Jatrorrhizine

Base Information

• Chemical Name: Jatrorrhizine
• CAS No.: 3621-38-3
• Molecular Formula: C20H20NO4
• Molecular Weight: 338.383
• Hs Code.: 2933990090
• European Community (EC) Number: 222-817-3
• UNII: 091S1F8V5Q
• DSSTox Substance ID: DTXSID40189767
• Wikipedia: Jatrorrhizine
• Wikidata: Q10910369
• Metabolomics Workbench ID: 67877
• ChEMBL ID: CHEMBL251055
• Mol file: 3621-38-3.mol

Synonyms:jatrorrhizine;jatrorrhizine chloride

Chemical Property of Jatrorrhizine

Chemical Property:

• Melting Point: 208～210℃
• PSA: 51.80000
• LogP: 3.08180
• Storage Temp.: 2-8°C
• Solubility.: Methanol (Slightly, Heated)
• XLogP3: 3.4
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 3
• Exact Mass: 338.13923312
• Heavy Atom Count: 25
• Complexity: 461

Purity/Quality:

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

Jatrorrhizine chloride ^*data from reagent suppliers

Safty Information:

• Pictogram(s): N
• Hazard Codes: N
• Statements: 50
• Safety Statements: 61

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
• Description: An alkaloid from Mahonia nepalensis DC. (Syn. Berberis nepalensis Spreng), this base is optically inactive and forms garnet-red crystals which decompose on heat_x0002_ing. The base contains 3.5 mole of H20 and still retains 1 mole even or prolonged drying at 100°C in vacuo. The salts are said to be orange or yellow.
• Uses: Jatrorrhizine, is an alkaloid extract from the Berberidaceae family of plants displaying antioxidant activity.

Technology Process of Jatrorrhizine

There total 5 articles about Jatrorrhizine 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: 83.0%

C28H29NO6 → Jatrorrhizine (3621-38-3)

Guidance literature:

C₂₈H₂₉NO₆; With methanesulfonyl chloride; triethylamine; In dichloromethane; at 20 ℃; for 6h;

With trifluoroacetic acid; In dichloromethane; at 20 ℃; for 2h;

Reference yield:

palmatine (3486-67-7) → Jatrorrhizine (3621-38-3)

Guidance literature:

With water; diethylamine; In acetonitrile; at 35 - 175 ℃; for 0.333333h; Inert atmosphere;

Reference yield:

C10H8ClNO2 → Jatrorrhizine (3621-38-3)

Guidance literature:

Multi-step reaction with 3 steps

1.1: potassium carbonate / tetrahydrofuran / 65 °C

2.1: sodium carbonate; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; XPhos / toluene; ethanol / 12 h / 110 °C / Inert atmosphere

3.1: triethylamine; methanesulfonyl chloride / dichloromethane / 6 h / 20 °C

3.2: 2 h / 20 °C

With tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; sodium carbonate; potassium carbonate; methanesulfonyl chloride; triethylamine; XPhos; In tetrahydrofuran; ethanol; dichloromethane; toluene;

upstream raw materials:

palmatine

Downstream raw materials:

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

Refernces

• 1、 -. "Bamahongting derived from cortex phellodendri salt roasted product as well as separation and preparation method and application thereof". Paragraph 0024; 0030-0035. . Retrieved 2021/03/24.