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13127-18-9

Basic Information
CAS No.: 13127-18-9
Name: ERYTHROMYCIN OXIME
Article Data: 13
Molecular Structure:
Molecular Structure of 13127-18-9 (ERYTHROMYCIN OXIME)
Formula: C37H68N2O13
Molecular Weight: 748.953
Synonyms: 9-Hydroxyiminoerythromycin;Erythromycin 9-ketoxime;Erythromycin A 9-oxime;Erythromycin A oxime;Erythromycin oxime;RU 28111;Erythromycin, 9-oxime;
EINECS: 204-040-1
Density: 1.28 g/cm3
Melting Point: 159-161?C
Boiling Point: 841 °C at 760 mmHg
Flash Point: 462.4 °C
Appearance: white to slightly yellow powder
Hazard Symbols: IrritantXi
Risk Codes: 36/37/38
Safety: 26-36
PSA: 209.43000
LogP: 2.04670
Synthetic route
114-07-8

erythromycin

13127-18-9

(9-E)-deoxo-9-hydroximinoerythromycin A

Conditions
ConditionsYield
With hydroxylamine; acetic acid In isopropyl alcohol at 50℃; for 24h;95%
With hydroxylamine hydrochloride; triethylamine In methanol Reflux;93%
With hydroxylamine hydrochloride; potassium carbonate In methanol at 20℃; for 48h; Solvent; Reagent/catalyst; Temperature;88.2%
114-07-8

erythromycin

A

13127-18-9

(9-E)-deoxo-9-hydroximinoerythromycin A

B

105882-69-7

8,9-anhydropseudoerythromycin A 6,9-hemiketal

Conditions
ConditionsYield
With hydroxylamine hydrochloride; sodium acetate In methanol at 50℃; for 13h;
7704-67-8

erythromycin A thiocyanate

13127-18-9

(9-E)-deoxo-9-hydroximinoerythromycin A

Conditions
ConditionsYield
With hydroxylamine hydrochloride In dichloromethane at 20℃; for 1.5h; pH=7; Beckmann Rearrangement;
With hydroxylamine hydrochloride; ammonium bicarbonate; sodium iodide In methanol at 56 - 60℃; Reagent/catalyst;89 g
1357466-70-6

erythromycin A oxime thiocyanate

13127-18-9

(9-E)-deoxo-9-hydroximinoerythromycin A

Conditions
ConditionsYield
With sodium hydroxide In dichloromethane; water at 38℃; Solvent; Temperature;
116-11-0

2-Methoxypropene

13127-18-9

(9-E)-deoxo-9-hydroximinoerythromycin A

999-97-3

1,1,1,3,3,3-hexamethyl-disilazane

119685-40-4

C44H84N2O14Si

Conditions
ConditionsYield
Stage #1: 2-Methoxypropene; (9-E)-deoxo-9-hydroximinoerythromycin A With Pyridine hydrobromide In dichloromethane at 7 - 17℃; for 2h;
Stage #2: 1,1,1,3,3,3-hexamethyl-disilazane In dichloromethane for 1h;
Stage #3: With sodium hydrogencarbonate In dichloromethane; water at 27 - 33℃; for 0.5h; Product distribution / selectivity;
96.9%
13127-18-9

(9-E)-deoxo-9-hydroximinoerythromycin A

342371-84-0

9-deoxo-6-deoxy-6,9-epoxy-9,9a-didehydro-9a-aza-homoerythromycin A

Conditions
ConditionsYield
With sodium hydrogencarbonate; p-toluenesulfonyl chloride In water; acetone at 0 - 20℃; for 4h;91.8%
With sodium hydrogencarbonate; p-toluenesulfonyl chloride In dichloromethane; water at 0 - 5℃; Product distribution / selectivity;
With sodium hydrogencarbonate; p-toluenesulfonyl chloride In dichloromethane at 20℃; for 1.5h;
With sodium hydrogencarbonate; methanesulfonyl chloride In water at 5℃; Temperature; Reagent/catalyst; Beckmann Rearrangement;
13127-18-9

(9-E)-deoxo-9-hydroximinoerythromycin A

26116-56-3

erythromycylamine

Conditions
ConditionsYield
With methanol; sodium tetrahydroborate at 20℃; for 8h; Reagent/catalyst; Temperature; Cooling with ice;85.03%
13127-18-9

