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DL-TARTARIC ACID

DL-Tartaric acid is a white, crystalline acid that is widely used as an intermediate or resolving agent in the pharmaceutical industry.
DL-Tartaric Acid is white powder, Widely used in the food industry, used as a foaming agent of beer, acid taste agent, taste modified agent, and is mainly used to make tartaric acid salts, like potassium sodium tartrate, it can also be served as a beer vesicant, foodstuff sourness agent and flavouring etc.Tartaric acid is a white crystalline organic acid that occurs naturally in many plants, most notably in grapes.Its salt, potassium bitartrate, commonly known as cream of tartar, develops naturally in the process of winemaking. 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 D-(-)-tartaric acid.

 

CAS no.: 133-37-9
EC Number: 205-105-7


IUPAC names
(+-)-Tartaric acid
(+-)-tartaric acid
(2R,3R)-2,3-dihydroxybutanedioic acid
(±)-tartaric acid
2, 3-Dihydroxybutanedioic Acid
2,3 dihydroxybutanedioic acid
2,3-Dihydroxybutanedioic acid
2,3-dihydroxybutanedioic acid
2,3-dihydroxysuccinic acid
Acide Tartrique Poudre
Butanedioic acid, 2,3-dihydroxy-, (2R,3R)-rel-
DL-Tartaric Acid
DL-Tartaric acid
DL-tartaric acid
Tartaric acid
tartaric acid


SYNONYMS: 
(+-)-Tartaric acid; (2RS,3RS)-Tartaric acid; Butanedioic acid, 2,3-dihydroxy-, (R*,R*)-; DL-Tartrate; Paratartaric acid; Racemic acid; Racemic tartaric acid; Resolvable tartaric acid; Tartaric acid D,L; Traubensaure; Uvic acid; dl-Tartaric acid; Butanedioic acid, 2,3-dihydroxy-, (2R,3R)-rel-; Butanedioic acid, 2,3-dihydroxy-, (R*,R*)-(+-)-; Butanedioic acid, 2,3-dihydroxy-, (theta,theta)-(+-)-; [ChemIDplus] dl-Weinsaure (German); Vogesensaure (German); [Merck Index]; Uvic acid;Sal tartar;DL-Tartaric;DL-TARTRATE;DL-Weinsαure;Traubensaure;Traubensαure;Vogesensαure;RACEMIC ACID;TARTARIC ACID;DL-Tartaric acid;tartaric acid;2,3-Dihydroxysuccinic acid;2,3-Dihydroxybutanedioic acid;133-37-9;526-83-0;Racemic acid;Uvic acid;Traubensaur;;Racemic tartaric acid;DL-Tartrate;Paratartaric acid;Paratartaric aicd;Threaric acid;Resolvable tartaric acid;BUTANEDIOIC ACID, 2,3-DIHYDROXY-;(+)-Tartaric acid;Natural tartaric acid;Acidum tartaricum;NSC62778;Tartaric acid D,L;tartrate;Tartaric acid, L-(+)-;Baros;CHEBI:15674;dl-2,3-dihydroxybutanedioic acid;Dextrotartaric acid;2RS,3RS)-Tartaric acid;MFCD00071626;NSC 148314;Butanedioic acid, 2,3-dihydroxy-, (2R,3R)-rel-;E-7050 (2S,3S)-2,3-dihydroxysuccinic acid;(2R,3R)-rel-2,3-Dihydroxysuccinic acid;DL-Tartaric acid, 99.5%;Butanedioic acid, 2,3-dihydroxy-(R*,R*)-(.+/-.)-;Butanedioic acid, 2,3-dihydroxy-, (R*,R*)-;868-14-4;Tartaric acid, L-;(2R,3R)-2,3-Dihydroxybernsteinsaeure;Tartaric acid (VAN);1007601-97-9;Kyselina vinna [Czech];NSC155080;Butanedioic acid, 2,3-dihydroxy- (2R,3R)-;Tartaric acid [USAN:JAN];(.+-.)-Tartaric acid,C4H6O6;(+)-(2R,3R)-Tartaric acid;d-alpha,beta-Dihydroxysuccinic acid;NSC-6277;Kyselina 2,3-dihydroxybutandiova [Czech];(+) tartaric acid;(-) tartaric acid;1,2-Dihydroxyethane-1,2-dicarboxylic acid;AI3-06298;1,2-dicarboxylic acid;(-) D-Tartaric acid;ACMC-209qpg;Sal tartar (Salt/Mix);Tartaric acid, (DL)-;Butanedioic acid, 2,3-dihydroxy- (R-(R*,R*));Butanedioic acid, 2,3-dihydroxy-, [S-(R*,R*)]-;Malic acid, 3-hydroxy-;laevo-(+)-tartaric acid;dextro,laevo-tartaric acid;Succinic acid,3-dihydroxy;SCHEMBL848,ACMC-209cz3;bmse000167;Succinic acid,3-dihydroxy-;(.+/-.)-Tartaric acid;DSSTox_CID_26986;DSSTox_RID_82036;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;L+Tartaric Acid FCC, NF, USP;2,3-bis(oxidanyl)butanedioic acid,HMS3370M15;(+)-2,3-dihydroxybutanedioic acid;(S,S)-Tartaric acid;Tartaric acid;BCP14303;Tox21_302052;BBL011588;MFCD00064206;s2997;STK387106;2,3-Dihydroxysuccinic acid, (DL)-;3-carboxy-2,3-dihydroxypropanoic acid;AKOS000120086;AKOS016844048;MCULE-3867000095;SMP2_000051;d-.alpha.,.beta.-Dihydroxysuccinic acid;NCGC00256063-01;NCGC00347131-03;AK105884;AK116146;AS-10983;CAS-133-37-9;NCI60_001102;(+)-2,3-dihydroxy-1,4-butanedioic acid;(+/-)-2,3-dihydroxy-1,4-butanedioic acid;1467-EP2269610A2;1467-EP2269986A1;1467-EP2269988A2;1467-EP2269989A1;1467-EP2269990A1;1467-EP2270003A1

