Case study for the synthesis of methyl salicylate studocu. Remove the patch and apply a new patch 1 or 2 times daily if needed. Synthesis of aspirin and oil of wintergreen revision f8 page 2 of 7 methyl salicylate is the active ingredient in oil of wintergreen. The product itself and its products of degradation are not toxic.
A single teaspoon 5ml of methyl salicylate contains 7g of salicylate. 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. Find patient medical information for methyl salicylate on webmd including its uses, side effects and safety, interactions, pictures, warnings and user ratings. Methyl salicylate is a natural ester that can be made organically or synthetically in the lab but is usually extracted via steam distillation of wintergreen leaves. It is a colorless, viscous liquid with a sweet fruity odor reminiscent of root beer. Methyl salicylate skin deep cosmetics database ewg. Methyl salicylate synthesis summer 2016 background. Methyl salicylate topical may be used up to 4 times daily or as directed on the medicine label. Nov 19, 2016 methyl salicylate is an organic compound present mainly in wintergreen oil obtained from gaultheria procumbens. Methyl salicylate c6h4 ho cooch3, also known as salicylic acid methyl ester, oil of wintergreen, is a natural product of many species of plants. This experiment was designed to be done using household chemicals.
Methyl salicylate oil of wintergreen is an organic ester. Although science in motion can provide concentrated sulfuric acid, we have decided that it is too dangerous to handle. Use of methyl salicylates as a trialing chemical agent. Learn about the uses, side effects, and safety tips for methyl salicylate. Demonstrates the use of diazonium salts for the replacement of an aromatic amine group by a phenolic hydroxyl. Experiment 22 synthesis of aspirin and oil of wintergreen. We offer halal and kosher methyl salicylate made in an iso9001, iso22000. 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. It also includes pleasant smells due to chemicals that are used for artificial flavorings. Mar 02, 2020 antiseptic eucalyptol, menthol, methyl salicylate, thymol mouthwash if this spl contains inactivated ndcs listed by the fda initiated compliance action, they will be specified as such. 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 two compounds we will be preparing, aspirin acetylsalicylic acid and oil of wintergreen methyl salicylate, are both organic esters.
Methyl salicylate mes cautionary response information common synonyms liquid colorless, yellowish or reddish wintergreen oanisic acid benzoic acid, 2methoxybetula or gaultheria oil omethoxybenzoic acid sweet birch oil teaberry or wintergreen oil keep people away. Methyl salicylate oil of wintergreen or wintergreen oil is an organic compound with the formula c 6 h 4 ohco 2 ch 3. However, the topical application of methyl salicylate in petroleumbased grease did not cause congenital defects when used at doses up to 6000 mgkgday 40. Methyl salicylate an overview sciencedirect topics. Methyl salicylate, which is commonly referred to as oil of wintergreen and smells minty, is a compound having an ester function.
And, it was soon discovered that methyl salicylate has analgesic eases pain. Other articles where methyl salicylate is discussed. Synthesis of oil of wintergreen cornell center for. Feb 04, 2020 applies to menthol methyl salicylate topical. Oil of wintergreen is the strongest, purest concentration of methyl salicylate. It has counter irritant and antiinflammatory effects. It is a colorless, viscous liquid with a sweet fruity. The purpose for the revision is to change the upper limit of the. Read more about the prescription drug methylsalicylatementhol bengay. Interestingly, methyl salicylate and methyl benzoate are both produced by methylation of salicylic and benzoic acids, respectively, controlled by the same gene in a. 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. Determination of methyl salicylate in pharmaceutical preparations.
Methyl salicylate is an organic ester responsible for the minty smell of wintergreen. Methyl salicylate is extracted from essential oil of wintergereen oil, ylang ylang oil and acacia oil. The synthesis of methyl salicylate is a safe and effective way to observe an amine diazotization. In tmvinoculated tobaccoleaves, benzoicacid accumulation 18 paralleled the induction of ba2h activity 26. Read more about the prescription drug methylsalicylatementhol bengay, icy hot, mentholatum d, salonpas.
Sp11 1021 synthesis of aspirin and oil of wintergreen. In methyl salicylate oil of wintergreen, the cooh group of salicylic acid is esterified with methanol ch3oh, whereas in acetylsalicylic acid aspirin the acid component of the ester is acetic acid, and salicylic acid contributes the phenolic. Twokey enzymes involvedin sabiosynthesis andmetabolism. It applied as fragrance ingredient on toothpaste, also using in. Rubbing alcohol wintergreen with methyl salicylate, 16 fl. This substance has caused adverse reproductive and fetal effects in animals. This provides first aid to help prevent the risk of infection. This structure is also available as a 2d mol file or as a computed 3d sd file the 3d. Necessary reagents methanol, ch 3oh salicylic acid, ohc 6h 4cooh. You will be able to see how two very different organic compounds can be made from the same common starting material. The sccs considers salicylic acid cas 69727 safe when used as. To remove this unwanted starting reactant, a thorough washing with aqueous sodium bicarbonate, nahco 3 aq, will be performed. Methylsalicylatementhol bengay, icy hot, mentholatum d, salonpas is a topical ointment to relieve muscle aches.
