| Revision as of 12:29, 15 February 2012 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Saving copy of the {{chembox}} taken from revid 475232701 of page Tartaric_acid for the Chem/Drugbox validation project (updated: ''). |
Latest revision as of 20:40, 16 December 2024 edit Citation bot (talk | contribs)Bots5,424,091 edits Altered title. Add: pmid, authors 1-1. Removed parameters. Some additions/deletions were parameter name changes. | Use this bot. Report bugs. | Suggested by Abductive | Category:Food antioxidants | #UCB_Category 18/32 |
| Line 1: |
Line 1: |
|
|
{{Short description|Organic acid found in many fruits}} |
|
{{ambox | text = This page contains a copy of the infobox ({{tl|chembox}}) taken from revid of page ] with values updated to verified values.}} |
|
|
{{chembox |
|
{{chembox |
|
| Watchedfields = changed |
|
| Watchedfields = changed |
|
| verifiedrevid = 470481910 |
|
| verifiedrevid = 476994374 |
|
| ImageFile_Ref = {{chemboximage|correct|??}} |
|
| ImageFile_Ref = {{chemboximage|correct|??}} |
|
| ImageFile = Tartaric acid.svg |
|
| ImageFile = Tartaric acid.svg |
|
|
| ImageClass = skin-invert-image |
|
| ImageFile1 = Tartaric-acid-3D-balls.png |
|
| ImageFile1 = Tartaric-acid-3D-balls.png |
|
|
| ImageCaption1 = Ball-and-stick model of <small>L</small>-(+)-tartaric acid |
|
| ImageSize = |
|
| ImageSize = |
|
|
| PIN = 2,3-Dihydroxybutanedioic acid <!-- Nomenclature of Organic Chemistry – IUPAC Recommendations and Preferred Names 2013 (Blue Book) --> |
|
| IUPACName = 2,3-dihydroxybutanedioic acid |
|
|
| OtherNames = 2,3-dihydroxysuccinic acid<br>threaric acid<br>racemic acid<br>uvic acid<br>paratartaric acid |
|
| OtherNames = Tartaric acid<br />2,3-Dihydroxysuccinic acid<br />Threaric acid<br />Racemic acid<br />Uvic acid<br />Paratartaric acid<br />Winestone |
|
| Reference = <ref>, ].</ref> |
|
| Reference = <ref name="pubchem">, ].</ref> |
|
|
|Section1={{Chembox Identifiers |
|
|- |
|
|
|
| index_label = |
|
| Section1 = {{Chembox Identifiers |
|
|
|
| index1_label = R,R-isomer |
|
| KEGG_Ref = {{keggcite|correct|kegg}} |
|
|
|
| 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}} |
|
| KEGG = C00898 |
|
| KEGG = C00898 |
|
| InChI = 1/C4H6O6/c5-1(3(7)8)2(6)4(9)10/h1-2,5-6H,(H,7,8)(H,9,10) |
|
| InChI = 1/C4H6O6/c5-1(3(7)8)2(6)4(9)10/h1-2,5-6H,(H,7,8)(H,9,10) |
| Line 18: |
Line 30: |
|
| ChEMBL_Ref = {{ebicite|correct|EBI}} |
|
| ChEMBL_Ref = {{ebicite|correct|EBI}} |
|
| ChEMBL = 333714 |
|
| ChEMBL = 333714 |
|
|
| ChEMBL5_Ref = {{ebicite|correct|EBI}}<!-- todo: which CASNo-index per Chembl? --> |
|
| ChEMBL2 = 1200861 |
|
|
|
| ChEMBL5 = 1200861 |
|
| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
|
| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
|
| StdInChI = 1S/C4H6O6/c5-1(3(7)8)2(6)4(9)10/h1-2,5-6H,(H,7,8)(H,9,10) |
|
| StdInChI = 1S/C4H6O6/c5-1(3(7)8)2(6)4(9)10/h1-2,5-6H,(H,7,8)(H,9,10) |
| Line 24: |
Line 37: |
|
| StdInChIKey = FEWJPZIEWOKRBE-UHFFFAOYSA-N |
|
| StdInChIKey = FEWJPZIEWOKRBE-UHFFFAOYSA-N |
|
| CASNo_Ref = {{cascite|correct|CAS}} |
|
| CASNo_Ref = {{cascite|correct|CAS}} |
|
|
| UNII_Ref = {{fdacite|correct|FDA}} |
|
| CASNo = 526-83-0 |
|
|
| PubChem = 875 |
|
| UNII = W4888I119H |
|
|
| CASNo1 = 87-69-4 |
|
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
|
|
|
| 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}} |
|
| ChemSpiderID = 852 |
|
| ChemSpiderID = 852 |
|
| MeSHName = tartaric+acid |
|
| MeSHName = tartaric+acid |
|
| DrugBank_Ref = {{drugbankcite|correct|drugbank}} |
|
| DrugBank_Ref = {{drugbankcite|correct|drugbank}} |
|
| DrugBank = DB01694 |
|
| DrugBank = DB01694 |
|
| ChEBI_Ref = {{ebicite|correct|EBI}} |
|
| ChEBI_Ref = {{ebicite|correct|EBI}} |
| Line 35: |
Line 58: |
|
| SMILES = O=C(O)C(O)C(O)C(=O)O |
|
| SMILES = O=C(O)C(O)C(O)C(=O)O |
|
}} |
|
}} |
|
| Section2 = {{Chembox Properties |
|
|Section2={{Chembox Properties |
|
