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23275

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Chloramphenicol

BioChemika, ≥99.0% (HPLC)

Synonym:Chloromycetin®, D-threo-2,2-Dichloro-N-[β-hydroxy-α-(hydroxymethyl)-4-nitrophenethyl]acetamide, D-(−)-threo-2,2-Dichloro-N-[β-hydroxy-α-(hydroxymethyl)-β-(4-nitrophenyl)ethyl]acetamide, D-(−)-threo-2-Dichloroacetamido-1-(4-nitrophenyl)-1,3-propanediol
CAS Number:56-75-7
Linear Formula:Cl2CHCONHCH(CH2OH)CH(OH)C6H4NO2
Molecular Weight:323.13
Beilstein Registry Number:2225532
EC Number:200-287-4
MDL number:MFCD00078159

Description

Biochem/physiol ActionsMode of Action: Inhibits translation on the 50S ribosomal subunit at the peptidyltransferase step (elongation inhibition). Bacteriostatic.
Mode of Resistance: Acetylation by chloramphenicol acetyltransferase (cat gene).
Other NotesInhibits protein biosynthesis by binding to the large subunit of the bacterial ribosome and by blocking the peptidyl transfer; chloramphenicol-resistance is a useful genetic marker for the selection of eukaryotic cells;1 Resistance is usually mediated by a chloramphenicol-acetyl-transferase, but there are exceptions;2 Review.3
Legal InformationChloromycetin is a registered trademark of Parke-Davis & Co.

Properties

product lineBioChemika
assay≥99.0% (HPLC)
optical activity[α]20/D +19.5±1°, c = 5% in ethanol
mp148-150 °C(lit.)
 149-151 °C

Safety

Personal Protective EquipmentEyeshields, Gloves, type P2 (EN 143) respirator cartridges
Hazard CodesT
Risk Statements45
Safety Statements53-45
WGK Germany3
RTECSAB6825000

Related Products

Replaced byC0378, Chloramphenicol

References

Cited Reference1. W. Shaw Meth. Enzymol. 53, 737, (1975)
 2. D.F. Gaffney et al. J. Gen. Microbiol. 125, 113, (1981) Abstract
 3. L.C. Vining, D.W.S. Westlake Drugs Pharm. Sci. 22, 387, (1984)
MerckMerck 13,2087
BeilsteinBeil. 13,IV,2742
referenceAldrich MSDS 1, 364:D / Corp MSDS 1 (1), 722:C / FT-IR 2 (2), 2987:A / FT-IR 1 (2), 362:D / FT-NMR 1 (2), 1380:A / IR-Spectra (3), 1074:A / IR-Spectra (2), 939:D / NMR-Reference 2 (2), 340:B / RegBook 1 (2), 2011:G / Sax 6, 668 / Sigma FT-IR 1 (1), 634:C / Structure Index 1, 321:A:2