Salicylic acid

Salicylic acid
Skeletal formula of salicylic acid	Ball-and-stick model of 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 crystals
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[dead link]
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). 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 (inactive 2024-04-11). ISBN 978-0-85404-182-4.{{cite book}}: CS1 maint: DOI inactive as of April 2024 (link)
^ ^a ^b ^c Haynes WM, ed. (2011). CRC Handbook of Chemistry and Physics (92nd ed.). Boca Raton, FL: 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 Nov 2023. Retrieved 19 Nov 2023.
^ ^a ^b ^c Atherton Seidell, William F. Linke (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.
^ Wishart DS, Djombou Feunang Y, Guo AC, Lo EJ, Marcu A, Grant JR, Sajed T, Johnson D, Li C, Sayeeda Z, Assempour N, Iynkkaran I, Liu Y, Maciejewski A, Gale N, Wilson A, Chin L, Cummings R, Le D, Pon A, Knox C, Wilson M. "Salycylic acid | DrugBank Online". DrugBank. 5.0.
^ "Salicylic acid". Archived from the original on 2017-02-15. Retrieved 2014-08-17.
^ 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 Sr RJ (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 (inactive 2024-04-11). ISBN 978-0-85404-182-4.{{cite book}}: CS1 maint: DOI inactive as of April 2024 (link)

[crc-2] Haynes WM, ed. (2011). CRC Handbook of Chemistry and Physics (92nd ed.). Boca Raton, FL: 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 Nov 2023. Retrieved 19 Nov 2023.

[sioc-4] Atherton Seidell, William F. Linke (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] Wishart DS, Djombou Feunang Y, Guo AC, Lo EJ, Marcu A, Grant JR, Sajed T, Johnson D, Li C, Sayeeda Z, Assempour N, Iynkkaran I, Liu Y, Maciejewski A, Gale N, Wilson A, Chin L, Cummings R, Le D, Pon A, Knox C, Wilson M. "Salycylic acid | DrugBank Online". DrugBank. 5.0.

[NIST-6] "Salicylic acid". Archived from the original on 2017-02-15. Retrieved 2014-08-17.

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

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