| Formula = C<sub>4</sub>H<sub>6</sub>O<sub>6</sub><small> (Basic formula)</small><br>HO<sub>2</sub>CCH(OH)CH(OH)CO<sub>2</sub>H <small>(Structural formula)</small> |
|
| Formula = C<sub>4</sub>H<sub>6</sub>O<sub>6</sub> (basic formula)<br>HO<sub>2</sub>CCH(OH)CH(OH)CO<sub>2</sub>H (structural formula) |
|
| MolarMass = 150.087 g/mol |
|
| MolarMass = 150.087{{nbsp}}g/mol |
|
| Appearance = white powder |
|
| Appearance = White powder |
|
| Density = 1.79 g/mL (H<sub>2</sub>O) |
|
| Density = 1.737 g/cm<sup>3</sup> (R,R- and S,S-)<br />1.79 g/cm<sup>3</sup> (racemate)<br />1.886 g/cm<sup>3</sup> (meso) |
|
| MeltingPt = 171–174 °C (''L or D''-tartaric; pure)<br>206 °C (''DL'', racemic)<br> 165-166°C ("meso-anhyrdous") <br> 146–148 °C (''meso-hydrous'')<ref>{{RubberBible86th}}</ref> <br> |
|
| MeltingPt = 169, 172 °C (R,R- and S,S-)<br />206 °C (racemate)<br />165-6 °C (meso) |
|
| BoilingPt = |
|
| BoilingPt = |
|
| Solubility = 133 g/100ml (20 °C) |
|
| Solubility = {{ubl |
|
|
| 1.33{{nbsp}}kg/L (''L or D''-tartaric) |
|
| pKa = L(+) 25 °C :<br>pK<sub>a1</sub>= 2.95 pK<sub>a2</sub>= 4.25<br>meso 25 °C:<br>pK<sub>a1</sub>= 3.22 pK<sub>a2</sub>= 4.85 |
|
|
|
| 0.21{{nbsp}}kg/L (''DL'', racemic) |
|
|
| 1.25{{nbsp}}kg/L ("meso") |
|
|
}} |
|
|
| pKa = L(+) 25{{nbsp}}°C :<br>pK<sub>a1</sub>= 2.89, pK<sub>a2</sub>= 4.40<br>meso 25{{nbsp}}°C:<br>pK<sub>a1</sub>= 3.22, pK<sub>a2</sub>= 4.85 |
|
|
<ref>Dawson, R.M.C. et al., ''Data for Biochemical Research'', Oxford, Clarendon Press, 1959.</ref> |
|
|
| ConjugateBase = ] |
|
|
| MagSus = −67.5·10<sup>−6</sup> cm<sup>3</sup>/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 = |
|
}} |
|
}} |
|
| Section3 = {{Chembox Hazards |
|
|Section4={{Chembox Related |
|
|
| OtherCations = ]<br />]<br />]<br />] |
|
| MainHazards = |
|
|
|
| OtherFunction_label = ]s |
|
|EUClass=Irritant('''Xi''') |
|
|
|
| OtherFunction = ]<br />]<br />]<br />]<br />]<br />] |
|
|RPhrases={{R36}} |
|
|
|
| OtherCompounds = ]<br />] |
|
| Autoignition = |
|
|
}} |
|
}} |
|
| Section4 = {{Chembox Related |
|
|
| OtherCations = ]<br />]<br />]<br />] |
|
|
| Function = ]s |
|
|
| OtherFunctn = ]<br />]<br />]<br />]<br />] |
|
|
| OtherCpds = ]<br />] |
|
|
}} |
|
}} |
|
|
|
|
|
|
'''Tartaric acid''' is a white, crystalline ] that occurs naturally in many fruits, most notably in ]s but also in ]s, ]s, ]s, and ].<ref name="pubchem"/> Its ], ], commonly known as cream of tartar, develops naturally in the process of ]. Potassium bitartrate is commonly mixed with ] and is sold as ] used as a ] in food preparation. The acid itself is added to foods as an ] ] and to impart its distinctive sour taste. ] tartaric acid is a useful raw material in ] ]. Tartaric acid, an alpha-hydroxy-], is ] and ] in acid characteristics and is a dihydroxyl derivative of ]. |
|
}} |
|
|
|
|
|
|
==History== |
|
|
Tartaric acid has been known to ] for centuries. However, the chemical process for extraction was developed in 1769 by the ] chemist ].<ref>Retzius, Anders Jahan (1770) (Experiments with cream of tartar and its acid), ''Kungliga Vetenskapsakademiens Handlingar'' (Proceedings of the Royal Academy of Sciences), '''31''' : 207–213. ''"§. 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 ]. This property of tartaric acid was first observed in 1832 by ], who observed its ability to rotate ].<ref>Biot (1835) (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 (Note: This article was read to the French Royal Academy of Sciences on 1832 November 5.)</ref><ref>Biot (1838) (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 , and spirit of wood ), ''Mémoires de l'Académie des sciences de l'Institut'', 2nd series, '''15''' : 93–279.</ref> ] continued this research in 1847 by investigating the shapes of ] 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) (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) , ''Annales de Chimie et de Physique'', 3rd series, '''28''' (3) : 56–99. See also (See also the report of the commission that was appointed to verify Pasteur's findings, pp. 99–117.) </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 == |
