Berberine

Base Information

• Chemical Name: Berberine
• CAS No.: 2086-83-1
• Deprecated CAS: 100414-97-9,11048-54-7,66414-49-1
• Molecular Formula: C20H18NO4
• Molecular Weight: 336.367
• Hs Code.: 2934999090
• European Community (EC) Number: 218-229-1
• UNII: 0I8Y3P32UF
• DSSTox Substance ID: DTXSID9043857
• Nikkaji Number: J7.320B
• Wikipedia: Berberine
• Wikidata: Q176525
• NCI Thesaurus Code: C83551
• Pharos Ligand ID: 29GMVN86KTRH
• Metabolomics Workbench ID: 38321
• ChEMBL ID: CHEMBL295124
• Mol file: 2086-83-1.mol

Synonyms:Berberine;Umbellatine

Chemical Property of Berberine

Chemical Property:

• Appearance/Colour: Yellow
• Melting Point: 204-206 °C (dec.)
• Refractive Index: 1.5800 (estimate)
• Boiling Point: 486.8°C (rough estimate)
• PKA: 2.47(at 25℃)
• PSA: 40.80000
• Density: 1.2976 (rough estimate)
• LogP: 3.09630
• Storage Temp.: Inert atmosphere,Room Temperature
• Water Solubility.: SOLUBLE IN COLD WATER
• XLogP3: 3.6
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 2
• Exact Mass: 336.12358306
• Heavy Atom Count: 25
• Complexity: 488

Purity/Quality:

97% ^*data from raw suppliers

9,10-Dimethoxy-5,6-dihydro-[1,3]dioxolo-[4,5-g]isoquinolino[3,2-a]isoquinolin-7-ium 95+% ^*data from reagent suppliers

Safty Information:

• Safety Statements: S24/25 :

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Other Uses -> Biochemical Research
• Drug Classes: Herbal and Dietary Supplements
• Canonical SMILES: COC1=C(C2=C[N+]3=C(C=C2C=C1)C4=CC5=C(C=C4CC3)OCO5)OC
• Recent ClinicalTrials: Treatment Benefits of Berberine Supplementation for Women With PCOS
• Recent NIPH Clinical Trials: Berberine for the intestinal metaplasia after endoscopic therapy for early-stage gastric cancer
• Description: Coptis chinensis was widely used in China as a folk medicine by Shennong around 3000 BC. Coptis chinensis was firstly described in the ancient Chinese medical book The Divine Farmer’s Herb-Root Classic. Coptis chinensis was used to treat intestinal bacterial infections and antipyretic analgesic for thousands of years agoCoptis chinensis also called zhilian, chuanlian, weilian, jizhualian, shanglian, and xuanlian in Chinese history. Coptis chinensis was accepted by most physicians, and the Chinese pharmacopoeia also uses Coptis chinensis as its official name . Coptis chinensis mainly grows in Anhui, Hunan, Sichuan, and Yunnan and has been cultivated in Sichuan since the Ming dynasty, which has a long history of cultivation. Other species of Coptis chinensis from different places were used as medicine. However, commodity circulation of wild Rhizoma coptidis has not been formed . Coptis chinensis is national three level protection plants at present and majorly produced in Shizhu of Chongqing, West Hubei, Shanxi, and Gansu.Berberine is a quaternary ammonium salt from the protoberberine group of isoquinoline alkaloids. It is found in some plants such as huanglian 黄连 (Rhizoma coptidis), huangbo黄柏 (Phellodendri Chinensis Cortex), sankezhen三颗针 (Berberidis Radix), and so on.The components of Coptis chinensis which have antibacterial and antiinflammatory effects are original alkaloid berberine class, including berberine, coptisine, palmatine, epiberberine, columbamine, jatrorrhizine, worenine, and magnoflorine, with berberine having the highest content (5–8%).
• Physical properties: Appearance: Berberine is odorless and yellow crystalline powder. Solubility: Berberine is soluble in hot water, slightly soluble in water or ethanol and in chloroform, and insoluble in ether. Melting point: Melting point of berberine is about 204–206?°C.?Berberine is heat labile.
• Uses: Antiseptic drug.Treat intestinal infection caused from dysentery bacillus and E.coil
• Clinical Use: Rhizoma coptidis, as the digestive tract disease medication, has a history of more than 3000?years in China and India. Berberine, as a cathartic nonprescription drug, is mainly used in the treatment of intestinal infection clinically. Clinical research showed that berberine has hypoglycemic effect and has very good prevention and treatment for diabetic patients with complications such as hypertension, hyperlipidemia, thrombosis, and inflammationThere are few oral side effects of berberine hydrochloride, accidentally appears nausea, vomiting, rash, and fever, which can disappear after withdrawal of drug. In patients with hemolytic anemia and lack of glucose-6-phosphate dehydrogenase, it was forbidden to be used. Berberine if used intravenously is toxic, but is only suitable for oral drug delivery .

