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Erythromycin A Enol Ether

CAS No.
33396-29-1
Chemical Name:
Erythromycin A Enol Ether
Synonyms
EM 523;Isoniazid Impurity 16;Erythromycin impurity B;Erythromycin Impurity 5;Erythromycin impurity 05;Erythromycin A Enol Ether;Erythromycin A Enol EtherI;JFVYXJKGJMUGRG-POECJHBWSA-N;Erythromycin Estolate Impurity E;Erythromycin A enol ether, EvoPure
CBNumber:
CB21176304
Molecular Formula:
C37H65NO12
Molecular Weight:
715.91
MDL Number:
MFCD09840536
MOL File:
33396-29-1.mol
Last updated:2023-09-04 15:51:00

Erythromycin A Enol Ether Properties

Melting point 133-1350C
Boiling point 791.6±60.0 °C(Predicted)
Density 1.20±0.1 g/cm3(Predicted)
storage temp. -20°C Freezer
solubility Chloroform (Slightly), Ethyl Acetate (Slightly), Methanol (Slightly)
form Solid
pka 13.45±0.70(Predicted)
color White to Pale Yellow
CAS DataBase Reference 33396-29-1
FDA UNII 32B40I7V7B

SAFETY

Risk and Safety Statements

WGK Germany  3

Erythromycin A Enol Ether price More Price(12)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Sigma-Aldrich 05238 Erythromycin A enol ether analytical standard 33396-29-1 5mg $655 2024-03-01 Buy
Cayman Chemical 17191 Erythromycin A enol ether ≥95% 33396-29-1 1mg $36 2024-03-01 Buy
Cayman Chemical 17191 Erythromycin A enol ether ≥95% 33396-29-1 5mg $155 2024-03-01 Buy
Cayman Chemical 17191 Erythromycin A enol ether ≥95% 33396-29-1 10mg $257 2024-03-01 Buy
TRC E649970 Erythromycin A enol ether 33396-29-1 50mg $910 2021-12-16 Buy
Product number Packaging Price Buy
05238 5mg $655 Buy
17191 1mg $36 Buy
17191 5mg $155 Buy
17191 10mg $257 Buy
E649970 50mg $910 Buy

Erythromycin A Enol Ether Chemical Properties,Uses,Production

Chemical Properties

White Solid

Uses

Erythromycin A Enol Ether (Erythromycin EP Impurity E) is an impurity of Erythromycin.

Uses

Erythromycin A enol ether is a degradation product of erythromycin formed under acidic conditions by C6–OH internal attack on the C9 ketone to produce a cyclic enol ether. The rearrangement results in a loss of antibiotic activity. This single reaction was the prime driver for the development of second and third generation erythromycins. Erythromycin A enol ether is an important standard for stability studies.

Definition

ChEBI: Erythromycin a enol ether is an aminoglycoside.

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.

Erythromycin A Enol Ether Preparation Products And Raw materials

Raw materials

Preparation Products

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Erythromycin A Enol Ether Spectrum

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 (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 Erythromycin A Enol Ether EM 523 Erythromycin impurity B JFVYXJKGJMUGRG-POECJHBWSA-N Erythromycin Impurity 5 Erythromycin EP Impurity E/Erythromycin A Enol Ether/(2R,3R,4S,5R,8R,9S,10S,11R,12R)-9-[(2,6-dideoxy-3- C-methyl-3-O-methyl-α-L-ribo-hexopyranosyl)oxy]- 5-ethyl-3,4-dihydroxy-2,4,8,10,12,14-hexamethyl- 11-[[3,4,6-trideoxy-3-(dimethylamino)-β-D-xylohexopyr Erythromycin Impurity 5(Erythromycin EP Impurity E) Erythromycin Impurit E:(erythromycin A enol ether) Erythromycin EP Impurity E (Erythromycin A Enol Ether) Erythromycin, 8,9-didehydro-9-deoxo-6-deoxy-6,9-epoxy- Isoniazid Impurity 16 Erythromycin A Enol EtherI Erythromycin Lactobionate EP Impurity E Inhibitor,inhibit,Acidic,Erythromycin A enol ether,degradation Erythromycin Estolate EP Impurity E Erythromycin Ethylsuccinate EP Impurity E Erythromycin Estolate Impurity E Erythromycin Stearate EP Impurity E Erythromycin impurity 05 Erythromycin A enol ether, EvoPure (2R,3R,4S,5R,8R,9S,10S,11R,12R)-9-[(2,6-dideoxy-3-C-methyl- 3-O-methyl-α-L-ribo-hexopyranosyl)oxy]-5-ethyl-3,4-dihydroxy- 2,4,8,10,12,14-hexamethyl-11-[[3,4,6-trideoxy-3-(dimethylamino)- β-D-xylohexopyranosyl]oxy]-6,15-dioxabicyclo[10.2.1]pentadec- 1(14)-en-7-one 33396-29-1 C37H65NO12 Intermediates & Fine Chemicals Metabolites & Impurities Pharmaceuticals Chromatography Drugs&Metabolites Forensic and Veterinary Standards Neat CompoundsAnalytical Standards Pharmacology Standards Metabolites & Impurities, Pharmaceuticals, Intermediates & Fine Chemicals Various Metabolites and Impurities