Editing Tartaric acid (section)

==History==
Tartaric acid has been known to [[winemakers]] for centuries. However, the chemical process for extraction was developed in 1769 by the [[Sweden|Swedish]] chemist [[Carl Wilhelm Scheele]].<ref>Retzius, Anders Jahan (1770) [https://babel.hathitrust.org/cgi/pt?id=mdp.39015039452886;view=1up;seq=605 "Försök med vinsten och dess syra"] (Experiments with cream of tartar and its acid), ''Kungliga Vetenskapsakademiens Handlingar'' (Proceedings of the Royal Academy of Sciences), '''31''' : 207–213.  [https://babel.hathitrust.org/cgi/pt?id=mdp.39015039452886;view=1up;seq=607 From p. 209:]  ''"§. 6.  Dessa försök omtalte jag för Hr. Carl Wilhelm Scheele (en snabb och lårgirug Pharmaciæ Studiosus) … "'' (§. 6. I mention  these experiments on behalf of Mr. Carl Wilhelm Scheele (a quick and studious student of pharmacology) … )</ref>

Tartaric acid played an important role in the discovery of [[chirality (chemistry)|chemical chirality]]. This property of tartaric acid was first observed in 1832 by [[Jean Baptiste Biot]], who observed its ability to rotate [[Polarization (waves)|polarized light]].<ref>Biot (1835) [http://gallica.bnf.fr/ark:/12148/bpt6k32283/f149.image "Mémoire sur la polarization circulaire et sur ses applications à la chimie organique"] (Memoir on circular polarization and on its applications to organic chemistry), ''Mémoires de l'Académie des sciences de l'Institut'', 2nd series, '''13''' :  39–175.  That tartaric acid (''acide tartarique cristallisé'') rotates plane-polarized light is shown in [http://gallica.bnf.fr/ark:/12148/bpt6k32283/f285.image Table G following p. 168.]  (Note:  This article was read to the French Royal Academy of Sciences on 1832 November 5.)</ref><ref>Biot (1838) [https://babel.hathitrust.org/cgi/pt?id=mdp.39015077785536;view=1up;seq=145 "Pour discerner les mélanges et les combinaisons chimiques définies ou non définies, qui agissent sur la lumière polarisée; suivies d'applications aux combinaisons de l'acide tartarique avec l'eau, l'alcool et l'esprit de bois"] (In order to discern mixtures and chemical combinations, defined or undefined, which act on polarized light; followed by applications to combinations of tartaric acid with water, alcohol [i.e., ethanol], and spirit of wood [i.e., methanol]), ''Mémoires de l'Académie des sciences de l'Institut'', 2nd series, '''15''' :  93–279.</ref> [[Louis Pasteur]] continued this research in 1847 by investigating the shapes of [[sodium ammonium tartrate]] crystals, which he found to be chiral. By manually sorting the differently shaped crystals, Pasteur was the first to produce a pure sample of levotartaric acid.<ref>{{cite journal |last1=Pasteur |first1=L. |title=Mémoire sur la relation qui peut exister entre la forme cristalline et la composition chimique, et sur la cause de la polarisation rotatoire |journal=Comptes rendus de l'Académie des Sciences de Paris |date=1848 |volume=26 |pages=535–538 |url=https://www.biodiversitylibrary.org/item/21163#page/545/mode/1up |trans-title=Memoir on the relationship which can exist between crystalline form and chemical composition, and on the cause of rotary polarization |language=French}}</ref><ref>L. Pasteur (1848) [https://books.google.com/books?id=gJ45AAAAcAAJ&pg=PA442 "Sur les relations qui peuvent exister entre la forme cristalline, la composition chimique et le sens de la polarisation rotatoire"] (On the relations that can exist between crystalline form, and chemical composition, and the sense of rotary polarization), ''Annales de Chimie et de Physique'', 3rd series, '''24''' : 442–459.</ref><ref>Pasteur, Louis (1850) [https://babel.hathitrust.org/cgi/pt?id=hvd.hx3dy7;view=1up;seq=66 "Recherches sur les propriétés spécifiques des deux acides qui composent l'acide racémique"] [Investigations into the specific properties of the two acids that compose racemic acid], ''Annales de Chimie et de Physique'', 3rd series, '''28''' (3) :  56–99. See also [https://babel.hathitrust.org/cgi/pt?id=hvd.hx3dy7;view=1up;seq=519 Plate II.] (See also the report of the commission that was appointed to verify Pasteur's findings, pp. 99–117.) [in French]</ref><ref>{{cite journal |author1=George B. Kauffman |author2=Robin D. Myers |year=1998 |url=http://192.129.24.144/licensed_materials/00897/papers/0003006/36kau897.pdf |title=Pasteur's resolution of racemic acid: A sesquicentennial retrospect and a new translation |journal=The Chemical Educator |volume=3 |issue=6 |pages=1–4 |doi=10.1007/s00897980257a |s2cid=95862598 |url-status=dead |archive-url=https://web.archive.org/web/20060117144722/http://192.129.24.144/licensed_materials/00897/papers/0003006/36kau897.pdf |archive-date=2006-01-17}}</ref><ref name=Flack>{{cite journal |author=Flack, H.D. |year=2009 |url=http://crystal.flack.ch/sh5092.pdf |title=Louis Pasteur's discovery of molecular chirality and spontaneous resolution in 1848, together with a complete review of his crystallographic and chemical work |journal=Acta Crystallographica A |volume=65 |issue=5 |pages=371–389 |pmid=19687573 |doi=10.1107/S0108767309024088 |bibcode=2009AcCrA..65..371F |url-status=dead |archive-url=https://wayback.archive-it.org/all/20120906001007/http://crystal.flack.ch/sh5092.pdf |archive-date=2012-09-06}}</ref>