH4 / methanol 2.1: 81 percent / mCPBA / CHCl3 / 20 °C 3.1: TFAA / CH2Cl2 / -30 - 20 °C 3.2: NaOAc / CH2Cl2; H2O / 0.5 h / 20 °C View Scheme
Multi-step reaction with 4 steps 1.1: 95 percent / methanol; H2O 2.1: NaBH4 3.1: 81 percent / mCPBA / CHCl3 / 20 °C 4.1: TFAA / CH2Cl2 / -30 - 20 °C 4.2: NaOAc / CH2Cl2; H2O / 0.5 h / 20 °C View Scheme
With sodium tetrahydroborate In pyridine at 20℃;

: 94272-85-2
C21H21NO6

: 2086-83-1
berberine

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 93 percent / silver carbonate / benzene / Heating 2: 96 percent / sodium cyanoborohydride / methanol View Scheme

: 84229-90-3
spirobenzylisoquinoline

: 2086-83-1
berberine

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: 94 percent / methanol / Ambient temperature 2: 93 percent / silver carbonate / benzene / Heating 3: 96 percent / sodium cyanoborohydride / methanol View Scheme

: 485-91-6
allocryptopine

: 2086-83-1
berberine

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: oxalyl dichloride / chloroform / 1 h / Reflux 2: dimethyl sulfoxide / 25.5 h / 115 - 120 °C View Scheme

: 47474-50-0
N-methyl-7,8-dihydroberberine

: 2086-83-1
berberine

Conditions

Conditions	Yield
In dimethyl sulfoxide at 115 - 120℃; for 25.5h;

: 483-15-8
7,8-dihydroberberine

: 2086-83-1
berberine

Conditions

Conditions	Yield
With iodine; potassium acetate In ethanol at 20℃; Inert atmosphere;	6.7 mg
Multi-step reaction with 2 steps 1: sodium tetrahydroborate / methanol / 2 h / 20 °C / Inert atmosphere 2: iodine / ethanol / 20 °C View Scheme
Multi-step reaction with 2 steps 1: diborane 2: iodine / ethanol / 20 °C View Scheme

: C21H21NO5

: 2086-83-1
berberine

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: Wilkinson's catalyst 2: iodine / ethanol / 20 °C View Scheme

: C21H20BrNO4

: 2086-83-1
berberine

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1: sodium formate; tetrakis(triphenylphosphine) palladium(0) / N,N-dimethyl-formamide; water / 1 h / 100 °C / Inert atmosphere 2: 9-borabicyclo[3.3.1]nonane dimer; sodium hydroperoxide 3: Wilkinson's catalyst 4: iodine / ethanol / 20 °C View Scheme
Multi-step reaction with 5 steps 1: sodium formate; tetrakis(triphenylphosphine) palladium(0) / N,N-dimethyl-formamide; water / 1 h / 100 °C / Inert atmosphere 2: tetrapropylammonium perruthennate; 4-methylmorpholine N-oxide / acetonitrile / 2 h / 50 °C / Inert atmosphere; Molecular sieve 3: Wilkinson's catalyst; diphenyl phosphoryl azide / diethylene glycol dimethyl ether / 12 h / 160 °C / Inert atmosphere 4: lithium aluminium tetrahydride; aluminum (III) chloride / diethyl ether / 2 h / Reflux; Inert atmosphere 5: potassium acetate; iodine / ethanol / 20 °C / Inert atmosphere View Scheme
Multi-step reaction with 6 steps 1: sodium formate; tetrakis(triphenylphosphine) palladium(0) / N,N-dimethyl-formamide; water / 1 h / 100 °C / Inert atmosphere 2: tetrapropylammonium perruthennate; 4-methylmorpholine N-oxide / acetonitrile / 2 h / 50 °C / Inert atmosphere; Molecular sieve 3: Wilkinson's catalyst; diphenyl phosphoryl azide / diethylene glycol dimethyl ether / 12 h / 160 °C / Inert atmosphere 4: lithium aluminium tetrahydride; aluminum (III) chloride / diethyl ether / 2 h / Reflux; Inert atmosphere 5: sodium tetrahydroborate / methanol / 2 h / 20 °C / Inert atmosphere 6: iodine / ethanol / 20 °C View Scheme
Multi-step reaction with 6 steps 1: sodium formate; tetrakis(triphenylphosphine) palladium(0) / N,N-dimethyl-formamide; water / 1 h / 100 °C / Inert atmosphere 2: tetrapropylammonium perruthennate; 4-methylmorpholine N-oxide / acetonitrile / 2 h / 50 °C / Inert atmosphere; Molecular sieve 3: Wilkinson's catalyst; diphenyl phosphoryl azide / diethylene glycol dimethyl ether / 12 h / 160 °C / Inert atmosphere 4: lithium aluminium tetrahydride; aluminum (III) chloride / diethyl ether / 2 h / Reflux; Inert atmosphere 5: diborane 6: iodine / ethanol / 20 °C View Scheme

