Erythromycin-9-oxime supplier

Name
ERYTHROMYCIN OXIME
EINECS 204-040-1
CAS No. 13127-18-9
Article Data13
CAS DataBase
Density 1.28 g/cm³
Solubility
Melting Point 159-161?C
Formula C₃₇H₆₈N₂O₁₃
Boiling Point 841 °C at 760 mmHg
Molecular Weight 748.953
Flash Point 462.4 °C
Transport Information
Appearance white to slightly yellow powder
Safety 26-36
Risk Codes 36/37/38
Molecular Structure
Hazard Symbols Xi
Synonyms 9-Hydroxyiminoerythromycin;Erythromycin 9-ketoxime;Erythromycin A 9-oxime;Erythromycin A oxime;Erythromycin oxime;RU 28111;Erythromycin, 9-oxime;
PSA 209.43000
LogP 2.04670

Synthetic route

: 114-07-8
erythromycin

: 13127-18-9
(9-E)-deoxo-9-hydroximinoerythromycin A

Conditions

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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%

...Expand

: 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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

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

: 13127-18-9
(9-E)-deoxo-9-hydroximinoerythromycin A

: C37H66N2O12

Conditions

Conditions	Yield
Stage #1: (9-E)-deoxo-9-hydroximinoerythromycin A With sodium hydrogencarbonate; p-toluenesulfonyl chloride In dichloromethane; water at 0 - 5℃; for 3h; Stage #2: With acetic acid In dichloromethane; water for 0.25h; pH=5.3 - 5.5; Stage #3: With sodium hydroxide In water pH=12 - 12.5; Product distribution / selectivity;	70%

: 13127-18-9
(9-E)-deoxo-9-hydroximinoerythromycin A

: 1138-80-3
N-(Benzyloxycarbonyl)glycine

: C47H77N3O16

Conditions

Conditions	Yield
With dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 3h;	65%

: 13127-18-9
(9-E)-deoxo-9-hydroximinoerythromycin A

: erythromycin A 6,9-imino ether

Conditions

Conditions	Yield
With sodium hydrogencarbonate; p-toluenesulfonyl chloride In water; acetone at -5 - 30℃; for 4.5h;	55.2%

: 13139-15-6
N-tert-butoxycarbonyl-L-leucine

: 13127-18-9
(9-E)-deoxo-9-hydroximinoerythromycin A

: C48H87N3O16

Conditions

Conditions	Yield
With dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 3h;	53.1%

: 13127-18-9
(9-E)-deoxo-9-hydroximinoerythromycin A

: 100-09-4
4-methoxybenzoic acid

: C45H74N2O15

Conditions

Conditions	Yield
With dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 3h;	51.2%

: 13127-18-9
(9-E)-deoxo-9-hydroximinoerythromycin A

: 121238-13-9
9-deoxo-11-deoxy-9,11-epoxy-9-nitroso-3'-des-N-methylerythromycin A

Conditions

Conditions	Yield
With N-Bromosuccinimide; sodium hydrogencarbonate In 1,2-dimethoxyethane; water for 2h; Ambient temperature;	42%

: 133-89-1
UDP-glucose

: 13127-18-9
(9-E)-deoxo-9-hydroximinoerythromycin A

: 2'-[O-(β-D-glucopyranosyl)]erythromycin A oxime

Conditions

Conditions	Yield
With magnesium(II) glycosylation by cell extract of Streptomyces hygroscopius ATCC 31080; pH 6.0-9.5;	50 mg

: 13127-18-9
(9-E)-deoxo-9-hydroximinoerythromycin A

: 106-89-8
epichlorohydrin

: 93488-70-1
erythromycin-9-[O-(2,3-epoxypropyl)]oxime

Conditions

Conditions	Yield
With potassium carbonate In acetone for 7h; Heating;

: 13127-18-9
(9-E)-deoxo-9-hydroximinoerythromycin A

: 134307-72-5
2-(((benzyloxy)carbonyl)amino)ethyl 1-methanesulfonate

A: 256420-10-7
C47H79N3O15

B: C47H79N3O15

Conditions

Conditions	Yield
With potassium carbonate In acetone for 24h; Heating;

