TARTARIC ACID

CAS No.: 526-83-0
EC No.: 205-105-7

Synonyms:
TARTARIC ACID; tartaric acid; TARTARİK ASİT; tartarik asit; 2,3-Dihydroxysuccinic acid; Threaric acid; Racemic acid; Uvic acid; Paratartaric acid; Winestone; DL-Tartaric acid; tartaric acid; 2,3-Dihydroxysuccinic acid; 2,3-Dihydroxybutanedioic acid; 133-37-9; 526-83-0; Racemic acid; Uvic acid; Traubensaure; Racemic tartaric acid; DL-Tartrate; Paratartaric acid; Paratartaric aicd; Resolvable tartaric acid; Tartaric acid D,L; BUTANEDIOIC ACID, 2,3-DIHYDROXY-; TARTARIC ACID; tartaric acid; TARTARİK ASİT; tartarik asit; TARTARIC ACID; tartaric acid; TARTARİK ASİT; tartarik asit; (2RS,3RS)-Tartaric acid; Threaric acid; NSC62778; tartrate; NSC 148314; Baros; CHEBI:15674; dl-2,3-dihydroxybutanedioic acid; Butanedioic acid, 2,3-dihydroxy-, (R*,R*)-; MFCD00071626; Natural tartaric acid; (+-)-Tartaric acid; Tartaric acid, L-(+)-; Butanedioic acid, 2,3-dihydroxy-, (2R,3R)-rel-; DL-Tartaric acid, 99.5%; CCRIS 8978; Butanedioic acid, 2,3-dihydroxy-(R*,R*)-(.+/-.)-; EINECS 205-105-7; 868-14-4; (2R,3R)-2,3-Dihydroxybernsteinsaeure; NSC155080; (.+-.)-Tartaric acid; (+)-(2R,3R)-Tartaric acid; NSC-62778; TARTARIC ACID; tartaric acid; TARTARİK ASİT; tartarik asit; TARTARIC ACID; tartaric acid; TARTARİK ASİT; tartarik asit; (+) tartaric acid; (-) tartaric acid; 1,2-Dihydroxyethane-1,2-dicarboxylic acid; 1,2-dicarboxylic acid; WLN: QVYQYQVQ; (-) D-Tartaric acid; ACMC-209qpg; Sal tartar (Salt/Mix); Tartaric acid, (DL)-; Butanedioic acid, 2,3-dihydroxy-, [S-(R*,R*)]-; TARTARIC ACID; tartaric acid; TARTARİK ASİT; tartarik asit; TARTARIC ACID; tartaric acid; TARTARİK ASİT; tartarik asit; Malic acid, 3-hydroxy-; laevo-(+)-tartaric acid; dextro,laevo-tartaric acid; Succinic acid,3-dihydroxy; Butanedioic acid, 2,3-dihydroxy-, (R*,R*)-(+-)-; SCHEMBL848; ACMC-209cz3; bmse000167; Succinic acid,3-dihydroxy-; (.+/-.)-Tartaric acid; Butanedioic acid, 2,3-dihydroxy-, (theta,theta)-(+-)-; DSSTox_CID_26986; DSSTox_RID_82036; TARTARIC ACID; tartaric acid; TARTARİK ASİT; tartarik asit; TARTARIC ACID; tartaric acid; TARTARİK ASİT; tartarik asit; 2,3-dihydroxy-succinic acid; DSSTox_GSID_46986; Oprea1_827092; TARTARIC ACID, (L); Tartaric acid, (.+-.)-; Butanedioic acid,3-dihydroxy-; CHEMBL333714; Dihydroxysuccinic acid, (DL)-; Tartaric acid, (.+/-.)