: 94143-83-6
5,6,7,8-tetrahydro-[1,3]dioxolo[4,5-g]isoquinoline

: 2086-83-1
berberine

Conditions

Conditions	Yield
Multi-step reaction with 6 steps 1: copper(l) iodide; benzoic acid / toluene / 12 h / 80 °C / Inert atmosphere; Molecular sieve 2: potassium carbonate / methanol / 0.5 h / 20 °C / Inert atmosphere 3: sodium formate; tetrakis(triphenylphosphine) palladium(0) / N,N-dimethyl-formamide; water / 1 h / 100 °C / Inert atmosphere 4: 9-borabicyclo[3.3.1]nonane dimer; sodium hydroperoxide 5: Wilkinson's catalyst 6: iodine / ethanol / 20 °C View Scheme
Multi-step reaction with 7 steps 1: copper(l) iodide; benzoic acid / toluene / 12 h / 80 °C / Inert atmosphere; Molecular sieve 2: potassium carbonate / methanol / 0.5 h / 20 °C / Inert atmosphere 3: sodium formate; tetrakis(triphenylphosphine) palladium(0) / N,N-dimethyl-formamide; water / 1 h / 100 °C / Inert atmosphere 4: tetrapropylammonium perruthennate; 4-methylmorpholine N-oxide / acetonitrile / 2 h / 50 °C / Inert atmosphere; Molecular sieve 5: Wilkinson's catalyst; diphenyl phosphoryl azide / diethylene glycol dimethyl ether / 12 h / 160 °C / Inert atmosphere 6: lithium aluminium tetrahydride; aluminum (III) chloride / diethyl ether / 2 h / Reflux; Inert atmosphere 7: potassium acetate; iodine / ethanol / 20 °C / Inert atmosphere View Scheme
Multi-step reaction with 8 steps 1: copper(l) iodide; benzoic acid / toluene / 12 h / 80 °C / Inert atmosphere; Molecular sieve 2: potassium carbonate / methanol / 0.5 h / 20 °C / Inert atmosphere 3: sodium formate; tetrakis(triphenylphosphine) palladium(0) / N,N-dimethyl-formamide; water / 1 h / 100 °C / Inert atmosphere 4: tetrapropylammonium perruthennate; 4-methylmorpholine N-oxide / acetonitrile / 2 h / 50 °C / Inert atmosphere; Molecular sieve 5: Wilkinson's catalyst; diphenyl phosphoryl azide / diethylene glycol dimethyl ether / 12 h / 160 °C / Inert atmosphere 6: lithium aluminium tetrahydride; aluminum (III) chloride / diethyl ether / 2 h / Reflux; Inert atmosphere 7: sodium tetrahydroborate / methanol / 2 h / 20 °C / Inert atmosphere 8: iodine / ethanol / 20 °C View Scheme
Multi-step reaction with 8 steps 1: copper(l) iodide; benzoic acid / toluene / 12 h / 80 °C / Inert atmosphere; Molecular sieve 2: potassium carbonate / methanol / 0.5 h / 20 °C / Inert atmosphere 3: sodium formate; tetrakis(triphenylphosphine) palladium(0) / N,N-dimethyl-formamide; water / 1 h / 100 °C / Inert atmosphere 4: tetrapropylammonium perruthennate; 4-methylmorpholine N-oxide / acetonitrile / 2 h / 50 °C / Inert atmosphere; Molecular sieve 5: Wilkinson's catalyst; diphenyl phosphoryl azide / diethylene glycol dimethyl ether / 12 h / 160 °C / Inert atmosphere 6: lithium aluminium tetrahydride; aluminum (III) chloride / diethyl ether / 2 h / Reflux; Inert atmosphere 7: diborane 8: iodine / ethanol / 20 °C View Scheme

