Editing Salicylic acid (section)

==History==
{{Main|History of aspirin}}
[[File:Thomé Salix alba clean.jpg|thumb|left|White willow (''[[Salix alba]]'') is a natural source of salicylic acid.]]

[[Willow]] has long been used for medicinal purposes. [[Pedanius Dioscorides|Dioscorides]], whose writings were highly influential for more than 1,500 years,<ref name=Dioscorides>{{cite web | vauthors = Dioscorides P | author-link=Pedanius Dioscorides |title=De Materia Medica |url=https://ia802907.us.archive.org/16/items/de-materia-medica/scribd-download.com_dioscorides-de-materia-medica.pdf}}</ref> used "Itea" (which was possibly a species of willow)  as a treatment for "painful intestinal obstructions", birth control, for "those who spit blood", to remove calluses and corns and, externally, as a "warm pack for gout". [[William Turner (naturalist)|William Turner]], in 1597, repeated this, saying that willow bark, "being burnt to ashes, and steeped in vinegar, takes away corns and other like risings in the feet and toes".<ref>{{cite web | vauthors = Turner W |title=The Herball, or Generall Historie of Plantes |url=https://www.exclassics.com/herbal/herbalv50587.htm |access-date=8 January 2022}}</ref> Some of these cures may describe the action of salicylic acid, which can be derived from the [[salicin]] present in willow. It is, however, a modern myth that Hippocrates used willow as a painkiller.<ref>{{cite web | vauthors = Martyr P |title=Hippocrates and willow bark? What you know about the history of aspirin is probably wrong |date=18 October 2020 |url=https://theconversation.com/hippocrates-and-willow-bark-what-you-know-about-the-history-of-aspirin-is-probably-wrong-148087 |access-date=9 January 2022}}</ref>

[[Hippocrates]], [[Galen]], [[Pliny the Elder]], and others knew that decoctions containing salicylate could ease pain and reduce fevers.<ref name=DMA>{{cite journal | vauthors = Norn S, Permin H, Kruse PR, Kruse E |title=From willow bark to acetylsalicylic acid | language = da | journal = Dansk Medicinhistorisk Årbog | volume = 37 | pages = 79–98 | year = 2009 | pmid = 20509453 | s2cid=10053542 }}</ref><ref>{{cite journal | vauthors = Vane JR | title=The fight against rheumatism: from willow bark to COX-1 sparing drugs | journal =  Journal of Physiology and Pharmacology | volume = 51 | pages = 573–586 | year=2000 | issue=4 Pt 1 | pmid=11192932 | url=https://pubmed.ncbi.nlm.nih.gov/11192932/ }}</ref>

It was used in Europe and China to treat these conditions.<ref name=ummc>{{cite web |url=http://www.umm.edu/altmed/articles/willow-bark-000281.htm |website=University of Maryland Medical Center |title=Willow bark |publisher=[[University of Maryland]] |access-date=19 December 2011 |archive-url=https://web.archive.org/web/20111224113137/http://www.umm.edu/altmed/articles/willow-bark-000281.htm |archive-date=24 December 2011 |url-status=live }}</ref> This remedy is mentioned in texts from [[Ancient Egypt]], [[Sumer]], and [[Assyria]].<ref name="Goldberg">{{cite journal| vauthors = Goldberg DR |title=Aspirin: Turn of the Century Miracle Drug|url=https://www.sciencehistory.org/distillations/magazine/aspirin-turn-of-the-century-miracle-drug|journal=Chemical Heritage Magazine|date=Summer 2009|volume=27|issue=2|pages=26–30|access-date=24 March 2018|archive-url=https://web.archive.org/web/20180320230715/https://www.sciencehistory.org/distillations/magazine/aspirin-turn-of-the-century-miracle-drug|archive-date=20 March 2018|url-status=live}}</ref>

