Salicylic acid - wikipedia 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 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 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 c1ccc ( c ( c1 ) C ( = O ) O ) O Properties Chemical formula C H O Molar mass 138.12 g mol Appearance colorless to white crystals Odor odorless Density 1.443 g / cm ( 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, CCl, 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 ( pK ) 1 = 2.97 ( 25 ° C ) 2 = 13.82 ( 20 ° C ) UV - vis ( λ ) 210 nm, 234 nm, 303 nm ( 4 mg % in ethanol ) Magnetic susceptibility ( χ ) - 72.23 10 cm / mol Refractive index ( n ) 1.565 ( 20 ° C ) Thermochemistry Std enthalpy of formation ( Δ H ) - 589.9 kJ / mol Std enthalpy of combustion ( Δ H ) 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 Eye hazard Severe irritation Skin hazard Mild irritation NFPA 704 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 ) : LD ( 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 verify ( what is ? ) Infobox references Salicylic acid ( from Latin salix, willow tree ) is a lipophilic monohydroxybenzoic acid, a type of phenolic acid, and a beta hydroxy acid ( BHA ). It has the formula C H O. 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 willow tree is the inner bark. It is on the WHO Model List of Essential Medicines, the most important medications needed in a basic health system. Contents 1 Uses 1.1 Medicine 1.2 Manufacturing 1.3 Chemistry 1.4 Other uses 2 Safety 2.1 Burns 2.2 Hearing 2.3 Pregnancy 2.4 Overdose 2.5 Allergy 2.6 Sun exposure 2.7 Reye 's syndrome 3 Mechanism of action 4 Plant hormone 5 Production 6 History 7 Dietary sources 8 See also 9 References 10 External links Uses Medicine Main article : Salicylic acid ( medical use ) Cotton pads soaked in salicylic acid can be used to chemically exfoliate skin 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. Manufacturing Salicylic acid is used in the production of other pharmaceuticals, including 4 - aminosalicylic acid sandulpiride landetimide ( via Salethamide ). Salicylic acid was one of the original starting materials for making acetylsalicylic acid ( aspirin ) in 1897. Bismuth subsalicylate, a salt of bismuth and salicylic acid, is the active ingredient in stomach relief aids such as Pepto - Bismol, is the main ingredient of Kaopectate and `` displays anti-inflammatory action ( due to salicylic acid ) and also acts as an antacid and mild antibiotic ''. Other derivatives include methyl salicylate used as a liniment to soothe joint and muscle pain and choline salicylate used topically to relieve the pain of mouth ulcers. Chemistry Salicylic acid has the formula C H ( OH ) COOH, where the OH group is ortho to the carboxyl group. It is also known as 2 - hydroxybenzoic acid. It is poorly soluble in water ( 2 g / L at 20 ° C ). Aspirin ( acetylsalicylic acid or ASA ) can be prepared by the esterification of the phenolic hydroxyl group of salicylic acid with the acetyl group from acetic anhydride or acetyl chloride. Salicylic acid can also be prepared using the Kolbe - Schmitt reaction. Other Uses Salicylic acid is used as a food preservative, a bactericidal and an antiseptic. Sodium salicylate is a useful phosphor in the vacuum ultraviolet, with nearly flat quantum efficiency for wavelengths between 10 and 100 nm. It fluoresces in the blue at 420 nm. It is easily prepared on a clean surface by spraying a saturated solution of the salt in methanol followed by evaporation. Safety Burns As a topical agent and as a beta - hydroxy acid ( and unlike alpha - hydroxy acids ), salicylic acid is capable of penetrating and breaking down fats and lipids, causing moderate chemical burns of the skin at very high concentrations. It may damage the lining of pores if the solvent is alcohol, acetone or an oil. Over-the - counter limits are set at 2 % for topical preparations expected to be left on the face and 3 % for those expected to be washed off, such as acne cleansers or shampoo. 17 % and 27 % salicylic acid, which is sold for wart removal, should not be applied to the face and should not be used for acne treatment. Even for wart removal, such a solution should be applied once or twice a day -- more frequent use may lead to an increase in side - effects without an increase in efficacy. Hearing When ingested, salicylic acid has a possible ototoxic effect by inhibiting prestin. It can induce transient hearing loss in zinc - deficient rats. An injection of salicylic acid induced hearing loss, while an injection of zinc reversed the hearing loss. An injection of magnesium in the zinc - deficient rats did not reverse the induced hearing loss. Pregnancy No studies examine topical salicylic acid in pregnancy. Oral salicylic acid is not associated with an