: 53811-50-0
6-bromo-2,3-dimethoxybenzaldehyde

: 2086-83-1
berberine

Conditions

Conditions	Yield
Multi-step reaction with 6 steps 1: copper(l) iodide; benzoic acid / toluene / 12 h / 80 °C / Inert atmosphere; Molecular sieve 2: potassium carbonate / methanol / 0.5 h / 20 °C / Inert atmosphere 3: sodium formate; tetrakis(triphenylphosphine) palladium(0) / N,N-dimethyl-formamide; water / 1 h / 100 °C / Inert atmosphere 4: 9-borabicyclo[3.3.1]nonane dimer; sodium hydroperoxide 5: Wilkinson's catalyst 6: iodine / ethanol / 20 °C View Scheme
Multi-step reaction with 7 steps 1: copper(l) iodide; benzoic acid / toluene / 12 h / 80 °C / Inert atmosphere; Molecular sieve 2: potassium carbonate / methanol / 0.5 h / 20 °C / Inert atmosphere 3: sodium formate; tetrakis(triphenylphosphine) palladium(0) / N,N-dimethyl-formamide; water / 1 h / 100 °C / Inert atmosphere 4: tetrapropylammonium perruthennate; 4-methylmorpholine N-oxide / acetonitrile / 2 h / 50 °C / Inert atmosphere; Molecular sieve 5: Wilkinson's catalyst; diphenyl phosphoryl azide / diethylene glycol dimethyl ether / 12 h / 160 °C / Inert atmosphere 6: lithium aluminium tetrahydride; aluminum (III) chloride / diethyl ether / 2 h / Reflux; Inert atmosphere 7: potassium acetate; iodine / ethanol / 20 °C / Inert atmosphere View Scheme
Multi-step reaction with 8 steps 1: copper(l) iodide; benzoic acid / toluene / 12 h / 80 °C / Inert atmosphere; Molecular sieve 2: potassium carbonate / methanol / 0.5 h / 20 °C / Inert atmosphere 3: sodium formate; tetrakis(triphenylphosphine) palladium(0) / N,N-dimethyl-formamide; water / 1 h / 100 °C / Inert atmosphere 4: tetrapropylammonium perruthennate; 4-methylmorpholine N-oxide / acetonitrile / 2 h / 50 °C / Inert atmosphere; Molecular sieve 5: Wilkinson's catalyst; diphenyl phosphoryl azide / diethylene glycol dimethyl ether / 12 h / 160 °C / Inert atmosphere 6: lithium aluminium tetrahydride; aluminum (III) chloride / diethyl ether / 2 h / Reflux; Inert atmosphere 7: sodium tetrahydroborate / methanol / 2 h / 20 °C / Inert atmosphere 8: iodine / ethanol / 20 °C View Scheme
Multi-step reaction with 8 steps 1: copper(l) iodide; benzoic acid / toluene / 12 h / 80 °C / Inert atmosphere; Molecular sieve 2: potassium carbonate / methanol / 0.5 h / 20 °C / Inert atmosphere 3: sodium formate; tetrakis(triphenylphosphine) palladium(0) / N,N-dimethyl-formamide; water / 1 h / 100 °C / Inert atmosphere 4: tetrapropylammonium perruthennate; 4-methylmorpholine N-oxide / acetonitrile / 2 h / 50 °C / Inert atmosphere; Molecular sieve 5: Wilkinson's catalyst; diphenyl phosphoryl azide / diethylene glycol dimethyl ether / 12 h / 160 °C / Inert atmosphere 6: lithium aluminium tetrahydride; aluminum (III) chloride / diethyl ether / 2 h / Reflux; Inert atmosphere 7: diborane 8: iodine / ethanol / 20 °C View Scheme

