118-57-0 Usage
Uses
Used in Pharmaceutical Industry:
2-Hydroxybenzoic acid 4-(acetylamino)phenyl ester is used as an analgesic and antipyretic agent for the relief of pain and reduction of fever. It is incorporated into various medications under different brand names, such as Acephen (G & W), Infants' Feverall (Actavis), Injectapap (Ortho-McNeil), Neopap (Polymedica), and Tylenol (McNeil). Its effectiveness in managing pain and fever is attributed to its ability to reduce inflammation and regulate body temperature.
Originator
Acetaminosal ,ZYF Pharm Chemical
Manufacturing Process
2 Methods of producing of acetyl salicylic acid ester of N-acetyl-paminophenol:
1. 65.0 g of N-acetyl-p-aminophenol were slurried with 400 ml of water and
cooled to 10°C. 125 ml of 20% sodium hydroxide were slowly added to the
mixture with stirring, the temperature being maintained 10°-15°C. To the
solution obtained, 75.0 g of acetyl salicylic chloride were added with vigorous
stirring over a period of 0.5 h, the solution being maintained at a temperature of about 10°C. Towards the end of the reaction the pH was checked and
adjusted to greater than 10 by the addition of a small amount of 20% sodium
hydroxide. After all the acid chloride had been added, vigorous stirring was
continued for 0.5 h during which time the crude product separated out. The
acetyl salicylic acid ester of N-acetyl-p-aminophenol was filtered off, washed
thoroughly with water and recrystallised from ethanol.
2. 65.0 g of sodium N-acetyl-p-aminophenol were slurried with 500.0 g of dry
benzene and 80.0 g of acetyl salicylic chloride added. The mixture was heated
under reflux for 4 h and filtered hot. The excess benzene was removed under
vacuum and the crude acetyl salicylic acid ester of N-acetyl-p-aminophenol
crystallized from ethanol.
Therapeutic Function
Analgesic, Antineuralgic, Antirheumatic, Antipyretic
Check Digit Verification of cas no
The CAS Registry Mumber 118-57-0 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 1,1 and 8 respectively; the second part has 2 digits, 5 and 7 respectively.
Calculate Digit Verification of CAS Registry Number 118-57:
(5*1)+(4*1)+(3*8)+(2*5)+(1*7)=50
50 % 10 = 0
So 118-57-0 is a valid CAS Registry Number.
InChI:InChI=1/C15H13NO4/c1-10(17)16-11-6-8-12(9-7-11)20-15(19)13-4-2-3-5-14(13)18/h2-9,18H,1H3,(H,16,17)
118-57-0Relevant articles and documents
Cleavage of Carboxylic Esters by Aluminum and Iodine
Sang, Dayong,Yue, Huaxin,Fu, Yang,Tian, Juan
, p. 4254 - 4261 (2021/03/09)
A one-pot procedure for deprotecting carboxylic esters under nonhydrolytic conditions is described. Typical alkyl carboxylates are readily deblocked to the carboxylic acids by the action of aluminum powder and iodine in anhydrous acetonitrile. Cleavage of lactones affords the corresponding ω-iodoalkylcarboxylic acids. Aryl acetylates undergo deacetylation with the participation of the neighboring group. This method enables the selective cleavage of alkyl carboxylic esters in the presence of aryl esters.
Evaluation of glycolamide esters and various other esters of aspirin as true aspirin prodrugs
Nielsen,Bundgaard
, p. 727 - 734 (2007/10/02)
A series of glycolamide, glycolate, (acyloxy)methyl, alkyl, and aryl esters of acetylsalicylic acid (aspirin) were synthesized and evaluated as potential prodrug forms of aspirin. N,N-Disubstituted glycolamide esters were found to be rapidly hydrolized in human plasma, resulting in the formation of aspirin as well as the corresponding salicylate esters. These in turn hydrolyzed rapidly to salicylic acid. The largest amount of aspirin formed from the esters were 50 and 55% in case of the N,N-dimethyl- and N,N-diethylglycolamide esters, respectively. Similar results were obtained in blood with the N,N-dimethyl- and N,N-diethylglycolamide esters. Unsubstituted and monosubstituted glycolamide esters as well as most other esters previously suggested to be aspirin prodrugs were shown to hydrolyze exclusively to the corresponding salicylic acid esters. Lipophilicity parameters and water solubilities of the esters were determined, and structural factors favoring ester prodrug hydrolysis at the expense of deacetylation to yield salicylate ester are discussed. The properties of some N,N-disubstituted glycolamide esters of aspirin are highlighted with respect to their use as potential aspirin prodrugs.
