31667
Chloramphenicol
VETRANAL®, analytical standard
Synonym(s):
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
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About This Item
Linear Formula:
Cl2CHCONHCH(CH2OH)CH(OH)C6H4NO2
CAS Number:
Molecular Weight:
323.13
Beilstein:
2225532
EC Number:
MDL number:
UNSPSC Code:
41116107
PubChem Substance ID:
NACRES:
NA.24
grade
analytical standard
Quality Level
product line
VETRANAL®
Assay
≥98% (HPLC)
shelf life
limited shelf life, expiry date on the label
technique(s)
HPLC: suitable
gas chromatography (GC): suitable
mp
149-153 °C (lit.)
solubility
H2O: insoluble 100% (practically)
application(s)
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
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.
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 Merck KGaA, Darmstadt, Germany
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Description
Pricing
Signal Word
Danger
Hazard Statements
Precautionary Statements
Hazard Classifications
Carc. 2 - Eye Dam. 1 - Repr. 2
WGK
WGK 3
Personal Protective Equipment
dust mask type N95 (US), Eyeshields, Gloves
Regulatory Information
监管及禁止进口产品
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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
Uwe Richter et al.
Current biology : CB, 23(6), 535-541 (2013-03-05)
Proliferating cells require coordinated gene expression between the nucleus and mitochondria in order to divide, ensuring sufficient organelle number in daughter cells [1]. However, the machinery and mechanisms whereby proliferating cells monitor mitochondria and coordinate organelle biosynthesis remain poorly understood.
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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