-; DTXSID5046986; CTK7J6041; L+Tartaric Acid FCC, NF, USP; 2,3-bis(oxidanyl)butanedioic acid; HMS3370M15; (+)-2,3-dihydroxybutanedioic acid; (S,S)-Tartaric acid;Tartaric acid; TARTARIC ACID; tartaric acid; TARTARİK ASİT; tartarik asit; TARTARIC ACID; tartaric acid; TARTARİK ASİT; tartarik asit; 1007601-97-9; BCP14303; Tox21_302052; BBL011588; NSC133735; NSC148314; NSC608773; STK387106; 2,3-Dihydroxysuccinic acid, (DL)-; 3-carboxy-2,3-dihydroxypropanoic acid; AKOS000120086; AKOS016844048; MCULE-3867000095; NE11122; NSC-133735; NSC-148314; TARTARIC ACID; tartaric acid; TARTARİK ASİT; tartarik asit; TARTARIC ACID; tartaric acid; TARTARİK ASİT; tartarik asit; NSC-608773; SMP2_000051; 2,3-Dihydroxysuccinic acid 526-83-0; d-.alpha.,.beta.-Dihydroxysuccinic acid; NCGC00256063-01; NCGC00347131-03; AK105884; AK116146; AS-10983; TARTARIC ACID; tartaric acid; TARTARİK ASİT; tartarik asit; TARTARIC ACID; tartaric acid; TARTARİK ASİT; tartarik asit; CAS-133-37-9; NCI60_001102; (+)-2,3-dihydroxy-1,4-butanedioic acid; DB-016129; DB-016159; DB-042899; TARTARIC ACID; tartaric acid; TARTARİK ASİT; tartarik asit; TARTARIC ACID; tartaric acid; TARTARİK ASİT; tartarik asit; LS-164466; AM20110247; FT-0624346; FT-0625514; FT-0628018; FT-0628243; FT-0656080; FT-0772946; FT-0773804; (+/-)-2,3-dihydroxy-1,4-butanedioic acid; 1467-EP2269610A2; 1467-EP2269986A1; TARTARIC ACID; tartaric acid; TARTARİK ASİT; tartarik asit; 1467-EP2269988A2; 1467-EP2269989A1; 1467-EP2269990A1; 1467-EP2270003A1; TARTARIC ACID; tartaric acid; TARTARİK ASİT; tartarik asit; 1467-EP2270006A1; 1467-EP2270008A1; 1467-EP2270011A1; 1467-EP2270014A1; 1467-EP2270505A1; TARTARIC ACID; tartaric acid; TARTARİK ASİT; tartarik asit; 1467-EP2272516A2; 1467-EP2272537A2; 1467-EP2272822A1; 1467-EP2272827A1; 1467-EP2272835A1; A22830; A22866; Butanedioic acid,3-dihydroxy- [R-(R*,R*)]-; TARTARIC ACID; tartaric acid; TARTARİK ASİT; tartarik asit; E-7050 (2S,3S)-2,3-dihydroxysuccinic acid; 133D379; A829202; Q194322; Butanedioic acid,3-dihydroxy-, (R*,R*)-(.+-.)