increase in malformations if used during the first trimester, but in late pregnancy has been associated with bleeding, especially intracranial bleeding. The risks of aspirin late in pregnancy are probably not relevant for a topical exposure to salicylic acid, even late in the pregnancy, because of its low systemic levels. Topical salicylic acid is common in many over-the - counter dermatological agents and the lack of adverse reports suggests a low teratogenic potential. Overdose Salicylic acid overdose can lead to salicylate intoxication, which often presents clinically in a state of metabolic acidosis with compensatory respiratory alkalosis. In patients presenting with an acute overdose, a 16 % morbidity rate and a 1 % mortality rate are observed. Allergy Some people are hypersensitive to salicylic acid and related compounds. Sun exposure The United States Food and Drug Administration ( FDA ) recommends the use of sun protection when using skincare products containing salicylic acid ( or any other BHA ) on sun - exposed skin areas. Reye 's Syndrome Data support an association between exposure to salicylic acid and Reye 's Syndrome. The National Reye 's Syndrome Foundation cautions against the use of these and other substances similar to aspirin on children and adolescents. Epidemiological research associated the development of Reye 's Syndrome and the use of aspirin for treating the symptoms of influenza - like illnesses, chicken pox, colds, etc. The U.S. Surgeon General, the FDA, the Centers for Disease Control and Prevention and the American Academy of Pediatrics recommend that aspirin and combination products containing aspirin not be given to children under 19 years of age during episodes of fever - causing illnesses. Mechanism of action Salicylic acid works through several different pathways. It produces its anti-inflammatory effects via suppressing the activity of cyclooxygenase ( COX ), an enzyme that is responsible for the production of pro-inflammatory mediators such as the prostaglandins. It does this not by direct inhibition of COX like most other non-steroidal anti-inflammatory drugs ( NSAIDs ) but instead by suppression of the expression of the enzyme through a mechanism not yet understood. Salicylic acid activates adenosine monophosphate - activated protein kinase ( AMPK ) and this action may play a role in the anticancer effects of the compound and its prodrugs aspirin and salsalate. The antidiabetic effects of salicylic acid are likely mediated by AMPK activation primarily through allosteric conformational change that increases levels of phosphorylation. Salicylic acid also uncouples oxidative phosphorylation, which leads to increased ADP : ATP and AMP : ATP ratios in the cell. As a consequence, salicylic acid may alter AMPK activity and work as an anti-diabetic by altering the energy status of the cell. AMPK knockout mice display an anti-diabetic effect, demonstrating at least one additional, yet unidentified action. Salicylic acid regulates c - Myc level at both transcriptional and post-transcription levels. Inhibition of c - Myc may be an important pathway by which aspirin exerts an anti-cancer effect, decreasing the occurrence of cancer in epithelial tissues. Plant hormone Salicylic acid ( SA ) is a phenolic phytohormone and is found in plants with roles in plant growth and development, photosynthesis, transpiration, ion uptake and transport. SA also induces specific changes in leaf anatomy and chloroplast structure. SA is involved in endogenous signaling, mediating in plant defense against pathogens. It plays a role in the resistance to pathogens by inducing the production of pathogenesis - related proteins. It is involved in the systemic acquired resistance ( SAR ) in which a pathogenic attack on one part of the plant induces resistance in other parts. The signal can also move to nearby plants by salicylic acid being converted to the volatile ester, methyl salicylate. Production Salicylic acid is biosynthesized from the amino acid phenylalanine. In Arabidopsis thaliana it can be synthesized via a phenylalanine - independent pathway. Sodium salicylate is commercially prepared by treating sodium phenolate ( the sodium salt of phenol ) with carbon dioxide at high pressure ( 100 atm ) and high temperature ( 390 K ) -- a method known as the Kolbe - Schmitt reaction. Acidification of the product with sulfuric acid gives salicylic acid : It can also be prepared by the hydrolysis of aspirin ( acetylsalicylic acid ) or methyl salicylate ( oil of wintergreen ) with a strong acid or base. History Main article : History of aspirin White willow ( Salix alba ) is a natural source of salicylic acid Hippocrates, Galen, Pliny the Elder and others knew that willow bark could ease pain and reduce fevers. It was used