|
|
]]] |
|
|
|
|
|
Naturally occurring form of the acid is '''dextro tartaric acid ''' or '''<small>L</small>-(+)-tartaric acid''' (obsolete name ]-tartaric acid). Because it is available naturally, it is cheaper than its ] and the ]. 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 | 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 ] 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 ] crystals. |
|
|
*Racemic tartaric acid forms ]<ref name=CRC49>CRC Handbook of Chemistry and Physics, 49th edition.</ref> and ] crystals (] 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 ]: 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 ] 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 (]) <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" | ] |
|
|
| width="150" | ] |
|
|
| width="270" | ] |
|
|
|} |
|
|
|
|
|
{{clear}} |
|
|
{| class="wikitable" |
|
|
|+ Forms of tartaric acid |
|
|
|- |
|
|
! ] |
|
|
! 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=]}}</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=]|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" |
|
|
! ] |
|
|
| {{PubChemCID|875}} |
|
|
| {{PubChemCID|439655}} |
|
|
| {{PubChemCID|444305}} |
|
|
| {{PubChemCID|78956}} |
|
|
| {{PubChemCID|5851}} |
|
|
|-align="center" |
|
|
! ] |
|
|
| |
|
|
| {{EINECS|205-695-6}} |
|
|
| {{EINECS|201-766-0}} |
|
|
| {{EINECS|205-696-1}} |
|
|
| {{EINECS|205-105-7}} |
|
|
|-align="center" |
|
|
! ] |
|
|
| 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 ], a solid byproduct of fermentations. The former byproducts mostly consist of potassium bitartrate ({{chem2|KHC4H4O6}}). This potassium salt is converted to ] ({{chem2|CaC4H4O6}}) upon treatment with ] ({{chem2|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> |
|
|
:{{chem2|KH(C4H4O6) + Ca(OH)2 -> Ca(C4H4O6) + KOH + H2O}} |
|
|
|
|
|
In practice, higher yields of calcium tartrate are obtained with the addition of ]. Calcium tartrate is then converted to tartaric acid by treating the salt with aqueous sulfuric acid: |
|
|
:{{chem2|Ca(C4H4O6) + H2SO4 -> H2(C4H4O6) + CaSO4}} |
|
|
|
|
|
===Racemic tartaric acid=== |
|
|
Racemic tartaric acid can be prepared in a multistep reaction from ]. In the first step, the maleic acid is ] by ] using {{ill|potassium tungstate|de|Kaliumwolframat}} as a catalyst.<ref name=Ullman/> |
|
|
:{{chem2|HO2CCH\dCHCO2H + H2O2 -> HO2C(CHCH)(O)CO2H + H2O}} |
|
|
|
|
|
In the next step, the epoxide is hydrolyzed. |
|
|
:{{chem2|HO2C(CHCH)(O)CO2H + H2O -> HO2CCH(OH)CH(OH)CO2H}} |
|
|
|
|
|
===''meso''-Tartaric acid=== |
|
|
A mixture of racemic acid and ''meso''-tartaric acid is formed when ''dextro''-Tartaric acid is heated in water at 165 °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> |
|
|
:{{chem2|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 ] salt. |
|
|
|
|
|
:HO<sub>2</sub>CCH(OH)CH(OH)CO<sub>2</sub>H + H<sub>2</sub>O<sub>2</sub> → HO<sub>2</sub>CC(OH)C(OH)CO<sub>2</sub>H + 2 H<sub>2</sub>O |
|
|
|
|
|
] can then be oxidized to ] 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 ] --> |
|
|
] |
|
|
] |
|
|
Important derivatives of tartaric acid include: |
|
|
*], the first material separated into its ]s |
|
|
*cream of tartar (]), used in ] |
|
|
*] (potassium sodium tartrate), which has unusual piezoelectric properties |
|
|
*] (antimony potassium tartrate), a ].<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> ] is used as a ] in asymmetric synthesis. |
|
|
|
|
|
Tartaric acid is a ] ], which works by inhibiting the production of ], and in high doses causes paralysis and death.<ref>{{Cite book|url=https://archive.org/details/medicaljurisprud00tayluoft|page=|title=Medical jurisprudence|author=Alfred Swaine Taylor, Edward Hartshorne|year=1861|publisher=Blanchard and Lea}}</ref> The ] (LD<sub>50</sub>) is about 7.5 grams/kg for a human, 5.3 grams/kg for rabbits, and 4.4 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 ]. As a ], tartaric acid is used as an ] with ] '''E334'''; ]s are other additives serving as antioxidants or ]. |
