Precautions
Salicylic Acid forms an intramolecular hydrogen bond. In aqueous solution, Salicylic Acid, being an organic acid, dissociates to lose a proton from the carboxylic acid functional group.
What type of hydrogen bond does salicylic acid form?
Salicylic Acid: a natural inducer of heat production in arum lilies. Science 237:1601–1602. ^ Malakar, Sreepurna; Gibson, Peter R.; Barrett, Jacqueline S.; Muir, Jane G. (1 April 2017). "Naturally occurring dietary salicylates: A closer look at common Australian foods".
What is salicylic acid?
In this reaction, salicylic acid is reacted with acetic anhydride in an acidic medium which leads to the acetylation of the hydroxyl group present in the salicylic acid, thereby resulting in the production of acetylsalicylic acid (aspirin).
What is the reaction between salicylic acid and acetic anhydride?
Salicylic acid acts as a keratolytic (it serves as a peeling agent). Salicylic acid facilitates and makes the outer layer of the skin to shed. The topical salicylic acid (for the skin) is used to treat acne, dandruff, seborrhea, or psoriasis and to remove cotton, calluses, and warts.
Is salicylic acid a keratolytic?
Does salicylic acid have intramolecular hydrogen bonding?
Salicylic acid is distinct among the derivatives of benzoic acid due to the presence of an intramolecular hydrogen bond.
What intermolecular forces are present in salicylic acid?
Two intermolecular interactions operate in salicylic acid, (i) dispersion forces which increase with the length of the molecule, and (ii) hydrogen bonding, which would occur between the carboxylate heads of 2 molecules.
Is aspirin ionic or covalent?
covalent compoundAspirin (C 9H 8O 4) is a covalent compound.
Is salicylic acid polar?
The -OH group is more polar than the ester so salicylic acid is more polar than aspirin.
What is intramolecular and intermolecular hydrogen bonding?
Hydrogen bonding can occur as both intermolecular and intramolecular forces. The main difference between intermolecular and intramolecular hydrogen bonding is that intermolecular bonding occurs between two neighbouring molecules whereas intramolecular hydrogen bonding occurs within the molecule itself.
How many hydrogen bonding sites are in salicylic acid?
two1 The molecular configurations of salicylic acid, guanidine and guanidinium salicylate. It is exhibited evidently that there are two non-covalent hydrogen bonds existing between the salicylate anion and guanidinium cation.
What type of bonds does aspirin form?
Homodimers of aspirin form hydrogen bonds with bond energies of 10 kcal/mol. Weak hydrogen bonds utilizing phenyl and methyl groups are also found.
Is acetylsalicylic acid polar covalent?
Aspirin is a polar molecule with dipole-dipole attraction bonds and an -OH (hydroxyl) segment as part of a carboxylic acid group.
What makes salicylic acid polar?
Since the two -OH bonds in the salicylic acid molecule are close to two of the carbon atoms and far away from the other four, and since the molecule is asymmetric, salicylic acid is polar.
What is the structure of salicylic acid?
C₇H₆O₃Salicylic acid / Formula
Why is salicylic acid hydrophobic?
The benzene ring of salicylic acid is highly hydrophobic, the same as the newly formed hexatomic ring between the carboxyl group and the phenolic hydroxyl group due to weakly intramolecular hydrogen bonding. However, the exocyclic the hydroxyl group of carboxyl group is hydrophilic.
What is salicylic acid chemistry?
Salicylic acid is the chemical compound with the formula C6H4(OH)CO2H, where the OH group is adjacent to the carboxyl group. It is also known as 2-hydroxybenzoic acid. Salicylic acid belongs to a group of medicines known as keratolytics.
What is the role of salicylic acid in plants?
Salicylic acid is a phenolic phytohormone, and is found in plants with roles in plant growth and development, photosynthesis, transpiration, and ion uptake and transport. Salicylic acid is involved in endogenous signaling, mediating plant defense against pathogens.
What is white willow bark?
White willow ( Salix alba) is a natural source of salicylic acid. Hippocrates, Galen, Pliny the Elder, and others knew that willow bark could ease pain and reduce fevers. It was used in Europe and China to treat these conditions. This remedy is mentioned in texts from Ancient Egypt, Sumer, and Assyria.
