Orellanine

Base Information

• Chemical Name: Orellanine
• CAS No.: 37338-80-0
• Molecular Formula: C10H8N2O6
• Molecular Weight: 252.183
• Hs Code.: 2933399090
• European Community (EC) Number: 805-586-9
• UNII: 082U1GSX3D
• Nikkaji Number: J18.373C
• Wikipedia: Orellanine
• Wikidata: Q420527
• ChEMBL ID: CHEMBL2152646
• Mol file: 37338-80-0.mol

Synonyms:orellanine

Chemical Property of Orellanine

Chemical Property:

• Boiling Point: 834.615 °C at 760 mmHg
• Flash Point: 458.558 °C
• PSA: 124.92000
• Density: 1.777 g/cm³
• LogP: -0.43720
• XLogP3: -1
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 1
• Exact Mass: 252.03823598
• Heavy Atom Count: 18
• Complexity: 507

Purity/Quality:

99%, ^*data from raw suppliers

Orellanine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: C1=CN(C(=C(C1=O)O)C2=C(C(=O)C=CN2O)O)O
• Recent ClinicalTrials: Study of Orellanine in Metastatic Clear-Cell or Papillary Renal Cell Carcinoma
• Recent EU Clinical Trials: A phase I/II, open label, single arm study on safety, tolerability and anti -tumour efficacy of orellanine treatment in patients with metastatic clear-cell or papillary renal cell carcinoma

Technology Process of Orellanine

There total 24 articles about Orellanine 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: 87.0%

orelline (72016-31-0) → 3,3',4,4'-tetrahydroxy-2,2'-bipyridine-1,1'-dioxide (37338-80-0)

Guidance literature:

With dihydrogen peroxide; for 8h; Ambient temperature;

DOI:10.1016/S0040-4020(01)87367-1

Reference yield: 77.0%

tetra-O-methylorellanine (101664-54-4) → 3,3',4,4'-tetrahydroxy-2,2'-bipyridine-1,1'-dioxide (37338-80-0)

Guidance literature:

With hydrogen bromide; acetic acid; for 5h; Heating;

Reference yield:

3,3',4,4'-tetramethoxy-2,2'-bipyridine (101664-55-5) → 3,3',4,4'-tetrahydroxy-2,2'-bipyridine-1,1'-dioxide (37338-80-0)

Guidance literature:

Multi-step reaction with 3 steps

1: m-chloroperbenzoic acid

2: m-chloroperbenzoic acid

3: 60 percent / 48percent HBr / 120 °C

With hydrogen bromide; 3-chloro-benzenecarboperoxoic acid;

upstream raw materials:

tetra-O-methylorellanine

orelline

3,3',4,4'-tetramethoxy-2,2'-bipyridine

2-bromo-3,4-dimethoxy pyridine

Downstream raw materials:

orelline

Refernces

• 1、 Tiecco,Tingoli,Testaferri,et al.. "Total synthesis of orellanine. The lethal toxin of Cortinarius orellanus Fries mushroom". . p. 1475 - 1485. Retrieved 2007/10/02.
• 2、 Dehmlow, Eckehard, V.,Schulz, Hans-Joachim. "SYNTHESIS OF ORELLANINE, THE LETHAL POISON OF A TOADSTOOL". . p. 4903 - 4906. Retrieved 2007/10/02.