633-65-8

Basic information

• Product Name: Berberine hydrochloride
• Synonyms: TIMTEC-BB SBB006488;NATURAL YELLOW 18 CHLORIDE;NATURAL YELLOW 18;UMBELLATINE;5,6-DIHYDRO-9,10-DIMETHOXY-BENZO[G]-1,3-BENZODIOXOLO[5,6-A]QUINOLIZINIUM, CHLORIDE;BERBERINE HCL;BERBERINE HYDROCHLORIDE;BERBERIN HCL
• CAS NO: 633-65-8
• Molecular Formula: C₂₀H₁₈NO₄*Cl
• Molecular Weight: 371.81
• EINECS: 211-195-9
• Product Categories: Natural Plant Extract;Aromatics;Heterocycles;Inhibitors;Intermediates & Fine Chemicals;Pharmaceuticals;Plant extracts;chemical reagent;pharmaceutical intermediate;phytochemical;reference standards from Chinese medicinal herbs (TCM).;standardized herbal extract
• Mol File: 633-65-8.mol

Chemical Properties

• Melting Point: 204-206 °C (dec.)
• Appearance: yellow crystalline powder
• Density: 1.654g/cm3
• Storage Temp.: +2C to +8C
• Solubility: methanol: soluble
• Water Solubility: SOLUBLE IN COLD WATER
• BRN: 3836585
• CAS DataBase Reference: Berberine hydrochloride(CAS DataBase Reference)
• NIST Chemistry Reference: Berberine hydrochloride(633-65-8)
• EPA Substance Registry System: Berberine hydrochloride(633-65-8)

Safety Data

• Hazard Codes: Xn
• Statements: 20/21/22-36/37/38
• Safety Statements: 24/25-36-26
• RIDADR: 1544
• WGK Germany: 2
• RTECS: DR9866400
• F: 3-10
• TSCA: Yes
• HazardClass: 6.1(b)
• PackingGroup: III
• Hazardous Substances Data: 633-65-8(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
Berberine hydrochloride is used as an active pharmaceutical ingredient for its various therapeutic properties, such as antiarrhythmic, alpha2 agonist, anticonvulsant, anti-inflammatory, antibacterial, antifungal, antitrypanosomal, antineoplastic, and immunostimulant activities. Its broad-spectrum action makes it a valuable compound in the development of drugs for treating a wide range of diseases and conditions.
Used in Ophthalmic Industry:
Berberine hydrochloride is used as an ingredient in some commercial eyewash products, where it can provide antibacterial and anti-inflammatory properties to help maintain eye health and hygiene.
Used in Cancer Prevention:
Berberine hydrochloride is used as a chemopreventive agent against colon tumor formation by inhibiting the enzyme cyclooxygenase-2 (COX-2), which is abundantly expressed in colon cancer cells. It also inhibits Activator Protein 1 (AP-1), a transcription factor that plays a critical role in inflammation and carcinogenesis. Treatment with berberine hydrochloride may potentially result in the reduced accumulation of chemotherapeutic drugs, thus offering a promising approach for cancer prevention and treatment.

Biochem/physiol Actions

An alkaloid with weak antibiotic properties. Substrate for MDR efflux pumps. Antimicrobial activities of berberine is potentiated by the MDR inhibitor 5′-methoxyhydnocarpin (5′-MHC). Berberine upregulates the expression of Pgp in hepatoma cells. Treatment with berberine potentially results in the reduced accumulation of chemotherapeutic drugs.

Safety Profile

Poison by intraperitoneal route.Slightly toxic by ingestion. Mutation data reported. Whenheated to decomposition it emits toxic vapors of NOx andCl-.

InChI:InChI=1/C20H18NO4.ClH/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;1H/q+1;

Upstream product

• 483-15-8 7,8-dihydroberberine 
• 1484-85-1 3,4-methylenedioxyphenylethylamine 
• 24677-78-9 2,3-dihydroxybenzaldehyde 
• 86-51-1 2,3-dimethyoxybenzaldehyde 
• 131543-46-9 Glyoxal 
• 120-80-9 benzene-1,2-diol 
• 274-09-9 Methylenedioxybenzene 
• 109032-33-9 1,2-bis(tert-butyldimethylsilanyloxy)-4-ethynylbenzene 

