N-((1R,2R)-1-((Acetyloxy)methyl)-2-hydroxy-2-(4-nitrophenyl)ethyl)-2,2-dichloroacetamide
Basic information
- CAS
10318-16-8- Standard SMILES
CC(=O)OC[C@@H](NC(=O)C(Cl)Cl)[C@H](O)c1ccc([N+](=O)[O-])cc1- InChIKey
VVOIFRARHIZCJD-GHMZBOCLSA-N- Molecular formula
- C13H14Cl2N2O6
- Average molar mass
- 365.16 g/mol
- Monoisotopic mass
- 364.0228916
Overview
Chloramphenicol 3-acetate is an acetate ester. It is functionally related to a chloramphenicol.
Names & identifiers
- Preferred name
- N-((1R,2R)-1-((Acetyloxy)methyl)-2-hydroxy-2-(4-nitrophenyl)ethyl)-2,2-dichloroacetamide
- IUPAC
- [(2R,3R)-2-[(2,2-dichloroacetyl)amino]-3-hydroxy-3-(4-nitrophenyl)propyl] acetate
- English name
- chloramphenicol 3-acetate
- Molecular formula
- C13H14Cl2N2O6
- Molecular weight
- 365.17
Names & synonyms
Chloramphenicol 3-acetate10318-16-83-Acetylchloramphenicol3'-O-acetylchloramphenicol(2R,3R)-2-[(dichloroacetyl)amino]-3-hydroxy-3-(4-nitrophenyl)propyl acetate[(2R,3R)-2-[(2,2-dichloroacetyl)amino]-3-hydroxy-3-(4-nitrophenyl)propyl] acetateCHEBI:16730N-[(1R,2R)-1-[(Acetyloxy)methyl]-2-hydroxy-2-(4-nitrophenyl)ethyl]-2,2-dichloroacetamide((2R,3R)-2-((2,2-dichloroacetyl)amino)-3-hydroxy-3-(4-nitrophenyl)propyl) acetate(2R,3R)-2-((dichloroacetyl)amino)-3-hydroxy-3-(4-nitrophenyl)propyl acetateN-((1R,2R)-1-((Acetyloxy)methyl)-2-hydroxy-2-(4-nitrophenyl)ethyl)-2,2-dichloroacetamideRefChem:926523
Show more names
Chloramphenicol Impurity 93-O-AcetylchloraMphenicol, ChloraMphenicol 3-acetateAcetamide, N-[(1R,2R)-1-[(acetyloxy)methyl]-2-hydroxy-2-(4-nitrophenyl)ethyl]-2,2-dichloro-
chloramphenicol acetateC13H14Cl2N2O63-Acetoxychloramphenicol; 3-Acetylchloramphenicol; 3-O-Monoacetylchloramphenicol; [R-(R*,R*)]-N-[1-[(acetyloxy)methyl]-2-hydroxy-2-(4-nitrophenyl)ethyl]-2,2-dichloroacetamide; D-threo-(-)-2,2-Dichloro-N-[beta-hydroxy-alpha-(hydroxymethyl)-p-nitrophenethyl]acetamide alpha-Acetate;orb2299212SCHEMBL4744337CHEMBL4177469DTXSID30908222MFCD28898459
Properties
Computed structural properties
- XLogP
- 1.7
- Topological polar surface area
- 121 Ų
- Hydrogen bond donors
- 2
- Hydrogen bond acceptors
- 6
- Rotatable bonds
- 7
- Heavy atoms
- 23
- Formal charge
- 0
- Complexity
- 435
Physicochemical properties
- Melting point
- 89 · 89-91oC
- Boiling point
- 589 · 589.0±50.0 °C(Predicted)
- Density
- 1.473 · 1.473±0.06 g/cm3(Predicted)
- storage temp.
- -20 °C · -20°C Freezer
- solubility
- Chloroform (Slightly), Methanol (Slightly)
- pka
- 10.85 · 10.85±0.46(Predicted)
- form
- Solid
- color
- White to Off-White
Chemistry & industry
Applications
DescriptionChloramphenicol acetate is an acetylated and inactive version of chloramphenicol. It is formed in E. coli and S. aureus by the inducible enzyme chloramphenicol acetyltransferase in the presence of acetyl coenzyme A (acetyl-CoA; ) to confer chloramphenicol resistance. Chloramphenicol acetate has no antibiotic activity against S. sonnei in a turbidimetric assay.
UsesChloramphenicol acetate is a naturally-occurring co-metabolite of chloramphenicol in Streptomyces venezuelae with albeit significantly lower potency. Chloramphenicol acetate is the major product of chloramphenicol acetyltransferase, the major resistance mechanism to chloramphenicol.
UsesChloramphenicol 3-Acetate is an Chloramphenicol (C325030) derivative found in metabolic decomposition of Chloramphenicol by Alcaligenes faecalis.
Additional notes
DefinitionChEBI: Chloramphenicol 3-acetate is an acetate ester. It is functionally related to a chloramphenicol.
Related reactions
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Compound notes
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