It is commonly extracted through steam distillation of wintergreen leaves. To apply a methyl salicylate topical skin patch, remove the liner and apply the patch to your skin over the area of pain. The two different functional groups on the aromatic ring are utilized in this lab. Find information on methyl salicylate use, treatment, drug class and molecular formula. Information contained in this data sheet is to the best of jmls knowledge correct at the time of publication. When an acid containing the cooh group reacts with an alcohol a compound containing an oh group formed an ester. Medicinal products methyl salicylate has antiinflammatory properties and is. First, the free carboxylic acid group will be produced when we hydrolyze the methyl salicylate. Synthesize methyl salicylate perform this part of the lab in a well ventilated area. Methyl salicylate oil of wintergreen or wintergreen oil is an organic ester. Lists the various brand names available for medicines containing methyl salicylate. Although science in motion can provide concentrated sulfuric acid, we have decided that it is too dangerous to handle. Methyl salicylate oil of wintergreen or wintergreen oil is an organic compound with the formula c 6 h 4 ohco 2 ch 3.
Physicians should be aware of the potential risks of salicylate dermal absorption and toxicity. 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 synthesis uses diazonium salts to replace the amine group of an aromatic amine with a hydroxyl group. Synthesis of salicylic acid from methyl salicylate kline. Methyl salicylate is a topical analgesic, as is capsaicin and menthol. 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. Our group has several manufacturing facilities spread across the world, supported by toll manufacturers and representatives in uae, europe, africa, usa. 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. According to webmd, methyl salicylate is found in many topical ointments bought over the counter for minor joint aches or muscular. Experiment 22 synthesis of aspirin and oil of wintergreen. Mediderm l with lidocaine rx methyl salicylate menthol capsaicin lidocaine cream if this spl contains inactivated ndcs listed by the fda initiated compliance action, they will be specified as such.
Synthesis of methyl salicylate from aspirin esters are a class of organic compounds. This substance has caused adverse reproductive and fetal effects in animals. Methyl salicylate is an ester easily recognized by its odor and is known as oil of wintergreen because of its natural source. Methyl salicylate is a natural ester that performs very similarly to menthol.
As a derivative of salicylic acid, it is used commonly in ointments for the relief of muscle. Monographs 1 expert committee has revised the methyl salicylate monograph. It is a colorless, viscous liquid with a sweet fruity odor reminiscent of root beer. Numbing might follow depending on the concentration of methyl salicylate is applied. You will be able to see how two very different organic compounds can be made from the same common starting material. The purpose for the revision is to change the upper limit of the. Abstract the purpose of this experiment was to determine if salicylic acid made from methyl salicylate was the same or different from salicylic acid made from benzene. Methyl salicylate is fully degradation biodegradable. Lab 6 report synthesis of salicylic acid from wintergreen. Remove the patch and apply a new patch 1 or 2 times daily if needed.
Sp11 1021 synthesis of aspirin and oil of wintergreen. It acts as an anticoagulant by interruption of the vitamin k1epoxide cycle. It is produced by many species of plants, particularly wintergreens. Salicylate toxicity from percutaneous absorption can occur, especially with methyl salicylate. Firefighting measures continued act in accordance with the internal emergency plan and the information sheets on actions to take after an accident or other. Methyl salicylate is absorbed through the skin and is applied topically in rheumatic conditions. Hanna mustaparta, marit stranden, in recent advances in phytochemistry, 2005. A contract research organization cro, inc research, inc. Methyl salicylate lactoside inhibits inflammatory response. It is also used in high concentrations as a rubefacient to treat joint, muscular pain and acute pain. Other articles where methyl salicylate is discussed.
This experiment was designed to be done using household chemicals. It is also synthetically produced, used as a fragrance, in foods and beverages, and in liniments. The product will be analyzed by melting point analysis and carbon nmr. The product itself and its products of degradation are not toxic. 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. Methyl salicylate oil of wintergreen is an organic ester. Methyl salicylate oral 5 mgkg nonapplicable 1 mgkg nonapplicable cas. A copy of the license is included in the section entitled gnu free documentation license.
Preparation of salicylic acid salicylic acid will be prepared by a basepromoted hydrolysis, or saponi. The use of methyl salicylate as a topical medical product is subject to a 2 in japan, methyl s alicylate which conforms to the standards of the japanese standards of cosmetic ingredients jsci has precedent for use at a maximum concentration of 0. The results proved the salicylic acid from methyl salicylate was the same as. Dailymed white flower analgesic balm camphor, menthol. On this page about methyl salicylate compound gold cross you will find information relating to side effects, age restrictions, food interactions, whether the medicine is available at a government subsidised price on the pharmaceutical benefits scheme pbs as well as other useful information. The hazard classification and labelling section shows the hazards of a substance through a standardised system of statements and pictograms, as has been established under clp classification labelling and packaging regulation. Methyl salicylate is made into liniments and ointments that are put on the skin to treat pain in the bones and rheumatism. Identification methyl salicylate stp 140 mgl fresh water 0. Permission is granted to copy, distribute andor modify this document under the terms of the gnu free documentation license, version 1. This section covers acetylsalicylic acid aspirin, choline salicylate, methyl salicylate oil.