DL-Tartaric acid has been used as food additives such as sour seasonings.
DL-Tartaric can also widely be used as industrial chemicals such as starting materials for detergents.
DL-Tartaric acid is a white, crystalline powder.
DL-Tartaric is mainly used in the food industry as an acidulant or ingredient producing emulsifier, and can be used as a starting material for pyruvate.
Its usage also covers the construction industry as a retarder, metal complexing agent for electroplating industry.


DL-Tartaric acid is a dicarboxylic acid available as a white crystalline powder.
DL-Tartaric acid can be used in areas below:
1) As an acidulant, or ingredient producing emulsifier in the food industry;
2) As retarder in the construction industry; 
3) As an intermediate, resolving agent or salt-forming agent in the pharmaceutical industry;
4) As a complexing agent, chelating agent or antiscaling agent in the electroplating and polishing industry;
5) As fruit acid in the cosmetic industry.

DL-Tartaric acid is a white, crystalline acid that is widely used as an intermediate or resolving agent in the pharmaceutical industry.
DL-Tartaric Acid is white powder, Widely used in the food industry, used as a foaming agent of beer, acid taste agent, taste modified agent, and is mainly used to make tartaric acid salts, like potassium sodium tartrate, it can also be served as a beer vesicant, foodstuff sourness agent and flavouring etc.

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

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.

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.
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.

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 DL-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.
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

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

Production
DL-Tartaric Acid
The DL-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):

KO2CCH(OH)CH(OH)CO2H + Ca(OH)2 → Ca(O2CCH(OH)CH(OH)CO2) + KOH + H2O
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:

Ca(O2CCH(OH)CH(OH)CO2) + H2SO4 → HO2CCH(OH)CH(OH)CO2H + CaSO4
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.

HO2CC2H2CO2H + H2O2 → OC2H2(CO2H) 2
In the next step, the epoxide is hydrolyzed.

OC2H2(CO2H)2 + H2O → (HOCH)2(CO2H)2
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:

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
DL-Tartaric Acid can participate in several reactions.
As shown in the reaction scheme below, dihydroxymaleic acid is produced upon treatment of DL-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.


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).
Diisopropyl tartrate is used as a co-catalyst in asymmetric synthesis.

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 colour 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).

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.

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.

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. 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.
DL-Tartaric Acid (2,3-Dihydroxysuccinic acid) is a white, crystalline organic acid isolated from many plants, particularly tamarinds and grapes and is used as an antioxidant and an additive agent to give a sour taste.


Tartaric acid is a white crystalline diprotic organic acid.
The compound occurs naturally in many plants, particularly in grapes, bananas, and tamarinds.
It is also one of the main acids found in wine.

