Berberine

• CAS: 2086-83-1
• Catalog Number: ACM2086831
• Category: Inhibitors
• Molecular Weight: 336.37
• Molecular Formula: C20H18NO4
• Description: Berberine (Natural Yellow 18) is an alkaloid isolated from the Chinese herbal medicine Huanglian, as an antibiotic. Berberine (Natural Yellow 18) induces reactive oxygen species (ROS) generation and inhibits DNA topoisomerase. Berberine (Natural Yellow 18) has antineoplastic properties.
• Synonyms: Berbericine
• IUPAC Name: 16,17-Dimethoxy-5,7-dioxa-13-azoniapentacyclo[11.8.0.02,10.04,8.015,20]henicosa-1(13),2,4(8),9,14,16,18,20-octaene
• Canonical SMILES: COC1=C(C2=C[N+]3=C(C=C2C=C1)C4=CC5=C(C=C4CC3)OCO5)OC
• InChI: InChI=1S/C20H18NO4/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/q+1
• InChI Key: YBHILYKTIRIUTE-UHFFFAOYSA-N
• Boiling Point: 486.8 °C
• Melting Point: 204-206 °C
• Density: 1.2976 g/cm³
• Appearance: White to yellow crystals
• Storage: Inert atmosphere, room temperature
• Complexity: 488
• Exact Mass: 336.12358306
• LogP: -0.99
• Monoisotopic Mass: 336.12358306
• pKa: 2.47(at 25 °C)
• PSA: 40.80000
• Refractive Index: 1.5800
• Shipping: Can be shipped at room temperature, where not in use may vary.
• Source: PlantsRanunculaceaeCoptis chinensis Franch.
• Topological Polar Surface Area: 40.8 Ų

Synthetic Use

Upstream Synthesis Route 1

• 29074-38-2

• 2086-83-1

Reference: [1] Chemistry - A European Journal, 2016, vol. 22, # 21, p. 7084 - 7089
[2] Tetrahedron, 2000, vol. 56, # 49, p. 9713 - 9723
[3] Journal of Biological Chemistry, 2012, vol. 287, # 51, p. 42972 - 42983

Upstream Synthesis Route 2

• 47474-50-0

• 2086-83-1

Reference: [1] Natural Product Research, 2014, vol. 28, # 7, p. 413 - 419

Upstream Synthesis Route 3

• 29074-38-2

• 549-21-3
• 2086-83-1
• 64939-64-6

Reference: [1] Helvetica Chimica Acta, 2002, vol. 85, # 4, p. 1069 - 1078

Downstream Synthesis Route 1

• 67-56-1
• 2086-83-1

• 61138-60-1

Reference: [1]Journal of the American Chemical Society,1976,vol. 98,p. 6714 - 6715

Downstream Synthesis Route 2

• 67-56-1
• 2086-83-1

• 71733-98-7

Reference: [1]Journal of Organic Chemistry,1979,vol. 44,p. 4343 - 4346

Downstream Synthesis Route 3

• 67-56-1
• 2086-83-1

• 71733-96-5

Reference: [1]Journal of Organic Chemistry,1979,vol. 44,p. 4343 - 4346

* For details of the synthesis route, please refer to the original source to ensure accuracy.