Wikipedia:WikiProject Chemicals/Chembox validation/VerifiedDataSandbox and Tartaric acid: Difference between pages

{{Short description|Organic acid found in many fruits}}

| verifiedrevid = 476994374

| ImageCaption1 = Ball-and-stick model of <small>L</small>-(+)-tartaric&nbsp;acid

| PIN = 2,3-Dihydroxybutanedioic acid <!-- Nomenclature of Organic Chemistry – IUPAC Recommendations and Preferred Names 2013 (Blue Book) -->

| OtherNames = Tartaric acid<br />2,3-Dihydroxysuccinic acid<br />Threaric acid<br />Racemic acid<br />Uvic acid<br />Paratartaric acid<br />Winestone

| Reference = <ref name="pubchem">[https://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?cid=875&loc=ec_rcs Tartaric Acid – Compound Summary], [[PubChem]].</ref>

|Section1={{Chembox Identifiers

| index_label =

| index1_label = R,R-isomer

| index2_label = S,S-isomer

| index3_label = racemic

| index4_label = meso-isomer

| index_comment =

| index1_comment = <!-- unused -->

| index2_comment =

| index3_comment =

| index4_comment =

| KEGG_Ref = {{keggcite|correct|kegg}}

| ChEMBL5_Ref = {{ebicite|correct|EBI}}<!-- todo: which CASNo-index per Chembl? -->

| ChEMBL5 = 1200861

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = W4888I119H

| CASNo1 = 87-69-4

| CASNo1_Comment =

| CASNo2 = 147-71-7

| CASNo2_Comment =

| CASNo3 = 133-37-9

| CASNo3_Comment =

| CASNo4 = 147-73-9

| CASNo4_Comment =

| PubChem = 875

| PubChem_Comment = unspecified isomer

| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}

| MeSHName = tartaric+acid

| DrugBank_Ref = {{drugbankcite|correct|drugbank}}

|Section2={{Chembox Properties

| Formula = C₄H₆O₆ (basic formula)<br>HO₂CCH(OH)CH(OH)CO₂H (structural formula)

| MolarMass = 150.087{{nbsp}}g/mol

| Appearance = White powder

| Density = 1.737 g/cm³ (R,R- and S,S-)<br />1.79 g/cm³ (racemate)<br />1.886 g/cm³ (meso)

| MeltingPt = 169, 172 °C (R,R- and S,S-)<br />206 °C (racemate)<br />165-6 °C (meso)

| BoilingPt =

| Solubility = {{ubl

| 1.33{{nbsp}}kg/L (''L or D''-tartaric)

| 0.21{{nbsp}}kg/L (''DL'', racemic)

| 1.25{{nbsp}}kg/L ("meso")

}}

| pKa = L(+) 25{{nbsp}}°C :<br>pK_a1= 2.89, pK_a2= 4.40<br>meso 25{{nbsp}}°C:<br>pK_a1= 3.22, pK_a2= 4.85

<ref>Dawson, R.M.C. et al., ''Data for Biochemical Research'', Oxford, Clarendon Press, 1959.</ref>

| ConjugateBase = [[Bitartrate]]

| MagSus = −67.5·10⁻⁶ cm³/mol}}

|Section3={{Chembox Hazards

| MainHazards =

| GHSPictograms = {{GHS corrosion}}

| GHSSignalWord = Danger

| HPhrases = {{HPhrases|H318}}

| PPhrases = {{PPhrases|P280|P305+P351+P338+P310}}

| GHS_ref= <ref>GHS: {{GESTIS|ZVG=33480}}</ref>| AutoignitionPt =

|Section4={{Chembox Related

| OtherCations = [[Monosodium tartrate]]<br />[[Sodium tartrate|Disodium tartrate]]<br />[[Potassium bitartrate|Monopotassium tartrate]]<br />[[Potassium tartrate|Dipotassium tartrate]]

| OtherFunction_label = [[carboxylic acid]]s

| OtherFunction = [[Butyric acid]]<br />[[Succinic acid]]<br />[[Dimercaptosuccinic acid]]<br />[[Malic acid]]<br />[[Maleic acid]]<br />[[Fumaric acid]]

| OtherCompounds = [[2,3-Butanediol]]<br />[[Cichoric acid]]

