Salicylic acid

Salicylic acid
Names
	Preferred IUPAC name 2-Hydroxybenzoic acid
Identifiers
CAS Number	69-72-7 ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:16914 ;
ChEMBL	ChEMBL424 ;
ChemSpider	331 ;
DrugBank	DB00936;
ECHA InfoCard	100.000.648
EC Number	200-712-3;
IUPHAR/BPS	4306;
KEGG	D00097 ;
PubChem CID	338;
RTECS number	VO0525000;
UNII	O414PZ4LPZ ;
CompTox Dashboard (EPA)	DTXSID7026368 ;
	InChI InChI=1S/C7H6O3/c8-6-4-2-1-3-5(6)7(9)10/h1-4,8H,(H,9,10) Key: YGSDEFSMJLZEOE-UHFFFAOYSA-N ; InChI=1/C7H6O3/c8-6-4-2-1-3-5(6)7(9)10/h1-4,8H,(H,9,10) Key: YGSDEFSMJLZEOE-UHFFFAOYAQ;
	SMILES O=C(O)c1ccccc1O;
Properties
Chemical formula	C7H6O3
Molar mass	138.122 g/mol
Appearance	Colorless to white crystalline powder
Odor	Odorless
Density	1.443 g/cm3 (20 °C)
Melting point	158.6 °C (317.5 °F; 431.8 K)
Boiling point	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)	2.97 (25 °C); 13.82 (20 °C);
UV-vis (λmax)	210 nm, 234 nm, 303 nm (4 mg/dL in ethanol)
Magnetic susceptibility (χ)	−72.23·10−6 cm3/mol
Refractive index (nD)	1.565 (20 °C)
Dipole moment	2.65 D
Thermochemistry
Std enthalpy of; formation (ΔfH⦵298)	−589.9 kJ/mol
Std enthalpy of; combustion (ΔcH⦵298)	−3.025 MJ/mol
Pharmacology
ATC code	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:
Pictograms
Signal word	Danger
Hazard statements	H302, H318
Precautionary statements	P280, P305+P351+P338
NFPA 704 (fire diamond)	2 1 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)
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
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). verify (what is ?) Infobox references

Salicylic acid is an organic compound with the formula HOC₆H₄COOH.^[3] A colorless (or white), bitter-tasting solid, it is a precursor to and a metabolite of acetylsalicylic acid (aspirin).^[3] It is a plant hormone,^[8] and has been listed by the EPA Toxic Substances Control Act (TSCA) Chemical Substance Inventory as an experimental teratogen.^[9] The name is from Latin salix for willow tree, from which it was initially identified and derived. It is an ingredient in some anti-acne products. Salts and esters of salicylic acid are known as salicylates.^[3]

^ "Front Matter". Nomenclature of Organic Chemistry: IUPAC Recommendations and Preferred Names 2013 (Blue Book). Cambridge: The Royal Society of Chemistry. 2014. p. 64. doi:10.1039/9781849733069-FP001. ISBN 978-0-85404-182-4.
^ ^a ^b ^c Haynes WM, ed. (2011). CRC Handbook of Chemistry and Physics (92nd ed.). Boca Raton, Florida: CRC Press. p. 3.306. ISBN 1-4398-5511-0.
^ ^a ^b ^c ^d ^e ^f ^g ^h ⁱ ^j ^k ^l ^m ⁿ ^o ^p "Salicylic acid". PubChem. US National Library of Medicine. 19 November 2023. Retrieved 19 November 2023.
^ ^a ^b ^c Seidell A, Linke WF (1952). Solubilities of Inorganic and Organic Compounds: A Compilation of Solubility Data from the Periodical Literature. Supplement to the third edition containing data published during the years 1939–1949. Van Nostrand.
^ Knox C, Wilson M, Klinger CM, Franklin M, Oler E, Wilson A, et al. "Salycylic acid | DrugBank Online". DrugBank. 6.0.
^ "Salicylic acid". NIST. Archived from the original on 15 February 2017. Retrieved 17 August 2014.
^ Sigma-Aldrich Co., Salicylic acid.
^ Boullard O, Leblanc H, Besson B (2000). "Salicylic Acid". Ullmann's Encyclopedia of Industrial Chemistry. doi:10.1002/14356007.a23_477. ISBN 3-527-30673-0.
^ Lewis RJ Sr (2008). Hazardous Chemicals Desk Reference. John Wiley & Sons. p. 1217. ISBN 978-0-470-33445-4.

[iupac2013-1] "Front Matter". Nomenclature of Organic Chemistry: IUPAC Recommendations and Preferred Names 2013 (Blue Book). Cambridge: The Royal Society of Chemistry. 2014. p. 64. doi:10.1039/9781849733069-FP001. ISBN 978-0-85404-182-4.

[crc-2] Haynes WM, ed. (2011). CRC Handbook of Chemistry and Physics (92nd ed.). Boca Raton, Florida: CRC Press. p. 3.306. ISBN 1-4398-5511-0.

[pubchem-3] ^ ^a ^b ^c ^d ^e ^f ^g ^h ⁱ ^j ^k ^l ^m ⁿ ^o ^p "Salicylic acid". PubChem. US National Library of Medicine. 19 November 2023. Retrieved 19 November 2023.

[sioc-4] Seidell A, Linke WF (1952). Solubilities of Inorganic and Organic Compounds: A Compilation of Solubility Data from the Periodical Literature. Supplement to the third edition containing data published during the years 1939–1949. Van Nostrand.

[drugbank-5] Knox C, Wilson M, Klinger CM, Franklin M, Oler E, Wilson A, et al. "Salycylic acid | DrugBank Online". DrugBank. 6.0.

[NIST-6] "Salicylic acid". NIST. Archived from the original on 15 February 2017. Retrieved 17 August 2014.

[sigma-7] Sigma-Aldrich Co., Salicylic acid.

[Ullmann-8] Boullard O, Leblanc H, Besson B (2000). "Salicylic Acid". Ullmann's Encyclopedia of Industrial Chemistry. doi:10.1002/14356007.a23_477. ISBN 3-527-30673-0.

[lewis08-9] Lewis RJ Sr (2008). Hazardous Chemicals Desk Reference. John Wiley & Sons. p. 1217. ISBN 978-0-470-33445-4.

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