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Key Documents

C0378

Sigma-Aldrich

Chloramphenicol

≥98% (HPLC)

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/REAXYS Number:
2225532
EC Number:
MDL number:
UNSPSC Code:
51102831
PubChem Substance ID:
NACRES:
NA.76

Quality Level

assay

≥98% (HPLC)

form

powder or crystals

pKa 

5.5

mp

149-153 °C (lit.)

antibiotic activity spectrum

Gram-negative bacteria
Gram-positive bacteria
mycobacteria
mycoplasma

mode of action

protein synthesis | interferes

storage temp.

room temp

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

Gene Information

human ... CYP1A2(1544)

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General description

Chemical structure: phenicole

Application

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

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

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.

Other Notes

Keep container tightly closed in a dry and well-ventilated place.

pictograms

Health hazardCorrosion

signalword

Danger

Hazard Classifications

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

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

ppe

Eyeshields, Faceshields, Gloves, type P3 (EN 143) respirator cartridges


Certificates of Analysis (COA)

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Development and Evaluation of an aroA/htrA Salmonella enteritidis Vector Expressing Eimeria maxima TRAP Family Protein EmTFP250 with CD 154 (CD 40L) as Candidate Vaccines against Coccidiosis in Broilers.
International Journal of Poultry Science, 9, 1031-1037 (2010)
Targeting antibacterial agents by using drug-carrying filamentous bacteriophages.
Yacoby I et al.
Antimicrobial Agents and Chemotherapy, 50, 2087-2087 (2006)
Kyle J Wayne et al.
Journal of bacteriology, 192(17), 4388-4394 (2010-07-14)
The WalRK two-component regulatory system coordinates gene expression that maintains cell wall homeostasis and responds to antibiotic stress in low-GC Gram-positive bacteria. Phosphorylated WalR (VicR) of the major human respiratory pathogen Streptococcus pneumoniae (WalR(Spn)) positively regulates transcription of several surface
Expression and Purification of the Arabidopsis E4 SUMO Ligases PIAL1 and PIAL2.
Tomanov K and Bachmair A
Bio-protocol null
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Cell reports, 27(2), 334-342 (2019-04-02)
We have previously described the existence of membranous nanotubes, bridging adjacent bacteria, facilitating intercellular trafficking of nutrients, cytoplasmic proteins, and even plasmids, yet components enabling their biogenesis remain elusive. Here we reveal the identity of a molecular apparatus providing a

Protocols

This procedure applies to products that have a specification for the enzymatic activity of chloramphenicol acetyltransferase.

A highly selective and sensitive analytical method was developed for chloramphenicol using a QuEChERS type sample preparation approach and LC-MS/MS detection.

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

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