These molecular entities were created by covalently linking two bioactive molecules, either niacin or salicylic acid, to an omega3 fatty acid. Synthesis and structure of new derivatives of salicylic acid hydrazide. 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. Since over 200 years salicylates have been used in medicine as analgesic, antipyretic and antiphlogistic drugs 1, 2.
Synthesis of aspirin in the first part of the experiment, aspirin was synthesized. Hippocrates discovery was lost over time, but rediscovered in the mid 1700s. Some people find even aspirin too acidic and prefer to use aspirin substitutes like acetaminophen and ibuprofen. Methyl salicylate c6h4 ho cooch3, also known as salicylic acid methyl ester, oil of wintergreen, is a natural product of many species of plants. A filter crucible and mortar and pestle were obtained from the instructor. Synthesis of some new azosulfonamides based on salicylic acid and thiosalicyclic acid, and having antibacterial and antifungal activity. Anthranylic acid derivatives are direct structural analogs of salicylic acid derivatives. C 2 o 4 ho another piece of evidence is the known decomposition of salicylic acid when heated with lime or. The synthesis of aetyllcsalicylic acidtt by jean w. The reactions were carried out in n,ndimethylformamide dmf in the presence of anhydrous potassium. The key step involved a sodium hydride promoted intramolecular lactonization in the presence of excess tmscl, which led to isolation of the natural product like lactone. At that time salicylic acid was known to ease pains and reduce fevers. Following promising pilot studies with highdose aspirin 2, salsalate 3, a prodrug of salicylic acid, produced a highly significant reduction in blood glucose, hemoglobina1c. Leeet at activation of the ba2h activity resulted in a significant increase in salevels in hydrogen peroxidetreated tobacco leaves j.
Synthesis of aspirin lab report and analysis odinity. The facile preparation of a novel 8membered polyhydroxylated salicylic acid lactone from 2,6dihydroxybenzoic acid and sodium thiodglucose is described. Another derivative of salicylic acid that has healing properties and is. Although salicylic acid is a good pain reliever, its acidic properties cause irritation in the moist membranes of the mouth, throat, and stomach. Mix salicylic acid solid with acetic anhydride liquid and a catalytic amount of h. Synthesis and antifungal activity of new salicylic acid. Salicylic acid and related compounds wiley online library. Salicylic acid 1 and its derivatives possess antiinflammatory activity due to their inhibition of cyclooxygenases and of nf. In fact, many cultures have used plants containing significant amounts of these compounds in medications to relieve. Your aspirin product as well as a commercial aspirin tablet will be compared to a standard 0. Salicylic acid from latin salix, willow tree is a lipophilic monohydroxybenzoic acid, a type of phenolic acid, and a beta hydroxy acid bha. According to the method, supported potassium carbonate is adopted as a catalyst, and salicylic acid is synthesized with phenol and supercritical carbon dioxide. Your use of this pdf, the bioone complete website, and all posted and associated.
Agrobacterium tumefaciens synthesizedsa via ocoumaric acid whereas the benzoic acid. Mix salicylic acid solid with acetic anhydride liquid and a catalytic amount of h2so4 heat for 10 min at 900c. Synthesis and characterization of fatty acid conjugates of. Hydrolysis of methyl salicylate naoh pka o h o h o o h o o o o o o salicylic acid mw 180. In this experiment, you will measure the melting point of your synthesized asa product, salicylic acid, a crushed aspirin tablet, and pure asa from a manufacturer. Pdf an improved synthesis of salicylic acid using water as solvent can be achieved using the ullmanngoldberg reaction conditions in presence of. A white powder, it could be taken orally, but it had an unfortunate side effect. Synthesis and use of organic compounds is an extremely important area of modern chemistry.
The rest of the pain relievers require multiple steps in their organic synthesis. Synthesis of oil of wintergreen cornell center for. The product will be analyzed by melting point analysis and carbon nmr. Dilution with water and cooling results in precipitation of aspirin, yet another white solid. Thus, salicylic acid can react with nucleophilic molecules like methanol in addition to reacting with electrophilic molecules like acetic anhydride. A 7080 c hot water bath was prepared by placing a 250 ml beaker on a hot plate with a thermometer to monitor temperature. A simple onestep procedure for synthesis of 1methoxy1oxoalkan2yl salicylates and 1methoxy1oxoalkan2yl 21methoxy1oxoalkan2yloxybenzoates by reaction of salicylic acid with several methyl 2bromoalkanoates was developed. Both salicylic acid and aspirin are sparingly soluble in water, making these procedures readily. This colorless crystalline organic acid is widely used in organic synthesis and functions as a plant hormone. It works as an exfoliant and mostly acts against comedonal acne by slowing follicular shedding of cells thus preventing clogging.