'''Tartaric acid''' is a white, crystalline [[organic acid]] that occurs naturally in many fruits, most notably in [[grape]]s but also in [[tamarind]]s, [[banana]]s, [[avocado]]s, and [[citrus]].<ref name="pubchem"/> Its [[salt (chemistry)|salt]], [[potassium bitartrate]], commonly known as cream of tartar, develops naturally in the process of [[winemaking|fermentation]]. Potassium bitartrate is commonly mixed with [[sodium bicarbonate]] and is sold as [[baking powder]] used as a [[leavening agent]] in food preparation. The acid itself is added to foods as an [[antioxidant]] [[E-numbers|E334]] and to impart its distinctive sour taste. [[Naturally occurring]] tartaric acid is a useful raw material in [[organic chemistry|organic]] [[chemical synthesis]]. Tartaric acid, an alpha-hydroxy-[[carboxylic acid]], is [[diprotic acid|diprotic]] and [[aldaric acid|aldaric]] in acid characteristics and is a dihydroxyl derivative of [[succinic acid]].

==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>

== Stereochemistry ==

[[File:TartrateCrystal.svg|thumb|left|Tartaric acid crystals drawn as if seen through an [[optical microscope]]]]

Naturally occurring form of the acid is '''dextro tartaric&nbsp;acid ''' or '''<small>L</small>-(+)-tartaric&nbsp;acid''' (obsolete name [[Descriptor (Chemistry)#dl|''d'']]-tartaric acid). Because it is available naturally, it is cheaper than its [[enantiomer]] and the [[meso isomer]]. The ''dextro'' and ''levo'' prefixes are archaic terms.<ref>{{Cite web |url=https://cosmolearning.org/video-lectures/stereochemical-nomenclature-racemization-and-resolution-6674/ |title=Lecture 28: Stereochemical Nomenclature; Racemization and Resolution &#124; CosmoLearning Chemistry |website=CosmoLearning}}</ref> Modern textbooks refer to the natural form as (2''R'',3''R'')-tartaric acid '''('''<small>L</small>'''-(+)-tartaric acid)''', and its enantiomer as (2''S'',3''S'')-tartaric acid '''('''D'''-(-)-tartaric acid)'''. The ''meso'' diastereomer is referred to as (2''R'',3''S'')-tartaric acid or (2''S'',3''R'')-tartaric acid.

*Dextro and levo form [[Crystal structure|monoclinic sphenoidal]] crystals<ref>{{cite journal |last1=W, T, Astbury |title=The Crystalline Structure and Properties of Tartaric Acid |journal=Proc. R. Soc. A |date=Feb 1923 |volume=102|issue=718 |pages=506–528 | doi=10.1098/rspa.1923.0010 |bibcode=1923RSPSA.102..506A |doi-access=free }}, based on P. Groth’s “Chemische Krystallographie".</ref> and [[orthorhombic]] crystals.

*Racemic tartaric acid forms [[monoclinic]]<ref name=CRC49>CRC Handbook of Chemistry and Physics, 49th edition.</ref> and [[triclinic]] crystals ([[space group]] P{{overline|1}}).<ref>{{cite web|date=2008 |last1=Samantha Callear and Michael Hursthouse |title=D-Tartaric acid |url=http://www.crystallography.net/cod/1519959.html |website=Crystallography Open Database}}</ref><ref>{{cite journal |display-authors=etal|last1=Paul Luner |title=(+-)-Tartaric acid |journal=Acta Crystallographica Section C |date=Jul 2002 |volume=58 |issue=6 |pages=o333–o335 |doi=10.1107/S0108270102006650 |pmid=12050433 |bibcode=2002AcCrC..58O.333L |url=https://www.researchgate.net/publication/11324000}}, {{cite web |title=(±)-Tartaric acid |url=http://www.crystallography.net/cod/2012731.html |website=Crystallography Open Database|year=2002 }}</ref>

*Anhydrous meso tartaric acid form two anhydrous [[polymorphism (materials science)|polymorphs]]: triclinic and orthorhombic.