Clean wounds with wintergreen rubbing alcohol with methyl salicylate. Methyl salicylate is also known to induce numbness when rubbed on affected area. 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 functions as a flavouring agent in chewing gums, syrups and ice creams. Most of these substances are used as fragrance and flavor ingredients. Methyl salicylate oral 5 mgkg nonapplicable 1 mgkg nonapplicable cas. This can also increase circulation of blood and furthermore fight the pain. Consult professionals if methyl salicylate need to be handled under some special conditions.
Methyl salicylate safety data sheet according to 19072006ec reach, 2015830eu section 5. Learn about side effects, drug interactions, recommended dosages, and storage information. When an acid containing the cooh group reacts with an alcohol a compound containing an oh group formed an ester. Dailymed antiseptic eucalyptol, menthol, methyl salicylate. Methyl salicylate is an antiinflammatory ingredient common in pain relief creams for muscles and joints. When salicylic acid reacts with methanol in the presence of an acid catalyst, methyl salicylate, or oil of wintergreen, is produced according to the. To apply a methyl salicylate topical skin patch, remove the liner and apply the patch to your skin over the area of pain. Mar 05, 2015 when methyl salicylate was given at doses of 200, 250, or 300 mgkgday, there was a reported alteration in renal pelvis and urine formation in rats. Notes that this experiment takes safety and noncarcinogenic reactants into account.
Methyl salicylate is fully degradation biodegradable. Methyl salicylate is an ester easily recognized by its odor and is known as oil of wintergreen because of its natural source. This procedure will use starting materials that can be found at a supermarket including aspirin, antifreeze, and drain cleaner. 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. Place the test tube in the hood in a water bath at 70 c for 15 minutes. Calculate the amount of methyl salicylate in both grams and ml that you will need to start with as part of your prelab. It is also found in the essential oils of cassie absolute, betula, tea tree and all plant species belonging to the genera spiraea, polygala, etc. Amended safety assessment of salicylic acid and salicylates as. Since the rld product has a matrix design that can be. 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. According to the national formulary nf, methyl salicylate contains not less. Methyl salicylate is commonly used in overthecounter medicines to temporarily relieve minor body aches and muscle and joint pain. Toxicology and teratology of the active ingredients of.
Synthesize methyl salicylate perform this part of the lab in a well ventilated area. Methyl salicylate is found in trees, legumes and exotic plants. Nov 09, 2018 methyl salicylate topical for the skin is used for temporary relief of muscle or joint pain caused by strains, sprains, arthritis, bruising, or backaches. Preparation of salicylic acid from methyl salicylate. Methyl salicylate c8h8o3 cid 43 structure, chemical names, physical and chemical properties, classification, patents, literature, biological activities. 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. 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. Even though it may be rare, some people may have very bad and sometimes deadly side effects when taking a drug. Application methyl salicylate has been used in the hyalinization of tissues for pulmonary angiography.
Methyl salicylate may be used by plants as a pheromone to warn other plants of pathogens such as tobacco mosaic virus. Find patient medical information for methyl salicylate nf topical on webmd including its uses, side effects and safety, interactions, pictures, warnings and user ratings. Pour 150 ml of methanol, 45 g of salicylic acid and slowly. Identification methyl salicylate stp 140 mgl fresh water 0. 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. We make ethyl rather than methyl salicylate, because methanol is toxic.
Remove the patch and apply a new patch 1 or 2 times. It comes in a 16 fl oz bottle that is easy to open and apply with a cotton ball. The hydrolysis reaction that occurs will form methanol, water, and the sodium salt of. In the case of methyl salicylate, there will also be unreacted salicylic acid drawn into the organic solvent. A toxicologic and dermatologic assessment of salicylates when used. Firefighting measures continued act in accordance with the internal emergency plan and the. In methyl salicylate oil of wintergreen, the cooh group of salicylic acid is esterified with methanol ch3oh, whereas in. Structurally, methyl salicylate is the methyl ester of salicylic acid, produced e. Hydrolyze the ester known as methyl salicylate under base conditions in order to synthesize salicylic acid, a carboxylic acid. This structure is also available as a 2d mol file or as a computed 3d sd file. Methyl salicylate is very hazardous in case of ingestion. Synthesis of oil of wintergreen pre lab discussion. Monographs 1 expert committee has revised the methyl salicylate monograph. Hazardous in case of skin contact irritant, of eye contact irritant, of inhalation.