Methyl salicylate, nf 119368 me170 spectrum chemical. 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. Simultaneous determination of the uvfilters benzyl salicylate, phenyl salicylate, octyl salicylate, homosalate, 34methylbenzylidene camphor and 3benzylidene camphor in human placental tissue by lcmsms. This substance has caused adverse reproductive and fetal effects in animals. The halflife of salicylate may be as long as 15 to 30 h at high therapeutic doses or when there is intoxication gilman et al. Methyl salicylate has a relatively weak phenol and carboxylic functional groups that are important in this experiment. The product chemistry data requirements for methyl salicylate are fully satisfied. Jsci has precedent for use at a maximum concentration of 0. Plasma analyses for methyl salicylate and free salicylate after oral administration of the ester to rats and dogs demonstrate. You will be able to see how two very different organic compounds can be made from the same common starting material.
Learn vocabulary, terms, and more with flashcards, games, and other study tools. Nov 23, 2016 in this study, a new series of 16 methyl salicylate derivatives bearing a piperazine moiety were synthesized and characterized. This colorless crystalline organic acid is widely used in organic synthesis and. Synthesis of salicylic acid from wintergreen oil essay. A novel methylation of tertiary amines with methyl salicylate. It acts as an anticoagulant by interruption of the vitamin k1epoxide cycle. The product will be analyzed by melting point analysis and carbon nmr. It also includes pleasant smells due to chemicals that are used for artificial flavorings. This can also increase circulation of blood and furthermore fight the pain. Synthesis of aspirin from methyl salicylate objective.
This is not the source of salicylic acid in the industrial synthesis of aspirin, but it is, nevertheless, a good one for laboratory use. Hydrolyze the ester known as methyl salicylate under base conditions in order to synthesize salicylic acid, a carboxylic acid. Computerguided design, synthesis, and protein kinase c a. It can be manufactured synthetically and it used as a fragrance, in foods, beverages, and liniments. Park sw, liu pp, forouhar f, vlot ac, tong l, tietjen k, klessig df.
The high degree of toxicity of this oil can make it fatal to human beings, but that means that it is fatal to bacteria and other microbes such as viruses, fungi and protozoa as well. In addition to serving as an important active metabolite. This colorless crystalline organic acid is widely used in organic synthesis and functions as a plant hormone. Synthesis of methyl salicylate via amine diazotization important references. Synthesis of salicylic acid from wintergreen oil abstract. The preparation of methyl benzoate and methyl salicylate. Exp5 hydrolysis of methyl salicylate synthesis of aspirin. Green synthesis of ultraviolet absorber 2ethylhexyl salicylate. Cosmetics cls categories except eyeliner preparations, in which it is not used. The purpose of this experiment is to take methyl salicylate wintergreen oil and by heating it under reflux with naoh as a solvent, and then cooling the mixture with h2so4. Methyl salicylate, nf is used to treat minor aches and pains of the muscles and joints.
Briefly describe the difference between an acid and an ester. Search results for methyl salicylate at sigmaaldrich. Involves two pleasantsmelling organic compounds, methyl anthranilate grape and methyl salicylate oil of wintergreen. 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. Plasma analyses for methyl salicylate and free salicylate after oral administration of the ester to rats and dogs demonstrate complete hydrolysis shortly after. 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. Synthesis of ethyl salicylate using household chemicals. Demonstrates the use of diazonium salts for the replacement of an aromatic amine group by a phenolic hydroxyl. Necessary reagents methanol, ch 3oh salicylic acid, ohc 6h 4cooh. Ethyl salicylate is synthesized, isolated, and characterized in a threestep process using simple equipment and household chemicals. Concise synthesis of xanthones by the tandem etherification.
Synthesis of methyl salicylate from aspirin esters are a class of organic compounds. On the metabolism and toxicity of methyl salicylate journal. Reregistration eligibility decision for methyl salicylate. 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 oil of wintergreen or wintergreen oil is an organic ester naturally produced by many species of plants, particularly wintergreens.
