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. Synthesis, characterization, and antiinflammatory activities. Nov 23, 2016 in this study, a new series of 16 methyl salicylate derivatives bearing a piperazine moiety were synthesized and characterized. Methyl salicylate is a benzoate ester that is the methyl ester of salicylic acid. See the mechanism and discussion in klein on saponification of esters, sections 21. To make sure we get the most product out of the reaction excess ensures product formation in high. 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. Synthesis of oil of wintergreen pre lab discussion. Synthesis of salicylic acid from wintergreen oil objective preparation of salicylic acid organic synthesis from methyl salicylate utilizing previously used procedure from the nineteenth century. This procedure will use starting materials that can be found at a.
Involves two pleasantsmelling organic compounds, methyl anthranilate grape and methyl salicylate. Preparation of aspirin, methyl salicylate and nylon. To observe the contrasts in appearance and odor of two different esters of salicylic acid, namely aspirin and methyl salicylate. Structurally, methyl salicylate is the methyl ester of salicylic acid, produced e. Tell your doctor about the allergy and what signs you had. Methyl salicylate c6h4 ho cooch3, also known as salicylic acid methyl ester, oil of wintergreen, is a natural product of many species of plants. The method involved distilling continuously or refluxing. Preparation of salicylic acid from methyl salicylate. First, acetylsalicylic acid is extracted from aspirin tablets with isopropyl alcohol, then hydrolyzed to salicylic acid with muriatic acid, and finally, the salicylic acid is esterified using ethanol and a boric acid catalyst. And, it was soon discovered that methyl salicylate has analgesic eases pain. Kyle johnson abstract methyl salicylate, or wintergreen oil, is an organic ester naturally produced by the wintergreen plant group, and commonly made by the esterification of salicylic acid with methanol. Preparation of salicylic acid salicylic acid will be prepared by a basepromoted hydrolysis, or saponi.
To remove this unwanted starting reactant, a thorough washing with aqueous sodium bicarbonate. It is a colorless, viscous liquid with a sweet fruity odor reminiscent of root beer. Salicylic acid is converted to the liquid ethyl salicylate by addition of ethanol. Methyl salicylate material safety data sheet cas no. In this lab you will you will hydrolyze methyl salicylate to salicylic acidafford and methanol, as shown below in scheme 1.
It has a role as a flavouring agent, a metabolite and an insect attractant. The two compounds we will be preparing, aspirin acetylsalicylic acid and oil of wintergreen methyl salicylate, are both organic esters. Methyl salicylate is the lr more expensive, not easy to remove because it is organic b. Methyl salicylate, which is commonly referred to as oil of wintergreen and smells minty, is a compound having an ester function. In this study, a new series of 16 methyl salicylate derivatives bearing a piperazine moiety were synthesized and characterized. Fda considered only some pk data, lmenthol levels, from trial fs6703l as valid. Salicylic acid from latin salix, willow tree is a lipophilic monohydroxybenzoic acid, a type of phenolic acid, and a beta hydroxy acid bha. To understand the structural basis of vvmje1 in discriminating meja and mesa, a homolog model of vvmje1 was made using the xray structure of tobacco sabp2, which encodes for methyl salicylate. In this experiment, this compound is synthesized using commercial aspirin tablets as the starting material. It also includes pleasant smells due to chemicals that are used for artificial flavorings. Preparation of salicylic acid santa monica college.
Discover methyl salicylate pharma, a seqens essential drug subtances product. Involves two pleasantsmelling organic compounds, methyl anthranilate grape and methyl salicylate oil of wintergreen. Packaging 1 kg in poly bottle 5, 10 kg in composite drum other notes download our flavors. Learn vocabulary, terms, and more with flashcards, games, and other study tools. Most of us are familiar with esters, but are not aware of their presence in our everyday life.
When an acid containing the cooh group reacts with an alcohol a compound containing an oh group formed an ester. A soluble, halogenfree oxalate from methyl salicylate for. Steam distillation of methyl salicylate oil of wintergreen. This structure is also available as a 2d mol file or as a computed 3d sd file. Methyl salicylate has been used in the hyalinization of tissues for pulmonary angiography.