in Europe and China to treat these conditions. This remedy is mentioned in texts from ancient Egypt, Sumer and Assyria. The Cherokee and other Native Americans used an infusion of the bark for fever and other medicinal purposes. In 2014, archaeologists identified traces of salicylic acid on 7th century pottery fragments found in east central Colorado. The Reverend Edward Stone, a vicar from Chipping Norton, Oxfordshire, England, noted in 1763 that the bark of the willow was effective in reducing a fever. The active extract of the bark, called salicin, after the Latin name for the white willow ( Salix alba ), was isolated and named by the German chemist Johann Andreas Buchner in 1828. A larger amount of the substance was isolated in 1829 by Henri Leroux, a French pharmacist. Raffaele Piria, an Italian chemist, was able to convert the substance into a sugar and a second component, which on oxidation becomes salicylic acid. Salicylic acid was also isolated from the herb meadowsweet ( Filipendula ulmaria, formerly classified as Spiraea ulmaria ) by German researchers in 1839. While their extract was somewhat effective, it also caused digestive problems such as gastric irritation, bleeding, diarrhea and even death when consumed in high doses. Dietary sources Salicylic acid occurs in plants as free salicylic acid and its carboxylated esters and phenolic glycosides. Several studies suggest that humans metabolize salicylic acid in measurable quantities from these plants ; one study found that vegetarians not taking aspirin had urinary levels of salicylic acid roughly 5 % those of patients taking 75 mg of aspirin per day, while the non-vegetarians had levels roughly one - third that of vegetarians. Dietary sources of salicylic acid and their interaction with drugs such as aspirin have not been well studied. Ongoing clinical studies of patients with aspirin - induced asthma have shown some benefits of a diet low in salicylic acid. Dietary salicylic acid may be partially responsible for the health benefits of a plant - based diet. Studies on the salicylic content of foods are sparse and have produced distinctly different results, creating controversy. Possible causes for the discrepancies include uncontrolled and often unreported factors such as cultivation area, crop species, and harvest methods, as well as inherent issues with the studies such as poor extraction and measurement procedures and limited or low - accuracy equipment. A recent study using best practice measurement methodology significantly reduced intra-sample measurement variability but has not yet been replicated or extended. Some results have been consistently reported. Meat, poultry, fish, eggs, oils, dairy products, sugar, cereals, and flour all have little to no salicylates. Measurable levels of salicylic acid have been found in fruits, vegetables, herbs, spices, nuts, and teas. See also Methyl salicylate Trolamine salicylate Salsalate References Jump up ^ Nomenclature of Organic Chemistry : IUPAC Recommendations and Preferred Names 2013 ( Blue Book ). Cambridge : The Royal Society of Chemistry. 2014. p. 64. ISBN 978 - 0 - 85404 - 182 - 4. doi : 10.1039 / 9781849733069 - FP001. ^ Jump up to : Haynes, William M., ed. ( 2011 ). CRC Handbook of Chemistry and Physics ( 92nd ed. ). Boca Raton, FL : CRC Press. p. 3.306. ISBN 1439855110. ^ Jump up to : `` Salicylic acid ''. ^ Jump up to : CID 338 from PubChem ^ Jump up to : Atherton Seidell ; William F. Linke ( 1952 ). Solubilities of Inorganic and Organic Compounds : A Compilation of Solubility Data from the Periodical Literature. Supplement. Van Nostrand. Jump up ^ Salicyclic acid. Drugbank.ca. Retrieved on 2012 - 06 - 03. Jump up ^ `` Salicylic acid ''. ^ Jump up to : Sigma - Aldrich Co., Salicylic acid. Retrieved on 2014 - 05 - 23. Jump up ^ `` 19th WHO Model List of Essential Medicines ( April 2015 ) '' ( PDF ). WHO. April 2015. Retrieved May 10, 2015. ^ Jump up to : `` Salicylic acid topical medical facts from Drugs.com ''. www.drugs.com. Retrieved 15 January 2017. Jump up ^ WHO Model Formulary 2008 ( PDF ). World Health Organization. 2009. p. 310. ISBN 9789241547659. Retrieved 8 January 2017. Jump up ^ Madan RK ; Levitt J ( April 2014 ). `` A review of toxicity from topical salicylic acid preparations ''. J Am Acad Dermatol. 70 ( 4 ) : 788 -- 92. PMID 24472429. doi : 10.1016 / j. jaad. 2013.12. 005. Jump up ^ Schrör, Karsten ( 2016 ). Acetylsalicylic Acid ( 2 ed. ). John Wiley & Sons. p. 9 - 10. ISBN 9783527685028. Jump up ^ `` Bismuth subsalicylate ''. PubChem. United States National Institutes of Health. Retrieved 24 January 2014. Jump up ^ `` Salicilyc acid ''. inchem.org. Retrieved 2008 - 10 - 13. Jump up ^ `` Definition of Salicylic acid ''. MedicineNet.com. Jump up ^ Samson, James ( 1976 ). Techniques of Vacuum Ultraviolet Spectroscopy. Wiley,. Jump up ^ salicylic acid 17 % Topical Liquid. Kaiser Permanente Drug Encyclopedia. Accessed 28 Sept 2011. Jump up ^ Wecker, H. ; Laubert, A. ( 2004 ). `` Reversible hearing loss in acute salicylate intoxication ''. HNO ( in German ). 