CAS Number633-65-8
Synonyms1,3-Benzodioxolo[5,6-a]benzo[g]quinolizinium, 5,6-dihydro-9,10-dimethoxy-, hydrochloride (1:1); EINECS 211-195-9; berberine hydrochloride; BERBERINE HCL; 5,6-dihydro-9,10-dimethoxy-1,3-benzodioxolo[5,6-a]benzo[g]quinolizinium chloride (1:1); MFCD00011939; 9,10-dimethoxy-5,6-dihydro[1,3]dioxolo[4,5-g]isoquino[3,2-a]isoquinolin-7-ium chloride; Berberine (chloride)
Molecular FormulaC20H18ClNO4
Molecular Weight371.81
Purity98.00%
Density1.654g/cm3
Melting Point200ºC
Appearancepowder
EINECS211-195-9
Symbol
Signal WordWarning
| Chemical & Physical Properties | |
|---|---|
| CAS Number | 633-65-8 |
| Catalog No. | 2A-9024620 |
| Chinese Name | 盐酸黄连素； 盐酸小檗碱 |
| Synonyms | 1,3-Benzodioxolo[5,6-a]benzo[g]quinolizinium, 5,6-dihydro-9,10-dimethoxy-, hydrochloride (1:1); EINECS 211-195-9; berberine hydrochloride; BERBERINE HCL; 5,6-dihydro-9,10-dimethoxy-1,3-benzodioxolo[5,6-a]benzo[g]quinolizinium chloride (1:1); MFCD00011939; 9,10-dimethoxy-5,6-dihydro[1,3]dioxolo[4,5-g]isoquino[3,2-a]isoquinolin-7-ium chloride; Berberine (chloride) |
| Molecular Formula | C20H18ClNO4 |
| Molecular Weight | 371.81 |
| Purity | 98.00 |
| Density | 1.654g/cm3 |
| Melting Point | 200ºC |
| Appearance | powder |
| Water Solubility | SOLUBLE IN COLD WATER |
| Storage Condition | Store in a cool, ventilated warehouse. Keep away f |
| Packaging | III |
| Application | Berberine hydrochloride can effectively inhibit the proliferation of various cancer cells, promote apoptosis, and affect the MAPK and Wnt/_beta_-catenin pathways. |
| EINECS | 211-195-9 |
| HTC | 3003409000 |
| PubChem ID | 24891691 |
| MDL Number | MFCD00011939 |
| SMILES | COC1=C(C=[N+](CCC2=C3C=C4C(OCO4)=C2)C3=C5)C5=CC=C1OC.[Cl-] |
| InChI | 1S/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;/p-1 |
| InChI Key | VKJGBAJNNALVAV-UHFFFAOYSA-M |
| Beilstein/REAXYS | 3836585 |
| NACRES Code | NA.32 |
| UNSPSC | 12171500 |
| Hazard Symbols | 6.1(b) |
| MSDS | msds/24620_1_633_65_8.pdf |
| Bioactivity | Berberine has shown to be effective in inhibiting cell proliferation and promoting apoptosis in various cancerous cells; MAPK and Wnt/β-catenin pathways affected by Berberine.IC50 value:Target: Anticancer agentThe plant-based alkaloid berberine has potential therapeutic applications for breast cancer, although a better understanding of the genes and cellular pathways regulated by this compound is needed to define the mechanism of its action in cancer treatment. In this review, the molecular targets of berberine in various cancers, particularly breast cancer, are discussed. Berberine was shown to be effective in inhibiting cell proliferation and promoting apoptosis in various cancerous cells. Some signaling pathways affected by berberine, including the MAP (mitogen-activated protein) kinase and Wnt/β-catenin pathways, are critical for reducing cellular migration and sensitivity to various growth factors [1]. Treatment with BBR(Berberine) in rats on the atherogenic diet reduced plasma total cholesterol and nonHDL cholesterol levels by 29%-33% and 31%-41%, respectively, with no significant differences being observed among the three doses [2]. Berberine induced both apoptotic and autophagic death of HepG2 cells, which was associated with a significant activation of AMPK and an increased expression of the inactive form of acetyl-CoA carboxylase (ACC) [3]. Berberine did not show major effects on viability of HEK-293 embryonic kidney and HCT116 colon carcinoma cells and was not toxic in concentrations up to 20 μM. Berberine inhibited β-catenin transcriptional activity and attenuated anchorage-independent growth. As a result of berberine treatment, cellular levels of active β-catenin were reduced concomitant with an increase in the expression of E-cadherin [4]. Related Catalog Signaling Pathways >> Stem Cell/Wnt >> β-catenin Signaling Pathways >> Stem Cell/Wnt >> Wnt Natural Products >> Alkaloid Research Areas >> Cancer References [1]. Jabbarzadeh Kaboli P, et al. Targets and mechanisms of berberine, a natural drug with potential to treat cancer with special focus on breast cancer. Eur J Pharmacol. 