Chloramphenicol
SIAL/31667 - VETRANAL®, analytical standard
Synonym: 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
CAS Number: 56-75-7
Empirical Formula (Hill Notation): C11H12Cl2N2O5
Molecular Weight: 323.13
EC Number: 200-287-4
MDL Number: MFCD00078159
Linear Formula: Cl2CHCONHCH(CH2OH)CH(OH)C6H4NO2
Product Type: Chemical
| application(s) | clinical testing |
| assay | ≥98% (HPLC) |
| format | neat |
| grade | analytical standard |
| InChI | 1S/C11H12Cl2N2O5/c12-10(1 |
| InChI key | WIIZWVCIJKGZOK-RKDXNWHRSA |
| mp | 148-150 °C (lit.) |
| product line | VETRANAL® |
| Quality Level | 100  |
| shelf life | limited shelf life, expiry date on the label |
| SMILES string | OC[C@@H](NC(=O)C(Cl)Cl)[C |
| solubility | H2O: insoluble 100% (practically) |
| technique(s) | gas chromatography (GC): suitable |
| HPLC: suitable |
| Application: | Chloramphenicol has been used as reference standard in the determination of the concentration of CAP residues in shrimp tissues using LC-MS technique and also in frozen chicken samples (liver, kidney and muscle) using HPLC. |
| 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. |
| General description: | Chloramphenicol (CAP) is an antibiotic which was first isolated from Streptomyces venezuelae. It has a nitrobenzene moiety which may be responsible for aplastic anaemia.1 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. This grade has the standard for Supelco MIP SPE cartridges. For more information request Supelco Literature T407075, T706024 |
| Legal Information: | VETRANAL is a registered trademark of Sigma-Aldrich Chemie GmbH |
| 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. |
| Symbol |   GHS05,GHS08 |
| Signal word | Danger |
| Hazard statements | H318 - H351 - H361fd |
| Precautionary statements | P202 - P280 - P305 + P351 + P338 - P308 + P313 - P405 - P501 |
| Hazard Codes | T |
| Risk Statements | 45 |
| Safety Statements | 53-45 |
| RIDADR | NONH for all modes of transport |
| WGK Germany | WGK 3 |
| Purity | ≥98% (HPLC) |
| mp | 148-150 °C (lit.) |
| UNSPSC | 41116107 |