Tartaric acid can be added to food when a sour taste is desired.
It is also used as an antioxidant. Salts of tartaric acid are known as tartarates.
The chemical is a dihydroxy derivative of succinic acid.

Tartaric acid is found in cream of tartar and baking powder.
The chemical compound is used in silvering mirrors, tanning leather, and Rochelle Salt.
In medical analysis, tartaric acid is used to make solutions for the determination of glucose.

Tartaric acid is a white, crystalline organic acid with anti-inflammatory and anti-oxidant properties that occur naturally in many fruits.
These properties help to stimulate overall helps to boost an individual’s immune systems.
Tartaric acid is a dicarboxylic acid, which is notably found in different fruits such as grapes, bananas, tamarind and citrus.
It is also obtained from wine fermentation by-products by salts, potassium bitartrate, also known as tartar cream.
Tartaric acid is an important ingredient in bakery items where, when mixed with baking powder, it acts as a leavening agent.
It also improves fruit flavours and in baked goods stabilizes batter structures and colour.
Tartaric acid extracts serve as buffers in the winemaking cycle to control antioxidant E334, acidity and preservatives; in other food items, they act as natural flavour enhancers and food emulsifiers.


Description: White solid;  Colorless or white odourless solid; [JECFA] White odourless crystalline powder; [Acros Organics MSDS]

Sources/Uses
Used as a synergist for antioxidants, acid, emulsifier, sequestrant, and flavouring agent; 

Tartaric Acid, also called dihydroxysuccinic acid [HOOC(CHOH)2COOH]), is a white crystalline naturally occurring carboxylic acid; melting at 171 C, soluble in water and alcohols.
It is obtained naturally as a by-product of wine fermentation along with its salts.
This natural acid is used as an antioxidant in food.
Tartaric acid has two asymmetrical carbon atoms and three chiral isomers; the dextro-, levo-, (optically active) and meso- forms (optically inactive).
DL-Tartaric Acid said to be enantiomorphs (each molecule is asymmetrical and has the mirror image of the other).
There are two asymmetrical carbon atoms in meso-tartaric acid, but the molecule is symmetrical and does not exhibit optical activity; the optical activity is internally compensated, the effect of one asymmetrical carbon atom balancing the effect of the other.
A pair of optical isomers such as dl-tartaric acid and meso-tartaric acid, which are not enantiomorphs, are called diastereoisomers. Tartaric Acid is a useful raw material for the synthesis of other chiral compounds.
DL-tartaric acid (called also d-2,3-dihydroxysuccinic acid or l-2,3-dihydroxybutanedioic acid) is chiefly found in many plant especially grape.
This form can be partially converted to the others by heating it with an aqueous alkali (potassium hydroxide) as the isomeric forms differ from each other in boiling points.
It can be synthesized by the reaction of maleic acids or fumaric acids with aqueous potassium permanganate.
Tartaric acid is biodegradable and no pollution problems are known.
Tartaric acid is used chiefly in the form of its salts, e.g., cream of tartar (potassium hydrogen tartrate), Rochelle salt (potassium sodium tartrate) and Tartar Emetic (antimony potassium tartrate).
It is used to enhance flavours in foods, confectionery and beverages.
It is used as a chemical intermediate and a sequestrant and in tanning, ceramics, photography, textile processing, mirror silvering, and metal colouring.


Tartaric Acid is a synergist for antioxidants, acids, emulsifiers, sequestrants, flavouring agents

FUNCTIONAL USES
Synergist for antioxidants, acid, emulsifier, sequestrant, flavouring agent

Solubility
Freely soluble in water; sparingly soluble in ethanol

Application Areas
Tartaric acid and its derivatives have a plethora of uses in the field of pharmaceuticals.
It has been used in the production of effervescent salts, in combination with citric acid, in order to improve the taste of oral medications.
The potassium antimonyl derivative of the acid known as tartar emetic is included, in small doses, in cough syrup as an expectorant.

Melting range
200 - 206 with decomposition when heated rapidly in a sealed capillary tube

substances
N potassium permanganate while keeping the solution at 20o. The colour of the solution does not disappear within 3 min.

Chemical Properties
Tartaric acid, HOOC(CHOH)2COOH, is a water- and alcohol-soluble colourless crystalline solid with an acid taste and a melting temperature of 170°C (338 OF).
It is also known as dihydroxy succinic acid.
Tartaric acid is used as a chemical intermediate and a sequestrant, as well as in tanning, effervescent beverages, baking powder, ceramics, photography, textile processing, mirror silvering, and metal colouring.


