Synthesis of aspirin and oil of wintergreen revision f8 page 2 of 7 methyl salicylate is the active ingredient in oil of wintergreen. Plasma analyses for methyl salicylate and free salicylate. Discover methyl salicylate pharma, a seqens essential drug subtances product. Design, synthesis and biological evaluation of hybrids of. The identification of salicylates as normal constituents of serum. Yields of salicylic acid week 1 and ethyl salicylate will be found, as well as the overall yield of the 2step conversion of acetyl salicylic acid to ethyl salicylate. Methyl salicylate may be used by plants as a pheromone to warn other plants of pathogens such as tobacco mosaic virus. 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.
Because of its concentrated liquid form, methyl salicylate ingestion can cause rapid onset salicylate. Most of us are familiar with esters, but are not aware of their presence in our everyday life. Preparation of monoesters of polyhydric alcohols download pdf. Methyl salicylate oil of wintergreen or wintergreen oil is an organic ester naturally produced by many species of plants, particularly wintergreens. Methyl salicylate possesses essentially the same ld5o in mice as sodium salicylate. 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.
Methyl salicylate c6h4 ho cooch3, also known as salicylic acid methyl ester, oil of wintergreen, is a natural product of many species of plants. Methyl salicylate an overview sciencedirect topics. In methyl salicylate oil of wintergreen, the cooh group of salicylic acid is esterified with methanol ch 3 oh, whereas in acetylsalicylic acid aspirin the acid component. Synthesis of oil of wintergreen pre lab discussion. The highest ineffective dose tested in any salmonella typhimurium strain was 333,000 ugplate. The hydrolysis reaction that occurs will form methanol, water, and the sodium salt of. The synthesis is described of several specifically labelled deuterium derivatives of salicylic acid needed. Methyl salicylate, for example, is oil of wintergreen. Methyl salicylate oil of wintergreen is an organic ester. Methyl salicylate is an organic ester responsible for the minty smell of wintergreen. Methyl salicylate was tested in as many as 5 salmonella typhimurium strains ta1535, ta1537, ta97, ta98, and ta100 in the presence and absence of rat and hamster liver s9, at doses of 1,000, 3,300,10,000, 33,300, 100,000, and 333,300 ugplate. Methyl salicylate type of posting revision bulletin posting date 28july2017 official date 01. Us3012064a preparation of monoesters of polyhydric alcohols.
Search results for methyl salicylate at sigmaaldrich. A zincii complex with tris2 n methylbenzimidazlylmethylamine and salicylate. Synthesis of the deoterospecific 4d and 6d methyl 3, 5. This procedure will use starting materials that can be found at a. Green synthesis of methyl salicylate using novel sulfated. Structurally, methyl salicylate is the methyl ester of salicylic acid, produced e. Chemical ecology, pheromones, pheromone, moth, moths, insect, sex, attractants, attractant, sexattractants, insects, entomology, behaviour, behavior, lepidoptera. Synthesis of methyl salicylate from aspirin pdf book. Sigmaaldrich offers a number of methyl salicylate products. Xjrbamwjdbpfimuhfffaoysan methyl vinyl ether chemical compound.
See the mechanism and discussion in klein on saponification of esters, sections 21. An ester compromises an organic or inorganic acid in which one or more hydroxy oh groups have been. The odor is often described as minty due to its use in mint candies. Fda considered only some pk data, lmenthol levels, from trial fs6703l as valid. Methyl salicylate type of posting revision bulletin. It is also synthetically produced, used as a fragrance, in foods and beverages, and in liniments the compound methyl salicylate. A zincii complex with tris2 n methylbenzimidazlylmethylamine. Wash your hands with soap and water immediately after applying methyl salicylate topical or. An ester compromises an organic or inorganic acid in which one or more hydroxy. Methyl salicylate synthesis summer 2016 background. Sp11 1021 synthesis of aspirin and oil of wintergreen.