What acid is used to make salicylic acid?
Acidification of the product with sulfuric acid gives salicylic acid: It can also be prepared by the hydrolysis of aspirin (acetylsalicylic acid) or methyl salicylate (oil of wintergreen) with a strong acid or base.
What is the active ingredient in Pepto Bismol?
Bismuth subsalicylate, a salt of bismuth and salicylic acid, is the active ingredient in stomach-relief aids such as Pepto-Bismol, is the main ingredient of Kaopectate, and "displays anti-inflammatory action (due to salicylic acid) and also acts as an antacid and mild antibiotic". Other derivatives include methyl salicylate used as a liniment ...
What is the name of the acid that is used to make aspirin?
Aspirin (acetylsalicylic acid or ASA) is prepared by the esterification of the phenolic hydroxyl group of salicylic acid with the acetyl group from acetic anhydride or acetyl chloride .
How is salicylate prepared?
Sodium salicylate is commercially prepared by treating sodium phenolate (the sodium salt of phenol) with carbon dioxide at high pressure (100 atm) and high temperature (115 °C) – a method known as the Kolbe-Schmitt reaction. Acidification of the product with sulfuric acid gives salicylic acid:
What is the chemical formula for salicylic acid?
Chemical compound. Salicylic acid is an organic compound with the formula HOC 6 H 4 CO 2 H. A colorless solid, it is a precursor to and a metabolite of aspirin (acetylsalicylic acid). It is a plant hormone. The name is from Latin salix for willow tree.
What is methyl salicylate used for?
It can be used for the preparation of salicylic acid. In this reaction, methyl salicylate is reacted with sodium hydroxide to lead to the formation of a sodium salt intermediate of salicylic acid, named disodium salicylate, which upon undergoing further reaction with sulphuric acid leads to the formation of salicylic acid.
What is the reaction between salicylic acid and acetic anhydride?
In this reaction, salicylic acid is reacted with acetic anhydride in an acidic medium which leads to the acetylation of the hydroxyl group present in the salicylic acid, thereby resulting in the production of acetylsalicylic acid (aspirin). Acetic acid is produced as a by-product of this reaction, which is also present as one ...
What is salicylic acid?
VIEW MORE. Salicylic Acid is a small aromatic acid whose chemical name is monohydroxybenzoic acid. It is lipophilic in nature. It was first derived from the bark of Willow Tree. It derives its common name from a variety of sources related to it with a similar name, e.g., it is derived as a metabolic product of salicin ...
Why is salicylic acid good for hair?
It is because salicylic acid prevents the deposition of sebum in the skin pores and around hair follicles. It helps in clearing away the dead and flaky skin cells from your scalp, thereby preventing the occurrence of dandruff.
What happens when salicylic acid dissociates?
In aqueous solution, Salicylic Acid, being an organic acid, dissociates to lose a proton from the carboxylic acid functional group. The resulting carboxylate ion (–COO –) undergoes intermolecular interaction with the hydrogen atom of the hydroxyl group (–OH), thereby leading to the formation of an intramolecular hydrogen bond.
What are the two methods of preparation of salicylic acid?
Methods of Preparation of Salicylic Acid. There are two most commonly used methods for the preparation of salicylic acid. These methods are discussed below: • From Phenol: When phenol is reacted with sodium hydroxide, it forms sodium phenoxide which is then further allowed to undergo distillation and dehydration.
What are the physical properties of salicylic acid?
Physical Properties of Salicylic Acid. • Salicylic Acid exist as clear white or colourless and odourless needle-shaped crystals at room temperature. • Salicylic Acid contains two hydrogen bond donors and three hydrogen bond acceptors in its molecule.
What is the chemical formula for salicylic acid?
Salicylic Acid is a type of beta hydroxy acid (BHA) and phenolic acid with a chemical formula C 7 H 6 O 3. It is a BHA found as a natural compound in plants. It functions as a plant hormone. This lipophilic monohydroxybenzoic acid is a derivative of salicin metabolism. It is a crystalline organic carboxylic acid with keratolytic, ...
What is salicylic acid used for?
The topical salicylic acid (for the skin) is used to treat acne, dandruff, seborrhea, or psoriasis and to remove cotton, calluses, and warts. Salicylic acid is found in many daily use products.
