A mimic of motilin
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Erythromycin A enol ether

Item No. 17191

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
8,9-didehydro-9-deoxo-6-deoxy-6,9-epoxy-erythromycin
CAS Number
33396-29-1
Synonyms
  • BRL 46357ER
  • EM-201
Molecular Formula
C37H65NO12
Formula Weight
715.9
Purity
≥95%
Formulation (Request formulation change)
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: 15 mg/mlDMSO: 15 mg/mlEthanol: 30 mg/mlEthanol:PBS(pH 7.2) (1:1): 0.5 mg/ml
λmax
209 nm
SMILES
O=C1[C@@H]([C@H]([C@@H]([C@]([H])([C@]2(CC(C)=C([C@@H]([C@H]([C@@](C)([C@H](O1)CC)O)O)C)O2)C)O[C@]3([C@@H]([C@H](C[C@H](O3)C)N(C)C)O)[H])C)O[C@@]4(O[C@H]([C@@H]([C@@](C)(C4)OC)O)C)[H])C
InChi Code
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
InChi Key
JFVYXJKGJMUGRG-KJPZRSJGSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    1 mg

    $40

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    5 mg

    $171

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    10 mg

    $283

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    Product Description

    Erythromycin A enol ether is a decomposition product of the macrolide antibiotic, erythromycin A (Item No. 16486).1 Erythromycin A enol ether does not retain the antibiotic properties of erythromycin A and has been identified as a β-turn mimic of the peptide hormone motilin, causing duodenal contractions and gastrointestinal distress.2 This compound has been used to determine the binding characteristics of ligands of the motilin receptor.2

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Pendela, M., Béni, S., Haghedooren, E., et al. Combined use of liquid chromatography with mass spectrometry and nuclear magnetic resonance for the identification of degradation compounds in an erythromycin formulation. Anal. Bioanal. Chem. 402(2), 781-790 (2012).

    2. Steinmetz, W.E., Shapiro, B.L., and Roberts, J.J. The structure of erythromycin enol ether as a model for its activity as a motilide. J. Med. Chem. 45(22), 4899-4902 (2002).