Tartaric acid

Last updated
Tartaric acid [1]
Tartaric acid.svg
Tartaric-acid-3D-balls.png
Ball-and-stick model of L-(+)-tartaric acid
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
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
DrugBank
ECHA InfoCard 100.121.903 OOjs UI icon edit-ltr-progressive.svg
E number E334 (antioxidants, ...)
KEGG
MeSH tartaric+acid
PubChem CID
  • 875  unspecified isomer
UNII
  • InChI=1S/C4H6O6/c5-1(3(7)8)2(6)4(9)10/h1-2,5-6H,(H,7,8)(H,9,10) Yes check.svgY
    Key: FEWJPZIEWOKRBE-UHFFFAOYSA-N Yes check.svgY
  • InChI=1/C4H6O6/c5-1(3(7)8)2(6)4(9)10/h1-2,5-6H,(H,7,8)(H,9,10)
    Key: FEWJPZIEWOKRBE-UHFFFAOYAZ
  • O=C(O)C(O)C(O)C(=O)O
Properties
C4H6O6 (basic formula)
HO2CCH(OH)CH(OH)CO2H (structural formula)
Molar mass 150.087 g/mol
AppearanceWhite powder
Density 1.737 g/cm3 (R,R- and S,S-)
1.79 g/cm3 (racemate)
1.886 g/cm3 (meso)
Melting point 169, 172 °C (R,R- and S,S-)
206 °C (racemate)
165-6 °C (meso)
  • 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
−67.5·10−6 cm3/mol
Hazards
GHS labelling: [3]
GHS-pictogram-acid.svg
Danger
H318
P280, P305+P351+P338+P310
Related compounds
Other cations
Monosodium tartrate
Disodium tartrate
Monopotassium tartrate
Dipotassium tartrate
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).
Yes check.svgY  verify  (what is  Yes check.svgYX mark.svgN ?)

Tartaric acid is a white, crystalline organic acid that occurs naturally in many fruits, most notably in grapes but also in tamarinds, bananas, avocados, and citrus. [1] Its salt, potassium bitartrate, commonly known as cream of tartar, develops naturally in the process of 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 E334 and to impart its distinctive sour taste. Naturally occurring tartaric acid is a useful raw material in organic chemical synthesis. Tartaric acid, an alpha-hydroxy-carboxylic acid, is diprotic and aldaric in acid characteristics and is a dihydroxyl derivative of succinic acid.

Contents

History

Tartaric acid has been known to winemakers for centuries. However, the chemical process for extraction was developed in 1769 by the Swedish chemist Carl Wilhelm Scheele. [4]

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. [5] [6] 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. [7] [8] [9] [10] [11]

Stereochemistry

Tartaric acid crystals drawn as if seen through an optical microscope TartrateCrystal.svg
Tartaric acid crystals drawn as if seen through an optical microscope

Naturally occurring form of the acid is dextro tartaric acid or L-(+)-tartaric acid (obsolete name 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. [12] 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 referred to as (2R,3S)-tartaric acid or (2S,3R)-tartaric acid.

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-Weinsaure Spiegel.svg
Forms of tartaric acid
Common name Tartaric acidLevotartaric acidDextrotartaric acidMesotartaric acidRacemic 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') [18]
(2R,3R)-tartaric acid
(R,R)-tartaric acid
(+)-tartaric acid
d-tartaric acid (obsolete)
L-tartaric acid
L-threaric acid
(‘natural isomer’) [19]
(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
PubChem CID 875 from PubChem CID 439655 from PubChem CID 444305 from PubChem CID 78956 from PubChem CID 5851 from PubChem
EINECS number 205-695-6 201-766-0 205-696-1 205-105-7
CAS number 526-83-0147-71-787-69-4147-73-9133-37-9

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 calcium hydroxide "milk of lime" (Ca(OH)2): [20]

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 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. [20]

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 °C for about 2 days. meso-Tartaric acid can also be prepared from dibromosuccinic acid using silver hydroxide: [21]

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. [22]

Derivatives

Tartar emetic Brechweinstein.jpg
Tartar emetic
Commercially produced tartaric acid CommercialTartaric.jpg
Commercially produced tartaric acid

Important derivatives of tartaric acid include:

Tartaric acid is a muscle toxin, which works by inhibiting the production of malic acid, and in high doses causes paralysis and death. [26] 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. [27] Given this figure, it would take over 500 g (18 oz) to kill a person weighing 70 kg (150 lb) with 50% probability, 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

Unpurified potassium bitartrate can take on the color of the grape juice from which it was separated. HomemadeTartaric.jpg
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 fruits

Grapes and tamarinds have the highest levels of tartaric acid concentration. Other fruits with tartaric acid are bananas, avocados, prickly pear fruit, apples, cherries, papayas, peaches, pears, pineapples, strawberries, mangoes and citrus fruits. [1] [28]

