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编号: 72927
• 分子式: C20H18ClNO4
• 平均质量: 371.81422
• 单一同位素质量: 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

名称和登记号

名称

• IUPAC标准名: 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传统名: 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
• 别名: 黄连素; 盐酸小檗碱 水合物; 氯化黄连素; 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

登记号

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

理论计算性质

• 质子受体: 4
• 质子供体: 0
• LogD (pH = 5.5): -1.2833123
• LogD (pH = 7.4): -1.2833123
• Log P: -1.2833123
• 摩尔折射率: 93.5233 cm^3
• 极化性: 38.453724 Å^3
• 极化表面积: 40.8 Å^2
• 可自由旋转的化学键: 2
• 里宾斯基五规则: true

分子性质

理化性质

• 溶解度: DMSO; Methanol
• 外观: Pale Yellow Solid
• 熔点: 193-196°C (dec.); 204-206 °C (dec.); ca 200°C dec.

安全信息

• 保存条件: -20°C; Refrigerator; Room Temperature (15-30°C)
• 保存注意事项: Light Sensitive
• RTECS编号: DR9866400
• 欧盟危险性物质标志: 刺激性(Irritant) (Xi)
• 德国WGK号: 2
• 危险公开号: R:36/37/38
• 安全公开号: S:20-25-26-37/39
• TSCA收录: 是
• 个人保护装置: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

产品相关信息

• 纯度: ≥90% (AT); 97%, water <17%
• 级别: technical
• 成盐信息: Hydrochloride
• Empirical Formula (Hill Notation): C20H18ClNO4 · xH2O

详细说明

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

包装
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

参考文献

• 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)