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Merck

B3251

Berberine chloride form

Synonyme(s) :

Benzodioxide, Berberine HCl, Natural Yellow 18

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A propos de cet article

Formule empirique (notation de Hill) :
C20H18ClNO4
Numéro CAS:
Poids moléculaire :
371.81
EC Number:
211-195-9
UNSPSC Code:
12171500
NACRES:
NA.32
PubChem Substance ID:
MDL number:
Colour Index Number:
75160
Beilstein/REAXYS Number:
3836585
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InChI key

VKJGBAJNNALVAV-UHFFFAOYSA-M

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

SMILES string

COC1=C(C=[N+](CCC2=C3C=C4C(OCO4)=C2)C3=C5)C5=CC=C1OC.[Cl-]

form

powder

solubility

methanol: soluble

Quality Level

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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.

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.

Classe de stockage

11 - Combustible Solids

wgk

WGK 2

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)


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Consulter la Bibliothèque de documents

Ying-Hong Li et al.
Journal of medicinal chemistry, 52(2), 492-501 (2008-12-19)
Twenty-nine derivatives of berberine (1) or pseudoberberine (2) were designed, semisynthesized, and evaluated for their up-regulatory activity on the low-density-lipoprotein receptor (LDLR) expression. SAR analysis revealed that (i) the methylenedioxy group at the 2- and 3-position is an essential element
Xiaoling Zhang et al.
Cancer research, 70(23), 9895-9904 (2010-10-12)
Berberine, a natural product derived from a plant used in Chinese herbal medicine, is reported to exhibit anticancer effects; however, its mechanism of action is not clearly defined. Herein, we demonstrate that berberine induces apoptosis in acute lymphoblastic leukemia (ALL)
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)
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

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