-; F2191-0230; Z1258943354; 1,2-Dihydroxyethane-1,2-dicarboxylic acid;2,3-Dihydrosuccinic acid; (2S,3S)-(-)-Tartaric acid; D(-)-Threaric acid; TARTARIC ACID; tartaric acid; TARTARİK ASİT; tartarik asit; D(-)-Dihydroxysuccinic acid; Copper, mixt. with [R-(R*,R*)]-2,3-dihydroxybutanedioic acid monopotassium salt; TARTARIC ACID; tartaric acid; TARTARİK ASİT; tartarik asit; TARTARIC ACID; tartaric acid; TARTARİK ASİT; tartarik asit; 2,3-Dihydroxysuccinic acid; Threaric acid; Racemic acid; Uvic acid; Paratartaric acid; Winestone; DL-Tartaric acid; tartaric acid; 2,3-Dihydroxysuccinic acid; 2,3-Dihydroxybutanedioic acid; 133-37-9; 526-83-0; Racemic acid; Uvic acid; Traubensaure; Racemic tartaric acid; DL-Tartrate; Paratartaric acid; Paratartaric aicd; Resolvable tartaric acid; Tartaric acid D,L; BUTANEDIOIC ACID, 2,3-DIHYDROXY-; TARTARIC ACID; tartaric acid; TARTARİK ASİT; tartarik asit; TARTARIC ACID; tartaric acid; TARTARİK ASİT; tartarik asit; (2RS,3RS)-Tartaric acid; Threaric acid; NSC62778; tartrate; NSC 148314; Baros; CHEBI:15674; dl-2,3-dihydroxybutanedioic acid; Butanedioic acid, 2,3-dihydroxy-, (R*,R*)-; MFCD00071626; Natural tartaric acid; (+-)-Tartaric acid; Tartaric acid, L-(+)-; Butanedioic acid, 2,3-dihydroxy-, (2R,3R)-rel-; DL-Tartaric acid, 99.5%; CCRIS 8978; Butanedioic acid, 2,3-dihydroxy-(R*,R*)-(.+/-.)-; EINECS 205-105-7; 868-14-4; (2R,3R)-2,3-Dihydroxybernsteinsaeure; NSC155080; (.+-.)-Tartaric acid; (+)-(2R,3R)-Tartaric acid; NSC-62778; TARTARIC ACID; tartaric acid; TARTARİK ASİT; tartarik asit; TARTARIC ACID; tartaric acid; TARTARİK ASİT; tartarik asit; (+) tartaric acid; (-) tartaric acid; 1,2-Dihydroxyethane-1,2-dicarboxylic acid; 1,2-dicarboxylic acid; WLN: QVYQYQVQ; (-) D-Tartaric acid; ACMC-209qpg; Sal tartar (Salt/Mix); Tartaric acid, (DL)-; Butanedioic acid, 2,3-dihydroxy-, [S-(R*,R*)]-; TARTARIC ACID; tartaric acid; TARTARİK ASİT; tartarik asit; TARTARIC ACID; tartaric acid; TARTARİK ASİT; tartarik asit; Malic acid, 3-hydroxy-; laevo-(+)-tartaric acid; dextro,laevo-tartaric acid; Succinic acid,3-dihydroxy; Butanedioic acid, 2,3-dihydroxy-, (R*,R*)-(+-)-; SCHEMBL848; ACMC-209cz3; bmse000167; Succinic acid,3-dihydroxy-; (.+/-.)-Tartaric acid; Butanedioic acid, 2,3-dihydroxy-, (theta,theta)-(+-)-; DSSTox_CID_26986; DSSTox_RID_82036; TARTARIC ACID; tartaric acid; TARTARİK ASİT; tartarik asit; TARTARIC ACID; tartaric acid; TARTARİK ASİT; tartarik asit; 2,3-dihydroxy-succinic acid; DSSTox_GSID_46986; Oprea1_827092; TARTARIC ACID, (L); Tartaric acid, (.+-.)-; Butanedioic acid,3-dihydroxy-; CHEMBL333714; Dihydroxysuccinic acid, (DL)-; Tartaric acid, (.+/-.)