Chemical Properties
Tartaric acid is odourless but has a characteristic acid taste.
Naturally occurring tartaric acid is generally of the L-configuration (based on the absolute configuration of D-glyceric acid).
The L-forms of tartrates are dextrorotatory in solution and thus are designated as L(+)-tartrates.
For a detailed description of this chemical, refer to Burdock (1997).

Occurrence
dl-Tartaric acid occurs in many fruits or other parts of the plant, free or combined with potassium, calcium or magnesium.
It is also reported found in raw, lean fish, white wine, red wine and port wine.

Preparation
The tartrates used in commerce are obtained as a by-product of wine manufacture and have the L(+) configuration.
Produced from argols or wine lees, which are formed in the manufacture of wine by extracting the potassium acid tartrate, transforming this into the calcium salt and then acidifying with dilute sulfuric acid; also by oxidation of d-glucose with nitric acid.
The dl-tartaric acid is obtained by boiling the d-tartaric acid with an aqueous solution of NaOH or by oxidation of fumaric acid.
The l- and the meso-tartaric acid are also known but are less important.

DL-Tartaric acid Preparation Products And Raw materials

Raw materials
CALCIUM TARTRATE Tungstic acid Maleic acid Maleic anhydride Hydrogen peroxide Sodium pyruvate (+/-)-TRANS-EPOXYSUCCINIC ACID D(-)-Tartaric acid CIS-EPOXYSUCCINIC ACID

Preparation Products
L(+)-Diethyl L-tartrate Potassium tartrate Disodium tartrate dihydrate L-Antimony potassium tartrate Ammonium L-tartrate Pyruvic acid Kitasamycin tartrate Potassium sodium tartrate (2S,3S)(-)-Dihydroxybutane-1,4-dioic acid diethyl ester Potassium Bitartrate 4-Hydroxy-D-(-)-2-phenylglycine


Tartaric acid is a white crystalline organic acid that occurs naturally in many plants, most notably in grapes.
Its salt, potassium bitartrate, commonly known as cream of tartar, develops naturally in the process of winemaking.
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 D-(-)-tartaric acid.


Application Areas

1. DL – TARTARIC ACID is widely used as beverages and other food acidifier, similar to the use and citric acid.
Combination of tartaric acid and tannin can be used as mordant acid dyes, but also for the photographic industry, and the fixation of certain imaging operations, which have a photosensitive iron salts, it can be used to produce a blueprint

2. DL - Tartaric acid with a variety of metal ions complexation can be used for metal surface cleaning agents and polishing agents

3. Potassium sodium tartrate (Rochelle salt) can be prepared Fehling, but also used in medicine as laxatives and diuretics, but also as a Sims can be fun intermediates

4. The crystal has piezoelectric properties can be used for the electronics industry

5. DL - TARTARIC ACID (CAS NO.147-71-7) is used for chromatographic analysis of reagent and a masking agent. And it also used as split agent for pharmaceutical, food additives, chemical and biological reagents

6. This product is widely used in food industry, such as beer foam, food sour agent, Jiao flavor agent and used in soft drinks, candy, fruit juice, sauces, cold dish, and baking powder and so on. This product is in line with Japanese food additives Kimisada book

DL Tartaric Acid is a colorless and semi-transparent or white powder, with a sour taste.
It is widely used in many fields such as foodstuff, medicine, the chemical and light industries etc., and is mainly used to make tartrates (tartaric acid salts), like antimony potassium tartrate, and potassium sodium tartrate.
It can be used as a beer vesicant, foodstuff sourness agent, and flavoring etc.
Its sourness is 1.3 times of that of citric acid, and it is especially suitable to be a sourness agent of grape juice.
It is also very important for the tannage, photograph, glass, enamel and telecommunication equipment industries.

Tartaric Acid is a white crystalline dicarboxylic acid found in many plants, particularly tamarinds and grapes.
Tartaric acid is used to generate carbon dioxide through interaction with sodium bicarbonate following oral administration.
Carbon dioxide extends the stomach and provides a negative contrast medium during double-contrast radiography.

