34005
m-Chloramphenicol
VETRANAL®, analytical standard
Synonym(s):
D-(−)-threo-2-Dichloroacetamido-1-(3-nitrophenyl)-1,3-propanediol
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About This Item
Empirical Formula (Hill Notation):
C11H12Cl2N2O5
CAS Number:
Molecular Weight:
323.13
UNSPSC Code:
41116107
PubChem Substance ID:
MDL number:
InChI
1S/C11H12Cl2N2O5/c12-10(13)11(18)14-8(5-16)9(17)6-2-1-3-7(4-6)15(19)20/h1-4,8-10,16-17H,5H2,(H,14,18)/t8-,9-/m1/s1
SMILES string
OC[C@@H](NC(=O)C(Cl)Cl)[C@H](O)c1cccc(c1)[N+]([O-])=O
InChI key
FTMJFHVKAXPFIY-RKDXNWHRSA-N
grade
analytical standard
description
threo-form
product line
VETRANAL®
shelf life
limited shelf life, expiry date on the label
technique(s)
HPLC: suitable, gas chromatography (GC): suitable, solid phase extraction (SPE): suitable
application(s)
forensics and toxicology
pharmaceutical (small molecule)
format
neat
storage temp.
2-8°C
Quality Level
Application
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.
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
Find a digital Reference Material for this product available on our online platform ChemisTwin® for NMR. You can use this digital equivalent on ChemisTwin® for your sample identity confirmation and compound quantification (with digital external standard). An NMR spectrum of this substance can be viewed and an online comparison against your sample can be performed with a few mouseclicks. Learn more here and start your free trial.
Legal Information
VETRANAL is a registered trademark of Merck KGaA, Darmstadt, Germany
Disclaimer
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.
signalword
Danger
hcodes
Hazard Classifications
Carc. 1B
Storage Class
6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects
wgk
WGK 3
ppe
Eyeshields, Gloves, type P3 (EN 143) respirator cartridges
Regulatory Information
涉药品监管产品
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Smriti Arora et al.
Nucleic acids research, 41(9), 4963-4975 (2013-03-27)
The accuracy of pairing of the anticodon of the initiator tRNA (tRNA(fMet)) and the initiation codon of an mRNA, in the ribosomal P-site, is crucial for determining the translational reading frame. However, a direct role of any ribosomal element(s) in
Riyaz Ahmad Shah et al.
Nucleic acids research, 47(4), 1908-1919 (2019-01-05)
Initiator tRNAs (i-tRNAs) possess highly conserved three consecutive GC base pairs (GC/GC/GC, 3GC pairs) in their anticodon stems. Additionally, in bacteria and eukaryotic organelles, the amino acid attached to i-tRNA is formylated by Fmt to facilitate its targeting to 30S
Benedikt M Markus et al.
mSphere, 4(3) (2019-06-28)
CRISPR-Cas9 technologies have enabled genome engineering in an unprecedented array of species, accelerating biological studies in both model and nonmodel systems. However, Cas9 can be inherently toxic, which has limited its use in some organisms. We previously described the serendipitous
Ying Xu et al.
Acta biochimica et biophysica Sinica, 50(8), 766-775 (2018-07-03)
Toxoplasma rhoptry protein 38 (TgROP38) is a new active kinase that modulates host cell signal transduction and TgROP38 expression shows strain-specificity and stage-specificity in different isolates. In the present study, we overexpressed ROP38 in the RH and prugniaud (PRU) strain
Conrad von Schubert et al.
PLoS biology, 8(9) (2010-10-12)
The protozoan parasite Theileria inhabits the host cell cytoplasm and possesses the unique capacity to transform the cells it infects, inducing continuous proliferation and protection against apoptosis. The transforming schizont is a multinucleated syncytium that resides free in the host
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