111321-02-9

Basic information

• Product Name: Erythromycin A Oxime
• Synonyms: Erythromycin A Oxime;(9E)-ErythroMycin A OxiMe;Erythromycin Impurity J;(3R,4S,5S,6R,7R,9R,11S,12R,13S,14R,E)-6-(((2S,3R,4S,6R)-4-(dimethylamino)-3-hydroxy-6-methyltetrahydro-2H-pyran-2-yl)oxy)-14-ethyl-7,12,13-trihydroxy-4-(((2R,4R,5S,6S)-5-hydroxy-4-methoxy-4,6-dimethyltetrahydro-2H-pyran-2-yl)oxy)-10-(hydroxyimino)-3,5,7,9;Azithromycin Impurity S ((9E)-Erythromycin A Oxime);(9E)-Erythromycin A Oxime Roxithromycin EP Impurity C;Roxithromycin EP Impurity C (Erythromycin Impurity J)
• CAS NO: 111321-02-9
• Molecular Formula: C₃₇H₆₈N₂O₁₃
• Molecular Weight: 748.94142
• Product Categories: Intermediates & Fine Chemicals;Pharmaceuticals;Chiral Reagents, Metabolites & Impurities, Pharmaceuticals, Intermediates & Fine Chemicals
• Mol File: 111321-02-9.mol

Chemical Properties

• Melting Point: 156-166 °C
• Boiling Point: 841°C at 760 mmHg
• Flash Point: 462.4°C
• Appearance: /
• Density: 1.28g/cm³
• Vapor Pressure: 7.27E-33mmHg at 25°C
• Refractive Index: 1.552
• Storage Temp.: Refrigerator
• Solubility: Chloroform (Slightly), DMSO (Slightly), Ethanol (Slightly), Methanol (Slightly,
• PKA: 11.96±0.70(Predicted)
• CAS DataBase Reference: Erythromycin A Oxime(CAS DataBase Reference)
• NIST Chemistry Reference: Erythromycin A Oxime(111321-02-9)
• EPA Substance Registry System: Erythromycin A Oxime(111321-02-9)

Safety Data

• Hazardous Substances Data: 111321-02-9(Hazardous Substances Data)

Usage

Uses

1. Used in Pharmaceutical Industry:
Erythromycin A Oxime is used as an intermediate for the synthesis of Azithromycin, a widely used antibiotic effective against a broad range of bacterial infections.
2. Used in Gastroenterology:
Erythromycin A Oxime is used as an antibacterial agent for treating infections caused by Helicobacter pylori, a bacterium that can lead to ulcers and other gastrointestinal issues.
3. Used in Research and Development:
As a semi-synthetic analogue of Erythromycin, Erythromycin A 9-oxime has been instrumental in the development of new macrolide antibiotics with improved properties, such as ring-expanded aza-erythromycins (e.g., Azithromycin) and oxime ethers (e.g., Roxithromycin).

InChI:InChI=1/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

Upstream product

• 114-07-8 erythromycin 

Downstream Products

• 227193-43-3 erythromycin A 9-[O-(3-phenoxypropyl)oxime] 
• 714960-38-0 2',4''-O-bis(benzoyl)erythromycin A 9-O-benzoyloxime 
• 76801-85-9 9-Deoxo-9a-aza-9a-homoerythromycin A 
• 26116-56-3 erythromycylamine 
• 13147-55-2 C₃₇H₇₀N₂O₁₂ 
• 76801-85-9 10-dihydro-10-deoxo-11-azaerythromycin A 
• 111247-90-6 C₄₅H₇₅N₃O₁₆S*ClH 
• 111247-87-1 C₄₄H₇₄N₂O₁₅S*ClH 
• 76820-32-1 erythromycin A lactam 
• 99290-97-8 C₃₇H₆₆N₂O₁₂ 
• 111266-72-9 C₄₃H₇₁ClN₂O₁₅S*ClH 
• 111247-89-3 C₄₃H₇₁IN₂O₁₅S*ClH 
• 83905-01-5 Zithromax(R) 
• 217500-96-4 (2R,3S,4R,5R,8R,10R,11R,12S,13S,14R)-13-[[2,6-dideoxy-3-C-methyl-3-Ο-methyl-4-C-[(propylamino)methyl]-α-L-ribohexopyranosyl]oxy]-2-ethyl-3,4,10-trihydroxy-3,5,8,10,12,14-hexamethyl-11-[[3,4,6-trideoxy-3-(dimethylamino)-β-D-xylohexopyranosyl]oxy]-1-oxa-6-azacyclopentadecan-15-one 

Relevant articles and documents

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A few examples of hybrids/conjugates/chimeras of erythromycin A derivatives and nucleobases (uracil and thymine) or thymidine-derived nucleosides are reported. Linkers and reaction conditions have been investigated to avoid the degradation of the macrolide moiety (glycoside hydrolysis, ring cleavage, dehydration, etc.). (C) 2000 Elsevier Science Ltd.

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