*Monohydrated meso tartaric acid crystallizes as monoclinic and triclinic polymorphys depending on the temperature at which crystallization from aqueous solution occurs.<ref>{{cite journal |last1=G. A. Bootsma and J. C. Schoone |title=Crystal Structures of Meso Tartaric Acid |journal=Acta Crystallogr. |date=1967 |volume=22|issue=4 |pages=522–532 | doi=10.1107/S0365110X67001070 |bibcode=1967AcCry..22..522B |url=https://scripts.iucr.org/cgi-bin/paper?a05502|doi-access=free }}</ref>

Tartaric acid in [[Fehling's solution]] binds to copper(II) ions, preventing the formation of insoluble hydroxide salts.

{| class="wikitable" style="text-align:center;"

|-

! colspan="2" | <small>DL</small>-tartaric acid ([[racemic acid]]) <small>(when in 1:1 ratio)</small>

! rowspan="2" | mesotartaric acid

|-

! dextrotartaric acid<br><small>(L-(+)-tartaric acid)</small>

! levotartaric acid<br><small>(D-(−)-tartaric acid)</small>

|-

| width="150" | [[File:L-tartaric acid.png]]

| width="150" | [[File:D-tartaric acid.png]]

| width="270" | [[File:Meso-Weinsäure Spiegel.svg|150 px]]

|}

{{clear}}

{| class="wikitable"

|+ Forms of tartaric acid

|-

! [[Common name]]

! Tartaric acid

! Levotartaric acid

! Dextrotartaric acid

! Mesotartaric acid

! Racemic acid

|-align="center"

! Synonyms

|

| style="vertical-align:top" | (2''S'',3''S'')-tartaric acid <br> (''S'',''S'')-tartaric acid <br> (−)-tartaric acid <br> ''l''-tartaric acid <small>''(obsolete)''</small> <br> levotartaric acid <br> <small>D</small>-tartaric acid <br> <small>D</small>-threaric acid <br>('unnatural isomer')<ref>{{Cite web|url=https://pubchem.ncbi.nlm.nih.gov/compound/439655|title=d-Tartaric acid|website=[[PubChem]]}}</ref>

| style="vertical-align:top" | (2''R'',3''R'')-tartaric acid <br> (''R'',''R'')-tartaric acid <br> (+)-tartaric acid <br> ''d''-tartaric acid <small>''(obsolete)''</small> <br> <small>L</small>-tartaric acid <br> <small>L</small>-threaric acid <br>(‘natural isomer’)<ref>{{Cite web|url=https://pubchem.ncbi.nlm.nih.gov/compound/L-tartaric_acid|title=L-(+)-Tartaric acid|website=[[PubChem]]|url-status=dead|archive-url=https://web.archive.org/web/20150516011103/https://pubchem.ncbi.nlm.nih.gov/compound/L-tartaric_acid#section=Top|archive-date=May 16, 2015}}</ref>

| style="vertical-align:top" | (2''R'',3''S'')-tartaric acid <br> ''meso''-tartaric acid <br> erythraric acid

| style="vertical-align:top" | ''rac''-(2''R'',3''S'')-tartaric acid <br> (2''RS'',3''SR'')-tartaric acid <br> (±)-tartaric acid <br> <small>DL</small>-tartaric acid <br> ''dl''-tartaric acid <small>''(obsolete)''</small> <br> paratartaric acid <br> uvic acid

|-align="center"

! [[PubChem]]

| {{PubChemCID|875}}

| {{PubChemCID|439655}}

| {{PubChemCID|444305}}

| {{PubChemCID|78956}}

| {{PubChemCID|5851}}

|-align="center"

! [[EINECS number]]

|

| {{EINECS|205-695-6}}

| {{EINECS|201-766-0}}

| {{EINECS|205-696-1}}

| {{EINECS|205-105-7}}

|-align="center"