-; DTXSID5046986; CTK7J6041; L+Tartaric Acid FCC, NF, USP; 2,3-bis(oxidanyl)butanedioic acid; HMS3370M15; (+)-2,3-dihydroxybutanedioic acid; (S,S)-Tartaric acid;Tartaric acid; TARTARIC ACID; tartaric acid; TARTARİK ASİT; tartarik asit; TARTARIC ACID; tartaric acid; TARTARİK ASİT; tartarik asit; 1007601-97-9; BCP14303; Tox21_302052; BBL011588; NSC133735; NSC148314; NSC608773; STK387106; 2,3-Dihydroxysuccinic acid, (DL)-; 3-carboxy-2,3-dihydroxypropanoic acid; AKOS000120086; AKOS016844048; MCULE-3867000095; NE11122; NSC-133735; NSC-148314; TARTARIC ACID; tartaric acid; TARTARİK ASİT; tartarik asit; TARTARIC ACID; tartaric acid; TARTARİK ASİT; tartarik asit; NSC-608773; SMP2_000051; 2,3-Dihydroxysuccinic acid 526-83-0; d-.alpha.,.beta.-Dihydroxysuccinic acid; NCGC00256063-01; NCGC00347131-03; AK105884; AK116146; AS-10983; TARTARIC ACID; tartaric acid; TARTARİK ASİT; tartarik asit; TARTARIC ACID; tartaric acid; TARTARİK ASİT; tartarik asit; CAS-133-37-9; NCI60_001102; (+)-2,3-dihydroxy-1,4-butanedioic acid; DB-016129; DB-016159; DB-042899; TARTARIC ACID; tartaric acid; TARTARİK ASİT; tartarik asit; TARTARIC ACID; tartaric acid; TARTARİK ASİT; tartarik asit; LS-164466; AM20110247; FT-0624346; FT-0625514; FT-0628018; FT-0628243; FT-0656080; FT-0772946; FT-0773804; (+/-)-2,3-dihydroxy-1,4-butanedioic acid; 1467-EP2269610A2; 1467-EP2269986A1; TARTARIC ACID; tartaric acid; TARTARİK ASİT; tartarik asit; 1467-EP2269988A2; 1467-EP2269989A1; 1467-EP2269990A1; 1467-EP2270003A1; TARTARIC ACID; tartaric acid; TARTARİK ASİT; tartarik asit; 1467-EP2270006A1; 1467-EP2270008A1; 1467-EP2270011A1; 1467-EP2270014A1; 1467-EP2270505A1; TARTARIC ACID; tartaric acid; TARTARİK ASİT; tartarik asit; 1467-EP2272516A2; 1467-EP2272537A2; 1467-EP2272822A1; 1467-EP2272827A1; 1467-EP2272835A1; A22830; A22866; Butanedioic acid,3-dihydroxy- [R-(R*,R*)]-; TARTARIC ACID; tartaric acid; TARTARİK ASİT; tartarik asit; E-7050 (2S,3S)-2,3-dihydroxysuccinic acid; 133D379; A829202; Q194322; Butanedioic acid,3-dihydroxy-, (R*,R*)-(.+-.)-; F2191-0230; Z1258943354; 1,2-Dihydroxyethane-1,2-dicarboxylic acid;2,3-Dihydrosuccinic acid; (2S,3S)-(-)-Tartaric acid; D(-)-Threaric acid; TARTARIC ACID; tartaric acid; TARTARİK ASİT; tartarik asit; D(-)-Dihydroxysuccinic acid; Copper, mixt. with [R-(R*,R*)]-2,3-dihydroxybutanedioic acid monopotassium salt; TARTARIC ACID; tartaric acid; TARTARİK ASİT; tartarik asit

