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
• Article Data: 16

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

Chemical Properties

yellow crystalline powder

Uses

Different sources of media describe the Uses of 633-65-8 differently. You can refer to the following data:
1. antiarrhythmic, alpha2 agonist, anticonvulsant, antiinflammatory, antibacterial, antifungal, antitrypanosomal, antineoplastic, immunostimulant
2. An isoqinoline alkaloid shown to have a chemopreventive property against colon tumor formation by inhibiting the enzyme cyclooxygenase-2 (cox-2) which is abundantly expressed in colon cancer cells. Al so inhibits Activator Protein 1 (AP-1), a transcription factor that plays a critical role in inflammation and carcinogenesis. Treatment with berberine potentially results in the reduced accumulation o f chemotherapeutic drugs.
3. An ingredient in some commercial eyewash products.

General Description

A highly potent and selective oxysterol EBI2 (GPR183) agonist (Kd) = 450 pM in a saturation binding assay, and EC50 = 140 pM over EC50 = 2.1 nM for its enantiomer, 7β,25-OHC, in a GTP-γS binding assay). Dose-dependently suppresses forskolin-induced cAMP accumulation in an EBI2-expressing SK-N-MC/CRE-β-galactosidase cell line (IC50 = 2 nM), but not in control cells. Stimulates migration of LPS-activated spleen B-cells and anti-CD3/CD28-activated CD4+ T-cells in a dose-dependent manner. In addition, pharmacological inhibition of its biosynthesis in vivo by Clotrimazole, a CYP7B1inhibitor, promotes the migration of adoptively transferred pre-activated B cells to the T/B boundary, mimicking the phenotype of pre-activated B cells in EBI2-deficient mice.

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 
• 289507-35-3 2-bromo-1-(6-bromobenzo[d][1,3]-dioxol-5-yl)ethan-1-one 
• 6543-34-6 benzo[1,3]dioxol-5-yl-acetaldehyde 
• 120-57-0 piperonal 
• 4512-88-3 7,8-dimethoxyisoquinolin-1(2H)-one 
• 7169-06-4 2,3-dimethoxybenzoyl chloride 
• 1521-38-6 2,3-dimethoxybenzoic acid 
• 119054-94-3 2-(2'-bromo-4',5'-methylenedioxyphenyl)ethanol 
• 1262680-50-1 C₁₀H₁₀O₃ 
• 75-09-2 dichloromethane 
• 549-21-3 oxyberberine 
• 109032-33-9 1,2-bis(tert-butyldimethylsilanyloxy)-4-ethynylbenzene 

Downstream Products

• 60716-41-8 N-benzylberberine chloride 
• 109855-57-4 Dihydro-8-(p-bromobenzyl)berberine 
• 1462359-81-4 C₃₀H₃₀NO₈S⁽¹⁺⁾*Cl^(1-) 
• 1462359-82-5 C₃₂H₃₄NO₉S⁽¹⁺⁾*Cl^(1-) 
• 1462359-80-3 C₂₈H₂₆NO₇S⁽¹⁺⁾*Cl^(1-) 
• 120834-89-1 7,14-dehydrocanadine 
• 2220-12-4 dehydrothalictricavine iodide 
• 2086-83-1 berberine 
• 96087-21-7 tetrahydrocoptisine hydrochloride 
• 50932-22-4 8-trichloromethyl dihydroberberine 
• 522-97-4 canadine 
• 522-97-4 (R)-(+)-canadine 
• 483-15-8 7,8-dihydroberberine 

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 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.