...Expand

: 13127-18-9
(9-E)-deoxo-9-hydroximinoerythromycin A

: 174626-34-7
N-(benzyloxycarbonyl)-3-amino-1-propyl methanesulfonate

A: 883739-43-3
C48H81N3O15

B: C48H81N3O15

Conditions

Conditions	Yield
With potassium carbonate In acetone for 24h; Heating;

...Expand

: 13127-18-9
(9-E)-deoxo-9-hydroximinoerythromycin A

: 75937-26-7
N-(benzyloxycarbonyl)-6-aminohexyl methanesulfonate

A: C51H87N3O15

B: C51H87N3O15

Conditions

Conditions	Yield
With potassium carbonate In acetone for 24h; Heating;

...Expand

: 13127-18-9
(9-E)-deoxo-9-hydroximinoerythromycin A

: 134833-89-9
6-(4-dimethylamino-3-hydroxy-6-methyl-tetrahydro-pyran-2-yloxy)-14-ethyl-7,12,13-trihydroxy-4-(5-hydroxy-4-methoxy-4,6-dimethyl-tetrahydro-pyran-2-yloxy)-3,5,7,9,11,13-hexamethyl-oxacyclotetradecane-2,10-dione 10-[O-(2-amino-ethyl)-oxime]

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: K2CO3 / acetone / 24 h / Heating 2: 100 percent / H2 / Pd/C / methanol / 20 °C View Scheme

: 13127-18-9
(9-E)-deoxo-9-hydroximinoerythromycin A

: 883739-48-8
6-(4-dimethylamino-3-hydroxy-6-methyl-tetrahydro-pyran-2-yloxy)-14-ethyl-7,12,13-trihydroxy-4-(5-hydroxy-4-methoxy-4,6-dimethyl-tetrahydro-pyran-2-yloxy)-3,5,7,9,11,13-hexamethyl-oxacyclotetradecane-2,10-dione 10-[O-(3-amino-propyl)-oxime]

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: K2CO3 / acetone / 24 h / Heating 2: 100 percent / H2 / Pd/C / methanol / 20 °C View Scheme

: 13127-18-9
(9-E)-deoxo-9-hydroximinoerythromycin A

: 883739-49-9
6-(4-dimethylamino-3-hydroxy-6-methyl-tetrahydro-pyran-2-yloxy)-14-ethyl-7,12,13-trihydroxy-4-(5-hydroxy-4-methoxy-4,6-dimethyl-tetrahydro-pyran-2-yloxy)-3,5,7,9,11,13-hexamethyl-oxacyclotetradecane-2,10-dione 10-[O-(6-amino-hexyl)-oxime]

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: K2CO3 / acetone / 24 h / Heating 2: 100 percent / H2 / Pd/C / methanol / 20 °C View Scheme

: 13127-18-9
(9-E)-deoxo-9-hydroximinoerythromycin A

: C50H86N6O18

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1: K2CO3 / acetone / 24 h / Heating 2: 100 percent / H2 / Pd/C / methanol / 20 °C 3: CH2Cl2; dimethylformamide / 20 °C 4: HF-pyridine / tetrahydrofuran / 0 - 4 °C View Scheme

: 13127-18-9
(9-E)-deoxo-9-hydroximinoerythromycin A

: C51H88N6O18

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1: K2CO3 / acetone / 24 h / Heating 2: 100 percent / H2 / Pd/C / methanol / 20 °C 3: CH2Cl2; dimethylformamide / 20 °C 4: HF-pyridine / tetrahydrofuran / 0 - 4 °C View Scheme

: 13127-18-9
(9-E)-deoxo-9-hydroximinoerythromycin A

: C54H94N6O18

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1: K2CO3 / acetone / 24 h / Heating 2: 100 percent / H2 / Pd/C / methanol / 20 °C 3: CH2Cl2; dimethylformamide / 20 °C 4: HF-pyridine / tetrahydrofuran / 0 - 4 °C View Scheme

