Pseudoerythromycin A enol ether

Pseudoerythromycin A enol ether

$150.00 - 1 mg

$525.00 - 5 mg

All prices in Australian dollars

Code
BIA-P1349
CAS #
105882-69-7
Molecular Formula
C37H65NO12
Molecular Weight
715.9
Purity
>95% by HPLC
Long Term Storage
-20°C
Solubility
Soluble in ethanol, methanol, DMF or DMSO. Good water solubility.

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Application Notes

Pseudoerythromycin A enol ether is a degradation product of erythromycin formed by a complex internal rearrangement of erythromycin A on exposure to neutral to weakly alkaline conditions. The C6–OH forms an internal enol ether with the C9 ketone of erythromycin, while the C11-OH attacks the carbonyl of the lactone to reduce the macrocycle from a 14- to an 11-membered macrolide. Synthetically, pseudoerythromycin A enol ether is prepared by reacting erythromycin enol ether with carbonate. Pseudoerythromycin A enol ether is devoid of antibiotic activity but is an important analytical standard for erythromycin A stability studies.

References

  • Study of the stability of erythromycin in neutral and alkaline solutions by liquid chromatography on poly(styrene-divinylbenzene). Paesen J. et al., Int. J. Pharm. 1994, 113, 215.
  • Synthesis of ring-contracted derivatives of erythromycin. Kirst H.A. et al., J. Org. Chem. 1987, 52, 4359.

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