What is Methyl Salicylate Definition Formula Reactions and Uses
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 Structure Properties and Preparation
1. What is methyl salicylate?
Methyl salicylate is an organic ester with the molecular formula C8H8O3, commonly known as oil of wintergreen. It is formed from salicylic acid and methanol and has a characteristic minty odor. Structurally, it contains:
- An aromatic benzene ring
- A hydroxyl (–OH) group
- An ester functional group (–COOCH3)
2. What is the chemical formula and structure of methyl salicylate?
The chemical formula of methyl salicylate is C8H8O3, and its condensed structural formula is C6H4(OH)COOCH3. Its structure consists of:
- A benzene ring (C6H4)
- An –OH group attached to the ring
- An ester group (–COOCH3) adjacent to the hydroxyl group
3. How is methyl salicylate prepared in the laboratory?
Methyl salicylate is prepared by Fischer esterification of salicylic acid with methanol in the presence of an acid catalyst. The balanced equation is: C7H6O3(s) + CH3OH(l) → C8H8O3(l) + H2O(l)
- Catalyst: Concentrated H2SO4
- Reaction type: Esterification reaction
- By-product: Water
4. What type of functional group is present in methyl salicylate?
Methyl salicylate contains an ester functional group (–COO–) along with a phenolic hydroxyl (–OH) group. Specifically, it includes:
- An ester linkage (–COOCH3)
- A phenol group attached to an aromatic ring
- An aromatic benzene ring
5. What is the molar mass of methyl salicylate?
The molar mass of methyl salicylate (C8H8O3) is 152.15 g·mol-1. It is calculated as:
- C: 8 × 12.01 = 96.08
- H: 8 × 1.008 = 8.06
- O: 3 × 16.00 = 48.00
6. Is methyl salicylate an acid, base, or neutral compound?
Methyl salicylate is generally considered a neutral organic compound, although it contains a weakly acidic phenolic –OH group. Unlike salicylic acid, it does not have a free carboxylic acid (–COOH) group because it is converted into an ester. Therefore:
- It does not strongly ionize in water
- It is much less acidic than salicylic acid
- It behaves mainly as a neutral ester in most reactions
7. What is the difference between salicylic acid and methyl salicylate?
The main difference is that salicylic acid contains a carboxylic acid (–COOH) group, while methyl salicylate contains an ester (–COOCH3) group. Key differences include:
- Salicylic acid: C7H6O3, acidic, contains –COOH
- Methyl salicylate: C8H8O3, ester, less acidic
- Methyl salicylate is formed by esterification of salicylic acid with methanol
8. What happens when methyl salicylate undergoes hydrolysis?
When methyl salicylate undergoes hydrolysis, it breaks down into salicylic acid and methanol. The balanced acid-catalyzed reaction is: C8H8O3(l) + H2O(l) → C7H6O3(aq) + CH3OH(aq)
- Reaction type: Ester hydrolysis
- Conditions: Acidic or basic medium
- Reverse of Fischer esterification
9. Why is methyl salicylate called oil of wintergreen?
Methyl salicylate is called oil of wintergreen because it naturally occurs in the leaves of the wintergreen plant and has a characteristic minty aroma. It can be:
- Extracted from plants such as Gaultheria procumbens
- Synthesized in the laboratory by esterification
- Used in liniments, balms, and flavorings
10. What are the common uses of methyl salicylate in chemistry and industry?
Methyl salicylate is commonly used as a topical analgesic, flavoring agent, and fragrance compound. Its major applications include:
- Pain relief creams due to its counterirritant properties
- Flavoring in small quantities for mint-like taste
- Fragrance in perfumes and cosmetics
- Intermediate in organic synthesis