In the first step, water is used to break the ester bond. Synthesis of acetylsalicylic acid aspirin from salicylic acid and acetic anhydride soriano, sosa, sualibios and tan department of chemistry, college of science, university of santo tomas, manila abstract this experiment was done in order to synthesize aspirin from the fischer esterification reaction of salicylic acid and acetic anhydride. Biosynthesis and metabolism of salicylic acid pnas. In the fume hood, add five drops of concentrated acid to the flask containing the salicylic acid and acetic anhydride and swirl to mix everything thoroughly. Aspirin is the common name for the compound acetylsalicylic acid, widely used as a fever reducer and as a pain killer. Salicylic acid sa has been shown to regulate various aspects of growth. In the presence of moisture, aspirin may decompose hydrolysis into salicylic acid and acetic acid. The reaction of a carboxylic acid with an alcohol, an esterification, its analogues, amidation for example, and the reverse reactions, ester hydrolysis for example, are essential to life as we know. Preparation of salicylic acid salicylic acid will be prepared by a basepromoted hydrolysis, or saponi.
Salicylic acid production by chemical means is energy intensive and generates many byproducts. Approximately half of all chemists work with organic chemicals. The addition of ferric chloride to salicylic acid produces a specific color caused by the reaction of salicylic acid with aqueous ferric feh the oh group on the salicylic acid together can form a complex with feh an intense violet color. Synthesis of a novel polyhydroxylated salicylic acid. A structure and antioxidant activity study of paracetamol. They possess analgesic, antiinflammatory, and feverreducing activity.
The synthesis of salicylic acid from wintergreen oil instructor guide learning objectives. Our starting material is aspirin acetylsalicylic acid. The structure of salicylic acid is shown in the figure below. Gtases is inhibited by cycloheximide, a protein synthesis inhibitor 41. Synthesis of aspirin background aspirin, which ranks as the most widely used drug in the united states, is one of a series of salicylic acid esters that has been known since antiquity to have therapeutic effects. Salicylic acid was found in the flowers of that tree. This reaction is the reverse of the synthesis reaction.
On the synthesis of salicylic acid by hermann kolbe. Synthesis of oil of wintergreen pre lab discussion. In addition to serving as an important active metabolite of aspirin, which acts in part as a prodrug to salicylic acid, it is probably best known for its use as a key ingredient in topical antiacne products. Salicylic acid is a milder and safer treatment for mild to moderate acne vulgaris, with fewer side effects. Cn105481685a onestep method for synthesizing salicylic. An illustrated equation showing compounds to be isolated. In 1875, the sodium salt of salicylic acid was used because it is less sour to the taste. Routh i of salicylate metabolism, the rate of in wiwo hydrolysis of the acetate portion of acetyl salicylate was of interest. In addition to serving as an important active metabolite of aspirin. In aspirin, the group which prevents the second bond from being formed.
The indications of a salicylic acid peeling agent include acne vulgarism, melasma. Synthesis of salicylic acid the purpose of this experiment is to synthesize salicylic acid, a white organic solid that was extracted from willow bark by hippocrates in the fifth century bc. In the field of medicinal chemistry, there is a growing interest in the use of small molecules. Methyl salicylate may be used by plants as a pheromone to warn other plants of. However, salicylic acid is more acidic than aspirin, and is especially irritating to the mouth and stomach. Preparation of salicylic acid smc faculty home pages. Perform typical organic synthesis chemistry laboratory techniques o equipment setup, refluxing, thermocouple controller use, crystallization, filtration, drying, perform hydrolysis reaction and neutralization. Salicylic acid h2 various preparations of salicylic acid have been used for peeling purposes for up to 50% 4. The maximum allowable amount of free salicylic acid in an aspirin sample is 0. Then add 2 drops of concentrated sulfuric acid, h 2 so 4, to the reaction mixture it acts as a catalyst.
Based on the mass of salicylic acid 2 g determine the maximum yield of aspirin theoretical yield from this amount of starting material. However, it still caused gastric discomfort problems. The purpose of this experiment was to perform a basecatalyzed hydrolysis reaction while converting oil of wintergreen to salicylic acid. Synthesis must always be accompanied by isolation and purification of the product. The synthesis of acetyl1c14salicylic acid pdf free. The synthesis of cool smelling molecules purpose to expand the use of the concept of nucleophilicity and electrophilicity, to introduce the reactivity of carbonyls, and to demonstrate a class of reactions that is vital to life as we know it by performing an esterification to make a cool molecule. Aspirin is produced from a reaction between acetic. Manydifferent types of hydroxybenzoic acid conjugates have been found in a wide range of plant species 33. This report describes the synthesis and preliminary biological characterization of novel fatty acid niacin conjugates and fatty acid salicylate conjugates. Experiment 22 synthesis of aspirin and oil of wintergreen. After synthesis and analysis, it will be determined if the crude and recrystallized samples were composed solely of either salicylic acid, acetylsalicylic acid, or a combination of both 3. After a brief overview of the information on salicylic acid and its. This hydrolysis reaction can be accomplished through either acid.
Synthesis of aspirin synthesis purification characterization. Salicylic acid is a lipophilic monohydroxybenzoic acid, a type of phenolic acid, and a beta hydroxy acid. Another derivative of salicylic acid that has healing properties and is also a simple onestep organic. This methodology allows the simultaneous intracellular delivery of two bioactives in order to.