Tartaric acid is an organic acid naturally found in fruits including grapes and tamarind.
It is a principal ingredient in wine and provides it with the characteristic tart taste.
Tartaric acid is primarily manufactured from natural raw materials; however, it can also be manufactured synthetically from maleic anhydride. Tartaric acid finds applications in the wine, food & beverages, construction, pharmaceutical, chemical, leather tanning, and metal finishing industries. It is used as an acidulant, pH control, and flavorant in wine. Tartaric acid is also used as an anti-microbial agent, anti-caking agent in bakery items and flavorant for fruit juices in the food & beverages industry. In the pharmaceutical industry, it is used as an excipient for drugs with poor solubility at higher pH levels. Tartaric acid is used as an anti-set agent in cement formulations in the construction industry.

DL tartaric acid is very useful in many applications,

·Tartaric Acid is widely used as antioxidant and acidity regulator in food production.
As antioxidant: in canned food to maintain flavor and appearance.
As acidity regulator: in canned food and confectionery to improve flavor.
·Beverage
Dl Tartaric Acid is widely used as antioxidant and acidity regulator in beverage.
As acidity regulator: in soft drink to improve flavor.
·Pharmaceutical
Dl Tartaric Acid is widely used as intermediate in Pharmaceutical.
As intermediate: in medicine manufacturing.
·Cosmetics
·Agriculture/Animal Feed
·Other Industries
DL-Tartaric Acid is widely used as an antioxidant in various other industries.
As antioxidant: in leather processing to soften the leather.
DL-Tartaric Acid is used in silvering mirrors, tanning leather, and in the making of Rochelle salt, which is sometimes used as a laxative.


Salts of Tartaric
Salts of tartaric acid are known as tartrates. It is a dihydroxyl derivative of succinic acid.

DESCRIPTION
In general, where biological molecules have optical isomers, only one of the isomers or forms will be active biologically.
The other will be unaffected by the enzymes in living cells. The meso form of the molecule is not affected by polarized light.


Application Areas
DL-Tartaric acid is found in cream of tartar, which is used in making candies and frostings for cakes.
DL-Tartaric acid is also used in baking powder where it serves as the source of acid that reacts with sodium bicarbonate (baking soda). This reaction produces carbon dioxide gas and lets products “rise,” but it does so without the “yeast” taste that can result from using active yeast cultures as a source of the carbon dioxide gas.

DL-Tartaric acid is used in silvering mirrors, tanning leather, and in the making of Rochelle Salt, which is sometimes used as a laxative.
Blueprints are made with ferric tartarte as the source of the blue ink.

In medical analysis, tartaric acid is used to make solutions for the determination of glucose.
Common esters of tartaric acid are diethyl tartarate and dibutyl tartrate. Both are made by reacting tartaric acid with the appropriate alcohol, ethanol or n-butanol.
In the reaction, the Hydrogen of the COOH acid group is replaced with an ethyl group (diethyl tartarate) or butyl group (dibutyl tartarate.
These esters are used in manufacturing lacquer and in dyeing textiles.

DL-Tartaric acid is a white crystalline organic acid. It occurs naturally in many plants, particularly grapes and tamarinds, and is one of the main acids found in wine.
It is added to other foods to give a sour taste and is used as an antioxidant. Salts of tartaric acid are known as tartrates.
It is a dihydroxy derivative of dicarboxylic acid.

DL-Tartaric acid was first isolated from potassium tartrate, known to the ancients as tartar, c. 800 by the Persian alchemist Jabir ibn Hayyan, who was also responsible for numerous other basic chemical processes still in use today.
The modern process was developed in 1769 by the Swedish chemist Carl Wilhelm Scheele.
The chirality of tartaric acid was discovered in 1832 by Jean Baptiste Biot, who observed its ability to rotate polarized light.
Louis Pasteur continued this research in 1847 by investigating the shapes of tartaric acid crystals, which he found to be asymmetric.
Pasteur was the first to produce a pure sample of levotartaric acid.

Stereochemistry
Naturally-occurring tartaric acid is chiral, meaning that it has molecules that are non-superimposable on its mirror images.
It is a useful raw material in organic chemistry for the synthesis of other chiral molecules.
The naturally occurring form of the acid is DL-Tartaric acid or dextrotartaric acid.
The mirror-image (enantiomeric) form, levotartaric acid or D-(−)-tartaric acid, and the achiral form, mesotartaric acid, can be made artificially.

They are abbreviations of dextro- and levo-, and nowadays should not be used.
Levotartaric and dextrotartaric acid are enantiomers, mesotartaric acid is a diastereomer of both of them.

