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C1919 Sigma-Aldrich

Chloramphenicol

BioReagent, suitable for plant cell culture

Synonym: 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, D-threo-2,2-Dichloro-N-[β-hydroxy-α-(hydroxymethyl)-4-nitrophenethyl]acetamide, Chloromycetin

  • 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

  •  PubChem Substance ID 24892448

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Properties

Related Categories A - K, Antibacterial, Antibiotics, Antibiotics A to Z, Antibiotics and Antimycotics,
InChI Key   WIIZWVCIJKGZOK-RKDXNWHRSA-N
product line   BioReagent
form   powder
application(s)   cell culture | plant: suitable
impurities   Endotoxin, tested
mp   148-150 °C (lit.)
solubility   ethanol: 50 mg/mL
suitability   suitable for plant cell culture
Featured Industry   Agriculture
Mode of action   protein synthesis | interferes
antibiotic activity spectrum   Gram-negative bacteria
  Gram-positive bacteria
  mycobacteria
  mycoplasma
Gene Information   human ... CYP1A2(1544)

Description

Application

Chloramphenicol is a synthetic antibiotic, isolated from strains of Streptomyces venezuelae. It is often used for bacterial selection in molecular biology applications at 10-20 μg/mL and as a selection agent for transformed cells containing chloramphenicol reistance genes.

Biochem/physiol Actions

Mode of Action: Chloramphenicol inhibits bacterial protein synthesis by blocking the peptidyl transferase step by binding to the 50S ribosomal subunit and preventing attachment of aminoacyl tRNA to the ribosome. It also inhibits mitochondrial and chloroplast protein synthesis and ribosomal formation of (p)ppGpp, de-pressing rRNA transcription.

Mode of Resistance: Use of chloramphenicol acetyltransferase will acetylate the product and inactivate it.

Antimicrobial Spectrum: This is a broad spectrum antibiotic against gram-positive and gram-negative bacteria, and is used mainly for ophthalmic and veterinary purposes.

Caution

Stock solutions should be stored at 2-8°C and are stable at 37°C for 5 days. Aqueous solutions are neutral and stable over a wide pH range, with 50% hydrolysis occurring after 290 days. Use of a borax buffered solution reduces this number to 14%. Solutions should be protected from light as photochemical decomposition results in a yellowing of the solution. Heating aqueous solutions at 115°C for 30 minutes results in a 10% loss of chloramphenicol.

Packaging

5, 25, 100 g in glass bottle

Preparation Note

Stock solutions can be prepared directly in the vial at any recommended concentration. A solution at 50 mg/mL in ethanol yields a clear, very faint, yellow solution. Degradation of chloramphenicol in aqueous solution is catalyzed by general acids and bases. This rate of degradation is independent of the ionic strength and pH.

General description

Chemical structure: phenicole

Other Notes

Keep container tightly closed in a dry and well-ventilated place, Light sensitive. Storage class (TRGS 510): Non-combustible, acute toxic Cat.3 / toxic hazardous materials or hazardous materials causing chronic effects

Safety & Documentation

Safety Information

Symbol 
GHS08  GHS08
Signal word 
Warning
Hazard statements 
Precautionary statements 
RIDADR 
NONH for all modes of transport
WGK Germany 
3
RTECS 
AB6825000

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Peer-Reviewed Papers
15

References

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