Iii, taking the kieselguhr load particles, adding dicyclohexylcarbodiimide, 4dimethylamino pyridine and ethyl alcohol, and preparing a solid composite catalyst. Methyl salicylate oil of wintergreen or wintergreen oil is an organic ester naturally produced by many species of plants, particularly wintergreens. Safety assessment of salicylic acid, butyloctyl salicylate, calcium. The method involved distilling continuously or refluxing. When salicylic acid reacts with methanol in the presence of an acid catalyst, methyl salicylate, or oil of wintergreen, is produced according to the following equation.
Synthesis and antifungal activity of new salicylic acid. A practical synthesis of flavones from methyl salicylate. The reaction of salicylic acid 1 with methyl 2bromoalkanoates 2a2c in dmf. The two step synthesis encompasses aqueous base hydrolysis of wintergreen oil methyl salicylate, ms to salicylic acid sa followed by acetylation to acetylsalicylic acid aspirin, asa. It appears that in lower animals the toxicity of methyl salicylate is essentially identical with that of salicylic. In this lab you will you will hydrolyze methyl salicylate to salicylic acidafford and methanol, as shown below in scheme 1. Permission is granted to copy, distribute andor modify this document under the terms of the gnu free documentation license, version 1.
The preparation of methyl benzoate and methyl salicylate on silica gel column o. An ester compromises an organic or inorganic acid in which one or more hydroxy. An investigation of the acid catalyzed esterification of benzoic acid and salicylic acid with methanol on silica gel solid support system was carried out. Your use of this pdf, the bioone complete website, and all posted and associated. Structurally, methyl salicylate is the methyl ester of salicylic acid, produced e. Olatunji department of chemistry, university of ilorin, pmb 1515, ilorin, nigeria. Effective immobilisation of lipase to enhance esterification potential.
The major site of hydrolysis of methyl salicylate in the rat, rabbit, dog and monkey is the liver, although intestine, kidney, pancreas, and spleen may play a minor role in such breakdown. It is a benzoate ester and a member of salicylates. Synthesis of oil of wintergreen cornell center for. Pdf synthesis and antifungal activity of new salicylic acid derivatives. The results of experiments using acetyllc14 salicylic acid, which was prepared by the following procedure, will be reported in a later publication. Methyl salicylate has a relatively weak phenol and carboxylic functional groups that are important in this experiment. The c nmr has extra signal compared to that of salicylic. An investigation of the acid catalyzed esterification of benzoic acid and salicylic. Compound 5 on treatment with tbutyldimethylsilyl chloride 6. Molecules free fulltext synthesis, characterization, and anti. The invention relates to a synthesis method of methyl salicylate, and the synthesis method comprises the following reaction steps. Cn105601512a efficient preparation method of methyl. Methyl salicylate material safety data sheet cas no. Request pdf synthesis of methyl salicylate over mesoporous aluminosilicate materials different from the traditional synthesis of methyl salicylate, the.
Learn more about these metrics article views are the countercompliant sum of full text article downloads. Maximization tests of methyl salicylate, ethylhexyl salicylate, and butyloctyl. Synthesis of methyl salicylate from aspirin esters are a class of organic compounds. Acetylsalicylic acid, marketed under the trade name aspirin by the bayer company, is one. Methyl salicylate c8h8o3 cid 43 structure, chemical names, physical. Gtases is inhibited by cycloheximide, a protein synthesis. Analysis of methyl salicylate and salicylic acid from. Article information, pdf download for safety assessment of salicylic acid. See the mechanism and discussion in klein on saponification of esters, sections 21.
A facile synthetic method has been developed for the conversion of methyl salicylate 5 into flavones 1ai in high yields. Tim sullivan, in annual reports in medicinal chemistry, 2012. It has direct activity as an antiinflammatory agent and acts as a topical antibacterial agent due to its ability to promote exfoliation. The type of reaction may be known as condensation reaction because the small molecule of h2o is eliminated from the reactants while the remaining bits of the. We ask that users who download significant portions of the database cite the. Methyl salicylate appears as colorless yellowish or reddish liquid with odor of wintergreen. This hydrolysis is catalyzed by base in this case naoh, and therefore the initial product of the reaction is the sodium salt of salicylic. This hypothesis was supported by studies of cellfree extracts. Salicylic acid is a beta hydroxy acid that occurs as a natural compound in plants. The preparation of methyl benzoate and methyl salicylate. Cn102267911a synthesis method of methyl salicylate. Methyl salicylate c6h4 ho cooch3, also known as salicylic acid methyl ester, oil of wintergreen, is a natural product of many species of plants. Article views are the countercompliant sum of full text article downloads since november 2008 both pdf and html across all institutions and individuals.
Methyl salicylate is a benzoate ester that is the methyl ester of salicylic acid. This procedure will use starting materials that can be found at a. Methyl salicylate oil of wintergreen or wintergreen oil is an organic compound with the formula c 6 h 4 ohco 2 ch 3. The method involved distilling continuously or refluxing the alcohol over the packed column. It is also synthetically produced, used as a fragrance, in foods and beverages, and in liniments the compound methyl salicylate.
This laboratory manual of organic chemistry has been compiled primarily to cover the. When salicylic acid reacts with methanol in the presence of an acid catalyst, methyl salicylate, or oil of. Pdf synthesis, characterization, and antiinflammatory. Biosynthesis and metabolism of salicylic acid pnas.
View methyl salicylate research papers on academia. Fda considered only some pk data, lmenthol levels, from trial fs6703l as valid. Acetylsalicylic acid an overview sciencedirect topics. General methyl salicylate from oil of wintergreen, and salicylic.
Methyl salicylate is an organic ester responsible for the minty smell of wintergreen. Methyl salicylate oil of wintergreen is an organic ester. Synthesizing aspirin and oil of wintergreen purpose in this experiment, you will synthesize acetylsalicylic acid, commonly known as aspirin, and methyl salicylate, oil of wintergreen, from salicylic acid. A practical synthesis of flavones from methyl salicylate sciencedirect. Synthesis of oil of wintergreen pre lab discussion.
Place the test tube in the hood in a water bath at 70. Nsf ccli project page 1 experiment oil of wintergreen. Methyl salicylate and salicylic acid were detected using an extraction solution of acetonitrile coupled with internal standard and then analyzed by hplcdiodearray detection. The synthesis of acetyl1c14salicylic acid pdf free. Methyl salicylate is an ester salicylic acid derivative found in many plants. Because of its concentrated liquid form, methyl salicylate ingestion can cause rapid onset salicylate toxicity. The synthesis of methyl salicylate methyl 2hydroxybenzoate and linalyl ferulate 3.
Experiment 22 synthesis of aspirin and oil of wintergreen. Discover methyl salicylate pharma, a seqens essential drug subtances product. An ester compromises an organic or inorganic acid in which one or more hydroxy oh groups have been. The synthesis of cool smelling molecules purpose to expand the use of the concept of nucleophilicity and electrophilicity, to introduce the reactivity of carbonyls, and to. When an acid containing the cooh group reacts with an alcohol a compound containing an oh group formed an ester. Synthesis of methyl salicylate over mesoporous aluminosilicate. Free as well as immobilized lipase was more specific to pnpp 20. In addition to the thermodynamics research center trc data available from this site, much more physical and chemical property data is available from the following trc products.