Chloramphenicol

SIGMA/C0857 - meets USP testing specifications

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

Catalog Number	PKG Qty.	Price


45-C0857-25G	25 g	$186.00 1/EA	Add To Favorites
45-C0857-100G	100 g	$624.00 1/EA	Add To Favorites
45-C0857-500G	500 g	$2260.00 1/EA	Add To Favorites

FT-NMR Spectra for Chloromycetin.

This picture is provided solely for illustration purposes. Optical properties of the actual product may deviate. Relevant product information is printed on labeled products and other accompanying or available information material.

This image depicts SKU: C0857-100G

Properties
Descriptions
Safety Info.
Basic Data

agency	meets USP testing specifications
	USP/NF
antibiotic activity spectrum	viruses
application(s)	pharmaceutical (small molecule)
assay	97.0-103.0%
form	crystalline
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
mode of action	protein synthesis \| interferes
mp	149-153 °C (lit.)
Quality Level	200
SMILES string	OC[C@@H](NC(=O)C(Cl)Cl)[C@H](O)c1ccc(cc1)[N+]([O-])=O
solubility	H₂O: insoluble 100% (practically)
storage temp.	2-8°C

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.
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.
General description:	Chemical structure: phenicole
Packaging:	25, 100, 500 g in poly bottle
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	97.0-103.0%
mp	149-153 °C (lit.)
Storage Temp.	2-8°C
UNSPSC	51102831

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