! [[CAS number]]

| 526-83-0

| 147-71-7

| 87-69-4

| 147-73-9

| 133-37-9

|}

==Production==

===<small>L</small>-(+)-Tartaric acid===

The <small>L</small>-(+)-tartaric acid isomer of tartaric acid is industrially produced in the largest amounts. It is obtained from [[Lees (fermentation)|lees]], a solid byproduct of fermentations. The former byproducts mostly consist of potassium bitartrate (KHC₄H₄O₆). This potassium salt is converted to [[calcium tartrate]] (CaC₄H₄O₆) upon treatment with [[calcium hydroxide]] "milk of lime" (Ca(OH)₂):<ref name=Ullman>J.-M. Kassaian "Tartaric acid" in Ullmann's Encyclopedia of Industrial Chemistry; VCH: Weinheim, Germany, 2002, 35, 671-678. {{doi|10.1002/14356007.a26_163}}</ref>

:<chem>KH(C4H4O6) + Ca(OH)2 -> Ca(C4H4O6) + KOH + H2O</chem>

In practice, higher yields of calcium tartrate are obtained with the addition of [[calcium sulfate]]. Calcium tartrate is then converted to tartaric acid by treating the salt with aqueous sulfuric acid:

:<chem>Ca(C4H4O6) + H2SO4 -> H2(C4H4O6) + CaSO4</chem>

===Racemic tartaric acid===

Racemic tartaric acid can be prepared in a multistep reaction from [[maleic acid]]. In the first step, the maleic acid is [[epoxide|epoxidized]] by [[hydrogen peroxide]] using [[potassium tungstate]] as a catalyst.<ref name=Ullman/>

:HO₂CC₂H₂CO₂H + H₂O₂ → OC₂H₂(CO₂H) ₂

In the next step, the epoxide is hydrolyzed.

:OC₂H₂(CO₂H)₂ + H₂O → (HOCH)₂(CO₂H)₂

===''meso''-Tartaric acid===

A mixture of racemic acid and ''meso''-tartaric acid is formed when ''dextro''-Tartaric acid is heated in water at 165&nbsp;°C for about 2 days. ''meso''-Tartaric acid can also be prepared from dibromosuccinic acid using silver hydroxide:<ref name=Aug>Augustus Price West. Experimental Organic Chemistry. World Book Company: New York, 1920, 232-237.</ref>

:HO₂CCHBrCHBrCO₂H + 2 AgOH → HO₂CCH(OH)CH(OH)CO₂H + 2 AgBr

''meso''-Tartaric acid can be separated from residual racemic acid by crystallization, the racemate being less soluble.

==Reactivity==

L-(+)-tartaric acid, can participate in several reactions. As shown the reaction scheme below, dihydroxymaleic acid is produced upon treatment of L-(+)-tartaric acid with hydrogen peroxide in the presence of a [[ferrous]] salt.

:HO₂CCH(OH)CH(OH)CO₂H + H₂O₂ → HO₂CC(OH)C(OH)CO₂H + 2 H₂O

[[Dihydroxymaleic acid]] can then be oxidized to [[tartronic acid]] with nitric acid.<ref name=Blair>{{cite encyclopedia | last1 = Blair | first1 = G. T. | last2 = DeFraties | first2 = J. J. | title = Hydroxy Dicarboxylic Acids | encyclopedia = Kirk Othmer Encyclopedia of Chemical Technology | year = 2000 | pages = 1–19 | doi = 10.1002/0471238961.0825041802120109.a01 | isbn = 0471238961 }}</ref>

==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]] (LD₅₀) 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.

==Tartaric acid in wine==

{{See also|Acids in wine|Tartrate}}{{More sources|date=November 2023}}[[File:HomemadeTartaric.jpg|thumb|Unpurified potassium bitartrate can take on the color of the grape juice from which it was separated.]]

Tartaric acid may be most immediately recognizable to wine drinkers as the source of "wine diamonds", the small [[potassium bitartrate]] crystals that sometimes form spontaneously on the [[cork (material)|cork]] or bottom of the bottle. These "tartrates" are harmless, despite sometimes being mistaken for broken glass, and are prevented in many wines through [[cold stabilization]] (which is not always preferred since it can change the wine's profile). The tartrates remaining on the inside of [[aging barrel]]s were at one time a major industrial source of potassium bitartrate.

Tartaric acid plays an important role chemically, lowering the pH of fermenting "must" to a level where many undesirable spoilage bacteria cannot live, and acting as a preservative after [[fermentation (wine)|fermentation]]. In the mouth, tartaric acid provides some of the tartness in the wine, although [[citric acid|citric]] and [[malic acid]]s also play a role.

