Chloramphenicol palmitate

Base Information

• Chemical Name: Chloramphenicol palmitate
• CAS No.: 530-43-8
• Molecular Formula: C27H42Cl2N2O6
• Molecular Weight: 561.546
• Hs Code.: 29414000
• European Community (EC) Number: 208-477-9
• UNII: 43VU4207NW
• DSSTox Substance ID: DTXSID9048699
• Nikkaji Number: J6.700H
• Wikidata: Q27106147
• NCI Thesaurus Code: C65313
• RXCUI: 20767
• Metabolomics Workbench ID: 53063
• ChEMBL ID: CHEMBL1506
• Mol file: 530-43-8.mol

Synonyms:chloramphenicol monopalmitate;chloramphenicol palmitate;chloramphenicol palmitate, diammonium salt;chloramphenicol palmitate, monoammonium salt;chloramphenicol palmitate, monopalmitate

Chemical Property of Chloramphenicol palmitate

Chemical Property:

• Appearance/Colour: white or slightly yellow crystalline powder
• Vapor Pressure: 4.43E-20mmHg at 25°C
• Melting Point: 90 °C
• Refractive Index: 1.525
• Boiling Point: 691.6 °C at 760 mmHg
• PKA: 10.69±0.46(Predicted)
• Flash Point: 372.1 °C
• PSA: 121.45000
• Density: 1.172 g/cm³
• LogP: 7.85530
• Storage Temp.: Store at RT.
• Solubility.: DMSO (Slightly), Ethanol (Sparingly), Ethyl Acetate (Slightly)
• Water Solubility.: 8.423ug/L(25 oC)
• XLogP3: 9
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 21
• Exact Mass: 560.2419925
• Heavy Atom Count: 37
• Complexity: 639

Purity/Quality:

99%, ^*data from raw suppliers

Chloramphenicol palmitate ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 40-36/37/38-20/21/22
• Safety Statements: 36/37-36-26

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CCCCCCCCCCCCCCCC(=O)OCC(C(C1=CC=C(C=C1)[N+](=O)[O-])O)NC(=O)C(Cl)Cl
• Isomeric SMILES: CCCCCCCCCCCCCCCC(=O)OC[C@H]([C@@H](C1=CC=C(C=C1)[N+](=O)[O-])O)NC(=O)C(Cl)Cl
• Description: Chloramphenicol palmitate is an orally bioavailable ester prodrug form of the antibiotic chloramphenicol. It is hydrolyzed in the small intestine to release chloramphenicol. Formulations containing chloramphenicol palmitate were previously used in the treatment of severe bacterial infections.
• Uses: Chloramphenicol Palmitate is a Chloramphenicol (C325030) derivative, a broad spectrum antibiotic obtained from cultures of the soil bacterium Streptomyces venezuelae. It has a broad spectrum of activity against Gram-positive and gram-negative bacteria. Antibacterial; antirickettsial. antibacterial, antirickettsial Chloramphenicol palmitate is prepared by acylation of chloramphenicol with palmitic acid. Although chloramphenicol palmitate is a more hydrophobic drug which should enhance bioavailability, the primary advantage of the ester is to mask the taste of chloramphenicol in oral formulations. Chloramphenicol palmitate is significantly less active than chloramphenicol but acts as a prodrug, being readily hydrolysed by acid and esterase in the gut to release chloramphenicol.
• Therapeutic Function: Antibacterial; Antirickettsial

Technology Process of Chloramphenicol palmitate

There total 17 articles about Chloramphenicol palmitate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 100.0%

3-nitro-1-palmitoyl-1H-1,2,4-triazole (1104640-94-9) + chloramphenicol (56-75-7,85666-84-8) → chloramphenicol Palmitate (530-43-8)

Guidance literature:

With triethylamine; In tetrahydrofuran; at 20 ℃; for 1h; regioselective reaction;

DOI:10.3987/COM-08-S(N)95

Reference yield: 99.0%

vinyl palmitate (693-38-9) + chloramphenicol (56-75-7,85666-84-8) → chloramphenicol Palmitate (530-43-8)

Guidance literature:

With palmitic acid imprinted Thermomyces lanuginosus Lypozyme TL 100L lipase nanogel; In acetonitrile; at 20 ℃; for 48h; Temperature; Concentration; Reagent/catalyst; regioselective reaction; Green chemistry; Enzymatic reaction;

DOI:10.1039/c3gc40465j

Reference yield: 91.9%

chloramphenicol (56-75-7,85666-84-8) + n-hexadecanoyl chloride (112-67-4) → chloramphenicol Palmitate (530-43-8)

Guidance literature:

With pyridine; In N,N-dimethyl-formamide; toluene; at -4 - 5 ℃; for 4.83333h; Solvent;

DOI:10.1021/op990200z

upstream raw materials:

dichloroacetic acid methyl ester

(1R,2R)-2-amino-1-(4-nitro-phenyl)-3-palmitoyloxy-propan-1-ol

(1R,2R)-2-amino-1-(4-nitro-phenyl)-3-palmitoyloxy-propan-1-ol; hydrochloride

dichloroacetic anhydride

Downstream raw materials:

chloramphenicol

1-hexadecylcarboxylic acid

Refernces

• 1、 Wang, Rui,Zhang, Yifei,Ge, Jun,Liu, Zheng. "Activation of enzyme nanogel in organic solvents by PEG-substrate joint imprinting". . p. 40301 - 40304. Retrieved 2015/01/09.
• 2、 Bizerra, Ayla M.C.,Montenegro, Tasso G.C.,Lemos, Telma L.G.,De Oliveira, Maria C.F.,De Mattos, Marcos C.,Lavandera, Iván,Gotor-Fernández, Vicente,De Gonzalo, Gonzalo,Gotor, Vicente. "Enzymatic regioselective production of chloramphenicol esters". supporting information; experimental part. p. 2858 - 2862. Retrieved 2011/05/12.