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Record Information
Version	2.0
Creation Date	2012-08-09 09:16:14 -0600
Update Date	2015-09-13 15:15:33 -0600
Secondary Accession Numbers	ECMDB21437
Identification
Name:	Salicylic acid
Description	Salicylic acid is a colorless, crystalline organic carboxylic acid. Salicylic acid is toxic if ingested in large quantities, but in small quantities is used as a food preservative and antiseptic in toothpaste. It is also the key additive in many skin-care products for the treatment of acne, psoriasis, callouses, corns, keratosis pilaris and warts. The carboxyl group (COOH) can react with alcohols, forming several useful esters. The name derives from the latin word for the willow tree (Salix), from whose bark it can be obtained. Salicylate is a known inducer of the multiple antibiotic resistance protein MarA
Structure	MOLSDF3D-SDFPDBSMILESInChI View 3D Structure × Structure for #<Compound:0xa56d6898> Close
Synonyms:	2-Carboxyphenol 2-HBA 2-Hydroxybenzenecarboxylate 2-Hydroxybenzenecarboxylic acid 2-Hydroxybenzoate 2-Hydroxybenzoic acid Advanced Pain Relief Callus Removers Advanced Pain Relief Corn Removers Clear away Wart Remover Compound W Dr. Scholl's Callus Removers Dr. Scholl's Corn Removers Dr. Scholl's Wart Remover Kit Duofil Wart Remover Duoplant Freezone Ionil Ionil Plus K 537 K 557 O-Carboxyphenol O-Hydroxybenzoate O-Hydroxybenzoic acid Phenol-2-carboxylate Phenol-2-carboxylic acid Psoriacid-S-Stift Retarder W Rutranex SA Salicylate Salicylate collodion Salicylate soap Salicylic acid collodion Salicylic acid Soap Saligel Salonil Stri-Dex Trans-Ver-Sal
Chemical Formula:	C7H6O3
Weight:	Average: 138.1207 Monoisotopic: 138.031694058
InChI Key:	YGSDEFSMJLZEOE-UHFFFAOYSA-N
InChI:	InChI=1S/C7H6O3/c8-6-4-2-1-3-5(6)7(9)10/h1-4,8H,(H,9,10)
CAS number:	69-72-7
IUPAC Name:	2-hydroxybenzoic acid
Traditional IUPAC Name:	salicylic
SMILES:	OC(=O)C1=CC=CC=C1O
Chemical Taxonomy
Description	belongs to the class of organic compounds known as salicylic acids. These are ortho-hydroxylated benzoic acids.
Kingdom	Organic compounds
Super Class	Benzenoids
Class	Benzene and substituted derivatives
Sub Class	Benzoic acids and derivatives
Direct Parent	Salicylic acids
Alternative Parents	Benzoic acids Benzoyl derivatives 1-hydroxy-4-unsubstituted benzenoids 1-hydroxy-2-unsubstituted benzenoids Vinylogous acids Monocarboxylic acids and derivatives Carboxylic acids Organooxygen compounds Organic oxides Hydrocarbon derivatives
Substituents	Salicylic acid Benzoic acid Benzoyl 1-hydroxy-4-unsubstituted benzenoid 1-hydroxy-2-unsubstituted benzenoid Phenol Vinylogous acid Monocarboxylic acid or derivatives Carboxylic acid Carboxylic acid derivative Organic oxygen compound Organic oxide Hydrocarbon derivative Organooxygen compound Aromatic homomonocyclic compound
Molecular Framework	Aromatic homomonocyclic compounds
External Descriptors	monohydroxybenzoic acid (CHEBI:16914 )
Physical Properties
State:	Solid
Charge:	-1
Melting point:	158 °C
Experimental Properties:	Property Value Source Water Solubility: 2.24 mg/mL at 25 oC [YALKOWSKY,SH & DANNENFELSER,RM (1992)] PhysProp LogP: 2.26 [HANSCH,C ET AL. (1995)] PhysProp
