Erythromycin A Oxime

Base Information

• Chemical Name: Erythromycin A Oxime
• CAS No.: 111321-02-9
• Molecular Formula: C37H68 N2 O13
• Molecular Weight: 748.953
• Mol file: 111321-02-9.mol

Synonyms:Oxacyclotetradecane,erythromycin deriv.; (9E)-Erythromycin A oxime; (E)-Erythromycin A oxime;(E)-Erythromycin oxime

Chemical Property of Erythromycin A Oxime

Chemical Property:

• Vapor Pressure: 7.27E-33mmHg at 25°C
• Melting Point: 156-166 °C
• Refractive Index: 1.552
• Boiling Point: 841°C at 760 mmHg
• PKA: 11.96±0.70(Predicted)
• Flash Point: 462.4°C
• PSA: 209.43000
• Density: 1.28g/cm³
• LogP: 2.04670
• Storage Temp.: Refrigerator
• Solubility.: Chloroform (Slightly), DMSO (Slightly), Ethanol (Slightly), Methanol (Slightly,

Purity/Quality:

99%, ^*data from raw suppliers

Erythromycin A oxime ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Description: (9E)-Erythromycin A oxime is a metabolite of the semisynthetic antibiotic roxithromycin .
• Uses: Intermediate of Azithromycin. Antibacterial agent. (9E)-Erythromycin A Oxime is a metabolite of Roxithromycin (R700850) in humans. It has anti-Helicobacter pylori activity Erythromycin A 9-oxime is a semi-synthetic analogue of erythromycin prepared as means of overcoming acid lability and improving oral absorption of erythromycin A while retaining comparable antibacterial and potency. Although not developed as a commercial product, erythromycin oxime was pivotal in the development of the ring expanded aza-erythromycins (e.g. azithromycin) and the oxime ethers (e.g. roxithromycin).

Technology Process of Erythromycin A Oxime

There total 4 articles about Erythromycin A Oxime 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: 100.0%

erythromycin (114-07-8) → erythromycin A 9-(E)-oxime (111321-02-9)

Guidance literature:

With hydroxylamine; acetic acid; In water; isopropyl alcohol; at 50 ℃; for 15h; Inert atmosphere;

DOI:10.1021/jm101593u

Reference yield:

→ Erythromycinoxim (13127-18-9,92470-22-9,111321-02-9,134931-01-4)

Guidance literature:

I, Hydroxylamin;

DOI:10.1016/S0040-4039(01)97664-6

Reference yield:

C37H68N2O13*CHNS → erythromycin A 9-(E)-oxime (111321-02-9)

Guidance literature:

With sodium hydroxide; In methanol; water; at 25 ℃; for 12h; pH=11; Solvent;

upstream raw materials:

erythromycin

Downstream raw materials:

C₄₃H₇₁ClN₂O₁₅S*ClH

C₃₇H₇₀N₂O₁₂

erythromycin A (9E)-(1-isopropoxycychex-1-yl)oxime

erythromycin A 9-[O-(3-phenoxypropyl)oxime]

Refernces

• 1、 Nam, Ghilsoo,Kim, Yang Soo,Choi, Kyung Il. "Synthesis and antibacterial activity of new 9-O-arylpropenyloxime ketolides". . p. 2671 - 2674. Retrieved 2010.
• 2、 Yang, Hongfen,Liu, Ke,Jin, Shouguang,Huigens III, Robert W.. "Design, synthesis and biological evaluation of a halogenated phenazine-erythromycin conjugate prodrug for antibacterial applications". . p. 1483 - 1487. Retrieved 2021.
• 3、 -. "HYDROGEN BOND FORMING FLUORO KETOLIDES FOR TREATING DISEASES". Page/Page column 31-32. . Retrieved 2012/03/27.