Name: Berberine
SKU: 2086-83-1

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Basic Information

Molecular Structure:
CAS No.:	2086-83-1
Name:	Berberine
Article Data:	11

Formula:	C₂₀H₁₈NO₄
Molecular Weight:	336.367
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;
EINECS:	218-229-1
Density:	1.2976 (rough estimate)
Melting Point:	204-206 °C (dec.)
Boiling Point:	486.8°C (rough estimate)
Solubility:	SOLUBLE IN COLD WATER
Appearance:	Yellow
Transport Information:	UN 1544
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

Raw Materials

633-65-8

29074-38-2

485-91-6

Downstream Products

483-15-8

3486-66-6

Total:126 Page 1 of 4 1 2 3 4 Next>>

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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.

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Specification