Experiment 22 synthesis of aspirin and oil of wintergreen. Synthesis of salicylic acid from wintergreen oil purpose of the experiment. Methyl salicylate is an herbivoreinduced plant volatile known to attract beneficial arthropods. This is not the source of salicylic acid in the industrial synthesis of aspirin, but it is, nevertheless, a good one for laboratory use. Molecules free fulltext synthesis, characterization, and anti. Feb 06, 2020 if you have an allergy to methyl salicylate, menthol, camphor or any other part of methyl salicylate, menthol, and camphor. The preparation of methyl benzoate and methyl salicylate on silica gel column o.
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. As a derivative of salicylic acid, it is used commonly in ointments for the relief of muscle. Transfer about 60 ml of methanol to the 125 ml erlenmeyer. If you have difficulty finding it under one name, then try the other. The reaction produces a strong odor or methyl salicylate and methanol vapor. Essay on synthesis of salicylic acid from wintergreen oil. In the case of methyl salicylate, there will also be unreacted salicylic acid drawn into the organic solvent. This demonstration is intended to be performed by persons with training in the handling and use of chemicals. Alban muller 9 za jean monnet 28630 fontenay sur eure france. Methyl salicylate is an organic ester responsible for the minty smell of wintergreen. This procedure will use starting materials that can be found at a supermarket including aspirin, antifreeze, and drain cleaner. Keep the tube in the hot water, and do not spill the contents. Seqens is a main actor in pharmaceutical synthesis and specialty ingredients.
This is not the source of salicylic acid in the industrial synthesis. Synthesis and biological evaluation of some new 2oxazoline and salicylic acid derivatives. Synthesis of an artificial flavor introduction esters occur naturally in plants and fruits. Us20070042009a1 topical composition for delivery of salicylates. While this is heating, fill an erlenmeyer flask about way full with water. Methyl salicylate oil of wintergreen or wintergreen oil is an organic compound with the formula c 6h 4 ohco 2ch 3. Hydrolyze the ester known as methyl salicylate under base conditions in order to synthesize salicylic acid, a carboxylic acid. Methyl salicylate is a naturally occurring compound that we will use to produce salicylic acid, which will then be used to make the wonder drug aspirin acetylsalicylic acid. Methyl salicylate is an ester salicylic acid derivative found in many plants. To remove this unwanted starting reactant, a thorough washing with aqueous sodium bicarbonate, nahco 3 aq, will be performed. Combine the extracts and dry over anhydrous magnesium sulphate. Methyl salicylate food and flavor ingredient, flavis no 9. Place the test tube in the hood in a water bath at 70 c for 15 minutes.
This hydrolysis is catalyzed by base in this case naoh, and therefore the initial product of the reaction is the sodium salt of salicylic acid. Search results for methyl salicylate at sigmaaldrich. Salicylates directly or indirectly affect most organ systems in the body by uncoupling oxidative phosphorylation, inhibiting krebs cycle enzymes, and inhibiting amino acid synthesis. Synthesis of an artificial flavor clemson university. Synthesis of methyl salicylate synthesis of methyl. More concentrated naoh in sm faster the reaction will go d. Methyl salicylate oil of wintergreen is an organic ester. H302, h402 synthesis of salicylic acid and aspirin. Olatunji department of chemistry, university of ilorin, pmb 1515, ilorin, nigeria. Methyl salicylate has an analgesic effect and is used in many overthecounter analgesic creams or gels designed only for topical use. 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. Synthesis of isopentyl acetate banana oil thermo fisher scientific. Preparation of methyl salicylate, by sciencemadness.
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. Methyl salicylate is one of the main volatile flavor components in tomatoes, sapodilla and unburned tobacco. The preparation of methyl benzoate and methyl salicylate. Another derivative of salicylic acid that has healing properties and is also a simple onestep organic synthesis is called methyl salicylate.
To recover the methyl salicylate, carefully extract the oily distillate with 15 ml of methylene chloride two times. You will be able to see how two very different organic compounds can be made from the same common starting material. Salicylic acid a methanol 1 methyl salicylate wintergreen. Preparation of oil of wintergreen from commercial aspirin tablets. This method is suitable for the synthesis of anomeric oligosides of phenols. Notes that this experiment takes safety and noncarcinogenic reactants into account. Methyl salicylate definition of methyl salicylate by. Topical composition for delivery of salicylates download pdf. It was first isolated in 1843 by extraction from a plant gaultheria spp. The synthesis uses diazonium salts to replace the amine group of an aromatic amine with a hydroxyl group. In this experiment, you will measure the melting point of your synthesized asa product, salicylic acid, a crushed aspirin tablet, and pure. Methyl salicylate is a major component of oil of wintergreen prepared by distillation from wintergreen leaves. Pdf antiinflammatory activity of methyl salicylate glycosides. How many moles of methyl salicylate does the procedure call for.