A rarely occurring optically inactive form of tartaric acid, DL-tartaric acid is a 1:1 mixture of levo and dextroforms.
It is distinct from mesotartaric acid and was called racemic acid (from Latin racemus - "a bunch of grapes").
The word racemic later changed its meaning, becoming a general term for 1:1 enantiomeric mixtures - racemates.


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).

DL-Tartaric acid is a muscle toxin, which works by inhibiting the production of malic acid, and in high doses causes paralysis and death.
The minimum recorded fatal dose for a human is about 12 grams. In spite of that, it is 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.
This is due to the fact that the tartrate solution can dissolve the layer of copper(II) oxide present on the surface of the coin.
Copper(II)-tartrate complex that is formed is easily soluble in water. 


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.
These "tartrates" are harmless, despite sometimes being mistaken for broken glass, and are prevented in many wines through cold stabilization.
The tartrates that remain on the inside of aging barrels were at one time a major industrial source of potassium bitartrate.

However, 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 that is currently out of fashion in the wine world, although citric and malic acids also play a role.
The modern practice of extended hang time, where grapes are allowed to sit on the vine nearly until they become raisins, can dramatically reduce the taste of tartaric acid in a wine, leaving it smoother but also potentially less compatible with food

Tartaric Acid
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.


Tartaric acid (2,3-dihydroxybutanedioic acid) is a naturally occurring dicarboxylic acid containing two stereocenters.


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.


Dl-Tartaric acid is an abundant constituent of many fruits such as grapes and bananas and exhibits a slightly astringent and refreshing sour taste. It is one of the main acids found in wine. It is added to other foods to give a sour taste and is normally used with other acids such as citric acid and malic acid as an additive in soft drinks, candies, and so on. It is produced by acid hydrolysis of calcium tartrate, which is prepared from potassium tartrate obtained as a by-product during wine production. Optically active tartaric acid is used for the chiral resolution of amines and also as an asymmetric catalyst.


The form of tartaric acid found naturally in grapes and often produced synthetically for use in handling is the dl-tartaric acid isomer.
This form is generally referred to as the ‘dextro form’ (Church and Blumberg,28 1951).
The D(-) form of tartaric acid is less common in nature and has almost no practical uses.
The third form is an achiral isomer, mesotartaric acid, that also can be manufactured

Properties of the Substance:
An organic acid, tartaric acid is an odourless, white crystalline solid (Smith and Hong-Shum, 2008).
The substance has a strong, tart taste and contributes to the flavours of many fruits (Furia, 1972).
It has a high Ka (acid-dissociation equilibrium constant; a measure of the strength of acidity) and possesses microbial stability.
It is found naturally in plants including grapes, bananas, and tamarinds

Specific Uses of the Substance:
Tartaric acid is a natural organic acid that is in many plants especially grapes, bananas, and tamarinds.
Tartaric acid can be used to create several different salts, including tartar emetic (antimony potassium tartrate), cream of tartar (potassium hydrogen tartrate), and Rochelle salt (potassium sodium tartrate).
The primary uses of tartaric acid are associated with its salts.
Tartaric acid and its salts have a very wide variety of uses. These include use as an acidulant, pH control agent, preservative, emulsifier, chelating agent, flavour enhancer and modifier, stabilizer, anti-caking agent, and firming agent.
It has been used in the preparation of baked goods and confectionaries, dairy products, edible oils and fats, tinned fruits and vegetables, seafood products, meat and poultry products, juice beverages and soft drinks, sugar preserves, chewing gum, cocoa powder, and alcoholic drinks.

As an acidulant and flavouring agent, tartaric acid is known to enhance the flavours of the fruits in which is a natural derivative.
Tartaric acid is commonly used to enhance grape flavors and to enhance flavours associated with raspberry, oranges, lemon, gooseberry, and currant.

Tartaric acid and its immediate byproducts are particularly useful in baking.
Due to its acidic properties,tartaric acid is used in baking powder in combination with baking soda (sodium bicarbonate).
When tartaric acid reacts with sodium bicarbonate, carbon dioxide gas is produced, causing various baking products to ‘rise’ without the use of active yeast cultures.
This action alters the texture of many foods. Tartaric acid and its salts are used in pancake, cookie, and cake mixes because of these properties
Cream of tartar is used to make cake frosting and candies.

