Rifamycin O

Base Information

• Chemical Name: Rifamycin O
• CAS No.: 14487-05-9
• Molecular Formula: C39H47NO14
• Molecular Weight: 753.8
• European Community (EC) Number: 238-493-1
• DSSTox Substance ID: DTXSID201023447
• Metabolomics Workbench ID: 21318
• Wikidata: Q27101853
• Mol file: 14487-05-9.mol

Synonyms:rifamycin O

Chemical Property of Rifamycin O

Chemical Property:

• Appearance/Colour: Yellow solid
• Melting Point: 171°C (dec.)
• Refractive Index: 1.607
• Boiling Point: 972.841 °C at 760 mmHg
• PKA: 4.61±0.70(Predicted)
• Flash Point: 542.155 °C
• PSA: 213.45000
• Density: 1.366 g/cm³
• LogP: 3.50260
• Storage Temp.: -20?C Freezer, Under Inert Atmosphere
• XLogP3: 4.5
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 14
• Rotatable Bond Count: 3
• Exact Mass: 753.29965517
• Heavy Atom Count: 54
• Complexity: 1640

Purity/Quality:

99% ^*data from raw suppliers

Rifamycin O ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1C=CC=C(C(=O)NC2=CC3(C4=C(C2=O)C(=C(C5=C4C(=O)C(O5)(OC=CC(C(C(C(C(C(C1O)C)O)C)OC(=O)C)C)OC)C)C)O)OCC(=O)O3)C
• Isomeric SMILES: C[C@H]1/C=C/C=C(\C(=O)NC2=CC3(C4=C(C2=O)C(=C(C5=C4C(=O)[C@](O5)(O/C=C/[C@@H]([C@H]([C@H]([C@@H]([C@@H]([C@@H]([C@H]1O)C)O)C)OC(=O)C)C)OC)C)C)O)OCC(=O)O3)/C
• Uses: Rifamycin O (Rifaximin EP Impurity F) is a Rifaximin intermediate.

Technology Process of Rifamycin O

There total 3 articles about Rifamycin O 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: 94.0%

rifamycin B (13929-35-6) → rifamycin O (14487-05-9)

Guidance literature:

With manganese(IV) oxide; In benzene; for 0.0833333h; Ambient temperature;

DOI:10.1246/cl.1982.627

Reference yield: 80.0%

Rifamycin B (13929-35-6) → rifamycin O (14487-05-9)

Guidance literature:

With air; Ambient temperature;

DOI:10.1021/jm970791o

Reference yield:

Rifamycin B (13929-35-6) → rifamycin S (62623-68-1,76188-88-0,81203-58-9,101978-28-3,13553-79-2) + rifamycin O (14487-05-9)

Guidance literature:

With ammonium persulfate; In methanol; aq. phosphate buffer; at 60 ℃; for 4h; Solvent; Reagent/catalyst;

DOI:10.1021/acs.oprd.5b00070

upstream raw materials:

rifamycin B

Rifamycin B

Downstream raw materials:

rifamycin S

rifamycin S

4-[(2R)-2-((S)-1-hydroxy-ethyl)-pyrrolidin-1-yl]-4-deoxy-rifamycin

4-(2-methoxy-phenylimino)-1-oxo-1,4-dihydro-1,4-dideoxy-rifamycin

Refernces

• 1、 L?w, Sebastian A.,Nestl, Bettina M.,Weissenborn, Martin J.,Zepeck, Ferdinand,Hauer, Bernhard. "Process Investigations on the One-Pot Synthesis of Rifamycin S Avoiding Chlorinated Solvents". . p. 1544 - 1547. Retrieved 2015/12/01.