Salicylate

Salicylic acid

Names
Preferred IUPAC name 2-Hydroxybenzoic acid
Identifiers
CAS Number	69-72-7 Y
3D model (Jmol)	Interactive image
ChEBI	CHEBI:16914 Y
ChEMBL	ChEMBL424 Y
ChemSpider	331 Y
DrugBank	DB00936 Y
ECHA InfoCard	100.000.648
EC Number	200-712-3
IUPHAR/BPS	4306
KEGG	D00097 Y
PubChem	338
RTECS number	VO0525000
UNII	O414PZ4LPZ Y
InChI InChI=1S/C7H6O3/c8-6-4-2-1-3-5(6)7(9)10/h1-4,8H,(H,9,10) Y Key: YGSDEFSMJLZEOE-UHFFFAOYSA-N Y InChI=1/C7H6O3/c8-6-4-2-1-3-5(6)7(9)10/h1-4,8H,(H,9,10) Key: YGSDEFSMJLZEOE-UHFFFAOYAQ
SMILES c1ccc(c(c1)C(=O)O)O
Properties
Chemical formula	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
Sublimation conditions	sublimes at 76 °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
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-vis (λmax)	210 nm, 234 nm, 303 nm (4 mg % in ethanol)
Magnetic susceptibility (χ)	-72.23·10−6 cm3/mol
Refractive index (nD)	1.565 (20 °C)
Thermochemistry
Std enthalpy of formation (ΔfHo298)	-589.9 kJ/mol
Std enthalpy of combustion (ΔcHo298)	3.025 MJ/mol
Pharmacology
ATC code	A01AD05 (WHO) B01AC06 (WHO) D01AE12 (WHO) N02BA01 (WHO) S01BC08 (WHO)
Hazards
Safety data sheet	MSDS
GHS pictograms
GHS signal word	Danger
GHS hazard statements	H302, H318
GHS precautionary statements	P280, P305+351+338
EU classification (DSD)	Xn
R-phrases	R22, R38, R41, R61
S-phrases	S22, S26, S36, S37, S39
Eye hazard	Severe irritation
Skin hazard	Mild irritation
NFPA 704	1 2 0
Flash point	157 °C (315 °F; 430 K) closed cup
Autoignition temperature	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).
Y  (what is YN ?)
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.