CAS 33396-29-1 Erythromycin A enol ether (HCID 83954)

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Basic information

CAS: 33396-29-1
Standard SMILES: CC[C@H]1OC(=O)[C@H](C)[C@@H](O[C@H]2C[C@@](C)(OC)[C@@H](O)[C@H](C)O2)[C@H](C)[C@@H](O[C@@H]2O[C@H](C)C[C@H](N(C)C)[C@H]2O)[C@@]2(C)CC(C)=C(O2)[C@H](C)[C@@H](O)[C@]1(C)O
InChIKey: JFVYXJKGJMUGRG-KJPZRSJGSA-N
Molecular formula: C37H65NO12
Average molar mass: 715.9 g/mol
Monoisotopic mass: 715.45067652

Overview

Erythromycin a enol ether is an aminoglycoside.

Names & identifiers

Preferred name: Erythromycin A enol ether
IUPAC: (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-one
English name: Erythromycin A Enol Ether
Molecular formula: C37H65NO12
Molecular weight: 715.91

Names & synonyms

Erythromycin A enol ether33396-29-1Erythromycin enol ether8,9-anhydroerythromycin A 6,9-hemiketalEM-20132B40I7V7BErythromycin, 8,9-didehydro-9-deoxo-6-deoxy-6,9-epoxy-BRL-46357ERRefChem:137779Erythromycin EP Impurity EME-4(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-one

Show more names

EM 523Isoniazid Impurity 16Erythromycin impurity BErythromycin Impurity 5Erythromycin impurity 05Erythromycin A Enol EtherIJFVYXJKGJMUGRG-POECJHBWSA-NErythromycin Stearate Impurity EErythromycin Estolate Impurity E

(2R,3R,4S,5R,8R,9S,10S,11R,12S)-5-ethyl-11-[(2S,3R,4S,6R)-4-[ethyl(methyl)amino]-3-hydroxy-6-methyloxan-2-yl]oxy-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-oneEM523EM-A enoletherUNII-32B40I7V7BME 4BRL 46357EREM 201Erythromycin-A enol ether

Properties

Computed structural properties

XLogP: 3.3
Topological polar surface area: 166 Å²
Hydrogen bond donors: 4
Hydrogen bond acceptors: 13
Rotatable bonds: 7
Heavy atoms: 50
Formal charge: 0
Complexity: 1,220

Physicochemical properties

Melting point: 133 · 133-1350C
Boiling point: 791.6 · 791.6±60.0 °C(Predicted)
Density: 1.2 · 1.20±0.1 g/cm3(Predicted)
storage temp.: -20 °C · -20°C Freezer
solubility: Chloroform (Slightly), Ethyl Acetate (Slightly), Methanol (Slightly)
form: Solid
pka: 13.45 · 13.45±0.70(Predicted)
color: White to Pale Yellow
CAS DataBase Reference: 33396 · 33396-29-1
FDA UNII: 32 B40I7V7B · 32B40I7V7B
WGK Germany: 3 · 3

Safety & regulation

GHS classification

GHS Classification · 4 items

Warning

H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]

P264, P270, P301+P317, P330, and P501 (click each P-code to see the statement)

The GHS information provided by 1 company from 1 notification to the ECHA C&L Inventory.

Safety data

wgk: 3

Chemistry & industry

Applications · 2 items

UsesErythromycin A Enol Ether (Erythromycin EP Impurity E) is an impurity of Erythromycin.

UsesErythromycin 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.