Jatrorrhizine hydrochloride

Base Information

• Chemical Name: Jatrorrhizine hydrochloride
• CAS No.: 6681-15-8
• Molecular Formula: C20H20 N O4 . Cl
• Molecular Weight: 373.836
• Hs Code.: 29399990
• European Community (EC) Number: 878-712-3
• NSC Number: 209410,150445,645313
• ChEMBL ID: CHEMBL274346
• Mol file: 6681-15-8.mol

Synonyms:jatrorrhizine;jatrorrhizine chloride

Chemical Property of Jatrorrhizine hydrochloride

Chemical Property:

• Melting Point: 208-210 °C(Solv: methanol (67-56-1))
• PSA: 51.80000
• LogP: 3.88380
• Storage Temp.: Inert atmosphere,Room Temperature
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 3
• Exact Mass: 373.1080858
• Heavy Atom Count: 26
• Complexity: 461

Purity/Quality:

95%-98% ^*data from raw suppliers

Jatrorrhizine chloride ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC1=C(C2=C[N+]3=C(C=C2C=C1)C4=CC(=C(C=C4CC3)O)OC)OC.[Cl-]
• Uses: Jaztorrhizine is an alkaloid extract from the Berberidaceae family of plants displaying antioxidant activity.

Technology Process of Jatrorrhizine hydrochloride

There total 2 articles about Jatrorrhizine hydrochloride 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:

2,9,10-trimethoxy-5,6-dihydroisoquinolino[2,1-b]isoquinolin-3-ol → jatrorrhizine hydrochloride (6681-15-8,960383-96-4)

Guidance literature:

2,9,10-trimethoxy-5,6-dihydroisoquinolino[2,1-b]isoquinolin-3-ol; With iodine; potassium acetate; In ethanol; at 20 ℃; for 1h; Inert atmosphere;

With hydrogenchloride; In methanol; water; Inert atmosphere;

DOI:10.1021/acs.orglett.8b01702

Reference yield:

5-(2-amino-ethyl)-2-methoxy-phenol (3213-30-7) + 2,3-dimethyoxybenzaldehyde (86-51-1) → jatrorrhizine hydrochloride (6681-15-8,960383-96-4)

Guidance literature:

Multi-step reaction with 2 steps

1.1: dichloromethane / 0.5 h / 20 °C / Inert atmosphere

1.2: 1 h / 0 °C / Inert atmosphere

2.1: potassium acetate; iodine / ethanol / 1 h / 20 °C / Inert atmosphere

2.2: Inert atmosphere

With iodine; potassium acetate; In ethanol; dichloromethane;

DOI:10.1021/acs.orglett.8b01702

Reference yield: 38.0%

jatrorrhizine hydrochloride (6681-15-8,960383-96-4) + Benzyl bromoacetate (5437-45-6) → 2,9,10-trimethoxy-3-benzyloxyformylmethylenoxyprotoberberine chloride

Guidance literature:

With potassium carbonate; In N,N-dimethyl-formamide;

DOI:10.3390/molecules23082084

upstream raw materials:

5-(2-amino-ethyl)-2-methoxy-phenol

2,3-dimethyoxybenzaldehyde

Downstream raw materials:

Jatrorrhizin

2,9,10-trimethoxy-berbin-3-ol

(+)-corypalmine

Refernces