TARTARIC ACID

Tartaric acid (2,3-dihydroxybutanedioic acid) is a naturally occurring dicarboxylic acid containing two stereocenters. It exists as a pair of enantiomers and an achiral meso compound. The dextrorotatory enantiomer of (R,R)-L-(+)-tartaric acid is widely distributed in nature. It is present in many fruits (fruit acid), and its monopotassium salt is found as a deposit during the fermentation of grape juice. Pure levorotatory (S,S)-d-(−)-tartaric acid is rare. Tartaric acid is a historical compound, dating back to when Louis Pasteur separated it into two enantiomers with a magnifying lens and a pair of tweezers more than 160 years ago.

It is manufactured from potassium hydrogen tartrate (wine tartar, cream of tartar – a by-product of the wine-making industry) via the calcium salt. (S,S)-Tartaric acid is also available commercially; it can be obtained from the racemic acid by several resolution procedures or from d-xylose. The highly functionalized and C2-symmetric tartaric acid molecule is perfectly tailored for applications as a resolving agent and chiral ligand. In fact, tartaric acid is the most frequently used resolving agent for racemic amines.1

Tartaric acid
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Tartaric acid[1]
Tartaric acid.svg
Tartaric-acid-3D-balls.png
Names
Preferred IUPAC name
2,3-Dihydroxybutanedioic acid
Other names
Tartaric acid
2,3-Dihydroxysuccinic acid
Threaric acid
Racemic acid
Uvic acid
Paratartaric acid
Winestone
Identifiers
CAS Number    
526-83-0 check
3D model (JSmol)    
Interactive image
ChEBI    
CHEBI:15674 check
ChEMBL    
ChEMBL333714 check
ChEMBL1200861 check
ChemSpider    
852 check
DrugBank    
DB01694 check
ECHA InfoCard    100.121.903 Edit this at Wikidata
E number    E334 (antioxidants, ...)
KEGG    
C00898 check
MeSH    tartaric+acid
PubChem CID    
875
CompTox Dashboard (EPA)    
DTXSID5046986 Edit this at Wikidata
InChI[show]
SMILES[show]
Properties
Chemical formula    C4H6O6 (Basic formula)
HO2CCH(OH)CH(OH)CO2H (Structural formula)
Molar mass    150.087 g/mol
Appearance    White powder
Density    1.79 g/mL (H2O)
Melting point    171 to 174 °C (340 to 345 °F; 444 to 447 K) (L or D-tartaric; pure)
206 °C (DL, racemic)
165–166 °C (meso-anhydrous)
146–148 °C (meso-hydrous)[3]
Solubility in water    
1.33 kg/L (L or D-tartaric)
0.21 kg/L (DL, racemic)
1.25 kg/L ("meso")
Acidity (pKa)    L(+) 25 °C :
pKa1= 2.89, pKa2= 4.40
meso 25 °C:
pKa1= 3.22, pKa2= 4.85
[2]

Conjugate base    Bitartrate
Magnetic susceptibility (χ)    −67.5·10−6 cm3/mol
Hazards
EU classification (DSD) (outdated)    Irritant(Xi)
R-phrases (outdated)    R36
Related compounds
Other cations    Monosodium tartrate
Disodium tartrate
Monopotassium tartrate
Dipotassium tartrate
Related carboxylic acids    Butyric acid
Succinic acid
Dimercaptosuccinic acid
Malic acid
Maleic acid
Fumaric acid
Related compounds    2,3-Butanediol
Cichoric acid
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references
Tartaric acid is a white, crystalline organic acid that occurs naturally in many fruits, most notably in grapes, but also in bananas, tamarinds, and citrus.[4] Its salt, potassium bitartrate, commonly known as cream of tartar, develops naturally in the process of fermentation. It 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 E334 and to impart its distinctive sour taste.

Tartaric acid is an alpha-hydroxy-carboxylic acid, is diprotic and aldaric in acid characteristics, and is a dihydroxyl derivative of succinic acid.

Contents
1    History
2    Stereochemistry
3    Production
3.1    L-(+)-Tartaric acid
3.2    Racemic tartaric acid
3.3    meso-Tartaric acid
4    Reactivity
5    Derivatives
6    Tartaric acid in wine
7    Tartaric acid in citrus
8    In superconductors
9    Applications
10    References
11    External links
History
Tartaric acid has been known to winemakers for centuries. Written record of its extraction from wine-making residues was made circa 800 AD, by the alchemist Jābir ibn Hayyān.[5] The chemical process for extraction was developed in 1769 by the Swedish chemist Carl Wilhelm Scheele.[6]

Tartaric acid played an important role in the discovery of chemical chirality. This property of tartaric acid was first observed in 1832 by Jean Baptiste Biot, who observed its ability to rotate polarized light.[7][8] 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.[9][10][11][12][13]

Stereochemistry
Tartaric acid crystals drawn as if seen through an optical microscope
Naturally occurring tartaric acid is chiral, and is a useful raw material in organic chemical synthesis. The naturally occurring form of the acid is dextrotartaric acid or L-(+)-tartaric acid (obsolete name d-tartaric acid). Because it is available naturally, it is slightly cheaper than its enantiomer and the meso isomer. The dextro and levo prefixes are archaic terms.[14] Modern textbooks refer to the natural form as (2R,3R)-tartaric acid (L-(+)-tartaric acid), and its enantiomer as (2S,3S)-tartaric acid (D-(-)-tartaric acid). The meso diastereomer is (2R,3S)-tartaric acid (which is identical with ‘(2S,3R)-tartaric acid’).