2014 Jun 26. pii: S0014-2999(14)00467-1. [2]. Wang Y, et al. Berberine decreases cholesterol levels in rats through multiple mechanisms, including inhibition of cholesterol absorption. Metabolism. 2014 Jun 4. pii: S0026-0495(14)00162-0. [3]. Yu R, et al. Berberine-induced apoptotic and autophagic death of HepG2 cells requires AMPK activation. Cancer Cell Int. 2014 Jun 11;14:49. [4]. Albring KF, et al. Berberine acts as a natural inhibitor of Wnt/β-catenin signaling--identification of more active 13-arylalkyl derivatives. Biofactors. 2013 Nov-Dec;39(6):652-62. Chemical & Physical Properties Density 1.654g/cm3 Melting Point 200ºC Molecular Formula C20H18ClNO4 Molecular Weight 372.822 Exact Mass 372.099701 PSA 40.80000 LogP 0.10030 InChIKey VKJGBAJNNALVAV-UHFFFAOYSA-M SMILES COc1ccc2cc3[n+](cc2c1OC)CCc1cc2c(cc1-3)OCO2.[Cl-] Water Solubility SOLUBLE IN COLD WATER |
| Use of | Properties Articles54 Name berberine chloride Synonym More Synonyms Berberine hydrochloride Biological Activity Related Catalog Signaling Pathways >> Stem Cell/Wnt >> β-catenin Signaling Pathways >> Stem Cell/Wnt >> Wnt Natural Products >> Alkaloid Research Areas >> Cancer References [1]. Jabbarzadeh Kaboli P, et al. Targets and mechanisms of berberine, a natural drug with potential to treat cancer with special focus on breast cancer. Eur J Pharmacol. 2014 Jun 26. pii: S0014-2999(14)00467-1. [2]. Wang Y, et al. Berberine decreases cholesterol levels in rats through multiple mechanisms, including inhibition of cholesterol absorption. Metabolism. 2014 Jun 4. pii: S0026-0495(14)00162-0. [4]. Albring KF, et al. Berberine acts as a natural inhibitor of Wnt/β-catenin signaling--identification of more active 13-arylalkyl derivatives. Biofactors. 2013 Nov-Dec;39(6):652-62. Chemical & Physical Properties Exact Mass 372.099701 PSA 40.80000 LogP 0.10030 InChIKey VKJGBAJNNALVAV-UHFFFAOYSA-M Water Solubility SOLUBLE IN COLD WATER |
| Transport Info | Shipping Name: UN |
| MSDS Transport Info | Module 14. Shipping information 14.1 UN dangerous goods number European Land Transport Dangerous Regulations: -International Maritime Dangerous Regulations: -International Air Transport Dangerous Regulations: - 14.2 United Nations shipping name European Land Transport Dangerous Regulations: Non-dangerous goods IMDG Code: Non-dangerous goods International air transport dangerous goods regulations: non-dangerous goods 14.3 Transport hazard categories European Land Transport Dangerous Regulations: -International Maritime Dangerous Regulations: -International Air Transport Dangerous Regulations: - 14.4 Package group European Land Transport Dangerous Regulations: -International Maritime Dangerous Regulations: -International Air Transport Dangerous Regulations: - 14.5 Environmental hazards European Land Transport Danger Regulations: No International Maritime Danger Regulations International Air Transport Danger Regulations: No Marine pollutants (yes/no): No 14.6 Special reminder to users No data available |
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