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31667 Supelco

Chloramphenicol

VETRANAL, analytical standard

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/REAXYS Number 2225532

  •  EC Number 200-287-4

  •  MDL number MFCD00078159

  •  PubChem Substance ID 329753874

  •  NACRES NA.24

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Properties

Related Categories Additional Standards, Analytical Standards, Analytical/Chromatography, Antibiotics Standards, Bacteriostatic,
Quality Level   100
grade   analytical standard
InChI Key   WIIZWVCIJKGZOK-RKDXNWHRSA-N
product line   VETRANAL
assay   ≥98% (HPLC)
form   neat
shelf life   limited shelf life, expiry date on the label
application(s)   HPLC: suitable
  gas chromatography (GC): suitable
mp   148-150 °C (lit.)
solubility   H2O: insoluble 100% (practically)
Featured Industry   Pharmaceutical (small molecule)
format   neat

Description

General description

Chloramphenicol (CAP) is an antibiotic which was first isolated from Streptomyces venezuelae. It has a nitrobenzene moiety which may be responsible for aplastic anaemia.1 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.
This grade has the standard for Supelco MIP SPE cartridges. For more information request Supelco Literature T407075, T706024

Application

Chloramphenicol has been used as reference standard in the determination of the concentration of CAP residues in shrimp tissues using LC-MS technique and also in frozen chicken samples (liver, kidney and muscle) using HPLC.

Refer to the product′s Certificate of Analysis for more information on a suitable instrument technique. Contact Technical Service for further support.

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.

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.

Legal Information

VETRANAL is a trademark of Sigma-Aldrich Chemie GmbH

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

Documents

Certificate of Analysis (COA)

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Protocols & Articles

Articles

HPLC Analysis of Antibacterials/Antifungals on Ascentis® C18

From our library of Articles, Sigma-Aldrich presents HPLC Analysis of Antibacterials/Antifungals on Ascentis® C18
Keywords: Antibiotics, Antifungals, Antimicrobials, Chromatography, High performance liquid chromatography, Pharmaceutical, Veterinary

HPLC Analysis of Antibacterials/Antifungals on Ascentis® RP-Amide (Formate Mobile Phase)

From our library of Articles, Sigma-Aldrich presents HPLC Analysis of Antibacterials/Antifungals on Ascentis® RP-Amide (Formate Mobile Phase)
Keywords: Antifungals, Chromatography, Clinical, High performance liquid chromatography, Pharmaceutical

LC/MS Analysis of Chloramphenicol in Shrimp on Ascentis® Express C18 after Dispersive SPE (QuEChERS) Cleanup using Supel™ QuE Z-Sep+

From our library of Articles, Sigma-Aldrich presents LC/MS Analysis of Chloramphenicol in Shrimp on Ascentis® Express C18 after Dispersive SPE (QuEChERS) Cleanup using Supel™ QuE Z-Sep+
Keywords: Antibiotics, Chromatography, High performance liquid chromatography, Liquid chromatography mass spectrometry, Mass spectrometry, Sample preparations, Solid phase extractions

Peer-Reviewed Papers
15

References

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41724 DL-threo-Chloramphenicol-d5, analytical standard

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