33396-29-1 Usage
Description
Erythromycin A Enol Ether is a degradation product of Erythromycin, an antibiotic, formed under acidic conditions through a chemical rearrangement involving the C6–OH group attacking the C9 ketone, resulting in the formation of a cyclic enol ether. This rearrangement leads to a loss of antibiotic activity, and the understanding of this reaction has been a significant factor in the development of second and third generation erythromycins. Erythromycin A Enol Ether is a white solid and serves as an important standard for stability studies in the pharmaceutical industry.
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.
Check Digit Verification of cas no
The CAS Registry Mumber 33396-29-1 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 3,3,3,9 and 6 respectively; the second part has 2 digits, 2 and 9 respectively.
Calculate Digit Verification of CAS Registry Number 33396-29:
(7*3)+(6*3)+(5*3)+(4*9)+(3*6)+(2*2)+(1*9)=121
121 % 10 = 1
So 33396-29-1 is a valid CAS Registry Number.
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
33396-29-1Relevant articles and documents
Design, synthesis, and evaluation of stable and taste-free erythromycin proprodrugs
Bhadra, Pranab K.,Morris, Gareth A.,Barber, Jill
, p. 3878 - 3884 (2005)
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 Ring-Contracted Derivatives of Erythromycin
Kirst, Herbert A.,Wind, Julie A.,Paschal, Jonathan W.
, p. 4359 - 4362 (1987)
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.
Translactonization in Erythromycins
Kibwage, Isaac O.,Busson, Roger,Janssen, Gerard,Hoogmartens, Jos,Vanderhaeghe, Hubert
, p. 990 - 996 (2007/10/02)
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.
