33396-29-1

Basic information

• Product Name: Erythromycin A Enol Ether
• Synonyms: 11-(4-Dimethylamino-3-hydroxy-6-methyl-tetrahydro-pyran-2-yloxy)-5-ethyl-3,4-dihydroxy-9-(5-hydroxy-4-methoxy-4,6-dimethyl-tetrahydro-pyran-2-yloxy)-2,4,8,10,12,14-hexamethyl-6,15-dioxa-bicyclo[10.2.1]pentadec-1(14)-en-7-one;Erythromycin A Enol Ether;EM 523;(6R)-6-Deoxy-9-deoxo-6,9-epoxy-8,9-didehydroerythromycin;6,9-Epoxy-8,9-didehydro-9-deoxo-6-deoxyerythromycin;6-Deoxy-9-deoxo-8,9-didehydro-6,9-epoxyerythromycin;6β,9-Epoxy-8,9-didehydro-9-deoxo-6-deoxyerythromycin;9-Deoxo-6-deoxy-6,9-epoxy-8,9-didehydroerythromycin
• CAS NO: 33396-29-1
• Molecular Formula: C₃₇H₆₅NO₁₂
• Molecular Weight: 715.916
• Product Categories: Various Metabolites and Impurities;Intermediates & Fine Chemicals;Metabolites & Impurities;Pharmaceuticals;Chromatography;Drugs&Metabolites;Forensic and Veterinary Standards;Neat CompoundsAnalytical Standards;Pharmacology Standards;Metabolites & Impurities, Pharmaceuticals, Intermediates & Fine Chemicals
• Mol File: 33396-29-1.mol
• Article Data: 6

Chemical Properties

• Melting Point: 133-1350C
• Boiling Point: 791.6°Cat760mmHg
• Flash Point: 432.6°C
• Appearance: /
• Density: 1.2g/cm³
• Vapor Pressure: 5.76E-29mmHg at 25°C
• Refractive Index: 1.542
• Storage Temp.: -20°C Freezer
• Solubility: Chloroform (Slightly), Ethyl Acetate (Slightly), Methanol (Slightly)
• PKA: 13.45±0.70(Predicted)
• CAS DataBase Reference: Erythromycin A Enol Ether(CAS DataBase Reference)
• NIST Chemistry Reference: Erythromycin A Enol Ether(33396-29-1)
• EPA Substance Registry System: Erythromycin A Enol Ether(33396-29-1)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 33396-29-1(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
Erythromycin A Enol Ether is used as an impurity standard for the quality control and stability testing of Erythromycin and its derivatives. Its presence in Erythromycin formulations is monitored to ensure the drug's efficacy and safety, as the formation of this enol ether indicates a loss of antibiotic activity.
Used in Research and Development:
Erythromycin A Enol Ether is utilized as a reference compound in the development of new generations of erythromycin antibiotics. Understanding its formation and the conditions that lead to its production have been crucial in the advancement of erythromycin-based treatments, leading to the creation of more stable and effective drugs.
Used in Quality Control:
Erythromycin A Enol Ether is employed as a benchmark in the quality control processes of pharmaceutical manufacturers. It helps in the assessment of the purity and stability of Erythromycin products, ensuring that they meet the required standards for therapeutic use.
Used in Analytical Chemistry:
As a known degradation product of Erythromycin, Erythromycin A Enol Ether is used in analytical chemistry for the development and validation of methods to detect and quantify impurities in pharmaceutical products. This helps in maintaining the quality and safety of the drugs available to patients.

Biological Activity

erythromycin a enol ether, also known as 8,9-anhydroerythromycin a 6,9 hemiketal, is a kind of catabolite of erythromycin a without its antibiotic properties.erythromycin a enol ether functions as a β-turn mimic of the peptide hormone motilin which leads to duodenal contractions. erythromycin a enol ether is also the agent of gastrointestinal (gi) distress [1].motilin is a kind of polypeptide hormone with 22-amino acid belonging to the motilin family. motilin could increase the migrating myoelectric complex of gastrointestinal motility, and stimulate the pepsin production. motilin could also improve peristalsis in the small intestine and empty the gut for the next meal. besides, motilin could facilitate the release of somatostatin and pancreatic polypeptide.

references

[1] steinmetz w e, shapiro b l, roberts j j, et al. the structure of erythromycin enol ether as a model for its activity as a motilide.[j]. journal of medicinal chemistry, 2002, 45(22): 4899-4902.