52 ( 4 ) : 347 -- 51. PMID 15143764. doi : 10.1007 / s00106 - 004 - 1065 - 5. Jump up ^ Rumack, CM ; Guggenheim, MA ; Rumack, BH ; Peterson, RG ; Johnson, ML ; Braithwaite, WR ( 1981 ). `` Neonatal intracranial hemorrhage and maternal use of aspirin ''. Obstetrics and gynecology. 58 ( 5 Suppl ) : 52S -- 6S. ISSN 0029 - 7844. PMID 7312229. Jump up ^ Acne and Pregnancy. Fetal-exposure.org. Retrieved on 2012 - 06 - 03. Jump up ^ Salicylate Toxicity at eMedicine Jump up ^ `` Beta Hydroxy Acids in Cosmetics ''. Archived from the original on 2007 - 12 - 21. Retrieved 2007 - 11 - 23. Jump up ^ `` Aspirin / Salicylates and Reye 's Syndrome ''. reyessyndrome.org. Retrieved 2009 - 05 - 22. Jump up ^ `` Anti-Inflammatory Activity of Aspirin -- It 's All About Salicylic Acid ''. American Chemical Society. Jump up ^ Hawley, S.A. ; Fullerton, M.D. ; Ross, F.A. ; Schertzer, J.D. ; Chevtzoff, C. ; Walker, K.J. ; Peggie, M.W. ; Zibrova, D. ; et al. ( 2012 ). `` The Ancient Drug Salicylate Directly Activates AMP - Activated Protein Kinase ''. Science. 336 ( 6083 ) : 918 -- 22. PMC 3399766. PMID 22517326. doi : 10.1126 / science. 1215327. Jump up ^ Raffensperger, Lisa ( 2012 - 04 - 19 ). `` Clues to aspirin 's anti-cancer effects revealed ''. New Scientist Jump up ^ Ai, G ; Dachineni, R ; Muley, P ; Tummala, H ; Bhat, GJ ( 2016 ). `` Aspirin and salicylic acid decrease c - Myc expression in cancer cells : a potential role in chemoprevention ''. Tumour Biol. 37 : 1727 -- 38. PMID 26314861. doi : 10.1007 / s13277 - 015 - 3959 - 0. Jump up ^ Hayat, S. & Ahmad, A. ( 2007 ). Salicylic acid -- A Plant Hormone. Springer. ISBN 1 - 4020 - 5183 - 2. Jump up ^ Van Huijsduijnen, R.A.M.H. ; Alblas, S.W. ; De Rijk, R.H. ; Bol, J.F. ( 1986 ). `` Induction by Salicylic Acid of Pathogenesis - related Proteins and Resistance to Alfalfa Mosaic Virus Infection in Various Plant Species ''. Journal of General Virology. 67 ( 10 ) : 2135 -- 2143. doi : 10.1099 / 0022 - 1317 - 67 - 10 - 2135. Jump up ^ Taiz, L. and Zeiger, Eduardo ( 2002 ) Plant Physiology, 3rd Edition, Sinauer Associates, p. 306, ISBN 0878938230. Jump up ^ `` Hydrolysis of ASA to SA ''. Retrieved July 31, 2007. Jump up ^ Norn, S. ; Permin, H. ; Kruse, P.R. ; Kruse, E. ( 2009 ). `` ( From willow bark to acetylsalicylic acid ) ''. Dansk Medicinhistorisk Årbog ( in Danish ). 37 : 79 -- 98. PMID 20509453. Jump up ^ `` Willow bark ''. University of Maryland Medical Center. University of Maryland. Retrieved 19 December 2011. Jump up ^ Seaman, David R. ( 19 July 2011 ). `` White Willow Bark : The Oldest New Natural Anti-Inflammatory / Analgesic Agent ''. The American Chiropractor. Retrieved 19 December 2011. Jump up ^ Hemel, Paul B. and Chiltoskey, Mary U. Cherokee Plants and Their Uses -- A 400 Year History, Sylva, NC : Herald Publishing Co. ( 1975 ) ; cited in Dan Moerman, A Database of Foods, Drugs, Dyes and Fibers of Native American Peoples, Derived from Plants. ( 1 ) A search of this database for `` salix AND medicine '' finds 63 entries. Jump up ^ `` 1,300 - Year - Old Pottery Found in Colorado Contains Ancient ' Natural Aspirin ' ''. Jump up ^ Stone, Edmund ( 1763 ). `` An Account of the Success of the Bark of the Willow in the Cure of Agues ''. Philosophical Transactions of the Royal Society of London. 53 : 195 -- 200. doi : 10.1098 / rstl. 1763.0033. Jump up ^ Buchner, A. ( 1828 ). `` Ueber das Rigatellische Fiebermittel und über eine in der Weidenrinde entdeckte alcaloidische Substanz ( On Rigatelli 's antipyretic ( i.e., anti-fever drug ) and on an alkaloid substance discovered in willow bark ) ''. Repertorium für die pharmacie... Bei J.L. Schrag. pp. 405 --. Noch ist es mir aber nicht geglückt, den bittern Bestandtheil der Weide, den ich Salicin nennen will, ganz frei von allem Färbestoff darzustellen. '' ( I have still not succeeded in preparing the bitter component of willow, which I will name salicin, completely free from colored matter Jump up ^ See : Leroux, H. ( 1830 ). `` Mémoire relatif à l'analyse de l'écorce de saule et à la découverte d'un principe immédiat propre à remplacer le sulfate de quinine '' ) ( Memoir concerning the analysis of willow bark and the discovery of a substance immediately likely to replace quinine sulfate ) ``. Journal de chimie médicale, de pharmacie et de toxicologie. Chez Béchet jeune. 6 : 340 -- 342. A report on Leroux 's presentation to the French Academy of Sciences also appeared in : Mémoires de l'Académie des sciences de l'Institut de France. Institut de France. 