Salicylic Acid

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Salicylic acid is a type of beta hydroxy acid that can be found naturally in nature or manufactured synthetically and used in skin treatment products. If you have ever had issues with acne, blackheads, whiteheads, or enlarged pores, then you are likely familiar with salicylic acid (SA). Even if you have not heard of it, you have probably used it, as it is the go-to solution for these types of skin problems, together with benzoyl peroxide. SA is an ingredient that is soluble in lipids, which means it can penetrate the pores of those who have oily or acne-prone skin, particularly those with “open comedones,” better known as blackheads. This makes it especially effective since it helps to keep the pores free of any substances that can cause acne.

Salicylic Acid (Wikipedia)

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.

Salicylic acid
Skeletal formula of salicylic acid
Ball-and-stick model of salicylic acid
Salicylic acid
Names
Preferred IUPAC name
2-Hydroxybenzoic acid
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
DrugBank
ECHA InfoCard 100.000.648 Edit this at Wikidata
EC Number
  • 200-712-3
KEGG
RTECS number
  • VO0525000
UNII
  • InChI=1S/C7H6O3/c8-6-4-2-1-3-5(6)7(9)10/h1-4,8H,(H,9,10) checkY
    Key: YGSDEFSMJLZEOE-UHFFFAOYSA-N checkY
  • InChI=1/C7H6O3/c8-6-4-2-1-3-5(6)7(9)10/h1-4,8H,(H,9,10)
    Key: YGSDEFSMJLZEOE-UHFFFAOYAQ
  • O=C(O)c1ccccc1O
Properties
C7H6O3
Molar mass 138.122 g/mol
Appearance Colorless to white crystals
Odor Odorless
Density 1.443 g/cm3 (20 °C)
Melting point 158.6 °C (317.5 °F; 431.8 K)
Boiling point 200 °C (392 °F; 473 K) decomposes
211 °C (412 °F; 484 K)
at 20 mmHg
Sublimes at 76 °C
  • 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
Solubility in benzene
  • 0.46 g/100 g (11.7 °C)
  • 0.775 g/100 g (25 °C)
  • 0.991 g/100 g (30.5 °C)
  • 2.38 g/100 g (49.4 °C)
  • 4.4 g/100 g (64.2 °C)
Solubility in chloroform
  • 2.22 g/100 mL (25 °C)
  • 2.31 g/100 mL (30.5 °C)
Solubility in methanol
  • 40.67 g/100 g (−3 °C)
  • 62.48 g/100 g (21 °C)
Solubility in olive oil 2.43 g/100 g (23 °C)
Solubility in acetone 39.6 g/100 g (23 °C)
log P 2.26
Vapor pressure 10.93 mPa
Acidity (pKa)
  1. 2.97 (25 °C)
  2. 13.82 (20 °C)
UV-vismax) 210 nm, 234 nm, 303 nm (4 mg/dL in ethanol)
−72.23·10−6 cm3/mol
1.565 (20 °C)
2.65 D
Thermochemistry
−589.9 kJ/mol
3.025 MJ/mol
Pharmacology
A01AD05 (WHO) B01AC06 (WHO) D01AE12 (WHO) N02BA01 (WHO) S01BC08 (WHO)
Hazards
Occupational safety and health (OHS/OSH):
Eye hazards
Severe irritation
Skin hazards
Mild irritation
GHS labelling:
GHS05: Corrosive GHS07: Exclamation mark
Danger
H302, H318
P280, P305+P351+P338
NFPA 704 (fire diamond)
2
1
0
Flash point 157 °C (315 °F; 430 K)
closed cup
540 °C (1,004 °F; 813 K)
Lethal dose or concentration (LD, LC):
480 mg/kg (mice, oral)
Safety data sheet (SDS) MSDS
Related compounds
Related compounds
Methyl salicylate,
Benzoic acid,
Phenol, Aspirin,
4-Hydroxybenzoic acid,
Magnesium salicylate,
Choline salicylate,
Bismuth subsalicylate,
Sulfosalicylic acid,
Salicylate synthase
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
checkY verify (what is checkY☒N ?)
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