: C21H21NO4

: 2086-83-1
berberine

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: 9-borabicyclo[3.3.1]nonane dimer; sodium hydroperoxide 2: Wilkinson's catalyst 3: iodine / ethanol / 20 °C View Scheme
Multi-step reaction with 4 steps 1: tetrapropylammonium perruthennate; 4-methylmorpholine N-oxide / acetonitrile / 2 h / 50 °C / Inert atmosphere; Molecular sieve 2: Wilkinson's catalyst; diphenyl phosphoryl azide / diethylene glycol dimethyl ether / 12 h / 160 °C / Inert atmosphere 3: lithium aluminium tetrahydride; aluminum (III) chloride / diethyl ether / 2 h / Reflux; Inert atmosphere 4: potassium acetate; iodine / ethanol / 20 °C / Inert atmosphere View Scheme
Multi-step reaction with 5 steps 1: tetrapropylammonium perruthennate; 4-methylmorpholine N-oxide / acetonitrile / 2 h / 50 °C / Inert atmosphere; Molecular sieve 2: Wilkinson's catalyst; diphenyl phosphoryl azide / diethylene glycol dimethyl ether / 12 h / 160 °C / Inert atmosphere 3: lithium aluminium tetrahydride; aluminum (III) chloride / diethyl ether / 2 h / Reflux; Inert atmosphere 4: sodium tetrahydroborate / methanol / 2 h / 20 °C / Inert atmosphere 5: iodine / ethanol / 20 °C View Scheme
Multi-step reaction with 5 steps 1: tetrapropylammonium perruthennate; 4-methylmorpholine N-oxide / acetonitrile / 2 h / 50 °C / Inert atmosphere; Molecular sieve 2: Wilkinson's catalyst; diphenyl phosphoryl azide / diethylene glycol dimethyl ether / 12 h / 160 °C / Inert atmosphere 3: lithium aluminium tetrahydride; aluminum (III) chloride / diethyl ether / 2 h / Reflux; Inert atmosphere 4: diborane 5: iodine / ethanol / 20 °C View Scheme

: C24H28BrNO4Si

: 2086-83-1
berberine

Conditions

Conditions	Yield
Multi-step reaction with 5 steps 1: potassium carbonate / methanol / 0.5 h / 20 °C / Inert atmosphere 2: sodium formate; tetrakis(triphenylphosphine) palladium(0) / N,N-dimethyl-formamide; water / 1 h / 100 °C / Inert atmosphere 3: 9-borabicyclo[3.3.1]nonane dimer; sodium hydroperoxide 4: Wilkinson's catalyst 5: iodine / ethanol / 20 °C View Scheme
Multi-step reaction with 6 steps 1: potassium carbonate / methanol / 0.5 h / 20 °C / Inert atmosphere 2: sodium formate; tetrakis(triphenylphosphine) palladium(0) / N,N-dimethyl-formamide; water / 1 h / 100 °C / Inert atmosphere 3: tetrapropylammonium perruthennate; 4-methylmorpholine N-oxide / acetonitrile / 2 h / 50 °C / Inert atmosphere; Molecular sieve 4: Wilkinson's catalyst; diphenyl phosphoryl azide / diethylene glycol dimethyl ether / 12 h / 160 °C / Inert atmosphere 5: lithium aluminium tetrahydride; aluminum (III) chloride / diethyl ether / 2 h / Reflux; Inert atmosphere 6: potassium acetate; iodine / ethanol / 20 °C / Inert atmosphere View Scheme
Multi-step reaction with 7 steps 1: potassium carbonate / methanol / 0.5 h / 20 °C / Inert atmosphere 2: sodium formate; tetrakis(triphenylphosphine) palladium(0) / N,N-dimethyl-formamide; water / 1 h / 100 °C / Inert atmosphere 3: tetrapropylammonium perruthennate; 4-methylmorpholine N-oxide / acetonitrile / 2 h / 50 °C / Inert atmosphere; Molecular sieve 4: Wilkinson's catalyst; diphenyl phosphoryl azide / diethylene glycol dimethyl ether / 12 h / 160 °C / Inert atmosphere 5: lithium aluminium tetrahydride; aluminum (III) chloride / diethyl ether / 2 h / Reflux; Inert atmosphere 6: sodium tetrahydroborate / methanol / 2 h / 20 °C / Inert atmosphere 7: iodine / ethanol / 20 °C View Scheme
Multi-step reaction with 7 steps 1: potassium carbonate / methanol / 0.5 h / 20 °C / Inert atmosphere 2: sodium formate; tetrakis(triphenylphosphine) palladium(0) / N,N-dimethyl-formamide; water / 1 h / 100 °C / Inert atmosphere 3: tetrapropylammonium perruthennate; 4-methylmorpholine N-oxide / acetonitrile / 2 h / 50 °C / Inert atmosphere; Molecular sieve 4: Wilkinson's catalyst; diphenyl phosphoryl azide / diethylene glycol dimethyl ether / 12 h / 160 °C / Inert atmosphere 5: lithium aluminium tetrahydride; aluminum (III) chloride / diethyl ether / 2 h / Reflux; Inert atmosphere 6: diborane 7: iodine / ethanol / 20 °C View Scheme

