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31667

Supelco

Chloramphenicol

VETRANAL®, analytical standard

Synonym(s):
D-(−)-threo-2-Dichloroacetamido-1-(4-nitrophenyl)-1,3-propanediol, D-(−)-threo-2,2-Dichloro-N-[β-hydroxy-α-(hydroxymethyl)-β-(4-nitrophenyl)ethyl]acetamide, Chloromycetin, D-threo-2,2-Dichloro-N-[β-hydroxy-α-(hydroxymethyl)-4-nitrophenethyl]acetamide
Linear Formula:
Cl2CHCONHCH(CH2OH)CH(OH)C6H4NO2
CAS Number:
Molecular Weight:
323.13
Beilstein:
2225532
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.24

Quality Level

grade

analytical standard

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

Clinical Testing

format

neat

SMILES string

OC[C@@H](NC(=O)C(Cl)Cl)[C@H](O)c1ccc(cc1)[N+]([O-])=O

InChI

1S/C11H12Cl2N2O5/c12-10(13)11(18)14-8(5-16)9(17)6-1-3-7(4-2-6)15(19)20/h1-4,8-10,16-17H,5H2,(H,14,18)/t8-,9-/m1/s1

InChI key

WIIZWVCIJKGZOK-RKDXNWHRSA-N

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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

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

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 registered trademark of Sigma-Aldrich Chemie GmbH

pictograms

CorrosionHealth hazard

signalword

Danger

Hazard Classifications

Carc. 2 - Eye Dam. 1 - Repr. 2

Storage Class Code

11 - Combustible Solids

WGK Germany

WGK 3

Personal Protective Equipment

dust mask type N95 (US),Eyeshields,Gloves

Certificate of Analysis

Certificate of Origin

Chloramphenicol residues in chicken liver, kidney and muscle: a comparison among the antibacterial residues monitoring methods of Four Plate Test, ELISA and HPLC.
Tajik H
Food And Chemical Toxicology, 48(8-9), 2464-2468 (2010)
Determination of chloramphenicol residues in shrimps by liquid chromatography-mass spectrometry.
Ramos M
Journal of Chromatography. B, Analytical Technologies in the Biomedical and Life Sciences, 791(1-2), 31-38 (2003)
Anthony J Brzoska et al.
PloS one, 8(2), e56090-e56090 (2013-02-15)
Members of the genus Acinetobacter have been the focus recent attention due to both their clinical significance and application to molecular biology. The soil commensal bacterium Acinetobacter baylyi ADP1 has been proposed as a model system for molecular and genetic...
David G Kirk et al.
Applied and environmental microbiology, 80(16), 5141-5150 (2014-06-15)
Clostridium botulinum produces heat-resistant endospores that may germinate and outgrow into neurotoxic cultures in foods. Sporulation is regulated by the transcription factor Spo0A and the alternative sigma factors SigF, SigE, SigG, and SigK in most spore formers studied to date....
J N de Almeida Júnior et al.
Clinical microbiology and infection : the official publication of the European Society of Clinical Microbiology and Infectious Diseases, 20(8), 784-790 (2013-12-21)
Trichosporon spp. have recently emerged as significant human pathogens. Identification of these species is important, both for epidemiological purposes and for therapeutic management, but conventional identification based on biochemical traits is hindered by the lack of updates to the species...

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