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34005

Supelco

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:
7411-65-6
Molecular Weight:
323.13
MDL number:
MFCD07370152
UNSPSC Code:
41116107
PubChem Substance ID:
329754750

grade

analytical standard

Quality Level

100

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

SMILES string

OC[C@@H](NC(=O)C(Cl)Cl)[C@H](O)c1cccc(c1)[N+]([O-])=O

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

InChI key

FTMJFHVKAXPFIY-RKDXNWHRSA-N

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.

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.

Recommended products

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

pictograms

Health hazard
GHS08

signalword

Danger

hcodes

H350

Hazard Classifications

Carc. 1B

Storage Class

6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

wgk_germany

WGK 3

ppe

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

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Certificates of Analysis (COA)

Lot/Batch Number
BCCF1657
BCBS4220V

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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
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
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
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
Masahiro Yamamoto et al.
The Journal of experimental medicine, 208(7), 1533-1546 (2011-06-15)
The ROP18 kinase has been identified as a key virulence determinant conferring a high mortality phenotype characteristic of type I Toxoplasma gondii strains. This major effector molecule is secreted by the rhoptries into the host cells during invasion; however, the
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