: 75767-29-2
Oxyberberine-13-carboxaldehyde

: 2086-83-1
berberine

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: Wilkinson's catalyst; diphenyl phosphoryl azide / diethylene glycol dimethyl ether / 12 h / 160 °C / Inert atmosphere 2: lithium aluminium tetrahydride; aluminum (III) chloride / diethyl ether / 2 h / Reflux; Inert atmosphere 3: potassium acetate; iodine / ethanol / 20 °C / Inert atmosphere View Scheme
Multi-step reaction with 4 steps 1: Wilkinson's catalyst; diphenyl phosphoryl azide / diethylene glycol dimethyl ether / 12 h / 160 °C / Inert atmosphere 2: lithium aluminium tetrahydride; aluminum (III) chloride / diethyl ether / 2 h / Reflux; Inert atmosphere 3: sodium tetrahydroborate / methanol / 2 h / 20 °C / Inert atmosphere 4: iodine / ethanol / 20 °C View Scheme
Multi-step reaction with 4 steps 1: Wilkinson's catalyst; diphenyl phosphoryl azide / diethylene glycol dimethyl ether / 12 h / 160 °C / Inert atmosphere 2: lithium aluminium tetrahydride; aluminum (III) chloride / diethyl ether / 2 h / Reflux; Inert atmosphere 3: diborane 4: iodine / ethanol / 20 °C View Scheme

: 549-21-3
oxyberberine

: 2086-83-1
berberine

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: lithium aluminium tetrahydride; aluminum (III) chloride / diethyl ether / 2 h / Reflux; Inert atmosphere 2: potassium acetate; iodine / ethanol / 20 °C / Inert atmosphere View Scheme
Multi-step reaction with 3 steps 1: lithium aluminium tetrahydride; aluminum (III) chloride / diethyl ether / 2 h / Reflux; Inert atmosphere 2: sodium tetrahydroborate / methanol / 2 h / 20 °C / Inert atmosphere 3: iodine / ethanol / 20 °C View Scheme
Multi-step reaction with 3 steps 1: lithium aluminium tetrahydride; aluminum (III) chloride / diethyl ether / 2 h / Reflux; Inert atmosphere 2: diborane 3: iodine / ethanol / 20 °C View Scheme

: C10H8ClNO2

: 2086-83-1
berberine

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: potassium carbonate / tetrahydrofuran / 65 °C 2: sodium carbonate; tris-(dibenzylideneacetone)dipalladium(0); XPhos / toluene; ethanol / 12 h / 110 °C / Inert atmosphere 3: triethylamine; methanesulfonyl chloride / dichloromethane / 6 h / 20 °C View Scheme

