Editing Tartaric acid (section)

==Derivatives==<!-- This section is linked from [[Napoleon I of France]] -->
[[File:Brechweinstein.jpg|thumb|Tartar emetic]]
[[File:CommercialTartaric.jpg|thumb|Commercially produced tartaric acid]]
Important derivatives of tartaric acid include:
*[[Sodium ammonium tartrate]], the first material separated into its [[enantiomer]]s
*cream of tartar ([[potassium bitartrate]]), used in [[cooking]]
*[[potassium sodium tartrate|Rochelle salt]] (potassium sodium tartrate), which has unusual piezoelectric properties
*[[antimony potassium tartrate|tartar emetic]] (antimony potassium tartrate), a [[resolving agent]].<ref>{{cite journal | doi = 10.1021/ic50125a033 | title = Crystal structure of l-tris(1,10-phenathroline)iron(II) bis(antimony(III) d-tartrate) octahydrate | year = 1973 | last1 = Zalkin | first1 = Allan | last2 = Templeton | first2 = David H. | last3 = Ueki | first3 = Tatzuo | journal = Inorganic Chemistry | volume = 12 | issue = 7 | pages = 1641–1646}}</ref><ref name="McCallum">{{cite journal | pmid =6804665 | year =1982 | last1 =Haq | first1 =I | last2 =Khan | first2 =C | title =Hazards of a traditional eye-cosmetic--SURMA | volume =32 | issue =1 | pages =7–8 | journal =The Journal of the Pakistan Medical Association}}</ref><ref>{{cite journal | pmc =1543508 | title =President's address. Observations upon antimony | year =1977 | volume =70 | issue =11 | pmid =341167 | last1 =McCallum | first1 =RI | pages =756–63 | journal =Proceedings of the Royal Society of Medicine| doi =10.1177/003591577707001103 }}</ref> [[Diisopropyl tartrate]] is used as a [[catalysis|co-catalyst]] in asymmetric synthesis.

Tartaric acid is a [[muscle]] [[toxin]], which works by inhibiting the production of [[malic acid]], and in high doses causes paralysis and death.<ref>{{Cite book|url=https://archive.org/details/medicaljurisprud00tayluoft|page=[https://archive.org/details/medicaljurisprud00tayluoft/page/61 61]|title=Medical jurisprudence|author=Alfred Swaine Taylor, Edward Hartshorne|year=1861|publisher=Blanchard and Lea}}</ref> The [[median lethal dose]] (LD<sub>50</sub>) is about 7.5 grams/kg for a human, 5.3&nbsp;grams/kg for rabbits, and 4.4&nbsp;grams/kg for mice.<ref>{{Cite book|url=https://books.google.com/books?id=6mGmxYqqiREC&pg=PA137|pages=137–138|title=Food additive toxicology|author=Joseph A. Maga, Anthony T. Tu|publisher=CRC Press|year=1995|isbn=0-8247-9245-9}}</ref> Given this figure, it would take over {{convert|500|g|abbr=on}} to kill a person weighing {{convert|70|kg|abbr=on}} with 50% probability, so it may be safely included in many foods, especially sour-tasting [[sweetness|sweets]]. As a [[food additive]], tartaric acid is used as an [[antioxidant]] with [[E number]] '''E334'''; [[tartrate]]s are other additives serving as antioxidants or [[emulsion|emulsifiers]].

When cream of tartar is added to water, a suspension results which serves to clean copper [[coin]]s very well, as the tartrate solution can dissolve the layer of copper(II) oxide present on the surface of the coin. The resulting copper(II)-tartrate complex is easily soluble in water.