Weigh the beaker and methyl salicylate and calculate the exact mass of methyl salicylate. Green synthesis of methyl salicylate using novel sulfated iron oxide. The toxicity and metabolism of methyl salicylate were investigated in the belief that it functions primarily as its hydrolytic product, free salicylate. Citations are the number of other articles citing this article, calculated by crossref and updated daily. Permission is granted to copy, distribute andor modify this document under the terms of the gnu free documentation license, version 1. Analysis of methyl salicylate and salicylic acid from. Request pdf green synthesis of methyl salicylate using novel sulfated iron oxidezirconia catalyst esters of salicylic acid are in demand for the synthesis of drugs, food preservatives. Nsf ccli project page 1 experiment oil of wintergreen. Find patient medical information for methyl salicylate nf topical on webmd including its uses, side effects and safety, interactions, pictures, warnings and user ratings. This structure is also available as a 2d mol file or as a computed 3d sd file the 3d structure may be viewed using java or javascript. An extract of acidified serum was derivatised using. Download synthesis of methyl salicylate from aspirin book pdf free download link or read online here in pdf. Preparation of methyl salicylate, by darkblade48 heres a simple synthesis of methyl salicylate oil of wintergreen, for those that just started organic chemistry though of course, even if you are a bit.
It is a colorless, viscous liquid with a sweet fruity odor reminiscent of root beer. Methyl salicylate c8h8o3 cid 43 structure, chemical names, physical and. Methyl salicylate topical may be used up to 4 times daily or as directed on the medicine label. When salicylic acid reacts with methanol in the presence of an acid catalyst, methyl salicylate, or oil of. Methyl salicylate is an ester easily recognized by its odor and is known as oil of wintergreen because of its natural source. Seqens is a main actor in pharmaceutical synthesis and specialty ingredients. Seqens is a main actor in pharmaceutical synthesis. Methyl salicylate was tested in as many as 5 salmonella typhimurium strains ta1535, ta1537, ta97, ta98, and ta100 in the presence and absence of rat and hamster liver s9, at doses of 1,000. Journal of chemical education, v65 n12 p1106 dec 1988.
These metrics are regularly updated to reflect usage leading up to the last few days. Read online synthesis of methyl salicylate from aspirin book pdf free download link book now. Salicylic acid is converted to the liquid ethyl salicylate by addition of ethanol. Us4754063a salicylates and process for their preparation. The two compounds we will be preparing, aspirin acetylsalicylic acid and oil of wintergreen methyl salicylate, are both organic esters. In the present study, motivated by important applications, we have focused on the synthesis of methyl 4r salicylate derivatives r c 5 nh 4, c 4 sh 3, c 4 seh 4 and elucidated their unique spectroscopic. Methyl salicylate oil of wintergreen or wintergreen oil is an organic compound with the formula c 6 h 4 ohco 2 ch 3.
Oswpmrlsedhdffuhfffaoysan methyl salicylate chemical compound. Methyl salicylate is an organic compound with the formula c6h4ohco2ch3. The purpose of this lab was to get students familiar with glass materials often used by organic chemists and how to reflux a mixture and to filter its precipitate, through teaching students how to create salicylic acid from methyl salicylate. Synthesis of oil of wintergreen cornell center for. Request pdf green synthesis of methyl salicylate using novel sulfated iron oxidezirconia catalyst esters of salicylic acid are in demand for. You will be able to see how two very different organic compounds can be made from the same common starting material. When an acid containing the cooh group reacts with an alcohol a compound containing an oh group formed an ester. Salicylates and process for their preparation download pdf.
This substance has caused adverse reproductive and fetal effects in animals. Methyl salicylate and salicylic acid were detected using an extraction solution of acetonitrile coupled with internal standard and then analyzed by hplcdiodearray detection. Article views are the countercompliant sum of full text article downloads since november 2008 both pdf and html across all institutions and individuals. Synthesis of methyl salicylate from aspirin esters are a class of organic compounds. A clear advantage of the use of ils in the synthesis of antioxidanttargeted compounds is the easy product purification and the possibility of reusing the il in subsequent reactions.