In the winemaking process, tartaric acid is used to alter acidity. Tartaric acid is a natural component of grapes, which are frequently used in the production of wine.
However, some wines are not made with grapes and a tablet of nonsynthetic or synthetic tartaric acid is added to wine to increase the mixture’s acidity.
In addition, organic acids, such as tartaric acid, are known to have antimicrobial properties which make them an important component in wine and other foods.
These antimicrobial properties are associated with the natural acidity of tartaric acid, which creates an unfavourable environment for microorganisms to survive and grow.
The typical concentrations of tartaric acid in wines range from 1500 to 4000 mg/L. Higher levels may cause an unpleasant and sour taste.

Industrial and manufacturing uses of tartaric acid and its derivatives include leather tanning, mirror silvering, ceramics, photography, and blueprinting (ferric tartrate serves as a source of blue ink).
Diethyl tartarate and dibutyl tartrate are common esters of tartaric acid and are used in dyeing textiles and the manufacture of lacquer.

DL-Tartaric acid is used in several medical applications including the manufacture of solutions that are used to determine glucose levels.
Rochelle Salt is occasionally used as a laxative. Tartaric acid also acts as a skin coolant and cream of tartar is an effective cleansing agent.
In non-permanent hair dyes, tartaric acid acts as a mild acid

The FDA classifies nonsynthetic DL-tartaric acid and its salts (i.e. L(+) potassium acid tartrate, DL sodium potassium tartrate acid) to be GRAS.
The FDA has compiled consumer data and determined that 6 mg each of tartaric acid and potassium acid tartrate added to foods is ingested daily per capita (a total of about 0.2 milligrams (mg) per kilogram (kg) in an adult).
These substances are not believed to be hazardous to the general public if used at levels that are now typical, or that might reasonably be expected in the future.
In 2006, the FDA ruled that a synthetic form of DL tartaric acid is also considered GRAS.
Synthetic DL tartaric acid is produced by the conversion of maleic anhydride to tartaric acid through the enzymatic action of the enzyme cis-epoxisuccinate hydrolase contained in immobilized Rhodococcus ruber cells.
The FDA also regulates the use of L(+) tartaric acid as an agent for compensating for the natural acidity of the fruit juice ingredient in fruit jellies, jams, preserves, butter, or related products.

Additionally, the use of DL-tartaric acid is permitted as a neutralizing agent in cocoa products, including chocolate liquor and breakfast cocoa 
The total amount of tartaric acid permitted for use in cocoa products is not to exceed 1.0 part by weight.

Action of the Substance:
Generally, only DL-tartaric acid is used in food applications. Tartaric acid increases the acidity of a solution and acts as an anti-microbial agent to preserve food.
The addition of tartaric acid (or products already known to contain tartaric acid) lowers the pH of a solution.
In fruit juices, tartaric acid helps to maintain the proper sugar/acid balance in fruit juices.
By lowering the pH of a solution, the tartaric acid acts as an effective antimicrobial agent by creating an environment too acidic for most microorganisms to grow.

Baking powder is used in many baking applications and tartaric acid produces carbon dioxide gas following reaction with sodium bicarbonate.
This action causes baking products to ‘rise’ without the use of active yeast cultures.
The use of baking powder containing tartaric acid alters the texture of many foods

As an emulsifier, tartaric acid acts by attaching to a surface and then links two repelling substances, such as oil and water.
This action is useful in the production of dairy products including milk because fats settle on the surface of the milk (i.e. a cream) and must be homogeneously mixed to create milk for drinking.
DL-Tartaric acid acts as a chelating agent and is used in the production of canned fruit products.
Chelates are formed when an organic acid binds with metal and prevents its reaction with another chemical.
Chelating agents prevent enzymatic browning through the formation of a complex free metal and inhibitors through an unshared pair of elec

Combinations of the Substance:
At the end of the winemaking process, DL-tartaric acid is an unwanted component.
In order to precipitate tartaric acid, winemakers add calcium hydroxide and potassium hydroxide to the mixture and then evaporate this solution, producing a white powder that contains calcium or potassium tartrate along with other chemical components.
The powder is sold to manufacturing facilities that purify DL-tartaric acid

DL-tartaric acid is used in combination with citric acid to impart tartness to many flavors, including wild cherry and sour apple flavors (Smith and Hong-Shum, 2003).
In food and beverages, DL-Tartaric acid us used a synergist to increase the antioxidant effect of other substances (Hui, 2006a).

