Salicylic Acid

2-Hydroxybenzoic acid or Salicylic Acid is a lipophilic mono-hydroxybenzoic acid, a type of phenolic acid, and a beta-hydroxy (BHA)  acids.

It has the formula C7H6O3

Salicylic Acid
2-Hydroxybenzoic acid

It is derived from the metabolism of salicin. In addition to serving as an important active metabolite of aspirin (acetylsalicylic acid), which acts in part as a prodrug to 2-Hydroxybenzoic acid, it is probably best known for its use as a key ingredient in topical anti-acne products. The salts and esters of salicylic acid are known as salicylates.

How do salicylates work on acne?

When your hair follicles (pores) get plugged with dead skin cells and oil, blackheads (open plugged pores), whiteheads (closed plugged pores), or pimples (pustules) often appear.

salicylates penetrate into the skin and work to dissolve the dead skin cells clogging your pores. It can take several weeks of use for you to see its full effect. Check with a dermatologist if you aren’t seeing results after 6 weeks.

PROPERTIES:

♦ Molecular formula: C7H6O3

♦ Molecular weight: 138.122 g·mol−1

♦ Colorless to white crystals & Odorless

Salicylic Acid
salicylates in solid states

♦ Boiling Point: 200 °C (392 °F; 473 K) decomposes; 211 °C (412 °F; 484 K) at 20 mmHg

♦ Melting Point: 158.6 °C

♦ SOLUBILITY (In Water): 1.24 g/L (0 °C)

2.48 g/L (25 °C)

4.14 g/L (40 °C)

17.41 g/L (75 °C)

77.79 g/L (100 °C)

♦ SOLUBILITY: Soluble in ether, CCl4, benzene, propanol, acetone, ethanol, oil of turpentine, toluene

♦ FLASHPOINT: 157 °C (315 °F; 430 K) closed cup

♦ Autoignition Temperature: 540 °C

♦ Std enthalpy of formation (ΔfH⦵298): −589.9 kJ/mol

♦ Std enthalpy of combustion (ΔcH⦵298): 3.025 MJ/mol

PRODUCTION:

Salicylates have the formula CH4(OH)COOH, where the OH group is ortho to the carboxyl group. It is also known as 2-hydroxybenzoic acid. It is poorly soluble in water (2 g/L at 20 °C).

Salicylate is biosynthesized from the amino acid phenylalanine. In Arabidopsis Thailand, it can be synthesized via a phenylalanine-independent pathway.

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 (390 K) – a method known as the Kolbe-Schmitt reaction. Acidification of the product with sulfuric acid gives salicylic acid:

Salicylic-Acid General Synthesis V.2.svg

Uses:

♦ This colorless crystalline organic acid is widely used in organic synthesis and functions as a plant hormone.

♦ used most commonly to help remove the outer layer of the skin. As such, it is used to treat warts, psoriasis, acne, ringworm, dandruff, and ichthyosis.

♦ It is a key ingredient in many skin care products for the treatment of seborrhoeic dermatitis, acne, psoriasis, calluses, corns, keratosis pilaris, acanthosis nigricans, ichthyosis, and warts.

♦ salicylates are used in the production of other pharmaceuticals, including 4-aminosalicylic acid, sulpiride, and landetimide (via Salethamide).

♦ It was one of the original starting materials for making acetylsalicylic acid (aspirin)

♦ Bismuth sub-salicylate, 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”

♦ Methyl salicylate used as a liniment to soothe joint and muscle pain and choline salicylate used topically to relieve the pain of mouth ulcers.

♦ salicylate is used as a food preservative, a bactericidal, and an antiseptic.

 

Action Mechanism: 

Salicylates modulates COX2 gene expression 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.

Salicylates work 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-diphosphoglucose (UDPG) competitively with nicotinamide adenosine dinucleotide (NAD) and noncompetitively with UDPG. It also competitively inhibits the transferring of the glucuronyl group of uridine-5-phosphoglucuronic acid (UDPGA) to the phenolic acceptor.

The wound-healing retardation action of salicylates is probably due mainly to its inhibitory action on mucopolysaccharide synthesis.

Side-effects of this drug:
There are some side-effects that may occur in the application of salicylic acid. But these causes at the very rear case. These are:

  • Slight burning,
  • skin redness,
  • peeling,
  • allergic reaction

If any of these effects worsen, tell your doctor or pharmacist immediately.

 

Reference:

Wikipedia, Healthline, WebMD,

 

*** NOTE: This article collected from the web. We’ve used some contents and images to make clear this article. So if there is any copyright issue here mean if you have any complaint against your copyright then please contact us. Your content and image will be removed. ***

 

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