|
|
|
|
|
When cream of tartar is added to water, a suspension results which serves to clean copper ]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}}] |
|
|
Tartaric acid may be most immediately recognizable to wine drinkers as the source of "wine diamonds", the small ] crystals that sometimes form spontaneously on the ] or bottom of the bottle. These "tartrates" are harmless, despite sometimes being mistaken for broken glass, and are prevented in many wines through ] (which is not always preferred since it can change the wine's profile). The tartrates remaining on the inside of ]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 ]. In the mouth, tartaric acid provides some of the tartness in the wine, although ] and ]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 ]s, ], ] fruit, ], ], ], ], ], ], ], ] and ].<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 ] and other ].<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 ] plants and ]. |
|
|
|
|
|
== 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 ] as an ]. |
|
|
|
|
|
Tartaric acid also has several applications for industrial use. The acid has been observed to ] 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 ] 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 '']'' hypothesized that the tartaric acid in grapes could be the cause of ].<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 |archive-url=http://web.archive.org/web/20210419032534/https://www.aaha.org/publications/newstat/articles/2021-04/what-causes-grape-toxicity-in-dogs-playdough-might-have-led-to-a-breakthrough |archive-date=19 April 2021}}</ref><ref>{{cite journal | title=Letters to the Editor | journal=Journal of the American Veterinary Medical Association | publisher=American Veterinary Medical Association (AVMA) | volume=258 | issue=7 | date=2021-04-01 | issn=0003-1488 | doi=10.2460/javma.258.7.704 | pages=704–707}}</ref> Other studies have observed tartaric acid toxicity in kidney cells of dogs, but not in human kidney cells.<ref>{{cite journal | last1=Coyne | first1=Sean R. | last2=Landry | first2=Greg M. | title=Tartaric acid induces toxicity in Madin–Darby canine kidney cells, but not human kidney-2 cells in vitro, and is prevented by organic anion transporter inhibition and human OAT-4 transfection | journal=Journal of Veterinary Emergency and Critical Care | volume=33 | issue=3 | date=2023 | issn=1479-3261 | doi=10.1111/vec.13294 | pages=298–304}}</ref> |
|
|
|
|
|
In dogs, the tartaric acid of ] causes ], 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> |
|
|
|
|
|
A review identified a relationship between grape ingestion and illness, though the specific type or quantity of grapes that cause toxicity remains unclear. Grape ingestion commonly leads to gastrointestinal and/or renal issues, with treatment depending on the symptoms; outcomes can vary.<ref>{{cite journal | last1=Downs | first1=Joshua | last2=Zoltowska | first2=Agnieszka | last3=Hackney | first3=Thomas | last4=Gardner | first4=David S. | last5=Ashmore | first5=Alison | last6=Brennan | first6=Marnie L. | title=Scoping review exploring the evidence base on Vitis vinifera toxicity in dogs after ingestion: Clinical effects, treatments and types of V. vinifera | journal=Veterinary Record | volume=195 | issue=7 | date=2024-10-05 | issn=0042-4900 | doi=10.1002/vetr.4536 | doi-access=free | page=| pmid=39183495 }}</ref> |
|
|
|
|
|
==References== |
|
|
{{reflist|30em}} |
|
|
|
|
|
==External links== |
|
|
{{commons}} |
|
|
* {{Webarchive|url=https://web.archive.org/web/20180920083516/http://xray.bmc.uu.se/hicup/MSE/ |date=2018-09-20 }} |
|
|
|
|
|
{{Authority control}} |
|
|
|
|
|
{{DEFAULTSORT:Tartaric Acid}} |
|
|
] |
|
|
] |
|
|
] |
|
|
] |
|
|
] |
|
|
] |
|
|
] |
|
|
] |
|
|
] |
|
|
] |