6,6',7-Trimethoxy-2,2'-dimethylberbaman-12-ol

Base Information

• Chemical Name: 6,6',7-Trimethoxy-2,2'-dimethylberbaman-12-ol
• CAS No.: 478-61-5
• Molecular Formula: C₃₇H₄₀N₂O₆
• Molecular Weight: 608.734
• European Community (EC) Number: 207-523-5
• NSC Number: 105131
• Wikipedia: Berbamine
• Wikidata: Q104978109
• NCI Thesaurus Code: C162341
• ChEMBL ID: CHEMBL1198334
• Mol file: 478-61-5.mol

Synonyms:(+)-berbamine;16h-1,24:6,9-dietheno-11,15-metheno-2H-pyrido(2',3':17,18)(1,11)dioxacycloeicosino(2,3,4-ij)isoquinolin-12-ol, 3,4,4a,5,16a,17,18,19-octahydro-21,22,26-trimethoxy-4,17-dimethyl-, (4aS,16aR)-;16h-1,24:6,9-dietheno-11,15-metheno-2H-pyrido(2',3':17,18)(1,11)dioxacycloeicosino(2,3,4-ij)isoquinolin-12-ol, 3,4,4a,5,16a,17,18,19-octahydro-21,22,26-trimethoxy-4,17-dimethyl-, (4aS-(4aR*,16aS*))-;16H-1,24:6,9-dietheno-11,15-metheno-2H-pyrido(2',3':17,18)(1,11)dioxacycloeicosino(2,3,4-ij)isoquinolin-12-ol, 3,4,4a,5,16a,17,18,19-octahydro-21,22,26-trimethoxy-4,17-dimethyl-, hydrochloride (1:2), (4aS,16aR)-;16H-1,24:6,9-dietheno-11,15-metheno-2H-pyrido(2',3':17,18)(1,11)dioxacycloeicosino(2,3,4-ij)isoquinolin-12-ol, 3,4,4a,5,16a,17,18,19-octahydro-21,22,26-trimethoxy-4,17-dimethyl-, hydrochloride, hydrate (1:1:4), (4aS,16aR)-;6,6',7-trimethoxy-2,2'-dimethylberbaman-12-ol;berbaman-12-ol, 6,6',7-trimethoxy-2,2'-dimethyl-;berbaman-12-ol, 6,6',7-trimethoxy-2,2'-dimethyl-, dihydrochloride;berbamine;berbamine dihydrochloride;berbamine hydrochloride;berbamine hydrochloride tetrahydrate;berbamine monohydrochloride;berbamine, (+);berbamine, (1'beta)-isomer;berbamine, (1beta)-isomer;berbamine, monohydrochloride, tetrahydrate;D-berbamine;penduline;pycnamine

Chemical Property of 6,6',7-Trimethoxy-2,2'-dimethylberbaman-12-ol

Chemical Property:

• Appearance/Colour: white crystal powder
• Vapor Pressure: 1.19E-20mmHg at 25°C
• Melting Point: 225°C
• Refractive Index: 1.601
• Boiling Point: 706.985 °C at 760 mmHg
• PKA: pKa (20°): 7.33 in aq methanol
• Flash Point: 381.371 °C
• PSA: 72.86000
• Density: 1.204 g/cm³
• LogP: 6.73520
• XLogP3: 6.1
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 3
• Exact Mass: 608.28863700
• Heavy Atom Count: 45
• Complexity: 963

Purity/Quality:

98%,99%, ^*data from raw suppliers

Berbamine ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi

MSDS Files:

Useful:

• Canonical SMILES: CN1CCC2=CC(=C3C=C2C1CC4=CC=C(C=C4)OC5=C(C=CC(=C5)CC6C7=C(O3)C(=C(C=C7CCN6C)OC)OC)O)OC
• Description: Berbamine is an alkaloid, separated from Berberidaceae, Menispermaceae, or Ranunculaceae plants. Most of Berberidaceae plants have medicinal value, including their root, root bark, and stem. The plants of Berberis L. and Mahonia Nutt. contain many alkaloids, the most important of which are berberine and a small amount of palmatine, jatrorrhizine, berbamine, oxyacanthine, and so on. These compounds have many biological activities and have been used to replace goldthread and golden cypress. Also they are well succedaneums of berberine in Chinese and Western medicine. Traditional Chinese medicine Oregon grape root has different therapeutic effects for dysentery, enteritis, children pneumonia, and chronic bronchitis. The major treatment diseases of Chinese mahonia are bacillary dysentery, acute gastritis, infectious hepatitis, pneumonia, tuberculosis, bronchitis, sore throat, and so on.
• Physical properties: Appearance: odorless and bitter white crystalline, powder, belongs to bisbenzylisoquinoline alkaloid. Melting point: 197–210?°C in petroleum ether. Solubility: easily soluble in dilute hydrochloric acid, sulfuric acid, ethanol, chloroform, and acetone; soluble in ether; slightly soluble in boiling water and petroleum ether; but insoluble in cold water, ammonia, sodium carbonate, and calcium hydroxide solution.
• Uses: antihypertensive, skeletal muscle relaxant
• Indications: Berbamine is contained in the 13th volume of the book, National Standards for Chemical Drugs.The current clinical dosage is berbamine hydrochloride tablets. It is used in the prevention and treatment of patients with cancer, which is due to radiotherapy- and chemotherapy-induced neutropenia or due to benzene poisoning, radioactive substances, and drug-induced neutropenia.
• Clinical Use: Berbamine is used for the prevention and treatment of cancer patients with neutropenia due to radiotherapy, chemotherapy , benzene poisoning, radioactive substances, and drug.

Technology Process of 6,6',7-Trimethoxy-2,2'-dimethylberbaman-12-ol

There total 1 articles about 6,6',7-Trimethoxy-2,2'-dimethylberbaman-12-ol 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:

→ berbamine (478-61-5,569-16-4,26137-45-1,64665-35-6)

Guidance literature:

Reference yield: 25.0%

berbamine (478-61-5,569-16-4,26137-45-1,64665-35-6) → (+)-penduline (26137-45-1)

Guidance literature:

With methanol; oxygen; at 40 ℃; for 24h; Product distribution; Mechanism; other bisbenzylisoquinoline alkaloids;

DOI:10.3987/COM-95-7155

Reference yield:

berbamine (478-61-5,569-16-4,26137-45-1,64665-35-6) → berbamine dihydrochloride (6078-17-7,26137-46-2,69475-26-9)

Guidance literature:

With hydrogenchloride; In water; for 0.5h; pH=1.5 - 3.5;

Downstream raw materials:

(+)-penduline

berbamine dihydrochloride

C₄₇H₅₁N₃O₇