23893-13-2

Basic information

• Product Name: ANHYDROERYTHROMYCIN A
• Synonyms: ANHYDROERYTHROMYCIN A;6,9,12-Anhydroerythromycin A;9-Deoxo-6,12-dideoxy-6,9:9,12-diepoxy-erythromycin;Anhydroerythromycin;BRL 46355ER;EM 202;Erythromycin Anhydride, Impurity D;Erythromycin anhydride
• CAS NO: 23893-13-2
• Molecular Formula: C37H65NO12
• Molecular Weight: 715.916
• Product Categories: Intermediates & Fine Chemicals;Pharmaceuticals
• Mol File: 23893-13-2.mol
• Article Data: 5

Chemical Properties

• Melting Point: 125-127°C
• Boiling Point: 787.2°Cat760mmHg
• Flash Point: 429.9°C
• Appearance: /
• Density: 1.21g/cm³
• Vapor Pressure: 1.23E-28mmHg at 25°C
• Refractive Index: 1.54
• Storage Temp.: −20°C
• Solubility: Chloroform (Slightly), Methanol (Sparingly)
• PKA: 13.46±0.70(Predicted)
• CAS DataBase Reference: ANHYDROERYTHROMYCIN A(CAS DataBase Reference)
• NIST Chemistry Reference: ANHYDROERYTHROMYCIN A(23893-13-2)
• EPA Substance Registry System: ANHYDROERYTHROMYCIN A(23893-13-2)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 23893-13-2(Hazardous Substances Data)

Usage

Chemical Properties

Off-White to Pale Yellow Solid

Uses

Anhydroerythromycin A is a degradation product of erythromycin formed by a complex internal rearrangement of erythromycin A on exposure to acidic conditions. In acid, erythromycin A forms the enol ether and then undergoes a second internal cyclisation of the C12–OH and C9 enol to afford the ketal, anhydroerythromycin A. Anhydroerythromycin A is an important analytical standard for erythromycin A stability studies.

InChI:InChI=1/C37H65NO12/c1-14-25-36(10)29(40)22(6)37(50-36)18(2)16-35(9,49-37)31(48-33-27(39)24(38(11)12)15-19(3)44-33)20(4)28(21(5)32(42)46-25)47-26-17-34(8,43-13)30(41)23(7)45-26/h18-31,33,39-41H,14-17H2,1-13H3/t18-,19-,20+,21-,22-,23+,24+,25-,26+,27-,28+,29-,30+,31-,33+,34-,35-,36-,37+/m1/s1

Upstream product

• 33396-29-1 8,9-anhydroerythromycin A 6,9-hemiacetal 
• 105882-69-7 pseudoerythromycin A enol ether 
• 105900-46-7 pseudoerythromycin A 6,9-hemiketal 
• 114-07-8 erythromycin A 
• 33396-29-1 erythromycin A enol ether 
• 114-07-8 erythromycin A 
• 30760-16-8 9-deoxo-9-iminoerythromycin A 
• 114-07-8 erythromycin 

Relevant articles and documents

Isomerization of erythromycin A in deuterium oxide and [2H6] dimethyl sulphoxide solutions: A 1H and 13C NMR study

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The Chemistry od Erythromycin. Reactions of Erythromycin A Imine and its 6-Methyl Ether with Aldehydes and Hydrazines

Erythromycin imine (3) and its 6-methyl ether (6) are multifunctional N-unsubstituted imines, which, in contrast to most unsubstituted imines, are readily isolable and relatively stable towards hydrolysis.With aldehydes in ethanol, the imines react quite differently: the imine (3) reacts with aliphatic and aromatic aldehydes to give predominantly the 9,11-cyclic imines (9), whereas the ether (6) reacts with aliphatic aldehydes to give N-(1-ethoxyalkyl)imines (13) and with benzaldehyde to give a 9,12-epoxy Schiff's base derivative (12).The imines also differ in their reactivities towards hydrazine derivatives: the imine (3) readily reacts with monosubstituted hydrazines to form erythromycin hydrazone derivatives, whereas the ether (6), in common with erythromycin (1), is unreactive towards these reagents.A rationale for the different modes of reaction of compounds (3) and (6) is discussed.

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.