Downstream Products

• 60716-41-8 N-benzylberberine chloride 
• 89369-10-8 2-[Hexylsulfanyl-(5-oxo-7,8-dihydro-5H-[1,3]dioxolo[4,5-g]isoquinolin-6-yl)-methyl]-3,4-dimethoxy-benzaldehyde 
• 73777-77-2 polyberbine 
• 80759-05-3 3,4-Dimethoxy-2-[methoxy-(5-oxo-7,8-dihydro-5H-[1,3]dioxolo[4,5-g]isoquinolin-6-yl)-methyl]-benzaldehyde 
• 522-97-4 canadine 
• 522-97-4 (R)-(+)-canadine 
• 485-91-6 allocryptopine 
• 17388-19-1 berberrubine 
• 1297302-68-1 9-O-(4-methoxybenzoyl)berberrubine chloride 
• 1297302-70-5 9-O-(4-methylthiobenzoyl)berberrubine chloride 
• 1297302-80-7 9-O-(2,4-diflourobenzoyl)berberrubine chloride 
• 1297302-82-9 9-O-(3,4-diflourobenzoyl)berberrubine chloride 
• 1297302-84-1 9-O-(2-flouro-4-triflouromethylbenzoyl)berberrubine chloride 
• 1297302-86-3 9-O-(4-flouro-2-triflouromethylbenzoyl)berberrubine chloride 

Relevant articles and documents

Thermodynamic study on the effects of β-cyclodextrin inclusion with berberine

The fluorescence enhancement of berberine (Berb) as a result of complex with β-cyclodextrin (β-CD) is investigated. The association constants of α-CD and β-CD with Berb are 60 and 137 M-1 at 20°C in pH 7.20 aqueous solution. Effects of temperature on the forming inclusion complexes of β-CD with Berb have been examined through using fluorescence titration. Enthalpy and entropy values calculated from fluorescence data are -33.7 kJ·mol-1 and 74.3 J·mol-1·K-1, respectively. It was found that the dielectric constant of β-CD cavity is about 24 in a rough analogy with absolute alcohol. These results suggest that the extrusion of 'high energy water' molecules from the cavity of β-CD and hydrophobic interaction upon the inclusion complex formation are the main forces of the inclusion reaction. Effect of pH on the association of β-CD with Berb was also studied. Mechanism of the inclusion of β-CD with Berb is further studied by absorption and NMR measurements. Results show that β-CD forms a 1:1 inclusion complex with Berb.

Modular and Divergent Syntheses of Protoberberine and Protonitidine Alkaloids

A modularly convergent and divergent strategy was established for the family synthesis of both protoberberine and protonitidine alkaloids. The robust, scalable, and flexible synthetic route featured a collective preparation of protoberberine and protonitidine alkaloids from a common isoquinoline assembled from pyridyne as the key synthon, which was based on the selective N-C or C-C cyclization via distinct processes. Through the strategy, 20 protoberberine alkaloids, 5 protonitidine alkaloids, and 11 analogues with diverse substituents were comprehensively aquired.

The total synthesis of berberine and selected analogues, and their evaluation as amyloid beta aggregation inhibitors

The total synthesis of berberine and selected analogues. And their evaluation as amyloid β (Aβ) aggregation inhibitors is described. The key step in the synthesis, the assembly of the berberine framework, was accomplished using an intermolecular Heck reaction. Berberine analog 17 incorporating a tertiary amine moiety showed good anti Aβ aggregation activity, water solubility, and almost no toxicity to nerve cells.

A synthetic preparation method for small carbags hydrochloric acid

The present invention belongs to the field of organic chemistry, relates to a method of synthesizing berberine hydrochloride, comprising: S1: with 5-halo-o-quinoastearaldehyde and piperine ethylamine to obtain N- [2-(3,4-dimethoxyphenyl-5-yl) ethyl] -1- (5-halo-2,3-dimethoxybenzyl) methylimide; S2: to obtain 2- (3,4-diimoxyphenyl) -N- (5-bromo-2,3-dimethoxybenzyl) ethylamine; S3: to obtain 2-(3,4-dimethoxyphenyl) -N- (5-bromo-2 S4: to obtain 12-halogenated berberine derivative; S5: to obtain berberine. The present invention is free from the application of the by-product o-vanillin synthesis of o-resveratal raw material constraints, synthesis of 5- substitute o-resveratal and piperine ethylamine, and the use of the two preparation of berberine hydrochloride, with raw materials readily available, mild reaction conditions, easy to operate, high chemical yield, low cost and other advantages.

The ring formation mechanism in cyclization of berberine

Berberine hydrochloride is a natural alkaloid with significant antitumor activities against many types of cancer cells, can be synthesized by cyclic reaction with hydrochloride condensate and glyoxal as raw materials and copper chloride as catalyst. In this study, the transition and energy change for the each reaction step was calculated by the density functional theory program Dmol3 in Materials Studio 2017. and the results testified that there are two ring formation in the cycliztion process, and according to the result we proposed the mechanism of this cyclization reaction. We also use infrared and ultraviolet spectroscopy to monitor the reaction process in real time and prove the ring formation process. The reaction mechanism was firstly proposed at the basic results of above.

