16,17-dimethoxy-5,7-dioxa-13λ5-azapentacyclo[11.8.0.02,10.04,8.015,20]henicosa-1(21),2(10),3,8,13,15,17,19-octaen-13-ylium chloride

• ChemBase ID: 72927
• Molecular Formular: C20H18ClNO4
• Molecular Mass: 371.81422
• Monoisotopic Mass: 371.09243574
• SMILES: c1c(c(c2c(c1)cc1[n+](c2)CCc2c1cc1c(c2)OCO1)OC)OC.[Cl-]
• Canonical SMILES: COc1c(OC)ccc2c1c[n+]1CCc3c(c1c2)cc1c(c3)OCO1.[Cl-]
• InChI: 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

NAMES AND DATABASE IDS

Names

• IUPAC name: 16,17-dimethoxy-5,7-dioxa-13λ^5-azapentacyclo[11.8.0.0^2,^1^0.0^4,^8.0^1^5,^2^0]henicosa-1(21),2(10),3,8,13,15,17,19-octaen-13-ylium chloride; 16,17-dimethoxy-5,7-dioxa-13$l^{5}-azapentacyclo[11.8.0.0^{2,10}.0^{4,8}.0^{15,20}]henicosa-1(21),2,4(8),9,13,15,17,19-octaen-13-ylium chloride; 16,17-dimethoxy-5,7-dioxa-13$l^{5}-azapentacyclo[11.8.0.0^{2,10}.0^{4,8}.0^{15,20}]henicosa-1(21),2(10),3,8,13,15,17,19-octaen-13-ylium chloride
• IUPAC Traditional name: 16,17-dimethoxy-5,7-dioxa-13λ^5-azapentacyclo[11.8.0.0^2,^1^0.0^4,^8.0^1^5,^2^0]henicosa-1(21),2(10),3,8,13,15,17,19-octaen-13-ylium chloride; berberine chloride; 16,17-dimethoxy-5,7-dioxa-13$l^{5}-azapentacyclo[11.8.0.0^{2,10}.0^{4,8}.0^{15,20}]henicosa-1(21),2(10),3,8,13,15,17,19-octaen-13-ylium chloride
• Synonyms: Berberine chloride form; 5,6-Dihydro-9,10-dimethoxybenzo[g]-1,3-benzodioxolo[5,6-a]quinolizinium Chloride; Berberine Chloride; 7,8,13,13a-Tetradehydro-9,10-dimethoxy-2,3-(methylenedioxy)berbinium Chloride; Berberine Hydrochloride; NSC 646666; Natural Yellow 18; C.I. 75160; BERBERINE CHLORIDE; Berberine chloride hydrate; Berberine Hydrochloride; 黄连素; 盐酸小檗碱 水合物; 氯化黄连素

Database IDs

• CAS Number: 633-65-8; 141433-60-5
• EC Number: 211-195-9
• MDL Number: MFCD00011939; MFCD00149998
• Beilstein Number: 3836585
• Merck Index: 141154
• PubChem SID: 24848471; 24891691; 162037847
• PubChem CID: 12456
• Color Index Number: 75160

CALCULATED PROPERTIES

• H Acceptors: 4
• H Donor: 0
• LogD (pH = 5.5): -1.2833123
• LogD (pH = 7.4): -1.2833123
• Log P: -1.2833123
• Molar Refractivity: 93.5233 cm^3
• Polarizability: 38.453724 Å^3
• Polar Surface Area: 40.8 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO; Methanol
• Apperance: Pale Yellow Solid
• Melting Point: 193-196°C (dec.); 204-206 °C (dec.); ca 200°C dec.

Safety Information

• Storage Condition: -20°C; Refrigerator; Room Temperature (15-30°C)
• Storage Warning: Light Sensitive
• RTECS: DR9866400
• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 2
• Risk Statements: R:36/37/38
• Safety Statements: S:20-25-26-37/39
• TSCA Listed: 是
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

Product Information

• Purity: ≥90% (AT); 97%, water <17%
• Grade: technical
• Salt Data: Hydrochloride
• Empirical Formula (Hill Notation): C20H18ClNO4 · xH2O

DETAILS

MP Biomedicals - 02195857

Chloride
Apoptosis Inhibitor.

Selleck Chemicals - S2271

Research Area: Cancer
Biological Activity:
Berberine is a quaternary ammonium salt from the group of isoquinoline alkaloids. It is found in such plants as Berberis, goldenseal (Hydrastis canadensis), and Coptis chinensis, usually in the roots, rhizomes, stems, and bark. Berberine is strongly yellow colored, which is why in earlier times berberis species were used to dye wool, leather and wood. Wool is still today dyed with berberine in Northern India. Under ultraviolet light, berberine shows a strong yellow fluorescence.[1] It inhibited the expression of IL-1beta and TNF-alpha in periodontal tissues in rats periodontitis model and promoted the regeneration of the periodontal tissues. [2]

Sigma Aldrich - B3251

Application
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.

Sigma Aldrich - 14050

Packaging
10, 50 g in glass bottle

Toronto Research Chemicals - B318150

An isoqinoline alkaloid shown to have a chemopreventive property against colon tumor formation by inhibiting the enzyme cyclooxygenase-2 (cox-2) which is abundantly expressed in colon cancer cells. Also inhibits Activator Protein 1 (AP-1), a transcription

REFERENCES

• Yu ZH et al. Hua Xi Kou Qiang Yi Xue Za Zhi. 2008 Feb;26(1):82-6.
• Zhang, X. et al.: Cancer Res., 70, 9895 (2010)
• Lin, H.L. et al.: Cancer 85, 1937(2010)
• Schumacher, M.A. et al.: Science, 294, 2158 (2010)
• Fukuda, K. et al.: J. Ethno., 66, 227(2010)