The [[Cherokee]] and other Native Americans use an infusion of the bark for fever and other medicinal purposes.<ref>{{cite book | vauthors = Hemel PB, Chiltoskey MU | title = Cherokee Plants and Their Uses – A 400 Year History | location = Sylva, North Carolina | publisher = [[The Sylva Herald|Herald Publishing Co.]] | date = 1975 }} Cited in {{cite web | vauthors = Moerman D | title = A Database of Foods, Drugs, Dyes and Fibers of Native American Peoples, Derived from Plants | url = http://herb.umd.umich.edu/ | archive-url = https://web.archive.org/web/20071206021817/http://herb.umd.umich.edu/ |archive-date=2007-12-06 }} A search of this database for "salix AND medicine" finds 63 entries.</ref> In 2014, archaeologists identified traces of salicylic acid on seventh-century pottery fragments found in east-central Colorado.<ref name=wdo>{{cite web|url=http://westerndigs.org/prehistoric-pottery-found-in-colorado-contains-ancient-natural-aspirin/|title=1,300-Year-Old Pottery Found in Colorado Contains Ancient 'Natural Aspirin'|date=12 August 2014|access-date=2014-08-13|archive-url=https://web.archive.org/web/20140813231049/http://westerndigs.org/prehistoric-pottery-found-in-colorado-contains-ancient-natural-aspirin/|archive-date=2014-08-13|url-status=live}}</ref>

[[Edward Stone (clergyman)|Edward Stone]], a vicar from [[Chipping Norton, Oxfordshire]], England, reported in 1763 that the bark of the willow was effective in reducing a fever.<ref name="RoyalSoc1763EdmundStone">{{cite journal | vauthors=Stone E | title=An Account of the Success of the Bark of the Willow in the Cure of Agues | journal=Philosophical Transactions of the Royal Society of London| year=1763 | pages=195–200 | volume=53 | url={{google books |plainurl=y |id=j0JFAAAAcAAJ|page=195}} | doi=10.1098/rstl.1763.0033| doi-access=free }}</ref>

[[File:Florence Nightingale salicylic silk letter.jpg|thumb|Letter from [[Florence Nightingale]] on "salicylic silk" as a dressing for cancer patients<ref>{{Cite web |title=2013.0503 |website=Collections Online |url=https://collections.thackraymuseum.co.uk/object-2013-0503 |access-date=2024-05-30 |publisher=Thackray Museum of Medicine}}</ref>]]
An extract of willow bark, called [[salicin]], after the [[Latin]] name for the white willow (''[[Salix alba]]''), was isolated and named by [[Germans|German]] chemist [[Johann Andreas Buchner]] in 1828.<ref name=buchner28>{{cite book|title=Repertorium für die Pharmacie|language=de|chapter-url={{google books |plainurl=y |id=r-40AQAAMAAJ|page=405}}|year=1828|publisher=Bei J. L. Schrag|pages=405– |first=A. |last=Buchner | author-link=Johann Andreas Buchner |chapter=Ueber das Rigatellische Fiebermittel und über eine in der Weidenrinde entdeckte alcaloidische Substanz |trans-chapter=On Rigatelli's antipyretic [i.e., anti-fever drug] and on an alkaloid substance discovered in willow bark |quote=<!--Don't use {{lang}} in CS1-->Noch ist es mir aber nicht geglückt, den bittern Bestandtheil der Weide, den ich ''Salicin'' nennen will, ganz frei von allem Färbestoff darzustellen. | trans-quote=I have still not succeeded in preparing the bitter component of willow, which I will name ''salicin'', completely free from colored matter}}</ref> A larger amount of the substance was isolated in 1829 by Henri Leroux, a French pharmacist.<ref name=leroux30>
* {{cite journal|journal=Journal de Chimie Médicale, de Pharmacie et de Toxicologie|url={{google books |plainurl=y |id=TYIDAAAAYAAJ|page=340}}|year=1830|last=Leroux |first=H. |title=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 | trans-title=Memoir concerning the analysis of willow bark and the discovery of a substance immediately likely to replace quinine sulfate |volume=6 |pages=340–342}}
* A report on Leroux's presentation to the French Academy of Sciences also appeared in: {{cite book|title=Mémoires de l'Académie des sciences de l'Institut de France|url={{google books |plainurl=y |id=EVKATMXxkCAC|page=20}}|year=1838|publisher=Institut de France|pages=20ff}}</ref> [[Raffaele Piria]], an [[Italy|Italian]] chemist, was able to convert the substance into a sugar and a second component, which on oxidation becomes salicylic acid.<ref>{{cite journal | author=Piria | year=1838 | url=http://gallica.bnf.fr/ark:/12148/bpt6k2965r/f621.image | title=Sur de neuveaux produits extraits de la salicine | archive-url=https://web.archive.org/web/20170727013453/http://gallica.bnf.fr/ark:/12148/bpt6k2965r/f621.image | archive-date=2017-07-27 | trans-title=On new products extracted from salicine | journal=[[Comptes rendus]] | volume=6 | pages=620–624 | quote-page=622}} Piria mentions "Hydrure de salicyle" (hydrogen salicylate, i.e., salicylic acid).</ref><ref>{{cite book | url = {{google books |plainurl=y |id=x-sL4iNQOgcC|page=38}}| isbn = 978-1-58234-600-7 | pages = 38–40 | last = Jeffreys |first=Diarmuid | year = 2005 | publisher = Bloomsbury | location = New York| title = Aspirin: the remarkable story of a wonder drug}}</ref>
Salicylic acid was also isolated from the herb meadowsweet (''[[Filipendula ulmaria]]'', formerly classified as ''Spiraea ulmaria'') by German researchers in 1839.<ref>{{cite journal|first1=C. |last1=Löwig |first2=S. |last2=Weidmann |journal=Annalen der Physik und Chemie; Beiträge zur Organischen Chemie |language=de |trans-journal=Contributions to Organic Chemistry |url={{google books |plainurl=y |id=iBcAAAAAMAAJ|page=57}}|year=1839|issue=46 |pages= 57–83|title=III. Untersuchungen mit dem destillierten Wasser der Blüthen von ''Spiraea Ulmaria'' | trans-title=III. Investigations of the water distilled from the blossoms of ''Spiraea ulmaria''}} Löwig and Weidman called salicylic acid {{lang|de|Spiräasäure}} (spiraea acid).</ref> Their extract caused digestive problems such as [[gastric irritation]], [[bleeding]], [[diarrhea]], and even death when consumed in high doses.

