C0378
Sigma-Aldrich

Chloramphenicol

Linear Formula:

Cl2CHCONHCH(CH2OH)CH(OH)C6H4NO2

Empform:

C11H12Cl2N2O5

Synonyms English:

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

Nacres: NA.76
Mdl No: MFCD00078159
Fw: 323.13
Pubchem Substance Id: 24892250
CAS Number: 56-75-7
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Properties

Properties
antibiotic activity spectrum Gram-negative bacteria
assay
assay range 98% (HPLC)
Description Chloramphenicol >=98% (HPLC)
format powder or crystals
glass tube l × o.d. × i.d. human ... CYP1A2(1544)
inchi key 1S/C11H12Cl2N2O5/c12-10(13)11(18)14-8(5-16)9(17)6-1-3-7(4-2-6)15(19)20/h1-48-1016-17H5H2(H1418)/t8-9-/m1/s1
indiff. to chromic acid WIIZWVCIJKGZOK-RKDXNWHRSA-N
MDM Code C0378-5G
Material Number C0378
Business Unit 777
CAS Number 56-75-7

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 10-20μg/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.

General description

Chemical structure: phenicole

Other Notes

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

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.

SAFETY INFORMATION

GHS05,GHS08

Signal Word

Danger

H318 - H351 - H361fd

P202 - P280 - P305 + P351 + P338 - P308 + P313 - P405 - P501

RIDADRRIDADR

WGK Germany

WGK 3

Flash Point (F)

Flash Point (C)

Target Organs

Risk Statement

Supplemental Hazard Statements

DOCUMENTATION

Certificate of Analysis View Sample COA
Certificate of Origin

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