: 3-chloro-7,8-dimethoxyisoquinoline

: 2086-83-1
berberine

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: sodium carbonate; tris-(dibenzylideneacetone)dipalladium(0); XPhos / toluene; ethanol / 12 h / 110 °C / Inert atmosphere 2: triethylamine; methanesulfonyl chloride / dichloromethane / 6 h / 20 °C View Scheme

: 2086-83-1
berberine

: 108275-17-8, 6847-93-4
berberrubine

Conditions

Conditions	Yield
In chloroform for 0.0833333h; microwave irradiation;	98%
In neat (no solvent) at 190℃; for 0.75h;	79%
at 180℃; for 1h;

: glycyrrhizic acid

: 2086-83-1
berberine

: C20H18NO4(1+)*C42H61O16(1-)

Conditions

Conditions	Yield
With sodium hydroxide In ethanol at 60 - 70℃; pH=7 - 8;	92%

: 471-53-4
enoxolone

: 2086-83-1
berberine

: C30H45O4(1-)*C20H18NO4(1+)

Conditions

Conditions	Yield
In ethanol at 60 - 70℃; pH=7 - 8;	86%

: 2086-83-1
berberine

: 29074-38-2
canadine

Conditions

Conditions	Yield
With indium; ammonium chloride In ethanol for 10h; Heating;	83%
With hydrogenchloride; zinc for 3h; Heating;	65%
With sodium tetrahydroborate
With sodium tetrahydroborate In water for 1h; Cooling with ice;
With sodium tetrahydroborate In methanol for 24.25h;

: 2086-83-1
berberine

: 483-15-8
7,8-dihydroberberine

Conditions

Conditions	Yield
With sodium tetrahydroborate; potassium carbonate; sodium hydroxide In methanol at 20℃; for 3h;	81%
With pyridine; sodium tetrahydroborate at 20℃; for 1h;
With sodium tetrahydroborate
With pyridine; sodium tetrahydroborate at 25℃;

: 2086-83-1
berberine

: 17388-19-1
berberrubine

Conditions

Conditions	Yield
With C60H54N2O10(2+) In N,N-dimethyl-formamide at 50 - 400℃; Solvent;	75%
at 190 - 200℃; under 20 - 30 Torr; for 0.5h;	75%
at 190 - 200℃; under 20 - 30 Torr; for 0.5h;	75%

: 2086-83-1
berberine

: 54313-01-8
Dehydro-berberubinium

Conditions

Conditions	Yield
at 190 - 200℃; under 20 - 30 Torr; for 0.5h;	75%

: Mangiferin

: 2086-83-1
berberine

: mangiferin-berberine salt

Conditions

Conditions	Yield
Stage #1: Mangiferin With sodium hydrogencarbonate In ethanol; water Stage #2: berberine In ethanol; water for 12h;	70.5%

: 5-(4-(2-bromoethoxy)benzyl)thiazolidine-2,4-dione

: 2086-83-1
berberine

: 9-(2-(4-((2,4-thiazolidinedione-5-yl)methyl)phenoxy)ethoxy)-O-berberine hydrobromide

Conditions

Conditions	Yield
With sodium hydride In dimethyl sulfoxide; mineral oil at 50℃; for 5h;	70%

: 5-(4-((2-bromoethyl)thio)benzyl)thiazolidine-2,4-dione

: 2086-83-1
berberine

: 9-(3-(4-((2,4-thiazolidinedione-5-yl)methyl)phenylthio)propoxy)-O-berberine hydrobromide

Conditions

Conditions	Yield
With sodium hydride In N,N-dimethyl-formamide at 50℃; for 8h;	69%

: 5-(4-(4-bromobutoxy)benzyl)thiazolidine-2,4-dione

: 2086-83-1
berberine

: 9-(4-(4-((2,4-thiazolidinedione-5-yl)methyl)phenoxy)butoxy)-O-berberine hydrobromide