Methyl salicylate compound gold cross healthdirect. This was done by performing the reaction for methyl salicylate, separation of salicylic acid, recrystallization, and then melting point analysis. Receptor neurons detecting the typical plant stress compound methyl salicylate have been identified in the moth m. We offer halal and kosher methyl salicylate made in an iso9001, iso22000 fssc22000 and cgmp certified facility. View lab report synthesis of methyl salicylate from aspirin. The hydrolysis reaction that occurs will form methanol, water, and the sodium salt of. Necessary reagents methanol, ch 3oh salicylic acid, ohc 6h 4cooh.
Interestingly, methyl salicylate and methyl benzoate are both produced by methylation of salicylic and benzoic acids, respectively, controlled by the same gene in a. Methyl salicylate is an ester and esters are formed from a carboxylic acid and an alcohol. Hydrolyze the ester known as methyl salicylate under base conditions in order to synthesize salicylic acid, a carboxylic acid. The two compounds we will be preparing, aspirin acetylsalicylic acid and oil of wintergreen methyl salicylate, are both organic esters. The clp regulation makes sure that the hazards presented by chemicals are clearly communicated to workers and consumers in. Acetylsalicylic acid, choline salicylate, methyl salicylate, salicylic acid. Use of the information, documents and data from the echa website is subject to. Methyl salicylate recommended jul 2014, revised oct 2016, oct 2018 this draft guidance, when finalized, will represent the current thinking of the food and drug. Renal dialysis patients are at increased risk for salicylism because salicylates are primarily excreted by the kidneys.
Synthesis of aspirin and oil of wintergreen revision f8 page 2 of 7 methyl salicylate is the active ingredient in oil of wintergreen. Methyl salicylate an overview sciencedirect topics. White flower analgesic balm camphor, menthol and methyl salicylate oil if this spl contains inactivated ndcs listed by the fda initiated compliance action, they will be specified as such. The odor is often described as minty due to its use in mint candies. Methyl salicylate and 1r,5smyrtenal stimulate specific olfactory cells in the primary rhinaria on the sixth and fifth antennal segments, respectively, of the black bean aphid. Methyl salicylate an ester can be hydrolyzed to produce salicylic acid. An ester compromises an organic or inorganic acid in which one or more hydroxy oh groups have been replaced by and alkoxy oalkyl group. Methyl salicylate has fdaspecified uses as indirect food additive cir, 2003. The foregoing data has been compiled for safety information only and does not form part of any selling specification. Menthol is slightly soluble in water and highly soluble in alcohol. 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. The pain relief capabilities of methyl salicylate are well established and. Salicylates inhibit cyclooxygenase, thereby reducing the formation of prostaglandins, and cause. In liquidliquid extraction, equilibrium concentrations of a.
Synthesis of ethyl salicylate using household chemicals. Methyl salicylate topical may be used up to 4 times daily or as directed on the medicine label. Methyl salicylate c8h8o3 cid 43 structure, chemical names, physical and. The aim of this study was to investigate the therapeutic effect of msl in mice with collageninduced arthritis cia and explore its underlying mechanism. Find patient medical information for methyl salicylate on webmd including its uses, side effects and safety, interactions, pictures, warnings and user ratings. For example, the simplest ester, methyl formate chooch 3, is. 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. Methyl salicylate safety data sheet according to 19072006ec reach, 2015830eu section 5. Methyl salicylate is an organic compound with the formula c6h4ohco2ch3. Methyl salicylate lactoside inhibits inflammatory response of. The synthesis of methyl salicylate is a safe and effective way to observe an amine diazotization.
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. Ethyl salicylate is synthesized, isolated, and characterized in a threestep process using simple equipment and household chemicals. 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. Methanol is the alcohol which is released by hydrolysis. Methyl salicylate is used as a flavoring agent and providing fragrance to products like chewing gum and mints. Salicylate toxicity from ingestion and continued dermal. It also includes pleasant smells due to chemicals that are used for artificial flavorings. Methyl salicylate, ms salicylic acid, sa salicylic acid mw 180. Pour 150 ml of methanol, 45 g of salicylic acid and slowly with mixing 30 ml of sulfuric acid. Methyl salicylate oil of wintergreen or wintergreen oil is an organic ester naturally produced by many species of plants, particularly wintergreens. Remove 70 ml of the methanol with a rotary evaporator, pour the mixture into a separatory funnel and. Preparation of salicylic acid santa monica college. The council of europe publications plants in cosmetics volume iii 2006 and active ingredients in cosmetics. 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.