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B3251

Sigma-Aldrich

Berberin Chlorid-Form

Synonym(e):

Natural Yellow 18

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About This Item

Empirische Formel (Hill-System):
C20H18ClNO4
CAS-Nummer:
633-65-8
Molekulargewicht:
371.81
Farbindexnummer:
75160
Beilstein:
3836585
EG-Nummer:
211-195-9
MDL-Nummer:
MFCD00011939
UNSPSC-Code:
12171500
PubChem Substanz-ID:
24891691
NACRES:
NA.32

Form

powder

Löslichkeit

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

InChIKey

VKJGBAJNNALVAV-UHFFFAOYSA-M

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Allgemeine Beschreibung

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.

Anwendung

Berberine Chloride is a fluorescent stain used to stain heparin in mast cells. Berberine upregulates the expression of Pgp in hepatoma cells.
Fluoreszenzfarbstoff für Heparin in Mastzellen

Biochem./physiol. Wirkung

Ein Alkaloid mit schwachen antibiotischen Eigenschaften. Substrat für MDR-Effluxpumpen. Antimikrobielle Aktivitäten von Berberin werden durch den MDR-Inhibitor 5´-Methoxyhydnocarpin (5´-MHC) potenziert. Berberin hochreguliert die Expression von Pgp in Hepatomzellen. Die Behandlung mit Berberin führt potenziell zu einer reduzierten Anreicherung von Chemotherapeutika.

Lagerklassenschlüssel

11 - Combustible Solids

WGK

WGK 2

Flammpunkt (°F)

Not applicable

Flammpunkt (°C)

Not applicable

Persönliche Schutzausrüstung

Eyeshields, Gloves, type N95 (US)

Analysenzertifikate (COA)

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Sigma-Aldrich

WH0001996M1

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Canadin phyproof® Reference Substance

PHL80378

Canadin

BERBERINE ACETONE ADDUCT AldrichCPR

S567574

BERBERINE ACETONE ADDUCT

Hydrastin phyproof® Reference Substance

PHL89511

Hydrastin

Dihydroberberin phyproof® Reference Substance

PHL80429

Dihydroberberin

BERBERINE BISULFATE AldrichCPR

S583634

BERBERINE BISULFATE

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)
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)
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
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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