Conditions

Conditions	Yield
With sodium hydride In dimethyl sulfoxide; mineral oil at 60℃; for 6h;	66%

: 5-(4-((4-bromobutyl)thio)benzyl)thiazolidine-2,4-dione

: 2086-83-1
berberine

: 9-(4-(4-((2,4-thiazolidinedione-5-yl)methyl)phenylthio)butoxy)-O-berberine hydrobromide

Conditions

Conditions	Yield
With sodium hydride In dimethyl sulfoxide; mineral oil at 55℃; for 7h;	65%

: 5-(4-((3-bromopropyl)thio)benzyl)thiazolidine-2,4-dione

: 2086-83-1
berberine

: 9-(3-(4-((2,4-thiazolidinedione-5-yl)methyl)phenylthio)butoxy)-O-berberine hydrobromide

Conditions

Conditions	Yield
With sodium hydride In dimethyl sulfoxide; mineral oil at 60℃; for 5h;	61.7%

: 124-13-0
Octanal

: 2086-83-1
berberine

: 947599-36-2
9,10-dimethoxy-13-octyl-5,6-dihydro-[1,3]dioxolo[4,5-g]isoquinolino[3,2-a]isoquinolin-7-ium chloride

Conditions

Conditions	Yield
Stage #1: berberine With sodium tetrahydroborate; potassium carbonate; sodium hydroxide In methanol at 20℃; for 2h; Stage #2: Octanal With acetic acid In ethanol at 90℃; for 6h;	51%

: 2086-83-1
berberine

A: 549-21-3
oxyberberine

B: 64939-64-6, 66408-44-4
3-<3,4-dihydro-1-oxo-6,7-(methylenedioxy)-2H-isoquinolin-2-yl>-4,5-dimethoxy-1(3H)-isobenzofuranone

C: 66408-27-3
13-hydroxy-8-oxo-berberine

Conditions

Conditions	Yield
With iodosylbenzene; tetra-(n-butyl)ammonium iodide In water; acetonitrile at 50℃; for 18h;	A 5% B 37% C 14%

...Expand

: 67-56-1
methanol

: 2086-83-1
berberine

: 61138-60-1
8-methoxyberberine phenolbetaine

Conditions

Conditions	Yield
(i) K3Fe(CN)6, (ii) /BRN= 1098229/, HCl; Multistep reaction;

: 67-56-1
methanol

: 2086-83-1
berberine

: 71733-98-7
1-[(3',4'-dimethoxy-2'-methylcarboxy)benzoyl]-6,7-methylenedioxyisoquinoline

Conditions

Conditions	Yield
(i) K3Fe(CN)6, (ii) Py*HCl, (iii) HCl, /BRN= 1098229/; Multistep reaction;

: 67-56-1
methanol

: 2086-83-1
berberine

: 71733-96-5, 95585-80-1
9,10,13a-trimethoxy-2,3-(methylenedioxy)-8,13-dioxo-5,6,13,13a-tetrahydro-8H-dibenzoquinolizine

Conditions

Conditions	Yield
(i) K3Fe(CN)6, (ii) Py*HCl, (iii) /BRN= 1098229/; Multistep reaction;

: 2086-83-1
berberine

: 71766-69-3
13a-hydroxy-9,10-dimethoxy-2,3-(methylenedioxy)-8,13-dioxo-5,6,13,13a-tetrahydro-8H-dibenzoquinolizine

Conditions

Conditions	Yield
(i) K3Fe(CN)6, (ii) Py*HCl; Multistep reaction;

: 2086-83-1
berberine

: 124-41-4
sodium methylate

: 60229-96-1
7,8-dihydro-8-methoxyberberine

Conditions

Conditions	Yield
In methanol Ambient temperature;

: 2086-83-1
berberine

: 3486-66-6
coptisine

Conditions

Conditions	Yield
Multistep reaction;