Trace amounts of tartaric acid have been found in cranberries and other berries. [29]

Tartaric acid is also present in the leaves and pods of Pelargonium plants and 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. [22] 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. [20]

Toxicity in canines

While tartaric acid is well-tolerated by humans and lab animals, an April 2021 letter to the editor of JAVMA hypothesized that the tartaric acid in grapes could be the cause of grape and raisin toxicity in dogs. [30]

In dogs, the tartaric acid of tamarind causes acute kidney injury, which can often be fatal. [31]

Related Research Articles

<span class="mw-page-title-main">Louis Pasteur</span> French chemist and microbiologist (1822–1895)

Louis Pasteur was a French chemist, pharmacist, and microbiologist renowned for his discoveries of the principles of vaccination, microbial fermentation, and pasteurization, the last of which was named after him. His research in chemistry led to remarkable breakthroughs in the understanding of the causes and preventions of diseases, which laid down the foundations of hygiene, public health and much of modern medicine. Pasteur's works are credited with saving millions of lives through the developments of vaccines for rabies and anthrax. He is regarded as one of the founders of modern bacteriology and has been honored as the "father of bacteriology" and the "father of microbiology".

<span class="mw-page-title-main">Optical rotation</span> Rotation of the plane of linearly polarized light as it travels through a chiral material

Optical rotation, also known as polarization rotation or circular birefringence, is the rotation of the orientation of the plane of polarization about the optical axis of linearly polarized light as it travels through certain materials. Circular birefringence and circular dichroism are the manifestations of optical activity. Optical activity occurs only in chiral materials, those lacking microscopic mirror symmetry. Unlike other sources of birefringence which alter a beam's state of polarization, optical activity can be observed in fluids. This can include gases or solutions of chiral molecules such as sugars, molecules with helical secondary structure such as some proteins, and also chiral liquid crystals. It can also be observed in chiral solids such as certain crystals with a rotation between adjacent crystal planes or metamaterials.

In chemistry, a racemic mixture or racemate, is one that has equal amounts of left- and right-handed enantiomers of a chiral molecule or salt. Racemic mixtures are rare in nature, but many compounds are produced industrially as racemates.

<span class="mw-page-title-main">Enantiomer</span> Stereoisomers that are nonsuperposable mirror images of each other

In chemistry, an enantiomer – also called optical isomer, antipode, or optical antipode – is one of two stereoisomers that are nonsuperposable onto their own mirror image. Enantiomers are much like one's right and left hands; without mirroring one of them, hands cannot be superposed onto each other. No amount of reorientation in three spatial dimensions will allow the four unique groups on the chiral carbon to line up exactly. The number of stereoisomers a molecule has can be determined by the number of chiral carbons it has.

<span class="mw-page-title-main">Winemaking</span> Production of wine

Winemaking or vinification is the production of wine, starting with the selection of the fruit, its fermentation into alcohol, and the bottling of the finished liquid. The history of wine-making stretches over millennia. There is evidence that suggests that the earliest wine production took place in Georgia and Iran around 6000 to 5000 B.C. The science of wine and winemaking is known as oenology. A winemaker may also be called a vintner. The growing of grapes is viticulture and there are many varieties of grapes.

<span class="mw-page-title-main">Fehling's solution</span> Chemical test for the reducibility of a sugar

In organic chemistry, Fehling's solution is a chemical reagent used to differentiate between water-soluble carbohydrate and ketone functional groups, and as a test for reducing sugars and non-reducing sugars, supplementary to the Tollens' reagent test. The test was developed by German chemist Hermann von Fehling in 1849.

<span class="mw-page-title-main">Potassium bitartrate</span> Chemical salt used in cooking as cream of tartar

Potassium bitartrate, also known as potassium hydrogen tartrate, with formula KC4H5O6, is a chemical compound with a number of uses. It is the potassium acid salt of tartaric acid (a carboxylic acid). In cooking, it is known as cream of tartar.

<span class="mw-page-title-main">Chirality (chemistry)</span> Geometric property of some molecules and ions

In chemistry, a molecule or ion is called chiral if it cannot be superposed on its mirror image by any combination of rotations, translations, and some conformational changes. This geometric property is called chirality. The terms are derived from Ancient Greek χείρ (cheir) 'hand'; which is the canonical example of an object with this property.

<span class="mw-page-title-main">Racemic acid</span>

Racemic acid is an old name for an optically inactive or racemic form of tartaric acid. It is an equal mixture of two mirror-image isomers (enantiomers), optically active in opposing directions. It occurs naturally in grape juice.

<span class="mw-page-title-main">Ammonium chlorate</span> Chemical compound

Ammonium chlorate is an inorganic compound with the formula NH4ClO3.

Arene substitution patterns are part of organic chemistry IUPAC nomenclature and pinpoint the position of substituents other than hydrogen in relation to each other on an aromatic hydrocarbon.