InChI:InChI=1/C37H65NO12/c1-14-25-37(10,43)30(40)20(4)28-18(2)16-36(9,50-28)32(49-34-27(39)24(38(11)12)15-19(3)45-34)21(5)29(22(6)33(42)47-25)48-26-17-35(8,44-13)31(41)23(7)46-26/h19-27,29-32,34,39-41,43H,14-17H2,1-13H3/t19-,20-,21+,22-,23+,24+,25+,26+,27-,29+,30-,31+,32-,34+,35-,36-,37-/m1/s1

Upstream product

• 114-07-8 erythromycin 
• 114-07-8 erythromycin A 
• 105900-46-7 pseudoerythromycin A 6,9-hemiketal 
• 105882-69-7 pseudoerythromycin A enol ether 

Downstream Products

• 23893-13-2 erythromycin A 6,9;9,12-spiroketal 
• 105882-69-7 pseudoerythromycin A enol ether 
• 23893-13-2 anhydroerythromycin A 
• 105882-69-7 8,9-anhydropseudoerythromycin A 6,9-hemiketal 
• 110479-62-4 2'-O-benzoyl-8,9-anhydroerythromycin A 6,9-hemiacetal 
• 110496-83-8 N-benzyl-8,9-anhydroerythromycin A 6,9-hemiacetal chloride 

Relevant articles and documents

Design, synthesis, and evaluation of stable and taste-free erythromycin proprodrugs

Erythromycin A is normally formulated for children as its 2′-ethyl succinate, a taste-free prodrug. Unfortunately, the prodrug hydrolyzes at a measurable rate in the medicine bottle, leading to the vile-tasting erythromycin. We have prepared derivatives of erythromycin B as putative paediatric prodrugs, taking advantage of the much improved acid stability of erythromycin B relative to erythromycin A. Thus, erythromycin B enol ether ethyl succinate is very poorly soluble in water, and its hydrolysis is undetectable in conditions resembling the medicine bottle. In acid, however, it converts rapidly to erythromycin B 2′-ethyl succinate, and this is in turn hydrolyzed to erythromycin B in neutral and basic conditions. Derivatives of erythromycin B enol ether are therefore proposed as taste-free proprodrugs of erythromycin B.

Synthesis of 8-fluorinated erythromycin cyclic 2',3'-carbamates

Methodology is described for the preparation of a 2',3'-carbamate-11,12- carbonate analog of flurithromycin and its 3-O-descladinosylflurithromycin analog from (9E)-erythromycin A 9-oxime. Phosgene was used for the carbonylation reactions. SelectfluorTM was an effective fluorinating agent of the intermediate 8,9-anhydro-N-demethylerythromycin A 2',3'-carbamate-11,12- carbonate-6,9-hemiketal under mild aqueous conditions.

Synthesis of Ring-Contracted Derivatives of Erythromycin

8,9-Anhydroerythromycin 6,9-hemiketal was converted by a translactonization process into a 12-membered-ring macrolide.Subsequent oxidative reactions have yielded several new derivatives which possess either 12-membered lactone or 11-membered dilactone rings.

Design and synthesis via click chemistry of 8,9-anhydroerythromycin A 6,9-hemiketal analogues with anti-MRSA and -VRE activity

An erythromycin analogue, 11,12-di-O-iso-butyryl-8,9-anhydroerythromycin A 6,9-hemiketal (1b), was found to be a potential anti-MRSA and anti-VRE agent. The use of copper catalyzed azide-acetylene cycloaddition, and click chemistry, readily provided 10 ty

Translactonization in Erythromycins

When erythromycin A is heated in diethylamine-acetic acid, an erythromycin hemiketal is obtained, which can be further transformed into a new enol ether and spiroketal.The new enol ether is also obtained in equilibrium with the normal one on heating erythromycin A or B in pyridine-acetic acid.The novel compounds, which will be called pseudoerythromycin derivatives, are characterized by a translactonization between the C11-hydroxyl and the lactone group.Their structure was proved by mass and 1H and 13C NMR spectrometry, by acetylation experiments, and by degradation with lead tetraacetate.