When an acid containing the cooh group reacts with an alcohol a compound containing an oh group formed an ester. Salicylic acid is converted to the liquid ethyl salicylate by addition of ethanol. Sigmaaldrich offers a number of methyl salicylate products. 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 of the ester is acetic acid, and salicylic acid contributes the phenolic. Remove the patch and apply a new patch 1 or 2 times daily if needed. 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. Synthesis of oil of wintergreen cornell center for. 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. Other derivatives include methyl salicylate used as a liniment to soothe joint and muscle pain and. To apply a methyl salicylate topical skin patch, remove the liner and apply the patch to your skin over the area of pain.
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. Most of us are familiar with esters, but are not aware of their presence in our everyday life. Article views are the countercompliant sum of full text article downloads since november 2008 both pdf and html across all institutions and individuals. An investigation of the acid catalyzed esterification of benzoic acid and salicylic acid with methanol on. Methyl salicylate synthesis summer 2016 background. Synthesis of oil of wintergreen cornell center for materials research. 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. Methyl salicylate material safety data sheet cas no 119368. The aim of this study was to investigate the therapeutic effect of msl in mice with collageninduced arthritis cia and explore its underlying mechanism. 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 more experienced. On the metabolism and toxicity of methyl salicylate journal. When methyl salicylate is applied to the skin, it causes a mild burning sensation which serves as a counterirritant for sore muscles.
An ester compromises an organic or inorganic acid in which one or more hydroxy oh groups have. 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. 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. Synthesis of methyl salicylate from aspirin esters are a class of organic compounds. When salicylic acid reacts with methanol in the presence of an acid catalyst. Citations are the number of other articles citing this article, calculated by crossref and updated daily. 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. Oacetylation of salicylic acid to give acetylsalicylate aspirin. Request pdf synthesis of methyl salicylate over mesoporous aluminosilicate materials different from the traditional synthesis of methyl salicylate, the. The toxicity and metabolism of methyl salicylate were investigated in the belief that it functions primarily as its hydrolytic product, free salicylate.
Methyl salicylate oil of wintergreen or wintergreen oil is an organic compound with the formula c 6 h 4 ohco 2 ch 3. Preparation of methyl salicylate, by sciencemadness. Methyl salicylate is a benzoate ester that is the methyl ester of salicylic acid. Information is presented in the monograph on methyl salicylate in the council of europe publications plants in cosmetics volume iii 2006 and active ingredients in cosmetics. A practical synthesis of flavones from methyl salicylate. Seqens is a main actor in pharmaceutical synthesis and specialty ingredients.
Safety data sheet according to 29cfr19101200 and ghs rev. The type of reaction may be known as condensation reaction because the small molecule of h 2 o is eliminated from the reactants while the remaining bits of the. See the mechanism and discussion in klein on saponification of esters, sections 21. Preparation of salicylic acid salicylic acid will be prepared by a basepromoted hydrolysis, or saponi. The preparation of methyl benzoate and methyl salicylate on silica. Synthesis of methyl salicylate ester hydrogen compounds scribd. Wash your hands with soap and water immediately after applying methyl. Preparation of salicylic acid santa monica college.
Wash your hands with soap and water immediately after applying methyl salicylate topical or handling. Methyl salicylate is also useful in synthesis as a generator of. Methyl salicylate definition of methyl salicylate by. Burning cold, heat these sensations can all work together so that when we apply methyl salicylate containing creams, lotions, or ointments we feel a warming sensation. Print student copies for the lab on the synthesis of wintergreen.
It is also found in the essential oils of cassie absolute. An ester compromises an organic or inorganic acid in which one or more. This substance has caused adverse reproductive and fetal effects in animals. Synthesis of methyl salicylate over mesoporous aluminosilicate. Nov 09, 2018 methyl salicylate topical may be used up to 4 times daily or as directed on the medicine label. The two compounds we will be preparing, aspirin acetylsalicylic acid and oil of wintergreen methyl salicylate, are both organic esters. Austin peay state university department of chemistry chem 1121 synthesis of aspirin and oil of wintergreen revision f8 page 2 of 7 methyl salicylate is the active ingredient in oil of wintergreen. This procedure will use starting materials that can be found at a supermarket including aspirin, antifreeze, and drain cleaner. Nsf ccli project page 1 experiment oil of wintergreen. 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 more.