Predicted Properties	Property Value Source Water Solubility 11.3 g/L ALOGPS logP 1.96 ALOGPS logP 1.98 ChemAxon logS -1.1 ALOGPS pKa (Strongest Acidic) 2.79 ChemAxon pKa (Strongest Basic) -6.3 ChemAxon Physiological Charge -1 ChemAxon Hydrogen Acceptor Count 3 ChemAxon Hydrogen Donor Count 2 ChemAxon Polar Surface Area 57.53 Ų ChemAxon Rotatable Bond Count 1 ChemAxon Refractivity 35.3 m³·mol⁻¹ ChemAxon Polarizability 12.81 ų ChemAxon Number of Rings 1 ChemAxon Bioavailability 1 ChemAxon Rule of Five Yes ChemAxon Ghose Filter Yes ChemAxon Veber's Rule Yes ChemAxon MDDR-like Rule Yes ChemAxon
Biological Properties
Cellular Locations:	Cytoplasm
Reactions:
SMPDB Pathways:	Collection of Reactions without pathways PW001891
KEGG Pathways:	Not Available
EcoCyc Pathways:	Not Available
Concentrations
	Not Available
Spectra
Spectra:	Spectrum Type Description Splash Key GC-MS GC-MS Spectrum - GC-MS (2 TMS) splash10-014i-3890000000-62eae168a9d7ab3ada6f View in MoNA GC-MS GC-MS Spectrum - EI-B (Non-derivatized) splash10-00du-9700000000-e1e2ee6b61d86c596403 View in MoNA GC-MS GC-MS Spectrum - GC-MS (Non-derivatized) splash10-014i-3890000000-62eae168a9d7ab3ada6f View in MoNA GC-MS GC-MS Spectrum - GC-EI-TOF (Non-derivatized) splash10-014i-2960000000-1b6b46cbb2b643b71448 View in MoNA Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive splash10-0079-8900000000-e8ee46d81fcc1ce3766e View in MoNA Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positive splash10-006x-8950000000-9ed3a56f2b2654ba281f View in MoNA Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive Not Available View in JSpectraViewer Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive Not Available View in JSpectraViewer LC-MS/MS LC-MS/MS Spectrum - Quattro_QQQ 10V, Negative (Annotated) splash10-059j-9600000000-54545731fceee84be340 View in MoNA LC-MS/MS LC-MS/MS Spectrum - Quattro_QQQ 25V, Negative (Annotated) splash10-00xu-9500000000-2f1c989b672669aaf083 View in MoNA LC-MS/MS LC-MS/MS Spectrum - Quattro_QQQ 40V, Negative (Annotated) splash10-0gb9-9000000000-a0049e982e8ecd7ab730 View in MoNA LC-MS/MS LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negative splash10-000i-0900000000-f1e71df6894bcc8dda74 View in MoNA LC-MS/MS LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negative splash10-0006-9200000000-f9fd317c182ec7ca90dc View in MoNA LC-MS/MS LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negative splash10-0006-9000000000-2b17aea4ee0ddd6321cf View in MoNA LC-MS/MS LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negative splash10-0006-9000000000-320b7cd879b61439cf42 View in MoNA LC-MS/MS LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negative splash10-0006-9000000000-7d1b96d60026076a7ecc View in MoNA LC-MS/MS LC-MS/MS Spectrum - ESI-TOF , Negative splash10-002b-0496100000-97708001d2a6d031beff View in MoNA LC-MS/MS LC-MS/MS Spectrum - ESI-TOF 10V, Negative splash10-002b-0496100000-97708001d2a6d031beff View in MoNA LC-MS/MS LC-MS/MS Spectrum - ESI-TOF , Negative splash10-002b-0496100000-97708001d2a6d031beff View in MoNA LC-MS/MS LC-MS/MS Spectrum - ESI-TOF 10V, Negative splash10-000i-0900000000-f88c693bac9b89416a52 View in MoNA LC-MS/MS LC-MS/MS Spectrum - LC-ESI-QFT , negative splash10-0006-9400000000-b0fb5458dfa73429b976 View in MoNA LC-MS/MS LC-MS/MS Spectrum - LC-ESI-QFT , negative splash10-0006-9400000000-b0fb5458dfa73429b976 View in MoNA