Technology Process of Berberine

There total 24 articles about Berberine which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 96.0%

C21H19NO6 (94272-86-3) → berberine (2086-83-1)

Guidance literature:

With sodium cyanoborohydride; In methanol;

Reference yield: 90.0%

canadine (29074-38-2) → berberine (2086-83-1)

Guidance literature:

With iodine; In ethanol; at 20 ℃;

DOI:10.1002/chem.201601245

Reference yield: 88.0%

2-{6-[(7,8-dimethoxyisoquinolin-3-yl)]benzo[d][1,3]-dioxol-5-yl}ethanol → berberine (2086-83-1)

Guidance literature:

With methanesulfonyl chloride; triethylamine; In dichloromethane; at 20 ℃; for 6h;

upstream raw materials:

C₂₁H₁₉NO₆

canadine

potassium cyanide

(+/-)-trans-canadine N-oxide

Downstream raw materials:

dimethoxy dihydroxy tetrahydroprotoberberine

berberrubine

Refernces

13-(2-methylbenzyl) berberine is a more potent inhibitor of MexXY-dependent aminoglycoside resistance than berberine

10.3390/antibiotics8040212

The research focused on synthesizing berberine derivatives to inhibit MexXY-dependent aminoglycoside resistance in Pseudomonas aeruginosa. The study synthesized 11 berberine derivatives and tested their inhibitory activities against MexXY in both MexXY-positive and MexXY-negative P. aeruginosa strains. The most potent derivative, 13-(2-methylbenzyl) berberine (13-o-MBB), was found to reduce the minimum inhibitory concentrations (MICs) of various aminoglycosides significantly in a multidrug-resistant P. aeruginosa strain. Experiments involved assessing MICs, determining fractional inhibitory concentration (FIC) indices to evaluate synergistic effects, and conducting time-kill assays to measure bactericidal activity. The analyses included NMR and mass spectrometry for compound characterization and CLSI standards for categorizing antibiotic susceptibility. The study concluded that 13-o-MBB is a more potent inhibitor of MexXY-dependent aminoglycoside resistance than berberine, offering a promising approach to overcoming antibiotic resistance in P. aeruginosa.

Structure-activity relationship of isoform selective inhibitors of Rac1/1b GTPase nucleotide binding

10.1016/j.bmcl.2009.08.037

The research aimed at synthesizing and evaluating a series of berberine, phenantridine, and isoquinoline derivatives for their inhibitory activity against Rho GTPase nucleotide binding, with a focus on the isoform selective inhibitors of Rac1/1b GTPase. The study concluded that the insertion of 19 amino acids in the Rac1b splice variant introduces a conformational difference that allows certain compounds, such as 4, 21, 22, and 26, to selectively inhibit Rac1b over Rac1. The chemicals used in the process included protoberberine series compounds like berberine, (±)-canadine, tetrahydroxy berberine analogs, and demethylene berberine, as well as phenantridine alkaloids like chelerythrine and sanguinarine, and 3-aryl-isoquinolines. These compounds were tested for their ability to inhibit Rac1, Rac1b, and Cdc42, with some showing selective inhibition and potential as isoform-selective Rac1b nucleotide binding inhibitors.