<span class="mw-page-title-main">Tartrate</span> Chemical compound

A tartrate is a salt or ester of the organic compound tartaric acid, a dicarboxylic acid. The formula of the tartrate dianion is OOC-CH(OH)-CH(OH)-COO or C4H4O62−.

<span class="mw-page-title-main">Calcium tartrate</span> Chemical compound

Calcium tartrate, exactly calcium L-tartrate, is a byproduct of the wine industry, prepared from wine fermentation dregs. It is the calcium salt of L-tartaric acid, an acid most commonly found in grapes. Its solubility decreases with lower temperature, which results in the forming of whitish crystalline clusters as it precipitates. As E number E354, it finds use as a food preservative and acidity regulator. Like tartaric acid, calcium tartrate has two asymmetric carbons, hence it has two chiral isomers and a non-chiral isomer (meso-form). Most calcium tartrate of biological origin is the chiral levorotatory (–) isomer.

Chiral resolution, or enantiomeric resolution, is a process in stereochemistry for the separation of racemic mixture into their enantiomers. It is an important tool in the production of optically active compounds, including drugs. Another term with the same meaning is optical resolution.

In enzymology, a tartrate epimerase is an enzyme that catalyzes the chemical reaction

<span class="mw-page-title-main">Acids in wine</span>

The acids in wine are an important component in both winemaking and the finished product of wine. They are present in both grapes and wine, having direct influences on the color, balance and taste of the wine as well as the growth and vitality of yeast during fermentation and protecting the wine from bacteria. The measure of the amount of acidity in wine is known as the “titratable acidity” or “total acidity”, which refers to the test that yields the total of all acids present, while strength of acidity is measured according to pH, with most wines having a pH between 2.9 and 3.9. Generally, the lower the pH, the higher the acidity in the wine. There is no direct connection between total acidity and pH. In wine tasting, the term “acidity” refers to the fresh, tart and sour attributes of the wine which are evaluated in relation to how well the acidity balances out the sweetness and bitter components of the wine such as tannins. Three primary acids are found in wine grapes: tartaric, malic, and citric acids. During the course of winemaking and in the finished wines, acetic, butyric, lactic, and succinic acids can play significant roles. Most of the acids involved with wine are fixed acids with the notable exception of acetic acid, mostly found in vinegar, which is volatile and can contribute to the wine fault known as volatile acidity. Sometimes, additional acids, such as ascorbic, sorbic and sulfurous acids, are used in winemaking.

<span class="mw-page-title-main">Antimony potassium tartrate</span> Chemical compound

Antimony potassium tartrate, also known as potassium antimonyl tartrate, potassium antimontarterate, or tartar emetic, has the formula K2Sb2(C4H2O6)2. The compound has long been known as a powerful emetic, and was used in the treatment of schistosomiasis and leishmaniasis. It is used as a resolving agent. It typically is obtained as a hydrate.

Chemical compounds that come as mirror-image pairs are referred to by chemists as chiral or handed molecules. Each twin is called an enantiomer. Drugs that exhibit handedness are referred to as chiral drugs. Chiral drugs that are equimolar (1:1) mixture of enantiomers are called racemic drugs and these are obviously devoid of optical rotation. The most commonly encountered stereogenic unit, that confers chirality to drug molecules are stereogenic center. Stereogenic center can be due to the presence of tetrahedral tetra coordinate atoms (C,N,P) and pyramidal tricoordinate atoms (N,S). The word chiral describes the three-dimensional architecture of the molecule and does not reveal the stereochemical composition. Hence "chiral drug" does not say whether the drug is racemic, single enantiomer or some other combination of stereoisomers. To resolve this issue Joseph Gal introduced a new term called unichiral. Unichiral indicates that the stereochemical composition of a chiral drug is homogenous consisting of a single enantiomer.

<span class="mw-page-title-main">Choline bitartrate</span> Choline bitartrate

Choline bitartrate is an organic compound with the chemical formula [(CH3)3NCH2CH2OH]+HOOC−CH(OH)−CH(OH)−COO. It is a white crystalline powder with an acid taste. It is hygroscopic when exposed to air. Modern texts refer to the choline salt of the natural form of tartaric acid, that is, the salt called choline dextrobitartrate, choline (2R,3R)-bitartrate or choline L-(+)-bitartrate.

<span class="mw-page-title-main">Sodium ammonium tartrate</span> Chemical compound

Sodium ammonium tartrate (NAT) is an organic compound with the formula Na(NH4)[O2CCH(OH)CH(OH)CO2]. The salt is derived from tartaric acid by neutralizing with ammonia and with sodium hydroxide. Louis Pasteur obtained enantiopure crystals of the tetrahydrate of NAT, via the process of spontaneous resolution. His discovery led to increased study of optical activity, which eventually was shown to have broad implications. Many modification of this salt have been investigated by X-ray crystallography, including the racemate, which crystallizes as the monohydrate.

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