LC-MS/MS LC-MS/MS Spectrum - LC-ESI-QFT , negative splash10-0006-9100000000-237ee14e8af5262c0dab View in MoNA LC-MS/MS LC-MS/MS Spectrum - LC-ESI-QFT , negative splash10-0006-9000000000-3ec5d7a9114e37b8af2a View in MoNA LC-MS/MS LC-MS/MS Spectrum - LC-ESI-QFT , negative splash10-0006-9000000000-d8fdab29114453b10280 View in MoNA LC-MS/MS LC-MS/MS Spectrum - LC-ESI-QFT , negative splash10-0006-9000000000-4a337e3639c9f42a9000 View in MoNA LC-MS/MS LC-MS/MS Spectrum - LC-ESI-QFT , negative splash10-0006-9000000000-2deb0e843e099fdcea99 View in MoNA LC-MS/MS LC-MS/MS Spectrum - LC-ESI-QFT , negative splash10-00kf-9000000000-951b374b351c5534628a View in MoNA LC-MS/MS LC-MS/MS Spectrum - LC-ESI-QFT , negative splash10-014l-9000000000-4ea52d5aa4344a40c007 View in MoNA LC-MS/MS LC-MS/MS Spectrum - LC-ESI-QQ , negative splash10-000i-0900000000-f1e71df6894bcc8dda74 View in MoNA LC-MS/MS LC-MS/MS Spectrum - LC-ESI-QQ , negative splash10-0006-9200000000-65f3f297188dc07b53be View in MoNA LC-MS/MS LC-MS/MS Spectrum - LC-ESI-QQ , negative splash10-0006-9000000000-2b17aea4ee0ddd6321cf View in MoNA LC-MS/MS LC-MS/MS Spectrum - LC-ESI-QQ , negative splash10-0006-9000000000-320b7cd879b61439cf42 View in MoNA MS Mass Spectrum (Electron Ionization) splash10-00du-9600000000-6d4a0ff2d48d814b5c54 View in MoNA 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 2D NMR [1H,1H] 2D NMR Spectrum Not Available View in JSpectraViewer 2D NMR [1H,13C] 2D NMR Spectrum Not Available View in JSpectraViewer
References
References:	Alanko K, Stubb S, Salo OP, Reitamo S: Suction blister fluid histamine in fixed drug eruption. Acta Derm Venereol. 1992;72(2):89-91. Pubmed: 1350413 Azaroual, Imbenotte M, Cartigny B, Lhermitte M, Vermeersch G: [Identification and quantification of exogenous metabolites in biological liquids with new development in NMR spectroscopy in one and two dimensions] Acta Clin Belg Suppl. 1999;1:97-100. Pubmed: 10216993 Baggott JE, Morgan SL, Ha T, Vaughn WH, Hine RJ: Inhibition of folate-dependent enzymes by non-steroidal anti-inflammatory drugs. Biochem J. 1992 Feb 15;282 ( Pt 1):197-202. Pubmed: 1540135 Benfeldt E, Serup J, Menne T: Microdialysis vs. suction blister technique for in vivo sampling of pharmacokinetics in the human dermis. Acta Derm Venereol. 1999 Sep;79(5):338-42. Pubmed: 10494706 Berkovitch M, Uziel Y, Greenberg R, Chen-Levy Z, Arcusin M, Marcus O, Pinto O, Evans S, Matias A, Lahat E: False-high blood salicylate levels in neonates with hyperbilirubinemia. Ther Drug Monit. 2000 Dec;22(6):757-61. Pubmed: 11128247 Flower R, Gryglewski R, Herbaczynska-Cedro K, Vane JR: Effects of anti-inflammatory drugs on prostaglandin biosynthesis. Nat New Biol. 1972 Jul 26;238(82):104-6. Pubmed: 4505422 Goussis OS, Theodoropoulos TJ: Dilantin and salicylate effects on hepatic thyroxine bio-availability and dialyzable thyroxine. Horm Metab Res. 1990 Jun;22(6):342-4. Pubmed: 2379917 Hazouard E, Grimbert M, Jonville-Berra AP, De Toffol MC, Legras A: [Salicylism and glaucoma: reciprocal augmentation of the toxicity of acetazolamide and acetylsalicylic acid] J Fr Ophtalmol. 1999 Feb;22(1):73-5. Pubmed: 10221197 Khan AZ, Aarons L: A note on the use of salicylate saliva concentration in clinical pharmacokinetic studies. J Pharm Pharmacol. 