Merging C-H Vinylation with Switchable 6π-Electrocyclizations for Divergent Heterocycle Synthesis

Pyridinium-containing polyheterocycles exhibit distinctive biological properties and interesting electrochemical and optical properties and thus are widely used as drugs, functional materials, and photocatalysts. Here, we describe a unified two-step strategy by merging Rh-catalyzed C-H vinylation with two switchable electrocyclizations, including aza-6π-electrocyclization and all-carbon-6π-electrocyclization, for rapid and divergent access to dihydropyridoisoquinoliniums and dihydrobenzoquinolines. Through computation, the high selectivity of aza-electrocyclization in the presence of an appropriate "HCl"source under either thermal conditions or photochemical conditions is shown to result from the favorable kinetics and symmetries of frontier orbitals. We further demonstrated the value of this protocol by the synthesis of several complex pyridinium-containing polyheterocycles, including the two alkaloids berberine and chelerythrine.

Method for fully synthesizing berberine

The invention discloses a method for fully synthesizing berberine, and relates to a drug synthesis method. The method realizes the industrial full synthesis production of the berberine and is made from a bulk organic raw material catechol, the raw material is easily available, and the price is low; 2,3-dimethoxybenzaldehyde is obtained through selective formylation and methylation of the catechol;after a piperonyl ring is obtained through a catechol methylenenation reaction, piperonyl amine is synthesized through a one-step catalytic addition reaction, so that the synthesis steps of the piperonyl amine are shortened, the use of toxic cyanide is avoided, and the process is green and sustainable; condensation hydrogenation and salification reactions adopt a 'one-pot method', and thus the time and the energy are saved, and the cost is decreased. Industrialized full synthesis production of the berberine opens up large-scale production of the berberine, meets the clinical and research needs of the berberine in current anti-tumor, anti-blood pressure, anti-heart rhythm, blood sugar reduction, treatment of Alzheimer's disease and the like, provides effective drugs for reducing pain of patients, and has remarkable economic and social benefits.

A Unified Strategy for the Syntheses of the Isoquinolinium Alkaloids Berberine, Coptisine, and Jatrorrhizine

Total syntheses of the antibacterial alkaloids berberine, coptisine, and jatrorrhizine have been achieved in four steps through a unified route. The key step of this strategy is an efficient intramolecular Friedel-Crafts alkoxyalkylation which, following oxidation, establishes the isoquinolinium core of these natural products. Herein, the design and development of this synthetic strategy, which has enabled the shortest and most efficient syntheses of these alkaloids reported to date, is described.

Fibrauretine synthetic method (by machine translation)

The invention relates to O-vanillin (11) as the starting material, by the acylation reaction generating 2 - acetoxy - 3 - methoxybenzaldehyde (12), by the bromo, hydrolysis reaction to produce the 2 - hydroxy - 6 - bromo - 3 - methoxybenzaldehyde (13), produced by the methylation reaction 6 - bromo - 2, 3 - dimethoxy benzaldehyde (14), produced by the condensation reaction of 2 - (6 - bromo - 2, 3 - dimethoxyphenyl) - 1, 3 - dioxolane (15); and then to 3, 4 - dimethoxy acetic acid (21) as raw materials, generated by the reduction reaction of the 3, 4 - dimethoxy ethanol (22), the acylation reaction generated by 3, 4 - dimethoxy new valeric acid environmentally (23), the acylation reaction is generated by the 2 - ethoxy - 3, 4 - dimethoxy new valeric acid environmentally (24), intermediate (15) and (24) after coupling, cyclized two-step reaction process for preparing the target product fibrauretin. (by machine translation)

A room-temperature protocol to access isoquinolines through Ag(i) catalysed annulation of o-(1-alkynyl)arylaldehydes and ketones with NH4OAc: Elaboration to berberine and palmatine

An efficient and mild protocol for the direct construction of aryl- and alkyl-substituted isoquinolines has been realized through silver nitrate catalyzed aromatic annulation of o-(1-alkynyl)arylaldehydes and ketones with ammonium acetate. The salient feature of this methodology is that this annulation could be effected at room temperature leading to a wide range of isoquinoline derivatives in good to excellent yields. Additionally, this approach has been employed to the synthesis of biologically important isoquinoline alkaloids such as berberine and palmatine.