Salicylic acid

Salicylic acid (frae Laitin salix, willow tree, frae the bark o which the substance uised tae be obtained) is a monohydroxybenzoic acid, a teep o phenolic acid an a beta hydroxy acid. It haes the formula C₇H₆O₃. This colourless crystalline organic acid is widely uised in organic synthesis an functions as a plant hormone. It is derived frae the metabolism o salicin. In addeetion tae bein an important active metabolite o aspirin (acetylsalicylic acid), which acts in pairt as a prodrug tae salicylic acid, it is probably best kent for its uise as a key ingredient in topical anti-acne products. The sauts an esters o salicylic acid are kent as salicylates.

Salicylic acid

Skeletal formula o salicylic acid Baw-an-stick model o salicylic acid
Names
IUPAC name 2-Hydroxybenzoic acid
Identifiers
CAS Nummer	69-72-7 Y
3D model (JSmol)	Interactive eemage
ChEBI	CHEBI:16914 Y
ChEMBL	ChEMBL424 Y
ChemSpider	331 Y
DrugBank	DB00936 Y
EC Nummer	200-712-3
IUPHAR/BPS	4306
KEGG	D00097 Y
PubChem CID	338
RTECS nummer	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	colourless tae white crystals
Odour	odorless
Density	1.443 g/cm3 (20 °C)[1]
Meltin pynt	158.6 °C (317.5 °F; 431.8 K)
Bylin pynt	200 °C (392 °F; 473 K) decomposes[2] 211 °C (412 °F; 484 K) at 20 mmHg[1]
Subleemation condeetions	sublimes at 76 °C[3]
Solubility in watter	1.24 g/L (0 °C) 2.48 g/L (25 °C) 4.14 g/L (40 °C) 17.41 g/L (75 °C)[2] 77.79 g/L (100 °C)[4]
Solubility	soluble in ether, CCl4, benzene, propanol, acetone, ethanol, ile o 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)[2][4]
Solubility in chloroform	2.22 g/100 mL (25 °C)[4] 2.31 g/100 mL (30.5 °C)[2]
Solubility in methanol	40.67 g/100 g (−3 °C) 62.48 g/100 g (21 °C)[2]
Solubility in olive ile	2.43 g/100 g (23 °C)[2]
Solubility in acetone	39.6 g/100 g (23 °C)[2]
log P	2.26
Vapour pressur	10.93 mPa[3]
Acidity (pKa)	1 = 2.97 (25 °C)[5] 2 = 13.82 (20 °C)[2]
λmax	210 nm, 234 nm, 303 nm (4 mg % in ethanol)[3]
Refractive index (nD)	1.565 (20 °C)[1]
Thermochemistry
Std enthalpy o formation ΔfHo298	-589.9 kJ/mol
Std enthalpy o combustion ΔcHo298	3.025 MJ/mol[6]
Hazards
Safety data sheet	MSDS
GHS pictograms	[7]
GHS signal wird	Danger
GHS hazard statements	H302, H318[7]
GHS precautionary statements	P280, P305+351+338[7]
Ee hazard	Severe irritation
Skin hazard	Mild irritation
NFPA 704	1 2 0
Flash pynt	157 °C (315 °F; 430 K) closed cup[3]
Autoigneetion temperatur	540 °C (1,004 °F; 813 K)[3]
Lethal dose or concentration (LD, LC):
LD50 (Median dose)	480 mg/kg (mice, oral)
Relatit compoonds
Relatit compoonds	Methyl salicylate, Benzoic acid, Phenol, Aspirin, 4-Hydroxybenzoic acid, Magnesium salicylate, Choline salicylate, Bismuth subsalicylate, Sulfosalicylic acid
Except whaur itherwise notit, data are gien for materials in thair staundart state (at 25 °C [77 °F], 100 kPa).
Y verify (whit is YN ?)
Infobox references

References

1. Haynes, William M., ed. (2011). CRC Handbook of Chemistry and Physics (92nt ed.). CRC Press. p. 3.306. ISBN 1439855110.
2. "Archived copy". Archived frae the original on 24 Mey 2014. Retrieved 30 September 2015.CS1 maint: archived copy as title (link)
3. PubChem 338
4. Seidell, Atherton; Linke, William F. (1952). [Google Books Solubilities of Inorganic and Organic Compounds] Check |url= value (help). Van Nostrand. Retrieved 29 Mey 2014.
5. Salicyclic acid. Drugbank.ca. Retrieved on 2012-06-03.
6. http://webbook.nist.gov/cgi/cbook.cgi?ID=C69727&Type=HCOMBS
7. Sigma-Aldrich Co. Retrieved on 2014-05-23.