1989 Oct;41(10):710-1. Pubmed: 2575150 Kocoshis SA, Wong CT: Sodium salicylate and bile acid-induced colonic secretion in the rat. Ann Clin Lab Sci. 1991 May-Jun;21(3):197-204. Pubmed: 2064304 Kunkel A, Watzig H: Pharmacokinetic investigations with direct injection of plasma samples: possible savings using capillary electrophoresis (CE). Arch Pharm (Weinheim). 1999 May;332(5):175-8. Pubmed: 10366903 Ndovi TT, Choi L, Caffo B, Parsons T, Baker S, Zhao M, Rohde C, Hendrix CW: Quantitative assessment of seminal vesicle and prostate drug concentrations by use of a noninvasive method. Clin Pharmacol Ther. 2006 Aug;80(2):146-58. Pubmed: 16890576 Owen SG, Francis HW, Roberts MS: Disappearance kinetics of solutes from synovial fluid after intra-articular injection. Br J Clin Pharmacol. 1994 Oct;38(4):349-55. Pubmed: 7833225 Pirola R, Bareggi SR, De Benedittis G: Determination of acetylsalicylic acid and salicylic acid in skin and plasma by high-performance liquid chromatography. J Chromatogr B Biomed Sci Appl. 1998 Feb 13;705(2):309-15. Pubmed: 9521569 Quaranta A, Portalatini P, Camporeale M, Sallustio V: Effects of salicylates on evoked otoacoustic emissions and remote masking in humans. Audiology. 1999 May-Jun;38(3):174-9. Pubmed: 10437688 Rutner M, Fitzek J, Jahnel-Kracht H, Otto J, Krause W: [Therapy of rheumatic disease with a hydroxyethylsalicylate gel. Results of 2 clinical studies of effectiveness and bioavailability] Fortschr Med. 1995 Mar 20;113(8):111-3. Pubmed: 7759034 Schmook FP, Meingassner JG, Billich A: Comparison of human skin or epidermis models with human and animal skin in in-vitro percutaneous absorption. Int J Pharm. 2001 Mar 14;215(1-2):51-6. Pubmed: 11250091 Singh P, Anliker M, Smith GA, Zavortink D, Maibach HI: Transdermal iontophoresis and solute penetration across excised human skin. J Pharm Sci. 1995 Nov;84(11):1342-6. Pubmed: 8587053 van der Werf, M. J., Overkamp, K. M., Muilwijk, B., Coulier, L., Hankemeier, T. (2007). "Microbial metabolomics: toward a platform with full metabolome coverage." Anal Biochem 370:17-25. Pubmed: 17765195 Vane JR: Inhibition of prostaglandin synthesis as a mechanism of action for aspirin-like drugs. Nat New Biol. 1971 Jun 23;231(25):232-5. Pubmed: 5284360 Vila MM, Tubino M, de Oliveira Neto G: Determination of salicylate in blood serum by flow injection with immobilized salicylate hydroxylase. J AOAC Int. 2001 Sep-Oct;84(5):1363-9. Pubmed: 11601455 Yoshida NH, Roberts MS: Prediction of cathodal iontophoretic transport of various anions across excised skin from different vehicles using conductivity measurements. J Pharm Pharmacol. 1995 Nov;47(11):883-90. Pubmed: 8708980 Zaugg S, Zhang X, Sweedler J, Thormann W: Determination of salicylate, gentisic acid and salicyluric acid in human urine by capillary electrophoresis with laser-induced fluorescence detection. J Chromatogr B Biomed Sci Appl. 2001 Mar 5;752(1):17-31. Pubmed: 11254191
Synthesis Reference:	Yin, Yingwu; Guo, Qingbin. Preparation of salicylic acid from phenol. Faming Zhuanli Shenqing Gongkai Shuomingshu (2005), 7pp.
Material Safety Data Sheet (MSDS)	Download (PDF)
Links
External Links:	Resource Link CHEBI ID 16914 HMDB ID HMDB01895 Pubchem Compound ID 338 Kegg ID C00805 ChemSpider ID 331 Wikipedia Salicylic acid BioCyc ID Not Available Ligand Expo SAL