What is a saline balm?
It is used in the treatment of acne, dandruff, and the wrath. It is used as a preservative. It is used in the production of drugs like aspirin. It is used as a balm to reduce muscle and joint pain.
Is salicylic acid safe to use?
Although the use of low-concentration household salicylic acid products is usually considered safe, salicylic acid can cause mild chemical burns at high concentrations. These chemicals can also cause dangerous intoxication if ingested.
Overview
Salicylic acid is used on the skin to treat psoriasis and other dry, scaly skin conditions. This medication is also used to help remove dead skin from warts, the palms of the hands, and the soles of the feet.
May Treat: Acne vulgaris · Calluses and corns · Dandruff · Hyperkeratosis · Keratoderma and more
Brand Names: Salex · Virasal · Bensal HP · Salvax · Keralyt and more
Drug Class: Acne Therapy Topical - Keratolytic · Dermatological - Keratolytic-Antimitotic Single Agents
Availability: Prescription sometimes needed
Pregnancy: Consult a doctor before using
Lactation: Consult a doctor before using
- Room temperature
- For adhesive patch, medicated products : Keep away from eyes, nose mouth, genitals or anus. Dispose patch by folding sticky sides together. Not recommended during pregnancy.
- For cream products : Do not use on moles or birth marks. Avoid contact with unaffected skin.
- Room temperature
- For adhesive patch, medicated products : Keep away from eyes, nose mouth, genitals or anus. Dispose patch by folding sticky sides together. Not recommended during pregnancy.
- For cream products : Do not use on moles or birth marks. Avoid contact with unaffected skin.
- For foam products : Wash hands before and after using. Shake foam canister well before spraying foam. Apply to affected areas and rub in well. Keep bottle upright.
- For gel products : Unless MD directs, do not use in kids less than 2. Apply a thin layer to affected areas. Do not increase dose or frequency or prolong use. Follow directions on best place to keep drug supply. Wash hands after applying. Keep medicine away from heat or flames. Call doctor if you are not getting better. Use only prescribed dura- tion. Ask MD if unsure.
- For pads, medicated products : Before first use, test for allergic reaction. Read directions carefully before start of therapy. Avoid contact with eyes, nose, mouth or genitals. Do not apply to raw skin or open wounds. Use at the same time(s) daily as directed. Apply after bath while skin still damp. Apply a thin layer and rub in. Protect from heat, light, & moisture.
- For shampoo products : Follow directions for use of shampoo on hair. Do not apply to large areas of body. Redness or irritation may occur at application site. Tell MD about other skin products you use.
Uses
Mechanism of action
Safety
Production and chemical reactions
Salicylic acid is an organic compound with the formula HOC6H4CO2H. A colorless, bitter-tasting solid, it is a precursor to and a metabolite of aspirin (acetylsalicylic acid). It is a plant hormone, and has been listed by the EPA Toxic Substances Control Act (TSCA) Chemical Substance Inventory as an experimental teratogen. The name is from Latin salix for willow tree. It is an ingredient in some anti-acne products. Salts and esters of salicylic acid are known as salicylates.
History
Salicylic acid as a medication is used commonly to remove the outer layer of the skin. As such, it is used to treat warts, psoriasis, acne vulgaris, ringworm, dandruff, and ichthyosis.
Similar to other hydroxy acids, salicylic acid is an ingredient in many skincare products for the treatment of seborrhoeic dermatitis, acne, psoriasis, calluses, corns, keratosis pilaris, acanthosis nigricans, ichthyosis, and warts.
Dietary sources
Salicylic acid modulates COX-1 enzymatic activity to decrease the formation of pro-inflammatory prostaglandins. Salicylate may competitively inhibit prostaglandin formation. Salicylate's antirheumatic (nonsteroidal anti-inflammatory) actions are a result of its analgesic and anti-inflammatory mechanisms.
Salicylic acid works by causing the cells of the epidermis to slough off more readily, preventing pores from clogging up, and allowing room for new cell growth. Salicylic acid inhibits the oxidation of uridine-5-diphosphogl…
Plant hormone
If high concentrations of salicylic ointment are applied to a large percentage of body surface, high levels of salicylic acid can enter the blood, requiring hemodialysis to avoid further complications.