: 2086-83-1
berberine

: 80665-65-2
9,10-dimethoxy-2,3-methylenedioxy-8,14-cycloberbin-13-one

: 2086-83-1
berberine

: 67-64-1
acetone

: 39024-13-0
acetoneberberine

Conditions

Conditions	Yield
With alkali

: 2086-83-1
berberine

: 77-78-1
dimethyl sulfate

: 32245-50-4
9,10-dimethoxy-7-methyl-5,8-dihydro-6H-[1,3]dioxolo[4,5-g]isoquino[3,2-a]isoquinolinium; methyl sulfate

Berberine Specification

The Berberine, with the CAS registry number 2086-83-1, is also known as 5,6-Dihydro-9,10-dimethoxybenzo[g]-1,3-benzodioxolo[5,6-a]quinolizinium. Its EINECS number is 211-195-9. This chemical's molecular formula is C₂₀H₁₈NO₄ and molecular weight is 336.37. What's more, its systematic name is 9,10-Dimethoxy-5,6-dihydro[1,3]dioxolo[4,5-g]isoquinolino[3,2-a]isoquinolin-7-ium. Its classification code is Mutation data. This chemical is used in histology for staining heparin in mast cells because of a strong yellow fluorescence. As a traditional medicine or dietary supplement, it has showed some activity against fungal infections, Candida albicans, yeast, parasites and bacterial/viral infections. Berberine is considered as an ineffective antibiotic and is a component of some eye drop formulations.

Physical properties of Berberine are: (1)ACD/LogP: 0.053; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 0.05; (4)ACD/LogD (pH 7.4): 0.05; (5)ACD/BCF (pH 5.5): 1.00; (6)ACD/BCF (pH 7.4): 1.00; (7)ACD/KOC (pH 5.5): 25.46; (8)ACD/KOC (pH 7.4): 25.46; (9)#H bond acceptors: 5; (10)#H bond donors: 0; (11)#Freely Rotating Bonds: 2; (12)Polar Surface Area: 40.8 Å².

Preparation: this chemical can be prepared by C₂₁H₁₉NO₆. This reaction will need reagent sodium cyanoborohydride and solvent methanol. The yield is about 96%.

Berberine can be prepared by C21H19NO6

Uses of Berberine: it can be used to produce 9,10-dimethoxy-5,8,13,13a-tetrahydro-6H-[1,3]dioxolo[4,5-g]isoquino[3,2-a]isoquinoline by heating. It will need reagents In, aq. NH₄Cl and solvent ethanol with the reaction time of 10 hours. The yield is about 83%.

Berberine can be used to produce 9,10-dimethoxy-5,8,13,13a-tetrahydro-6H-[1,3]dioxolo[4,5-g]isoquino[3,2-a]isoquinoline by heating

You can still convert the following datas into molecular structure:
(1)SMILES: O1c2c(OC1)cc5c(c2)c4cc3ccc(OC)c(OC)c3c[n+]4CC5
(2)Std. InChI: InChI=1S/C20H18NO4/c1-22-17-4-3-12-7-16-14-9-19-18(24-11-25-19)8-13(14)5-6-21(16)10-15(12)20(17)23-2/h3-4,7-10H,5-6,11H2,1-2H3/q+1
(3)Std. InChIKey: YBHILYKTIRIUTE-UHFFFAOYSA-N

The toxicity data is as follows:

Organism	Test Type	Route	Reported Dose (Normalized Dose)	Source
mouse	LD50	oral	329mg/kg (329mg/kg)	Yakugaku Zasshi. Journal of Pharmacy. Vol. 82, Pg. 726, 1962.
mouse	LD50	subcutaneous	18mg/kg (18mg/kg)	Russian Pharmacology and Toxicology Vol. 31, Pg. 129, 1968.
rabbit	LDLo	subcutaneous	100mg/kg (100mg/kg)	"Abdernalden's Handbuch der Biologischen Arbeitsmethoden." Vol. 4, Pg. 1289, 1935.
rat	LD	intraperitoneal	> 500mg/kg (500mg/kg)	National Academy of Sciences, National Research Council, Chemical-Biological Coordination Center, Review. Vol. 5, Pg. 17, 1953.

Product Name

Berberine

Synthetic route

Berberine Specification

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