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B3251

Sigma-Aldrich

Berberine chloride form

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Synonym(s):
Benzodioxide, Berberine HCl, Natural Yellow 18
Empirical Formula (Hill Notation):
C20H18ClNO4
CAS Number:
633-65-8
Molecular Weight:
371.81
Colour Index Number:
75160
Beilstein:
3836585
EC Number:
211-195-9
MDL number:
MFCD00011939
PubChem Substance ID:
24891691
NACRES:
NA.32

form

powder

Quality Level

200

solubility

methanol: soluble

SMILES string

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

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This Item
20027500900585Y0001149
Berberine chloride form

Sigma-Aldrich

B3251

Berberine chloride form

Berberine Chloride 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).

Sigma-Aldrich

200275

Berberine Chloride

Berberine chloride primary reference standard

00900585

Berberine chloride

Berberine chloride European Pharmacopoeia (EP) Reference Standard

Y0001149

Berberine chloride

solubility

methanol: soluble

solubility

water: 1 mg/mL, DMSO: 10 mg/mL

solubility

-

solubility

-

General description

Berberine Chloride form or Natural Yellow 18, is also known as 5,6-dihydro-9,10-dimethoxybenzo(g)-1,3-benzodioxolo (5,6-a) quinolizinium is a benzyl tetra isoquinoline plant alkaloid. Berberine contains a quaternary base and is commercially available in berberine chloride form.

Application

Berberine Chloride is a fluorescent stain used to stain heparin in mast cells. Berberine upregulates the expression of Pgp in hepatoma cells.
Fluorescent stain for heparin in mast cells

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.

Storage Class Code

11 - Combustible Solids

WGK

WGK 2

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Canadine phyproof® Reference Substance

PHL80378

Canadine

BERBERINE ACETONE ADDUCT AldrichCPR

S567574

BERBERINE ACETONE ADDUCT

Hydrastine phyproof® Reference Substance

PHL89511

Hydrastine

Dihydroberberine phyproof® Reference Substance

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BERBERINE BISULFATE AldrichCPR

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BERBERINE BISULFATE

Gil Belofsky et al.
Journal of natural products, 69(2), 261-264 (2006-02-28)
Two new 2-arylbenzofuran aldehydes (1 and 2) and three known phenolic compounds (3-5) were isolated from organic extracts of Dalea spinosa. These compounds were evaluated for their intrinsic antimicrobial activity and their ability to perform as multidrug-resistance inhibitors by potentiating
Siritron Samosorn et al.
Bioorganic & medicinal chemistry, 17(11), 3866-3872 (2009-05-08)
Conjugation of the NorA substrate berberine and the NorA inhibitor 5-nitro-2-phenyl-1H-indole via a methylene ether linking group gave the 13-substituted berberine-NorA inhibitor hybrid, 3. A series of simpler arylmethyl ether hybrid structures were also synthesized. The hybrid 3 showed excellent
Inhibitors of prolyl oligopeptidases for the therapy of human diseases: defining diseases and inhibitors.
Janice Lawandi et al.
Journal of medicinal chemistry, 53(9), 3423-3438 (2010-01-12)
Yan Ma et al.
Bioorganic & medicinal chemistry, 16(16), 7582-7591 (2008-08-05)
A series of 9-N-substituted berberine derivatives (2a-j) were synthesized and evaluated as a new class of G-quadruplex binding ligands. G-quadruplex of DNA had been proven to be the transcription controller of human c-myc gene. The interaction of 9-N-substituted berberine derivatives
Anding Shi et al.
Bioorganic & medicinal chemistry, 19(7), 2298-2305 (2011-03-15)
A series of novel triazole-containing berberine derivatives were synthesized via the azide-alkyne cycloaddition reaction. Their biological activity as inhibitors of both acetylcholinesterase (AChE) and butyrylcholinesterase (BuChE) were evaluated. Among them, compound 16d, which featured a diisopropylamino substitution at the 4-position
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