When an acid containing the cooh group reacts with an alcohol a compound containing an oh group formed an ester. Methyl salicylate is a colorless, yellowish or reddish, oily liquid with the odor and taste of wintergreen. 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, nothing beats a minty smelling. Methyl salicylate, an organic ester, is naturally produced by wintergreens, among other plants chebi, 2017. Synthesis, characterization, and antiinflammatory activities of methyl salicylate derivatives bearing piperazine moiety. The in vivo antiinflammatory activities of target compounds were investigated against xylolinduced ear edema and carrageenaninduced paw edema in mice. 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.
Preparation of salicylic acid salicylic acid will be prepared by a basepromoted hydrolysis, or saponi. Methyl salicylate, ms salicylic acid, sa salicylic acid mw 180. The in vivo antiinflammatory activities of target compounds were investigated against xylol. Since this is a preparation, or synthesis, lab you must have a reaction equation with structures in your notebook for both the conversion of methyl salicylate to the dianion of salicylic acid and for the conversion of the dianion to salicylic acid see the middle of page 8 of the looseleaf pages. It is often helpful to make an outline of the days activities from the procedures so. Sp11 1021 synthesis of aspirin and oil of wintergreen. Salicylic acid is converted to the liquid ethyl salicylate by addition of ethanol. Sodium benzoate is an ester used in the modification of. Synthesis of oil of wintergreen pre lab discussion. Synthesis, solubility characteristics, in vitro enzymatic hydrolysis rates, and blood levels of total salicylate following. Record the mass of methyl salicylate in the data section.
Methyl salicylate synthesis summer 2016 background. Synthesis of bismuth iii oxide salicylate from nitrate solutions for. Methyl salicylate may be used by plants as a pheromone to warn other plants of pathogens such as tobacco mosaic virus. An ester compromises an organic or inorganic acid in which one or more hydroxy. Methyl salicylate as a selective methylation agent for the. 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. Methyl salicylate oil of wintergreen is an organic ester. This methyl salicylate is the focus of this project.
The synthesis of methyl salicylate is a safe and effective way to observe an amine diazotization. Methyl salicylate is also useful in synthesis as a generator of reactive inter corresponding author. In this lab you will you will hydrolyze methyl salicylate to salicylic acidafford and methanol, as shown below in scheme 1. Methyl salicylate is used as a flavoring agent and providing fragrance to products like chewing gum and mints. Preparation of aspirin, methyl salicylate and nylon.
Synthesis of salicylic acid from methyl salicylate kline. The more detail you propose for any mechanism the more support you must have. 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. Nsf ccli project page 1 experiment oil of wintergreen.
This procedure will use starting materials that can be found at a supermarket including aspirin, antifreeze, and drain cleaner. Salicylic acid from latin salix, willow tree is a lipophilic monohydroxybenzoic acid, a type of phenolic acid, and a beta hydroxy acid bha. The invention belongs to the technical field of preparation of organic compounds and relates to a method for catalytic synthesis of salicylate alkyl ester by using ionic liquid under microwave promotion. Notes that this experiment takes safety and noncarcinogenic reactants into account. Successful methyl salicylate synthesis in the reaction cocktail by esterification reaction using alginateimmobilized lipase was confirmed by hplc. Permission is granted to copy, distribute andor modify this document under the terms of the gnu free documentation license, version 1. Spectrum chemical nf products are manufactured, packaged and stored under current good manufacturing practices cgmp per 21cfr part 211 in fda registered and inspected facilities. 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.
The compound was first extracted and isolated from plant species gaultheria procumbens in 1843. The synthesis uses diazonium salts to replace the amine group of an aromatic amine with a hydroxyl group. The synthesis of multisubstituted xanthones 1 by the intermolecular cyclization of salicylates 2 and diaryl iodoniums 3. For quantities of 55 gallons, we will contact you with a shipping quote prior to processing your order. Methyl salicylate is an organic ester responsible for the minty smell of wintergreen. Methyl salicylate pesticide chemical code 076601 is the major constituent of oil of wintergreen which is a natural fragrant oil. Salicylic acid is a lipophilic monohydroxybenzoic acid, a type of phenolic acid, and a beta hydroxy acid bha. 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 beaker, boiled for 20 min and autoclaved for for 1 h. Functional analysis of a tomato salicylic acid methyl transferase and. It is often used in perfumes, toothpaste, tooth powder, mouthwash, and sunburn lotions. The two compounds we will be preparing, aspirin acetylsalicylic acid and oil of wintergreen methyl salicylate, are both organic esters. An ester compromises an organic or inorganic acid in which one or more hydroxy oh groups have been replaced by and alkoxy oalkyl group. View lab report exp5 hydrolysis of methyl salicylate from chem 210 at miracosta college.