Find patient medical information for methyl salicylatementhol topical on webmd including its uses, side effects and safety, interactions, pictures, warnings and user ratings. You will be able to see how two very different organic compounds can be made from the same common starting material. Unlike many organic chemistry labs, this experiment does not expose students to carcinogenics, nor does it smell bad. 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 oil of wintergreen is an organic ester.
Methyl salicylate topical may be used up to 4 times daily or as directed on the medicine label. Methyl salicylate lactoside inhibits inflammatory response of. Methyl salicylate is an organic ester responsible for the minty smell of wintergreen. Methyl salicylate is an organic compound present mainly in wintergreen oil obtained from gaultheria procumbens. General methyl salicylate from oil of wintergreen, and salicylic acid from latin salix, willow tree are both natural products. Philadelphia collegeof pharmacy and science, philadelphia, pa.
The product will be analyzed by melting point analysis and. Oct 04, 2019 to apply a methyl salicylate topical skin patch, remove the liner and apply the patch to your skin over the area of pain. November 2017 olume 2 umber 1 e2017 bacterial transformation we began by adding 50 ml distilled water and 1 g lb broth. Structurally, methyl salicylate is the methyl ester of salicylic acid, produced e. An ester compromises an organic or inorganic acid in which one or more hydroxy. Bronsted acidic ionic liquids ils 1 butyl3methylimidazolium hydrogen. Methyl salicylate oil of wintergreen is used as a flavoring agent and it is also used in rubbing compounds, like ben gay. Fda considered only some pk data, lmenthol levels, from trial fs6703l as valid. 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. 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. Search results for methyl salicylate at sigmaaldrich.
The two step synthesis encompasses aqueous base hydrolysis of wintergreen oil methyl salicylate, ms to salicylic acid sa. Methyl salicylate, for example, is oil of wintergreen, isopentenyl acetate is oil of banana or pear, butyl butanoate smells like pineapple, propyl2methylpropanoate smells like rum and p. Synthesis of oil of wintergreen pre lab discussion. Notes that this experiment takes safety and noncarcinogenic reactants into account. Salicylic acid is a lipophilic monohydroxybenzoic acid, a type of phenolic acid, and a beta hydroxy acid bha. Synthesis of methyl salicylate free download as word doc.
This colorless crystalline organic acid is widely used in organic synthesis and. Green synthesis of methyl salicylate using novel sulfated iron oxide. These metrics are regularly updated to reflect usage leading up to the last few days. A larger size patch 10 cm x 14 cm, with the same ingredients, was approved on november 5, 2012 for the same. Green synthesis of methyl salicylate using novel sulfated. Methyl salicylate may be used by plants as a pheromone to warn other plants of pathogens such as tobacco mosaic virus. Plasma analyses for methyl salicylate and free salicylate after oral administration of the ester to rats and dogs demonstrate complete hydrolysis shortly after. 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. Hydrolysis of methyl salicylate oil of wintergreen to give salicylic acid. Methyl salicylate c6h4 ho cooch3, also known as salicylic acid methyl ester, oil of wintergreen, is a natural product of many species of. Methyl salicylate an overview sciencedirect topics.
Request pdf green synthesis of methyl salicylate using novel sulfated iron oxidezirconia catalyst esters of salicylic acid are in demand for. It is a colorless, viscous liquid with a sweet fruity odor reminiscent of root beer. Place the test tube in the hood in a water bath at 70 c for 15 minutes. Olatunji department of chemistry, university of ilorin, pmb 1515, ilorin, nigeria. The traditional catalysts used for the synthesis of salicylate were concentrated. It is a benzoate ester and a member of salicylates.
An ester is a compound that is formed when an acid containing the cooh group reacts with an alcohol a compound containing an oh group. Sp11 1021 synthesis of aspirin and oil of wintergreen. Discover methyl salicylate pharma, a seqens essential drug subtances product. The type of reaction may be known as condensation reaction because the small molecule of h 2 o is eliminated from the reactants while the remaining bits of the reactants condense together to give the main product. Methyl salicylate material safety data sheet cas no.
It has a role as a flavouring agent, a metabolite and an insect attractant. Demonstrates the use of diazonium salts for the replacement of an aromatic amine group by a. Hydrolyze the ester known as methyl salicylate under base conditions in order to synthesize salicylic acid, a carboxylic acid. Experiment 22 synthesis of aspirin and oil of wintergreen.
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