Oil of Wintergreen
Methyl salicylate or wintergreen oil or oil of wintergreen can be described as a natural ester produced by different plant species, specifically wintergreens. The plant species Gaultheria procumbens was first used in 1843 for extracting and isolating this compound. So, what is methyl salicylate, it is a compound produced synthetically while used in the form of a fragrance in liniments, beverages, and food.
Methyl salicylate forms a reddish, or yellow or completely colourless liquid. It has a specific taste and odour and is used as an analgesic and rubefacient in some deep heating liniments used for treating muscular and acute joint pain. It is even used in the form of a flavouring element in mints and chewing gums but in small quantities. You can also add this compound as an antiseptic in different mouthwash solutions.
Structure and Uses of Methyl Salicylate
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When it comes to the uses of methyl salicylate, it is suitable for treating minor pains and aches of muscle joints. These include sprains, backaches, and arthritis. Methyl salicylate uses can even be found in chewing gums, candies, toothpaste and cough drops but in minimal concentrations. Methyl salicylate and menthol work in coordination by making the skin feel warm and cool. Such feelings on the skin distract individuals from the feelings of pains and ache of the joints and muscles.
Wintergreen oil uses do not end there. It serves as a warming element in cosmetics and products meant for sports massage. The oil is also ideal for aromatherapy. It is incorporated into ointments and liniments in the form of an anti-inflammatory agent. Nevertheless, it is crucial to understand that you need to keep this product from children below 18 years of age.
Coming to the oil of wintergreen structure, this syrupy tasting member of the family of aspirins is probably one of the most extensively utilised counter-irritants in the market. It is a salicylic acid ester where acidic carboxylate moiety is completely methylated without changing the phenolic hydroxyl. Methyl salicylate structure is very similar to the structure of salicylic acid.
Properties of Methyl Salicylate
First of all, we will have a look at the physical properties of methyl salicylate. The properties are as under:
Minty cool odour
Reddish to yellow or colourless liquid appearance.
Slightly soluble in water. Methyl salicylate is also soluble in the majority of the organic solvents.
Vapor pressure: 0.0343mm Hg@ 25 deg C.
The Chemical Properties of Methyl Salicylate are:
The compound undergoes the process of hydrolysis if there is an aqueous base present. The hydrolysis of methyl salicylate results in the formation of methanol and salicylic acid.
Methyl Salicylate Structural Formula
Methyl salicylate formula is C8H8O3. Its average mass is 152.147 Da, and its monoisotopic mass is 152.047348 Da. Now that you know the oil of wintergreen formula and also understand the structure of the oil of wintergreen, you need to know the methyl salicylate IUPAC name. The IUPAC name of methyl salicylate is methyl 2- hydroxybenzoate. Methyl salicylate boiling point is 220 degrees C, and the methyl salicylate melting point is -9 degree C.
Methyl Salicylate Side Effects
It should be kept away from the reach of children below 18 years of age. It is also worth noting that the product should not be used without the advice of a healthcare professional. Failing to do so might result in several methyl salicylate side effects. Some of the significant side effects of methyl salicylate are as follows:
Mild itching, irritation, and redness at the spot of the application might appear. If any of these problems get worse or last for long, consult a pharmacist or doctor immediately.
Swelling or blistering at the site of application or unusual or increased pain along with vomiting and nausea or ringing in the ears are conditions that require immediate medical attention. You must stop using this product if you experience these problems.
Serious allergic reactions to methyl salicylate are rare, but if any symptoms are noticed like swelling, itching, trouble breathing, or severe dizziness, they must be reported to a doctor instantly.
Other side effects might also take place. So, consulting a healthcare professional is always advisable. Remember, if your doctor has asked you to use methyl salicylate, he or she has already judged its advantages for you rather than the risks of the side effects. So, it is quite possible for individuals not to experience methyl salicylate side effects.
FAQs on Methyl Salicylate
1. What is methyl salicylate and what are its common names?
Methyl salicylate is a natural organic ester produced by many species of plants, particularly wintergreens. It is commonly known as oil of wintergreen or wintergreen oil. Its official IUPAC name is methyl 2-hydroxybenzoate. It is often produced synthetically for commercial use in foods, fragrances, and liniments.