Preparation of salicylic acid from methyl salicylate. Heat the mixture until boiling, then gently boil for 15 minutes more. If methyl salicylate is present in the test environment, it may be able to relieve stress. In this study, a new series of 16 methyl salicylate derivatives bearing a piperazine moiety were synthesized and characterized. Experiment 22 synthesis of aspirin and oil of wintergreen. And, it was soon discovered that methyl salicylate has analgesic eases pain. Synthesis, characterization, and antiinflammatory activities. Near, and daryl staveness departments of chemistry and chemical and systems biology, stanford university, stanford, california 94305, united states. Different phenol content ranges seeking one purpose. Methyl salicylate possesses essentially the same ld5o in mice as sodium salicylate. Methyl salicylate is a selective and inexpensive methylating agent for the esterification of carboxylic acids with a wide range of functional group tolerance. Show the chemical reaction for the hydrolysis of the ester, ethyl.
Methyl salicylate or oil of wintergreen is a counterirritant, local anesthetic, disinfected, ultraviolet absorber and odorant. This was demonstrated when its thermal decomposition generated orthoquinoketene, a benzyne precursor, badea et al. A copy of the license is included in the section entitled gnu free documentation license. The reaction of several amines with methyl salicylate z o salicylate colourless needles m. The method is carried out according to the following reaction formula and comprises the following steps. 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. Pour 150 ml of methanol, 45 g of salicylic acid and slowly with mixing 30 ml of sulfuric acid. Randomised double blind trials report that evidence of its effectiveness is weak, but stronger for acute pain than chronic pain, and that effectiveness may be due entirely to counterirritation. Methyl salicylate is also known to induce numbness when rubbed on affected area. Metabolism orally administered methyl salicylate is nearly completely hydrolysed to. 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.
Percutaneous absorption, disposition, and exposure assessment of homosalate, a uv filtering agent, in rats. It was first isolated in 1843 by extraction from a plant gaultheria spp. Find patient medical information for methyl salicylate nf topical on webmd including its uses, side effects and safety, interactions, pictures, warnings and user ratings. Methyl salicylate, which is commonly referred to as oil of wintergreen and smells minty, is a compound having an ester function. Methyl salicylate is used in high concentrations as a rubefacient and analgesic in deep heating liniments such as bengay to treat joint and muscular pain. The intramolecular hydrogen bonds between the carboxylate and hydroxyl groups in methyl salicylate are essential for the transformation. Methyl salicylate pharma further down the salicylic acid chain, seqens eds offers a comprehensive portfolio of methyl salicylate grades.
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. The extent to which methyl salicylate is required for. As a derivative of salicylic acid, it is used commonly in ointments for the relief of muscle. Methyl salicylate c6h4 ho cooch3, also known as salicylic acid methyl ester, oil of wintergreen, is a natural product of many species of plants. In order to elaborate the mechanism of mesa synthesis in tomato, we screened a set of o.
It is also used in high concentrations as a rubefacient to treat joint, muscular pain and acute pain. Preparation of salicylic acid santa monica college. Synthesis of oil of wintergreen cornell center for. During our study on the synthesis of heterocycles with diaryliodonium salts 8, we envisioned that the diaryliodonium salts 3 could be attacked by methyl salicylate 2 to give 2methoxylcarbonyl diaryl ether 4 9, which. The toxicity and metabolism of methyl salicylate were investigated in the belief that it functions primarily as its hydrolytic product, free salicylate. Synthesis of aspirin and oil of wintergreen revision f8 page 2 of 7 methyl salicylate is the active ingredient in oil of wintergreen.
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