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Salicylic acid

Salicylic acid
Skeletal formula of salicylic acid
Ball-and-stick model of salicylic acid
Salicylic acid
Names
Preferred IUPAC name
2-Hydroxybenzoic acid
Identifiers
69-72-7 YesY
3D model (Jmol) Interactive image
ChEBI CHEBI:16914 YesY
ChEMBL ChEMBL424 YesY
ChemSpider 331 YesY
DrugBank DB00936 YesY
ECHA InfoCard 100.000.648
EC Number 200-712-3
4306
KEGG D00097 YesY
PubChem 338
RTECS number VO0525000
UNII O414PZ4LPZ YesY
Properties
C7H6O3
Molar mass 138.12 g·mol−1
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 % in ethanol)
-72.23·10−6 cm3/mol
1.565 (20 °C)
Thermochemistry
-589.9 kJ/mol
3.025 MJ/mol
Pharmacology
A01AD05 (WHO) B01AC06 (WHO) D01AE12 (WHO) N02BA01 (WHO) S01BC08 (WHO)
Hazards
Safety data sheet MSDS
GHS pictograms The corrosion pictogram in the Globally Harmonized System of Classification and Labelling of Chemicals (GHS)The exclamation-mark pictogram in the Globally Harmonized System of Classification and Labelling of Chemicals (GHS)
GHS signal word Danger
H302, H318
P280, P305+351+338
Harmful Xn
R-phrases R22, R38, R41, R61
S-phrases S22, S26, S36, S37, S39
Eye hazard Severe irritation
Skin hazard Mild irritation
NFPA 704
Flammability code 1: Must be pre-heated before ignition can occur. Flash point over 93 °C (200 °F). E.g., canola oil Health code 2: Intense or continued but not chronic exposure could cause temporary incapacitation or possible residual injury. E.g., chloroform Reactivity code 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g., liquid nitrogen Special hazards (white): no codeNFPA 704 four-colored diamond
Flash point 157 °C (315 °F; 430 K)
closed cup
540 °C (1,004 °F; 813 K)
Lethal dose or concentration (LD, LC):
LD50 (median dose)
480 mg/kg (mice, oral)
Related compounds
Related compounds
Methyl salicylate,
Benzoic acid,
Phenol, Aspirin,
4-Hydroxybenzoic acid,
Magnesium salicylate,
Choline salicylate,
Bismuth subsalicylate,
Sulfosalicylic acid
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
YesY  (what is YesYN ?)
Infobox references

Salicylic acid (from Latin salix, willow tree) is a monohydroxybenzoic acid, a type of phenolic acid, and a beta hydroxy acid. It has the formula C7H6O3. This colorless crystalline organic acid is widely used in organic synthesis and functions as a plant hormone. 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 salicylic 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. The medicinal part of the plant is the inner bark.

It is on the WHO Model List of Essential Medicines, the most important medications needed in a basic health system.

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

As with other hydroxy acids, salicylic acid 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.


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Wikipedia

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