Whereas the two chiral stereoisomers rotate plane polarized light in opposite directions, solutions of meso-tartaric acid do not rotate plane-polarized light. The absence of optical activity is due to a mirror plane in the molecule [segmented line in picture below].[15][16]

Tartaric acid in Fehling's solution binds to copper(II) ions, preventing the formation of insoluble hydroxide salts.
DL-tartaric acid (racemic acid) (when in 1:1 ratio)    mesotartaric acid
dextrotartaric acid
(L-(+)-tartaric acid)    levotartaric acid
(D-(−)-tartaric acid)
L-tartaric acid.png    D-tartaric acid.png    Meso-Weinsäure Spiegel.svg
Forms of tartaric acid
Common name    Tartaric acid    Levotartaric acid    Dextrotartaric acid    Mesotartaric acid    Racemic acid
Synonyms        (2S,3S)-tartaric acid
(S,S)-tartaric acid
(−)-tartaric acid
l-tartaric acid (obsolete)
levotartaric acid
D-tartaric acid
D-threaric acid
('unnatural isomer')[17]    (2R,3R)-tartaric acid
(R,R)-tartaric acid
(+)-tartaric acid
d-tartaric acid (obsolete)
L-tartaric acid
L-threaric acid
(‘natural isomer’)[18]    (2R,3S)-tartaric acid
meso-tartaric acid
erythraric acid    rac-(2R,3S)-tartaric acid
(2RS,3SR)-tartaric acid
(±)-tartaric acid
DL-tartaric acid
dl-tartaric acid (obsolete)
paratartaric acid
uvic acid
Production
L-(+)-Tartaric acid
The L-(+)-tartaric acid isomer of tartaric acid is industrially produced in the largest amounts. It is obtained from 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 milk of lime (Ca(OH)2):[19]

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

Racemic tartaric acid
Racemic tartaric acid (i.e.: a 50:50 mixture of D-(−)-tartaric acid and L-(+)-tartaric acid molecules, racemic acid) can be prepared in a multistep reaction from maleic acid. In the first step, the maleic acid is epoxidized by hydrogen peroxide using potassium tungstate as a catalyst.[19]
In the next step, the epoxide is hydrolyzed.
meso-Tartaric acid
meso-Tartaric acid is formed via thermal isomerization. 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:[20]

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.

Derivatives

Tartar emetic

Commercially produced tartaric acid
Important derivatives of tartaric acid include its salts, cream of tartar (potassium bitartrate), Rochelle salt (potassium sodium tartrate, a mild laxative), and tartar emetic (antimony potassium tartrate).[22][23][24] Diisopropyl tartrate is used as a 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.[25] The median lethal dose (LD50) is about 7.5 grams/kg for a human, 5.3 grams/kg for rabbits, and 4.4 grams/kg for mice.[26] Given this figure, it would take over 500 g (18 oz) to kill a person weighing 70 kg (150 lb), so it may be safely included in many foods, especially sour-tasting sweets. As a food additive, tartaric acid is used as an antioxidant with E number E334; tartrates are other additives serving as antioxidants or emulsifiers.

When cream of tartar is added to water, a suspension results which serves to clean copper coins 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 and Tartrate

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 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 barrels 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. In the mouth, tartaric acid provides some of the tartness in the wine, although citric and malic acids also play a role.

Tartaric acid in citrus
Results from a study showed that in citrus, fruits produced in organic farming contain higher levels of tartaric acid than fruits produced in conventional agriculture.[27]

In superconductors
Tartaric acid seems to increase the critical temperature in certain superconductors, by supposedly raising the oxidation grade, while the mechanism of this phenomenon is still not precisely known.[28]

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.[21] 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 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.[19]

Tartaric Acid
Tartaric acid has a stronger, sharper taste than citric acid. Although it is renowned for its natural occurrence in grapes, it also occurs in apples, cherries, papaya, peach, pear, pineapple, strawberries, mangos, and citrus fruits. Tartaric acid is used preferentially in foods containing cranberries or grapes, notably wines, jellies, and confectioneries. Commercially, tartaric acid is prepared from the waste products of the wine industry and is more expensive than most acidulants, including citric and malic acids. Tartaric acid is one of the least antimicrobial of the organic acids known to inactivate fewer microorganisms and inhibit less microbial growth in comparison with most other organic acids (including acetic, ascorbic, benzoic, citric, formic, fumaric, lactic, levulinic, malic, and propionic acids) in the published scientific literature. Furthermore, when dissolved in hard water, undesirable insoluble precipitates of calcium tartrate can form.