1838. pp. 20 --. Jump up ^ Piria ( 1838 ) `` Sur de neuveaux produits extraits de la salicine '' ( On new products extracted from salicine ), Comptes rendus... 6 : 620 -- 624. On page 622, Piria mentions `` Hydrure de salicyle '' ( hydrogen salicylate, i.e., salicylic acid ). Jump up ^ Jeffreys, Diarmuid ( 2005 ). Aspirin : the remarkable story of a wonder drug. New York : Bloomsbury. pp. 38 -- 40. ISBN 978 - 1 - 58234 - 600 - 7. Jump up ^ Löwig, C. ; Weidmann, S. ( 1839 ). `` III. Untersuchungen mit dem destillierten Wasser der Blüthen von Spiraea Ulmaria ( III. Investigations of the water distilled from the blossoms of Spiraea ulmaria ). Löwig and Weidman called salicylic acid Spiräasaure ( spiraea acid ) ''. Annalen der Physik und Chemie ; Beiträge zur organischen Chemie ( Contributions to organic chemistry ). J.A. Barth. ( 46 ) : 57 -- 83. ^ Jump up to : Malakar, Sreepurna ; Gibson, Peter R. ; Barrett, Jacqueline S. ; Muir, Jane G. ( 1 April 2017 ). `` Naturally occurring dietary salicylates : A closer look at common Australian foods ''. Journal of Food Composition and Analysis. 57 : 31 -- 39. doi : 10.1016 / j. jfca. 2016.12. 008. Jump up ^ Lawrence, JR ; Peter, R ; Baxter, GJ ; Robson, J ; Graham, AB ; Paterson, JR ( 28 May 2017 ). `` Urinary excretion of salicyluric and salicylic acids by non-vegetarians, vegetarians, and patients taking low dose aspirin ''. Journal of Clinical Pathology. 56 ( 9 ) : 651 -- 653. ISSN 0021 - 9746. Jump up ^ Race, Sharla. `` Salicylate in Food ''. The Salicylate Handbook : Your Guide to Understanding Salicylate Sensitivity. Sharla Race. ISBN 9781907119040. Jump up ^ `` Food Guide ''. Salicylate Sensitivity. Jump up ^ Sommer, Doron D. ; Rotenberg, Brian W. ; Sowerby, Leigh J. ; Lee, John M. ; Janjua, Arif ; Witterick, Ian J. ; Monteiro, Eric ; Gupta, Michael K. ; Au, Michael ; Nayan, Smriti ( April 2016 ). `` A novel treatment adjunct for aspirin exacerbated respiratory disease : the low - salicylate diet : a multicenter randomized control crossover trial ''. International Forum of Allergy & Rhinology. 6 ( 4 ) : 385 -- 391. doi : 10.1002 / alr. 21678. Jump up ^ Greger, Michael. `` Inflammation, Diet, and `` Vitamin S '' NutritionFacts.org ``. NutritionFacts.org. Jump up ^ `` Salicylates in foods '' ( PDF ). Retrieved 2014 - 05 - 09. External links Wikimedia Commons has media related to Salicylic acid. Salicylic acid MS Spectrum Safety MSDS data International Chemical Safety Cards CDC / NIOSH ( 2 ) English Translation of Hermann Kolbe 's seminal 1860 German article in Annalen der Chemie und Pharmacie. English title : ' On the syntheses of salicylic acid ' ; German title `` Ueber Synthese der Salicylsäure ''. Acne - treating agents ( D10 ) Antibacterial Azelaic acid Benzoyl peroxide 8 - Hydroxyquinoline Blue light therapy Tea tree oil Keratolytic Glycolic acid Salicylic acid Sulfur Benzoyl peroxide Anti-inflammatory Nicotinamide Ibuprofen Aspirin Red light therapy Antibiotics Clindamycin Dapsone Erythromycin Sulfacetamide Tetracyclines ( Lymecycline Minocycline Doxycycline ) Hormonal Antiandrogens Bicalutamide Cyproterone acetate Drospirenone Flutamide Spironolactone ) Estrogens Estradiol Ethinylestradiol Retinoids Adapalene Isotretinoin Motretinide Tazarotene Tretinoin Other Benzamycin Epristeride Mesulfen Pelretin Stridex Tioxolone Combinations Adapalene / benzoyl peroxide Benzoyl peroxide / clindamycin Clindamycin / tretinoin Erythromycin / isotretinoin Sulfacetamide / sulfur WHO - EM Withdrawn from market Clinical trials : Phase III Never to phase III Ancient anaesthesia Plants / animals Aconitum ( aconite ) Atropa belladonna ( belladonna ) Cannabis medical use Castoreum Coca Conium ( hemlock ) Datura innoxia ( thorn - apple ) Datura metel ( devil 's trumpet ) Hyoscyamus niger ( henbane ) Lactucarium Mandragora officinarum ( mandrake ) Opium Saussurea ( saw - wort ) Willow People Abulcasis Avenzoar Avicenna Celsus Dioscorides Galen Hippocrates Rhazes Sabuncuoğlu Sushrutha Theophrastus Zhang Compounds Aconitine Atropine Cocaine Coniine Hyoscine Δ9 - THC Hyoscyamine Morphine Salicylate Antifungals ( D01 and J02 ) Wall / membrane Ergosterol inhibitors Azoles ( lanosterol 14α - demethylase inhibitors ) Imidazoles Topical : bifonazole butoconazole chlormidazole clotrimazole croconazole eberconazole econazole fenticonazole flutrimazole isoconazole ketoconazole luliconazole miconazole neticonazole omoconazole oxiconazole sertaconazole sulconazole tioconazole Systemic : ketoconazole Triazoles Topical : efinaconazole fluconazole fosfluconazole terconazole Systemic : fluconazole hexaconazole isavuconazole itraconazole posaconazole voriconazole Unknown : albaconazole ravuconazole Thiazoles Topical : abafungin Polyene antimycotics ( ergosterol binding ) Topical : hamycin natamycin nystatin Systemic : amphotericin B, hamycin Squalene monooxygenase inhibitors Allylamines Topical : naftifine terbinafine Systemic : terbinafine Benzylamines Topical : butenafine Others Topical : amorolfine β - glucan synthase inhibitors echinocandins ( anidulafungin biafungin caspofungin cilofungin micafungin ) Intracellular Pyrimidine analogues / thymidylate synthase inhibitors flucytosine Mitotic inhibitors griseofulvin Aminoacyl tRNA synthetase inhibitors tavaborole Others bromochlorosalicylanilide chlorophetanol chlorphenesin ciclopirox crystal violet dimazole ethylparaben haloprogin polynoxylin potassium iodide salicylic acid selenium disulfide sodium thiosulfate sulbentine taurolidine ticlatone tolciclate tolnaftate tribromometacresol undecylenic acid Whitfield 's ointment citronella oil lemon grass lemon myrtle orange oil patchouli tea tree oil PCP : atovaquone dapsone pentamidine WHO - EM Withdrawn from market Clinical trials : Phase III Never to phase III Nonsteroidal anti-inflammatory drugs ( NSAIDs ) ( primarily M01A and M02A, also N02BA ) Pyrazolones / Pyrazolidines Aminophenazone Ampyrone Azapropazone Clofezone Difenamizole Famprofazone Feprazone Kebuzone Metamizole Mofebutazone Morazone Nifenazone Oxyphenbutazone Phenazone Phenylbutazone Propyphenazone Sulfinpyrazone Suxibuzone Salicylates Aspirin ( acetylsalicylic acid ) Aloxiprin Benorylate Carbasalate calcium Diflunisal Dipyrocetyl Ethenzamide Guacetisal Magnesium salicylate Methyl salicylate Salsalate Salicin Salicylamide Salicylic acid ( salicylate ) Sodium salicylate Acetic acid derivatives and related substances Aceclofenac Acemetacin Alclofenac Amfenac Bendazac Bromfenac Bumadizone Bufexamac Diclofenac Difenpiramide Etodolac Felbinac Fenclozic acid Fentiazac Indomethacin Indomethacin farnesil Isoxepac Ketorolac Lonazolac Oxametacin Prodolic acid Proglumetacin Sulindac Tiopinac Tolmetin Zomepirac Oxicams Ampiroxicam Droxicam Isoxicam Lornoxicam Meloxicam Piroxicam Tenoxicam Propionic acid derivatives ( profens ) Alminoprofen Benoxaprofen Carprofen Dexibuprofen Dexketoprofen Fenbufen Fenoprofen Flunoxaprofen Flurbiprofen Ibuprofen Ibuproxam Indoprofen Ketoprofen Loxoprofen Miroprofen Naproxen Oxaprozin Pirprofen Suprofen Tarenflurbil Tepoxalin Tiaprofenic acid Vedaprofen COX - inhibiting nitric oxide donator : Naproxcinod N - Arylanthranilic acids ( fenamates ) Azapropazone Clonixin Etofenamate Flufenamic acid Flunixin Meclofenamic acid Mefenamic acid Morniflumate Niflumic acid Tolfenamic acid Flutiazin Coxibs Apricoxib Celecoxib Cimicoxib Deracoxib Etoricoxib Firocoxib Lumiracoxib Mavacoxib Parecoxib Robenacoxib Rofecoxib Valdecoxib Other Aminopropionitrile Benzydamine Chondroitin sulfate Diacerein Fluproquazone Glucosamine Glycosaminoglycan Hyperforin Nabumetone Nimesulide Oxaceprol Proquazone Superoxide dismutase / Orgotein Tenidap Items listed in bold indicate initially developed compounds of specific groups. WHO - EM Withdrawn drugs. Veterinary use medications. Analgesics ( N02A, N02B ) Opioids Opiates / opium Codeine ( + paracetamol, + aspirin ) Morphine ( + naltrexone ) Opium Laudanum Paregoric Semisynthetic Acetyldihydrocodeine Benzylmorphine Buprenorphine ( + naloxone ) Desomorphine Diamorphine ( heroin ) Dihydrocodeine ( + paracetamol ) Dihydromorphine Ethylmorphine Hydrocodone ( + paracetamol, + ibuprofen, + aspirin ) Hydromorphinol Hydromorphone Nicocodeine Nicodicodeine Nicomorphine Oxycodone ( + paracetamol, + aspirin, + ibuprofen, + naloxone, + naltrexone ) Oxymorphone Thebacon Synthetic Alfentanil Alphaprodine Anileridine Butorphanol Carfentanil Dextromoramide Dextropropoxyphene Dezocine Fentanyl ( + fluanisone ) Ketobemidone Levorphanol Lofentanil Meptazinol Methadone Nalbuphine NFEPP Pentazocine Pethidine ( meperidine ) Phenadoxone Phenazocine Piminodine Piritramide Propiram Remifentanil Sufentanil Tapentadol Tilidine Tramadol Paracetamol - type Acetanilide Bucetin Butacetin Paracetamol ( acetaminophen ) Parapropamol Phenacetin Propacetamol NSAIDs Propionates Fenoprofen Flurbiprofen Ibuprofen Ketoprofen Naproxen Oxaprozin Oxicams Meloxicam Piroxicam Acetates Diclofenac Indometacin Ketorolac Nabumetone Sulindac Tolmetin COX - 2 inhibitors Celecoxib Etoricoxib Lumiracoxib Parecoxib Rofecoxib Valdecoxib Fenamates Meclofenamic acid Mefenamic acid Salicylates Aspirin ( acetylsalicylic acid ) ( + paracetamol / caffeine ) Benorylate Diflunisal Ethenzamide Magnesium salicylate Salicin Salicylamide Salsalate Wintergreen ( methyl salicylate ) Pyrazolones Aminophenazone Ampyrone Metamizole ( dipyrone ) Nifenazone Phenazone Propyphenazone ( + paracetamol / caffeine ) Others Glafenine Cannabinoids Cannabidiol Cannabis Nabilone Nabiximols Tetrahydrocannabinol ( dronabinol ) Ion channel modulators Calcium blockers Gabapentin Gabapentin enacarbil Pregabalin Ziconotide