Protopine

Base Information

• Chemical Name: Protopine
• CAS No.: 130-86-9
• Molecular Formula: C20H19NO5
• Molecular Weight: 353.375
• Hs Code.: 29391900
• European Community (EC) Number: 204-999-6
• UNII: UIW569HT35
• DSSTox Substance ID: DTXSID90156282
• Nikkaji Number: J40.085H
• Wikipedia: Protopine
• Wikidata: Q390706
• Metabolomics Workbench ID: 38412
• ChEMBL ID: CHEMBL453019
• Mol file: 130-86-9.mol

Synonyms:4,6,7,14-tetrahydro-5-methyl-bis(1,3)benzodioxolo(4,5-c-5',6'-g)azecin-13(5H)-one;fumarine;protopine;protopine hydrochloride;protopine mesylate

Chemical Property of Protopine

Chemical Property:

• Appearance/Colour: Off-white solid
• Vapor Pressure: 4.86E-12mmHg at 25°C
• Melting Point: 211oC
• Refractive Index: 1.613
• Boiling Point: 547.479 °C at 760 mmHg
• Flash Point: 284.905 °C
• PSA: 57.23000
• Density: 1.324 g/cm³
• LogP: 2.49520
• Storage Temp.: Refrigerator
• Water Solubility.: Insoluble in water
• XLogP3: 2.8
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 0
• Exact Mass: 353.12632271
• Heavy Atom Count: 26
• Complexity: 542

Purity/Quality:

≥99% ^*data from raw suppliers

Protopine ^*data from reagent suppliers

Safty Information:

• Safety Statements: 24/25

MSDS Files:

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CN1CCC2=CC3=C(C=C2C(=O)CC4=C(C1)C5=C(C=C4)OCO5)OCO3
• Uses: Protopine is a Ca2+ channel blocker and antiplatelet agent. Immunomodulator

Technology Process of Protopine

There total 14 articles about Protopine 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: 78.0%

Dihydroprotopine (64191-02-2) → protopine (130-86-9)

Guidance literature:

With sodium acetate; pyridinium chlorochromate; In dichloromethane; at 20 ℃; for 2h;

DOI:10.1021/jo071038y

Reference yield: 50.0%

bis(2,3,9,10-dioxolo)-7-methyl-5,6,7,8-tetrahydrodibenzazecine N-oxide (128967-32-8) → protopine (130-86-9)

Guidance literature:

With hydrogenchloride; acetic acid; at 50 ℃; for 1h;

DOI:10.1002/jhet.5570270327

Reference yield:

1-[2-bromo-4,5-(methylenedioxy)benzyl]-7,8-(methylenedioxy)-3-methyl-1,2,4,5-tetrahydro-3H-3-benzazepin-2-one (952196-33-7) → protopine (130-86-9)

Guidance literature:

Multi-step reaction with 4 steps

1: 27 percent / P₂O₅; POCl₃ / 2 h / Heating

2: 99 percent / Rose Bengal; O₂ / methanol; CH₂Cl₂ / 0.33 h / 18 °C / UV-irradiation

3: 99 percent / LiAlH₄ / tetrahydrofuran / 15 h / Heating

4: 78 percent / NaOAc; pyridinium chlorochromate / CH₂Cl₂ / 2 h / 20 °C

With lithium aluminium tetrahydride; oxygen; sodium acetate; phosphorus pentoxide; rose bengal; pyridinium chlorochromate; trichlorophosphate; In tetrahydrofuran; methanol; dichloromethane;

DOI:10.1021/jo071038y

upstream raw materials:

bis(2,3,9,10-dioxolo)-7-methyl-5,6,7,8-tetrahydrodibenzazecine N-oxide

(S)-N-methylstylopine

Dihydroprotopine

1-[2-bromo-4,5-(methylenedioxy)benzyl]-7,8-(methylenedioxy)-3-methyl-1,2,4,5-tetrahydro-3H-3-benzazepin-2-one

Downstream raw materials:

protopine methiodide

dihydrosanguinarine

coptisine chloride

Stylopine

Refernces

Chemical evaluation of Betula species in Japan. I. Constituents of Betula ermanii

10.1248/cpb.43.1937

The research focused on the chemical evaluation of Betula species in Japan, specifically the constituents of Betula ermanii. The purpose of the study was to identify and characterize the chemical compounds present in different parts of the tree, including the fresh leaves, outer bark, inner bark, and root bark. The research concluded that the tree contained a variety of dammarane-type triterpenes, lignans, triterpenes, phenolics, and caffeoyl esters. Some of the key chemicals identified were 20(S),24(R)-epoxydammaran-3,11x,25-triol and its derivatives, betulin, betulin 3-caffeate, oleanolic acid, and various lignans such as (+)-lyoniresinol and (-)-lyoniresinol. The study also reported several new compounds, including 2, 3, 4, 6, 19, and 21, which were dammarane-type glycosides isolated for the first time from the leaves of Betula species. This comprehensive analysis of Betula ermanii's chemical constituents contributes to the understanding of its potential medicinal value, building on the known traditional uses of other Betula species in medicine and cosmetics.