2. What is the chemical formula and structure of methyl salicylate?
The chemical formula for methyl salicylate is C₈H₈O₃. Structurally, it is an ester of salicylic acid. The molecule consists of a benzene ring with two functional groups attached: a hydroxyl (-OH) group and a methyl ester (-COOCH₃) group. It is formed by the methylation of the carboxyl group of salicylic acid.
3. What are the main uses of methyl salicylate?
Methyl salicylate has several common applications, primarily due to its analgesic and aromatic properties. Its main uses include:
- Topical Analgesic: It is a key active ingredient in deep heating liniments to provide temporary relief from minor muscle and joint pain, such as from arthritis, backaches, and sprains.
- Flavouring Agent: In very small, controlled concentrations, it is used to give a minty flavour to products like chewing gum, candies, and toothpaste.
- Fragrance: Its distinct minty scent makes it a popular fragrance component in cosmetics and aromatherapy products.
- Antiseptic: It is sometimes added to mouthwash solutions for its antiseptic qualities.
4. What are the key physical and chemical properties of methyl salicylate?
Methyl salicylate exhibits several distinct properties:
- Appearance: It is a colourless to yellow or reddish liquid.
- Odour: It has a characteristic strong, minty odour, famously known as the scent of wintergreen.
- Solubility: It is only slightly soluble in water but dissolves well in most organic solvents.
- Boiling and Melting Points: Its boiling point is approximately 220°C, and its melting point is -9°C.
- Chemical Reactivity: It undergoes hydrolysis in the presence of an aqueous base to yield salicylic acid and methanol.
5. What are the potential side effects of using methyl salicylate topically?
When applied to the skin, methyl salicylate can cause some side effects, although most are mild. Common reactions include mild itching, redness, or irritation at the application site. However, more serious side effects can occur and require immediate medical attention, such as blistering, swelling, increased pain, nausea, or ringing in the ears. It is important to use this product as directed and consult a doctor if adverse reactions persist or worsen.
6. How is methyl salicylate prepared in a laboratory setting?
In the laboratory, methyl salicylate is typically synthesized through a process called Fischer esterification. This reaction involves heating salicylic acid with an excess of methanol in the presence of a strong acid catalyst, such as concentrated sulfuric acid (H₂SO₄). The acid protonates the carboxyl group of salicylic acid, making it more susceptible to nucleophilic attack by methanol, resulting in the formation of the ester (methyl salicylate) and water as a byproduct.
7. What is the difference between methyl salicylate and salicylic acid?
The primary difference lies in their functional groups. Both molecules contain a benzene ring and a hydroxyl (-OH) group. However, salicylic acid has a carboxylic acid group (-COOH). In methyl salicylate, this carboxylic acid group has been converted into a methyl ester group (-COOCH₃) through esterification. This structural change significantly alters their properties; for instance, methyl salicylate is a fragrant liquid used as a topical analgesic, while salicylic acid is a solid crystal used in skincare for its keratolytic properties.
8. Why is methyl salicylate considered a counter-irritant for pain relief?
Methyl salicylate acts as a counter-irritant by creating a surface-level irritation on the skin where it is applied. This action produces a warming or cooling sensation that serves as a distraction. The sensory signals from the skin override or 'distract' the nervous system from the deeper, more persistent signals of muscle or joint pain. Essentially, it tricks the brain into paying attention to the new sensation on the skin rather than the underlying ache.
9. Why is it dangerous to ingest methyl salicylate, even in small amounts?
Ingesting methyl salicylate is extremely dangerous because it is highly toxic. Upon ingestion, the body rapidly hydrolyzes it back into salicylic acid. A very small amount of methyl salicylate (as little as one teaspoon) can be equivalent to ingesting a toxic overdose of aspirin tablets. This leads to a severe condition called salicylism or salicylate poisoning, which can cause symptoms like nausea, vomiting, rapid breathing, convulsions, coma, and can be fatal.