(9-E)-deoxo-9-hydroximinoerythromycin A

76801-85-9

9-Deoxo-9a-aza-9a-homoerythromycin A

Conditions
ConditionsYield
Stage #1: (9-E)-deoxo-9-hydroximinoerythromycin A With calcium(II) bis(trifluoromethanesulfonyl)imide; tert-butylammonium hexafluorophosphate(V) In 1,2-dimethoxyethane; 1,2-dichloro-ethane at 80℃; for 5h;
Stage #2: With sodium tetrahydroborate In methanol at 0 - 20℃; for 51h;
78%
Multi-step reaction with 2 steps
1: p-toluenesulfonyl chloride; sodium hydrogencarbonate / acetone; water / 4 h / 0 - 20 °C
2: sodium tetrahydroborate; methanol / 24 h / 0 - 20 °C
View Scheme
1132-95-2

1,1-diisopropoxycyclohexane

13127-18-9

(9-E)-deoxo-9-hydroximinoerythromycin A

129288-91-1

9-{O-[1-(1-methylethoxy)-cyclohexyl]oxime}-erythromycin

Conditions
ConditionsYield
With pyridine hydrochloride In dichloromethane at 20℃; for 42h;71%
15761-38-3

L-N-Boc-Ala

13127-18-9

(9-E)-deoxo-9-hydroximinoerythromycin A

C45H81N3O16

Conditions
ConditionsYield
With dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 3h;70%
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Chemistry

Empirical Formula of Erythromycin, 9-oxime (CAS NO.13127-18-9): C37H68N2O13
Molecular Weight: 748.9414
Nominal Mass: 748 Da
Average Mass: 748.9414 Da
Monoisotopic Mass: 748.47214 Da 
Index of Refraction: 1.552
Molar Refractivity: 185.92 cm3
Molar Volume: 581.1 cm3
Surface Tension: 41.3 dyne/cm
Density: 1.28 g/cm3
Flash Point: 462.4 °C
Enthalpy of Vaporization: 139 kJ/mol
Boiling Point: 841 °C at 760 mmHg
Vapour Pressure: 7.27E-33 mmHg at 25 °C
Structure of Erythromycin, 9-oxime (CAS NO.13127-18-9):
               
IUPAC Name: (2R,3S,4S,5R,6R,8R,9E,10S,11R,12S,13R)-5-[(2S,3R,4S,6R)-4-(Dimethylamino)-3-hydroxy-6-methyloxan-2-yl]oxy-13-ethyl-6,11,12-trihydroxy-9-hydroxyimino-3-[(2R,4R,5S,6S)-5-hydroxy-4-methoxy-4,6-dimethyloxan-2-yl]oxy-2,4,6,8,10,12-hexamethyl-14-oxacyclotetradecan-1-one
Canonical SMILES: CCC1C(C(C(C(=NO)C(CC(C(C(C(C(C(=O)O1)C)OC2CC(C(C(O2)C)O)(C)OC)C)OC3C(C(CC(O3)C)N(C)C)O)(C)O)C)C)O)(C)O
Isomeric SMILES: CC[C@@H]1[C@@]([C@@H]([C@H](/C(=N/O)/[C@@H](C[C@@]([C@@H]([C@H]([C@@H]([C@H](C(=O)O1)C)O[C@H]2C[C@@]([C@H]([C@@H](O2)C)O)(C)OC)C)O[C@H]3[C@@H]([C@H](C[C@H](O3)C)N(C)C)O)(C)O)C)C)O)(C)O
InChI: InChI=1S/C37H68N2O13/c1-14-25-37(10,45)30(41)20(4)27(38-46)18(2)16-35(8,44)32(52-34-28(40)24(39(11)12)15-19(3)48-34)21(5)29(22(6)33(43)50-25)51-26-17-36(9,47-13)31(42)23(7)49-26/h18-26,28-32,34,40-42,44-46H,14-17H2,1-13H3/b38-27+/t18-,19-,20+,21+,22-,23+,24+,25-,26+,28-,29+,30-,31+,32-,34+,35-,36-,37-/m1/s1
InChIKey: KYTWXIARANQMCA-ZTILBQITSA-N

Safety Profile

Hazard Codes of Erythromycin, 9-oxime (CAS NO.13127-18-9): IrritantXi
Risk Statements: 36/37/38 
R36/37/38:Irritating to eyes, respiratory system and skin.
Safety Statements: 26-36 
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. 
S36:Wear suitable protective clothing.

Specification

 Erythromycin, 9-oxime , its cas register number is 13127-18-9. It also can be called Erythromycin-9-oxime ; and Erythromycin oxime .