== Tartaric acid in fruits ==

Grapes and tamarinds have the highest levels of tartaric acid concentration. Other fruits with tartaric acid are [[banana]]s, [[avocado|avocados]], [[Opuntia ficus-indica|prickly pear]] fruit, [[apple|apples]], [[cherry|cherries]], [[papaya|papayas]], [[peach|peaches]], [[pear|pears]], [[pineapple|pineapples]], [[strawberry|strawberries]], [[mango|mangoes]] and [[citrus|citrus fruits]].<ref name="pubchem"/><ref>J.B. Gurtler, T.L. Mai, in Encyclopedia of Food Microbiology (Second Edition), 2014. PRESERVATIVES | Traditional Preservatives – Organic Acids: Tartaric Acid.</ref>

Trace amounts of tartaric acid have been found in [[cranberry|cranberries]] and other [[berry|berries]].<ref>Phytochemicals of Cranberries and Cranberry Products: Characterization, Potential Health Effects, and Processing Stability https://www.researchgate.net/publication/44573816_Phytochemicals_of_Cranberries_and_Cranberry_Products_Characterization_Potential_Health_Effects_and_Processing_Stability</ref>

Tartaric acid is also present in the leaves and pods of [[Pelargonium]] plants and [[Phaseolus vulgaris|beans]].

== Applications ==

Tartaric acid and its derivatives have a plethora of uses in the field of pharmaceuticals. For example, it has been used in the production of effervescent salts, in combination with citric acid, to improve the taste of oral medications.<ref name="Blair" /> The potassium antimonyl derivative of the acid known as tartar emetic is included, in small doses, in [[cough syrup]] as an [[expectorant]].

Tartaric acid also has several applications for industrial use. The acid has been observed to [[Chelation|chelate]] metal ions such as calcium and magnesium. Therefore, the acid has served in the farming and metal industries as a chelating agent for complexing micronutrients in soil [[fertilizer]] and for cleaning metal surfaces consisting of aluminium, copper, iron, and alloys of these metals, respectively.<ref name=Ullman/>

== Toxicity in canines ==

While tartaric acid is well-tolerated by humans and lab animals, an April 2021 letter to the editor of ''[[Journal of the American Veterinary Medical Association|JAVMA]]'' hypothesized that the tartaric acid in grapes could be the cause of [[grape and raisin toxicity in dogs]].<ref>{{Cite web|url=https://www.aaha.org/publications/newstat/articles/2021-04/what-causes-grape-toxicity-in-dogs-playdough-might-have-led-to-a-breakthrough/|title=What causes grape toxicity in dogs? Playdough might have led to a breakthrough|website=American Animal Hospital Association|first=Tony|last=McReynolds|date=April 1, 2021}}</ref>

In dogs, the tartaric acid of [[tamarind]] causes [[acute kidney injury]], which can often be fatal.<ref>{{cite journal |last1=Wegenast |first1=CA |title=Acute kidney injury in dogs following ingestion of cream of tartar and tamarinds and the connection to tartaric acid as the proposed toxic principle in grapes and raisins |journal=J Vet Emerg Crit Care |date=2022 |volume=32 |issue=6 |pages=812–816 |doi=10.1111/vec.13234|pmid=35869755 |s2cid=250989489 }}</ref>

==References==

{{reflist|30em}}

==External links==

{{commons}}

*[http://xray.bmc.uu.se/hicup/MSE/ PDB file for MSE] {{Webarchive|url=https://web.archive.org/web/20180920083516/http://xray.bmc.uu.se/hicup/MSE/ |date=2018-09-20 }}

{{Authority control}}

{{DEFAULTSORT:Tartaric Acid}}

[[Category:Crystals in space group 14]]

[[Category:Chirality]]

[[Category:Racemic mixtures]]

[[Category:Food antioxidants]]

[[Category:Food acidity regulators]]

[[Category:Acids in wine]]

[[Category:Alpha hydroxy acids]]

[[Category:Dicarboxylic acids]]

[[Category:Vicinal diols]]

[[Category:E-number additives]]