C1919

Sigma-Aldrich

Chloramphenicol

BioReagent, suitable for plant cell culture

Synonym(s):
D-threo-2,2-Dichloro-N-β-hydroxy-α-(hydroxymethyl)-4-nitrophenethylacetamide, D-(−)-threo-2-Dichloroacetamido-1-(4-nitrophenyl)-1,3-propanediol, D-(−)-threo-2,2-Dichloro-N-β-hydroxy-α-(hydroxymethyl)-β-(4-nitrophenyl)ethylacetamide, Chloromycetin
Linear Formula:
Cl2CHCONHCH(CH2OH)CH(OH)C6H4NO2
CAS Number:
Molecular Weight:
323.13
Beilstein/REAXYS Number:
2225532
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.76
Pricing and availability is not currently available.

product line

BioReagent

form

powder

application(s)

cell culture | plant: suitable

impurities

Endotoxin, tested

mp

148-150 °C (lit.)

solubility

ethanol: 50 mg/mL

Featured Industry

Agriculture

Mode of action

protein synthesis | interferes

antibiotic activity spectrum

Gram-negative bacteria
Gram-positive bacteria
mycobacteria
mycoplasma

SMILES string

OCC@@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

Packaging

5, 25, 100 g in glass bottle

Application

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

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.

Other Notes

Keep container tightly closed in a dry and well-ventilated place, Light sensitive. Storage class (TRGS 510): Non-combustible, acute toxic Cat.3 / toxic hazardous materials or hazardous materials causing chronic effects

Pictograms

CorrosionHealth hazard

Signal Word

Danger

Hazard Statements

Personal Protective Equipment

dust mask type N95 (US),Eyeshields,Gloves

Hazard Codes

T

Risk Statement

45

Safety Statement

53-45

RIDADR

NONH for all modes of transport

WGK Germany

WGK 3

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....
David H Kwan et al.
Journal of the American Chemical Society, 137(17), 5695-5705 (2015-04-15)
Blood transfusions are critically important in many medical procedures, but the presence of antigens on red blood cells (RBCs, erythrocytes) means that careful blood-typing must be carried out prior to transfusion to avoid adverse and sometimes fatal reactions following transfusion....
Chloramphenicol eye drops: a dangerous drug?
J Diamond et al.
The Practitioner, 239(1555), 608-611 (1995-10-01)
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...
Stephan Born et al.
The Journal of neuroscience : the official journal of the Society for Neuroscience, 33(1), 201-213 (2013-01-04)
Bitter taste is a basic taste modality, required to safeguard animals against consuming toxic substances. Bitter compounds are recognized by G-protein-coupled bitter taste receptors (TAS2Rs). The human TAS2R10 responds to the toxic strychnine and numerous other compounds. The mechanism underlying...
Articles
Antibiotic kill curve is a dose response experiment in which mammalian cells are subjected to increasing amounts of selection antibiotic
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