Erythromycin A Enol Ether

Names

[ Name ]:
Erythromycin A Enol Ether

[Synonym ]:
9-Deoxo-6-deoxy-6,9-epoxy-8,9-didehydroerythromycin
8,9-anhydroerythromycin A 6,9-hemiacetal
6,9-Epoxy-8,9-didehydro-9-deoxo-6-deoxyerythromycin
8,9-anhydroerythromycin A 6,9-hemiketal
erythromycin hemiketal
8,9-anhydroerythromycin 6,9-hemiketal
6-Deoxy-9-deoxo-8,9-didehydro-6,9-epoxyerythromycin
8,9-anhydroerythromycin A
EM 523
Erythromycin Impurity 5

Biological Activity

[Description]:

Erythromycin A enol ether is an acidic degradation product of Erythromycin A (macrolide antibiotic) and has no antibacterial effect[1][2].

[Related Catalog]:

Research Areas >> Infection

Signaling Pathways >> Others >> Others

[References]

[1]. A Deubel, et al. Development of an enhanced separation of erythromycin and its related substances by liquid chromatography. J Pharm Biomed Anal. 2007 Jan 17;43(2):493-8.

[2]. Abdolreza Hassanzadeh, et al. Mechanism for the degradation of erythromycin A and erythromycin A 2'-ethyl succinate in acidic aqueous solution. J Phys Chem A. 2007 Oct 11;111(40):10098-104.

Chemical & Physical Properties

[ Density]:
1.2g/cm3

[ Boiling Point ]:
791.6ºC at 760mmHg

[ Melting Point ]:
133-135ºC

[ Molecular Formula ]:
C₃₇H₆₅NO₁₂

[ Molecular Weight ]:
715.91100

[ Flash Point ]:
432.6ºC

[ Exact Mass ]:
715.45100

[ PSA ]:
165.84000

[ LogP ]:
2.89230

[ Index of Refraction ]:
1.542

[ Storage condition ]:
-20°C Freezer

Safety Information

[ Personal Protective Equipment ]:
Eyeshields;Gloves;type N95 (US);type P1 (EN143) respirator filter

[ RIDADR ]:
NONH for all modes of transport

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Articles

Sensitive high-performance liquid chromatographic determination of EM523, a new erythromycin derivative, in human plasma and urine with ultraviolet detection using column switching.

J. Chromatogr. A. 616(1) , 144-50, (1993)

A sensitive high-performance liquid chromatographic (HPLC) method using column switching is described for the determination of EM523 (I), a new erythromycin derivative, in human plasma and urine. The ...

Comparison of the motor-stimulating action of EM523, an erythromycin derivative, and prostaglandin F2 alpha in conscious dogs.

Jpn. J. Pharmacol. 63(2) , 209-17, (1993)

The effect of EM523 [de(N-methyl)-N-ethyl-8,9-anhydroerythromycin A 6,9-hemiacetal], an erythromycin derivative, on gastrointestinal motility was investigated using conscious dogs in the fasting state...

EM523L, a nonpeptide motilin agonist, stimulates gastric emptying and pancreatic polypeptide secretion.

Peptides 17(6) , 895-900, (1996)

We investigated the efficacy and the mechanism of action of EM523L, a nonpeptide motilin agonist (motilide), on the stimulation of gastric emptying and on the release of gut peptides after ingestion o...