Erythromycin A Enol Ether

Product Name: 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 Stearate Impurity E;Erythromycin Estolate Impurity E
CBNumber: CB21176304
Molecular Formula: C37H65NO12
Formula Weight: 715.91
MOL File: 33396-29-1.mol

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Erythromycin A Enol Ether Property

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

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Safety

WGK Germany: 3

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Hazard and Precautionary Statements (GHS)

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N-Bromosuccinimide Price

Sigma-Aldrich

Product number: 05238
Product name: Erythromycin A enol ether
Purity: analytical standard
Packaging: 5mg
Price: $655
Updated: 2024/03/01

Cayman Chemical

Product number: 17191
Product name: Erythromycin A enol ether
Purity: ≥95%
Packaging: 1mg
Price: $36
Updated: 2024/03/01

Cayman Chemical

Product number: 17191
Product name: Erythromycin A enol ether
Purity: ≥95%
Packaging: 5mg
Price: $155
Updated: 2024/03/01

Cayman Chemical

Product number: 17191
Product name: Erythromycin A enol ether
Purity: ≥95%
Packaging: 10mg
Price: $257
Updated: 2024/03/01

TRC

Product number: E649970
Product name: Erythromycin A enol ether
Packaging: 50mg
Price: $910
Updated: 2021/12/16

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Erythromycin A Enol Ether Chemical Properties,Usage,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 Suppliers

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33396-29-1, Erythromycin A Enol EtherRelated Search:

ERYTHROMYCIN B 1,2-Bis(4-pyridylcarbonyl)hydrazine 3,6-DI-4-PYRIDYL-1,2,4,5-TETRAZINE 2,5-BIS(4-PYRIDYL)-1,3,4-OXADIAZOLE 3,6-di(4-pyridinyl)-1,4-dihydro-1,2,4,5-tetraazine N-Demethyl-N-Propanoyl Erythromycin erythronolide B Erythromycin EDiscontinued ANHYDROERYTHROMYCIN A N-DEMETHYL ERYTHROMYCIN A 16-Hydroxyerythromycin Erythromycin ERYTHROMYCIN IMP. E (EP): ERYTHROMYCIN A ENOL ETHER PSEUDO ERYTHROMYCIN A ENOL ETHER Idremcinal Erythromycin A Enol Ether

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 Lactobionate Impurity E

Erythromycin Ethylsuccinate Impurity E

Erythromycin Stearate Impurity E

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

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Various Metabolites and Impurities