B3251
Berberine chloride form
Synonym(s):
Benzodioxide, Berberine HCl, Natural Yellow 18
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About This Item
Empirical Formula (Hill Notation):
C20H18ClNO4
CAS Number:
Molecular Weight:
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
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
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
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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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)
Danuta Tomkiewicz et al.
Antimicrobial agents and chemotherapy, 54(8), 3219-3224 (2010-05-26)
Hybrid antimicrobials containing an antibacterial linked to a multidrug resistance (MDR) pump inhibitor make up a promising new class of agents for countering efflux-mediated bacterial drug resistance. This study explores the effects of varying the relative orientation of the antibacterial
Ling Huang et al.
Bioorganic & medicinal chemistry, 18(3), 1244-1251 (2010-01-09)
By targeting the dual active sites of acetylcholinesterase (AChE), a new series of berberine derivatives was designed, synthesized, and evaluated as AChE inhibitors. Most of the derivatives inhibited AChE in the sub-micromolar range. Compound 8c, berberine linked with phenol by
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
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