Erythromycin A enol ether

HCID 83954CAS 33396-29-1

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Grundinformationen

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
Summenformel: C37H65NO12
Durchschnittliche Molmasse: 715,9 g/mol
Monoisotopische Masse: 715,45067652

Überblick

Erythromycin a enol ether is an aminoglycoside.

Namen und Bezeichner

Bevorzugter 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
Englischer Name: Erythromycin A Enol Ether
Summenformel: C37H65NO12
Molmasse: 715.91

Namen und Synonyme

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

Weitere Namen anzeigen

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

Datenbank-Bezeichner

CAS: 33396-29-1
PubChem CID: 83954
DTXSID: DTXSID801371991
ChEMBL: CHEMBL300004
ChEBI: CHEBI:184048
UNII: 32B40I7V7B
EC Number: 641-788-1
Nikkaji: J247.117E

Eigenschaften

Berechnete Struktureigenschaften

XLogP: 3,3
Polarare Oberfläche (TPSA): 166 Å²
H-Brücken-Donoren: 4
H-Brücken-Akzeptoren: 13
Frei drehbare Bindungen: 7
Schwere Atome: 50
Formalladung: 0
Komplexität: 1.220

Physikochemische Eigenschaften

Schmelzpunkt: 133 · 133-1350C
Siedepunkt: 791.6 · 791.6±60.0 °C(Predicted)
Dichte: 1.2 · 1.20±0.1 g/cm3(Predicted)
storage temp.: -20 °C · -20°C Freezer
Löslichkeit: Chloroform (Slightly), Ethyl Acetate (Slightly), Methanol (Slightly)
Aggregatzustand: Solid
pka: 13.45 · 13.45±0.70(Predicted)
Farbe: White to Pale Yellow
CAS Datenbank: 33396 · 33396-29-1

Sicherheit und Regulatorisches

GHS-Klassifizierung

GHS Classification · 4 Einträge

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.

Sicherheitsdaten

wgk: 3

Chemie und Industrie

Anwendungen · 1 Eintrag

VerwendenErythromycin 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.