In 1874 the Scottish physician [[Thomas John MacLagan|Thomas MacLagan]] experimented with salicin as a treatment for acute [[rheumatism]], with considerable success, as he reported in ''The Lancet'' in 1876.<ref>{{cite journal | vauthors = MacLagan TJ | author-link=Thomas John MacLagan |title=The treatment of acute rheumatism by salicin |journal=The Lancet |date=28 October 1876 |volume=108 | issue=2774 |page=383 |doi=10.1016/S0140-6736(02)49509-8 |url=https://www.thelancet.com/journals/lancet/article/PIIS0140-6736(02)49509-8/fulltext}}</ref> Meanwhile, German scientists tried sodium salicylate with less success and more severe side effects.<ref>{{cite journal | vauthors = MacLagan T |title=The treatment of acute rheumatism |journal=The Lancet |date=1900 |volume=155 |issue=3998 |page=1904 |doi=10.1016/S0140-6736(01)70583-1 |s2cid=58103130 }}</ref><ref>{{cite journal | vauthors = Buchanan WW, Kean WF | title = The Treatment of Acute Rheumatism by Salicin, by T. J. Maclagan – The Lancet, 1876 | journal = The Journal of Rheumatology | volume = 29 | issue = 6 | pages = 1321–1323 | date = June 2002 | pmid = 12064852 }}</ref>

In 1979, salicylates were found to be involved in induced defenses of [[tobacco]] against [[tobacco mosaic virus]].<ref name=raskin92>{{cite journal | vauthors = Raskin I | title = Salicylate, A New Plant Hormone | journal = Plant Physiology | volume = 99 | issue = 3 | pages = 799–803 | date = July 1992 | pmid = 16669002 | pmc = 1080546 | doi = 10.1104/pp.99.3.799 }}</ref> In 1987, salicylic acid was identified as the long-sought signal that causes [[thermogenic plant]]s, such as the voodoo lily, ''[[Sauromatum guttatum]]'', to produce heat.<ref name=raskin87>{{cite journal | vauthors = Raskin I, Ehmann A, Melander WR, Meeuse BJ | title = Salicylic Acid: A Natural Inducer of Heat Production in ''Arum'' Lilies | journal = Science | volume = 237 | issue = 4822 | pages = 1601–02 | date = September 1987 | pmid = 17834449 | doi = 10.1126/science.237.4822.1601 | bibcode = 1987Sci...237.1601R | s2cid = 3108513 }}</ref>