Synthesis of ethyl salicylate using household chemicals. Ethyl salicylate is synthesized, isolated, and characterized in a threestep process using simple equipment and household chemicals. The in vivo antiinflammatory activities of target compounds were investigated against xylolinduced ear edema and carrageenaninduced paw edema in mice. Methyl salicylate functions as a flavouring agent in chewing gums, syrups and ice creams. A microscale experiment highlighting acyl substitutions a singlepot.
This substance has caused adverse reproductive and fetal effects in animals. Esters were traditionally named by combining the name of the alcohol with the. 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. The final product will then be evaluated in comparison to salicylic acid made from benzene.
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. View lab report synthesis of methyl salicylate from aspirin. Request pdf preparation of oil of wintergreen from commercial aspirin tablets. 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. Make certain there are no open flames or other ignition sources nearby. Techniques hydrolysis of an ester heating under reflux filtration crystallization melting point theory methyl salicylate is an ester easily recognized by its odor and is known as oil of. An ester compromises an organic or inorganic acid in which one or more hydroxy. Methyl salicylate oil of wintergreen or wintergreen oil is an organic compound with the formula c 6 h 4 ohco 2 ch 3. Peptobismol 236 mg of nonaspirin salicylate per 15 ml pathophysiology 1. The results showed that both methyl salicylate glycosides dosedependently inhibited.
An investigation of the acid catalyzed esterification of benzoic acid and salicylic acid with methanol on silica gel solid support system was carried out. The purpose of this experiment is to synthesize isopentyl acetate 3methylbutyl acetate. 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. Transfer about 60 ml of methanol to the 125 ml erlenmeyer flask. A new oxalate ester made from methyl salicylate oil of wintergreen was found to be an excellent replacement for the typical halogenated oxalate ester bis2,4,6trichlorophenyl oxalate used in. This colorless crystalline organic acid is widely used in organic synthesis and functions as a plant hormone. Demonstrates the use of diazonium salts for the replacement of an aromatic amine group by a phenolic hydroxyl.
Combine and dry the ether extracts with anhydrous sodium sulfate. Among the volatile blend released upon aphid infestation are chemicals including. The synthesis of methyl salicylate is a safe and effective way to observe an amine diazotization. Methyl salicylate synthesis summer 2016 background. It has counter irritant and antiinflammatory effects. The product will be analyzed by melting point analysis and. Starting from methyl salicylate and 2amino2hydroxymethylpropane1,3diol 1a, or 2amino. Synthesis of oil of wintergreen cornell center for. 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 is found in trees, legumes and exotic plants. Find patient medical information for methyl salicylate on webmd including its uses, side effects and safety, interactions, pictures, warnings and user ratings. If you are allergic to methyl salicylate, menthol, and camphor. Sp11 1021 synthesis of aspirin and oil of wintergreen.
Methyl salicylate has fdaspecified uses as indirect food additive cir, 2003. The council of europe publications plants in cosmetics volume iii 2006 and active ingredients in cosmetics. November 2017 olume 2 umber 1 e2017 bacterial transformation we began by adding 50 ml distilled water and 1 g lb broth powder to the. Structure, properties, spectra, suppliers and links for. Methyl salicylate is an ester easily recognized by its odor and is known as oil of wintergreen because of its natural source. Synthesis of methyl salicylate chemistry 236 april 12, 2016 vincent guzman lab partner. Synthesis of methyl salicylate from aspirin esters are a class of organic compounds. Methyl salicylate naturally found in the bark of sweet birch tree betula lenta round bottom flask condenser 2 rubber tubings separatory funnel vials bunsen burner tripod water bath clamps iron stand slowly add small portions of 20% sodium carbonate solution with constant. Pour 150 ml of methanol, 45 g of salicylic acid and slowly. Methyl salicylate an overview sciencedirect topics. Methyl salicylate appears as colorless yellowish or reddish liquid with odor of wintergreen. Medicinal products methyl salicylate has antiinflammatory properties and is still used. The hydrolysis reaction that occurs will form methanol, water, and the sodium salt of. Brand names of formulations containing methyl salicylate are balmosa, monphytol, phytex, radian b and salonpas.
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