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C0378

Sigma-Aldrich

Chloramphenicol

≥98% (HPLC)

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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
Linear Formula:
Cl2CHCONHCH(CH2OH)CH(OH)C6H4NO2
CAS Number:
Molecular Weight:
323.13
Beilstein:
2225532
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.76

Assay

≥98% (HPLC)

form

powder or crystals

pKa 

5.5

mp

148-150 °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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This Item
C7795C08571107004
Chloramphenicol ≥98% (HPLC)

Sigma-Aldrich

C0378

Chloramphenicol

Chloramphenicol γ-irradiated

Sigma-Aldrich

C7795

Chloramphenicol

Chloramphenicol meets USP testing specifications

Sigma-Aldrich

C0857

Chloramphenicol

Chloramphenicol United States Pharmacopeia (USP) Reference Standard

USP

1107004

Chloramphenicol

form

powder or crystals

form

powder

form

crystalline

form

-

mp

148-150 °C (lit.)

mp

148-150 °C (lit.)

mp

148-150 °C (lit.)

mp

148-150 °C (lit.)

antibiotic activity spectrum

Gram-negative bacteria, Gram-positive bacteria, mycobacteria, mycoplasma

antibiotic activity spectrum

Gram-negative bacteria, Gram-positive bacteria, mycobacteria, mycoplasma

antibiotic activity spectrum

viruses

antibiotic activity spectrum

-

mode of action

protein synthesis | interferes

mode of action

protein synthesis | interferes

mode of action

protein synthesis | interferes

mode of action

-

storage temp.

room temp

storage temp.

2-8°C

storage temp.

-

storage temp.

-

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

CorrosionHealth hazard

Signal Word

Danger

Hazard Statements

Hazard Classifications

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

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Chloramphenicol United States Pharmacopeia (USP) Reference Standard

USP

1107004

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Protocols

Enzymatic Assay of Chloramphenicol Acetyltransferase

To measure chloramphenicol acetyltransferase activity, this procedure uses DTNB and coenzyme A. The reaction of DTNB with the –SH group on CoA results in a colorimetric increase at 412 nm.

Plasmid DNA Preparation

Preparation of Plasmid DNA by Alkaline Lysis with SDS: Maxipreparation between Cold Spring Harbor Laboratory Press and our research team.

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