: 13127-18-9
(9-E)-deoxo-9-hydroximinoerythromycin A

: 883739-50-2
C56H100N6O18Si

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: K2CO3 / acetone / 24 h / Heating 2: 100 percent / H2 / Pd/C / methanol / 20 °C 3: CH2Cl2; dimethylformamide / 20 °C View Scheme

: 13127-18-9
(9-E)-deoxo-9-hydroximinoerythromycin A

: 883739-51-3
C57H102N6O18Si

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: K2CO3 / acetone / 24 h / Heating 2: 100 percent / H2 / Pd/C / methanol / 20 °C 3: CH2Cl2; dimethylformamide / 20 °C View Scheme

: 13127-18-9
(9-E)-deoxo-9-hydroximinoerythromycin A

: 883739-52-4
C60H108N6O18Si

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: K2CO3 / acetone / 24 h / Heating 2: 100 percent / H2 / Pd/C / methanol / 20 °C 3: CH2Cl2; dimethylformamide / 20 °C View Scheme

: 13127-18-9
(9-E)-deoxo-9-hydroximinoerythromycin A

A: 722495-12-7
3-O-descladinosyl-3-OH-6-O-allyl-erythromycin A 9-oxime

B 3-halide-4-methyl-thiophene: 3-halide-4-methyl-thiophene

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1.1: 71 percent / pyridine hydrochloride / CH2Cl2 / 42 h / 20 °C 2.1: 90 percent / dimethylaminopyridine / pyridine / 3 h / 20 °C 3.1: 56 percent / potassium tert-butoxide / dimethylsulfoxide; tetrahydrofuran / 4 h 4.1: HCl / ethanol; H2O / 6 h / 50 °C 4.2: 72 percent / K2CO3 / methanol / 12 h / 50 °C View Scheme

: 13127-18-9
(9-E)-deoxo-9-hydroximinoerythromycin A

: (3R,4S,5S,6R,7R,9R,11S,12R,13S,14R)-6-((2S,3R,4S,6R)-4-Dimethylamino-3-hydroxy-6-methyl-tetrahydro-pyran-2-yloxy)-14-ethyl-4,12,13-trihydroxy-3,5,7,9,11,13-hexamethyl-7-[(E)-3-(4-methyl-thiophen-3-yl)-allyloxy]-oxacyclotetradecane-2,10-dione 10-oxime

Conditions

Conditions	Yield
Multi-step reaction with 5 steps 1.1: 71 percent / pyridine hydrochloride / CH2Cl2 / 42 h / 20 °C 2.1: 90 percent / dimethylaminopyridine / pyridine / 3 h / 20 °C 3.1: 56 percent / potassium tert-butoxide / dimethylsulfoxide; tetrahydrofuran / 4 h 4.1: HCl / ethanol; H2O / 6 h / 50 °C 4.2: 72 percent / K2CO3 / methanol / 12 h / 50 °C 5.1: triethylamine / palladium (II) acetate; triphenylphosphine / acetonitrile / 16 h / Heating View Scheme

Yield

Multi-step reaction with 5 steps
1.1: 71 percent / pyridine hydrochloride / CH2Cl2 / 42 h / 20 °C
2.1: 90 percent / dimethylaminopyridine / pyridine / 3 h / 20 °C
3.1: 56 percent / potassium tert-butoxide / dimethylsulfoxide; tetrahydrofuran / 4 h
4.1: HCl / ethanol; H2O / 6 h / 50 °C
4.2: 72 percent / K2CO3 / methanol / 12 h / 50 °C
5.1: triethylamine / palladium (II) acetate; triphenylphosphine / acetonitrile / 16 h / Heating
View Scheme

Erythromycin-9-oxime Chemical Properties

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

Erythromycin-9-oxime Safety Profile

Hazard Codes of Erythromycin, 9-oxime (CAS NO.13127-18-9): Irritant Xi
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.

Erythromycin-9-oxime Specification

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

Product Name

ERYTHROMYCIN OXIME

Synthetic route

Erythromycin-9-oxime Chemical Properties

Erythromycin-9-oxime Safety Profile

Erythromycin-9-oxime Specification

Related Products

Hot Products