Erythromycin A enol ether

SKU
E-2465
  • CAS:33396-29-1
  • Formula:C37H65NO12
  • MW:715.9 Da
  • Appearance:White solid
  • Purity:>98% by HPLC
Product Name Qty
Erythromycin A enol ether
1 mg
$148.07
Erythromycin A enol ether
5 mg
$517.14

Description

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.

 

 

More Information
Alternate Name/Synonyms
8,9-anhydroerythromycin A 6,9-hemiketal; Erythromycin enol ether; EM-A enolether
SKU
E-2465
CAS #
33396-29-1
Chemical Name
(2R,3R,4S,5R,8R,9S,10S,11R,12R)-11-[(2S,3R,4S,6R)-4-(dimethylamino)-3-hydroxy-6-methyloxan-2-yl]oxy-5-ethyl-3,4-dihydroxy-9-[(2R,4R,5S,6S)-5-hydroxy-4-methoxy-4,6-dimethyloxan-2-yl]oxy-2,4,8,10,12,14-hexamethyl-6,15-dioxabicyclo[10.2.1]pentadec-1(14)-en-7
Chemical Formula
C37H65NO12
Molecular Weight
715.9 Da
Appearance
White solid
Purity
>98% by HPLC
Solubility
Soluble in ethanol, methanol, DMF or DMSO. Limited water solubility.
Melting Point
143-145 °C
Storage Temp
-20°C
USE
An impurity of erythromycin A
MDL NUMBER
MFCD09840536
INCHI
InChI=1S/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
SMILES
CC[C@@H]1[C@@]([C@@H]([C@H](C2=C(C[C@@](O2)([C@@H]([C@H]([C@@H]([C@H](C(=O)O1)C)O[C@H]3C[C@@]([C@H]([C@@H](O3)C)O)(C)OC)C)O[C@H]4[C@@H]([C@H](C[C@H](O4)C)N(C)C)O)C)C)C)O)(C)O
Handling
Handle in accordance with good industrial hygiene and safety practice. Corrosive hazard. Wear protective gloves/clothing and eye/face protection.
HandlingHandle in accordance with good industrial hygiene and safety practice. Corrosive hazard. Wear protective gloves/clothing and eye/face protection.
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