Sodium blockers Carbamazepine Lacosamide Local anesthetics ( e.g., cocaine, lidocaine ) Mexiletine Nefopam Tricyclic antidepressants ( e.g., amitriptyline ) Na 1.7 / 1.8 - selective : DSP - 2230 Funapide PF - 05089771 Raxatrigine Potassium openers Flupirtine Myorelaxants Carisoprodol Chlorzoxazone Cyclobenzaprine Mephenoxalone Methocarbamol Orphenadrine Others Analgesic adjuvant Analgecine Camphor Capsaicin Clonidine Ketamine Menthol Methoxyflurane Nefopam Proglumide Tricyclic antidepressants ( e.g., amitriptyline ) WHO - EM Withdrawn from market Clinical trials : Phase III Never to phase III Plant hormones Abscisic acid Auxins Cytokinins Ethylene Gibberellins Brassinosteroids Florigen Jasmonates Karrikins Plant peptide hormones Polyamine Salicylic acid Strigolactones Salicylates Salicylic acid Aspirin Aloxiprin Methyl salicylate Magnesium salicylate Ethyl salicylate Bismuth subsalicylate Sodium salicylate Salicylamide Salicin Benorilate Salsalate Ethenzamide Diflunisal Trolamine salicylate Homosalate Salicylmethylecgonine Octyl salicylate Aluminon Benzyl salicylate Copper aspirinate Potassium salicylate Phenolic acids ( C6 - C1 ) and their glycosides Monohydroxybenzoic acids 3 - Hydroxybenzoic acid 4 - Hydroxybenzoic acid Salicylic acid ( 2 - Hydroxybenzoic acid ) Glycosides p - Hydroxybenzoic acid glucoside Acetylated Methylparaben ( Methyl p - hydroxybenzoic acid ) Dihydroxybenzoic acids 2, 3 - Dihydroxybenzoic acid ( Hypogallic acid ) 2, 4 - Dihydroxybenzoic acid 2, 5 - Dihydroxybenzoic acid ( Gentisic acid ) 2, 6 - Dihydroxybenzoic acid 3, 4 - Dihydroxybenzoic acid ( Protocatechuic acid ) 3, 5 - Dihydroxybenzoic acid Acetylated Ethyl protocatechuate Orsellinic acid Trihydroxybenzoic acids Gallic acid Phloroglucinol carboxylic acid Glycosides Bergenin Norbergenin Theogallin Chebulic acid Acetylated Ethyl gallate Eudesmic acid Methyl gallate Syringic acid Prostanoid signaling modulators Receptor ( ligands ) DP ( D ) DP Agonists : Prostaglandin D Treprostinil Antagonists : Asapiprant Laropiprant Vidupiprant DP Agonists : Indometacin Prostaglandin D Antagonists : ADC - 3680 AZD - 1981 Bay U3405 Fevipiprant MK - 1029 MK - 7246 QAV - 680 Ramatroban Setipiprant Timapiprant TM30089 Vidupiprant EP ( E ) EP Agonists : Beraprost Enprostil Iloprost ( ciloprost ) Latanoprost Lubiprostone Misoprostol Prostaglandin E ( alprostadil ) Prostaglandin E ( dinoprostone ) Sulprostone Antagonists : AH - 6809 ONO - 8130 SC - 19220 SC - 51089 SC - 51322 EP Agonists : Butaprost Misoprostol Prostaglandin E ( alprostadil ) Prostaglandin E ( dinoprostone ) Treprostinil Antagonists : AH - 6809 PF - 04418948 TG 4 - 155 EP Agonists : Beraprost Carbacyclin Cicaprost Enprostil Iloprost ( ciloprost ) Isocarbacyclin Latanoprost Misoprostol Prostaglandin D Prostaglandin E ( alprostadil ) Prostaglandin E ( dinoprostone ) Remiprostol Sulprostone Antagonists : L - 798106 EP Agonists : Lubiprostone Misoprostol Prostaglandin E ( alprostadil ) Prostaglandin E ( dinoprostone ) TCS - 2510 Antagonists : Grapiprant GW - 627368 L - 161982 ONO - AE3 - 208 Unsorted Agonists : 16, 16 - Dimethyl Prostaglandin E Aganepag Carboprost Evatanepag Gemeprost Nocloprost Omidenepag Prostaglandin F ( dinoprost ) Simenepag Taprenepag FP ( F ) Agonists : Alfaprostol Bimatoprost Carboprost Cloprostenol Enprostil Fluprostenol Latanoprost Prostaglandin D Prostaglandin F ( dinoprost ) Sulotroban Tafluprost Travoprost Unoprostone IP ( I ) Agonists : ACT - 333679 AFP - 07 Beraprost BMY - 45778 Carbacyclin Cicaprost Iloprost ( ciloprost ) Isocarbacyclin MRE - 269 NS - 304 Prostacyclin ( prostaglandin I, epoprostenol ) Prostaglandin E ( alprostadil ) Ralinepag Selexipag Taprostene TRA - 418 Treprostinil Antagonists : RO1138452 TP ( TX ) Agonists : Carbocyclic thromboxane A I - BOP Thromboxane A U-46619 Vapiprost Antagonists : 12 - HETE 13 - APA AA - 2414 Argatroban Bay U3405 BMS - 180,291 Daltroban Domitroban EP - 045 GR - 32191 ICI - 185282 ICI - 192605 Ifetroban Imitrodast L - 655240 L - 670596 Linotroban Mipitroban ONO - 3708 ONO - 11120 Picotamide Pinane thromboxane A Ramatroban Ridogrel S - 145 Samixogrel Seratrodast SQ - 28,668 SQ - 29,548 Sulotroban Terbogrel Terutroban TRA - 418 Unsorted Arbaprostil Ataprost Ciprostene Clinprost Cobiprostone Delprostenate Deprostil Dimoxaprost Doxaprost Ecraprost Eganoprost Enisoprost Eptaloprost Esuberaprost Etiproston Fenprostalene Flunoprost Froxiprost Lanproston Limaprost Luprostiol Meteneprost Mexiprostil Naxaprostene Nileprost Nocloprost Ornoprostil Oxoprostol Penprostene Pimilprost Piriprost Posaraprost Prostalene Rioprostil Rivenprost Rosaprostol Spiriprostil Tiaprost Tilsuprost Tiprostanide Trimoprostil Viprostol Enzyme ( inhibitors ) COX ( PTGS ) Salicylic acids : Aloxiprin Aspirin ( acetylsalicylic acid ) Benorilate ( benorylate ) Carbasalate calcium Diflusinal Dipyrocetyl Ethenzamide Guacetisal Magnesium salicylate Mesalazine ( 5 - aminosalicylic acid ) Methyl salicylate Salacetamide Salicin Salicylamide Salicylate ( salicylic acid ) Salsalate Sodium salicylate Triflusal ; Acetic acids : Aceclofenac Acemetacin Aclofenac Amfenac Alclofenac Bendazac Bromfenac Bufexamac Bumadizone Cinmetacin Clometacin Diclofenac Difenpiramide Etodolac Felbinac Fenclofenac Fentiazac Glucametacin Indometacin ( indomethacin ) Indometacin farnesil Ketorolac Lonazolac Mofezolac Nabumetone Oxametacin Oxindanac Proglumetacin Sulindac Sulindac sulfide Tolmetin Zidometacin Zomepirac ; Propionic acids : Alminoprofen Benoxaprofen Bucloxic acid ( blucloxate ) Butibufen Carprofen Dexibuprofen Dexindoprofen Dexketoprofen Fenbufen Fenoprofen Flunoxaprofen Flurbiprofen Ibuprofen Ibuproxam Indoprofen Ketoprofen Loxoprofen Miroprofen Naproxen Naproxcinod Oxaprozin Pirprofen Pranoprofen Suprofen Tarenflurbil Tepoxalin Tiaprofenic acid ( tiaprofenate ) Vedaprofen ; Anthranilic acids ( fenamic acids ) : Etofenamic acid ( etofenamate ) Floctafenic acid ( floctafenate ) Flufenamic acid ( flufenamate ) Meclofenamic acid ( meclofenamate ) Mefenamic acid ( mefenamate ) Morniflumic acid ( morniflumate ) Niflumic acid ( niflumate ) Talinflumic acid ( talinflumate ) Tolfenamic acid ( tolfenamate ) ; Pyrazolones : Azapropazone Dipyrone Isopyrin Oxyphenbutazone Phenylbutazone ; Enolic acids ( oxicams ) : Ampiroxicam Droxicam Enolicam Isoxicam Lornoxicam Meloxicam Piroxicam Tenoxicam ; 4 - Aminoquinolines : Antrafenine Floctafenine Glafenine ; Quinazolines : Fluproquazone Proquazone ; Aminonicotinic acids : Clonixeril Clonixin Flunixin ; Sulfonanilides : Flosulide Nimesulide ; Aminophenols ( anilines ) : Acetanilide AM - 404 ( N - arachidonoylaminophenol ) Bucetin Paracetamol ( acetaminophen ) Parapropamol Phenacetin Propacetamol ; Selective COX - 2 inhibitors ( coxibs ) : Apricoxib Celecoxib Cimicoxib Deracoxib Etoricoxib Firocoxib Lumiracoxib Mavacoxib Parecoxib Polmacoxib Robenacoxib Rofecoxib Tilmacoxib Valdecoxib ; Others / unsorted : Anitrazafen Clobuzarit Curcumin DuP - 697 FK - 3311 Flumizole FR - 122047 Glimepiride Hyperforin Itazigrel L - 655240 L - 670596 Licofelone Menatetrenone ( vitamin K ) NCX - 466 NCX - 4040 NS - 398 Pamicogrel Resveratrol Romazarit Rosmarinic acid Rutecarpine Satigrel SC - 236 SC - 560 SC - 58125 Tenidap Tiflamizole Timegadine Trifenagrel Tropesin PGD S Retinoids Selenium ( selenium tetrachloride, sodium selenite, selenium disulfide ) PGES HQL - 79 PGFS Bimatoprost PGI S Tranylcypromine TXAS Camonagrel Dazmegrel Dazoxiben Furegrelate Isbogrel Midazogrel Nafagrel Nicogrelate Ozagrel Picotamide Pirmagrel Ridogrel Rolafagrel Samixogrel Terbogrel U63557A Others Precursors : Linoleic acid γ - Linolenic acid ( gamolenic acid ) Dihomo - γ - linolenic acid Diacylglycerol Arachidonic acid Prostaglandin G Prostaglandin H See also Receptor / signaling modulators Leukotriene signaling modulators Nuclear receptor modulators LCCN : sh85116754 GND : 4178954 - 4 NDL : 00570211 Retrieved from `` https://en.wikipedia.org/w/index.php?title=Salicylic_acid&oldid=800054589 '' Categories : Nonsteroidal anti-inflammatory drugs Antiseptics Salicylic acids Plant hormones Anti-acne preparations Monohydroxybenzoic acids World Health Organization essential medicines Chelating agents Hidden categories : PubChem ID ( CID ) same as Wikidata CS1 German - language sources ( de ) CS1 Danish - language sources ( da ) ECHA InfoCard ID from Wikidata Chembox having GHS data Articles containing unverified chemical infoboxes All articles with unsourced statements Articles with unsourced statements from June 2016 All articles with specifically marked weasel - worded phrases Articles with specifically marked weasel - worded phrases from August 2014 Wikipedia articles with LCCN identifiers Wikipedia articles with GND identifiers Talk Contents About Wikipedia Беларуская Български Bosanski Català Čeština Dansk Deutsch Eesti Español Esperanto Euskara فارسی Français Gaeilge Gaelg Galego 한국어 Հայերեն हिन्दी Bahasa Indonesia Íslenska Italiano עברית Latviešu Magyar Македонски മലയാളം Nederlands 日本 語 Norsk Polski Português Română Русский Scots Simple English Slovenčina Slovenščina Српски / srpski Srpskohrvatski / српскохрватски Suomi Svenska తెలుగు ไทย Türkçe Українська اردو 粵語 中文 Edit links This page was last edited on 11 September 2017, at 08 : 33. Text is available under the Creative Commons Attribution - ShareAlike License ; additional terms may apply. By using this site, you agree to the Terms of Use and Privacy Policy. Wikipedia ® is a registered trademark of the Wikimedia Foundation, Inc., a non-profit organization. About Wikipedia

Question: what is a natural source of salicylic acid
Answer: willow tree