Status

Historic Use:
The ancient Greeks and Romans first identified DL-tartaric acid as a by-product of winemaking; however, the product was not harnessed for use because a wine was not traditionally stored in wooden casks or containers suitable for the sediment that contains the crude tartar.
As the use of wooden casks for the collection of wine increased, so did the collection of crude tartar.
Some winemakers exclusively using wooden casks for the storage of wine so that crude tartar could be collected more efficiently.

In the 1400s, Paracelsus identified the use of tartar as medicine but was incorrect in his analysis of the chemical.
The chemical was first isolated in the mid-1700s after the cream of tartar was boiled with chalk and treated with sulfuric acid.
DL-Tartaric acid is used to restore acidity in foods that contain fruit juices and also act as a neutralizer in cocoa products.
Additional food products made using DL-tartaric acid include bakery products, gelatin, soft drinks, and confectionery products.

Synthetic tartaric acid is currently available for commercial use and is manufactured primarily by the conversion of maleic anhydride to tartaric acid using the enzymatic action of cis-eposxisuccinate hydrolase contained in immobilized Rhodococcus ruber cells (FDA, 2009).


Nonsynthetic tartaric acid is also available for commercial use and is produced following precipitation from sediment and wine wastes obtained during the production of grape wines.
Tartaric acid is a naturally occurring organic acid found in grapes and it is estimated that the average concentration of tartaric acid in winery waste is approximately 50 to 75 kg/ton in grape pomace and approximately 100 to 150 kg/ton in yeast lees (Nerantzis and Tartaridis, 2006).
Tartaric acid is observed at the end of the winemaking in the form of crystals.
These crystals form after potassium and calcium present naturally in wine combine with tartaric acid and form the compounds potassium bitartrate and calcium tartrate, respectively.
During fermentation, these compounds precipitate out and evidence of this action is noted in the formation of crystals.


DL-tartaric acid is found as a secondary organic acid in many fruits including grapes, cherries, apples, mangos, raspberries, and strawberries. In tamarinds, tartaric acid is a predominant organic acid.
The nonsynthetic form of tartaric acid used for many food and industrial applications is
derived from the wastes associated with winemaking. Grape growers and winemakers produce a significant amount of waste materials and tartaric acid is contained in grape pomace and yeast lees.
DL-Tartaric acid can be precipitated out of wastes and the actual wine solution by adding potassium hydroxide or calcium hydroxide.
After evaporation, tartaric acid in the form of crystals remains and can be sent for purification 


Nonsynthetic DL- tartaric acid and its salts (i.e. L(+) potassium acid tartrate, L(+) sodium-potassium
308 tartrate acid) are classified by the FDA to be GRAS. These substances are not believed to be hazardous to
309 the general public if used at levels that are now current (a total of about 0.2mg per kg in an adult),
310 or that might reasonably be expected in the future.


One of the many functions of DL- tartaric acid is the ability to act as a preservative.
The other primary functions of DL- tartaric acid are discussed in more detail in the sections on Specific Uses and the Action of the Substance.

DL-Tartaric acid acts as an effective preservative by controlling the pH of a variety of food products by altering the acidity and preventing the growth of spoilage microbes.
The first dissociation constant or pK1 of tartaric acid is equal to 2.98 and the second dissociation constant or pK2 is equal to 4.34.
Typically an acidic environment causes a loss in enzymatic function in spoilage microbes, thereby destroying them.
Tartaric acid is used to alter the acidity of milk, margarine, meat and poultry products, fruit preserves, jellies, and jams, canned fruits, sherbets, beverages (including fruit juices), and soft drinks.
A small amount of tartaric acid is added to a solution (1-3% of the total solution) that meat carcasses are dipped in for the reduction of microbial populations present on the carcass.

DL-tartaric acid is used to improve flavours, colours, and textures lost in food processing (Smith and Hong344 Shum, 2009).

As an acidulant, DL-tartaric acid is used to improve the taste and enhance flavours of fruit-flavoured products and can add intensity to the sweetness of sucrose (Heath, 1981).
A wide variety of products may contain tartaric acid, including fruit-flavoured carbonated and noncarbonated beverages, dry beverage powders, low-calorie beverages, candies, fruit gums, and thermally processed fruits. Specifically, tartaric acid enhances lime, cranberry, and grape flavours.

DL-Tartaric acid is also considered a chelating agent and prevents discolouration that might occur during food processing.
Chelating agents are capable of binding metal ions and in doing so improve colour, aroma, and texture.
DL-Tartaric acid is added to canned fruit products because it increases the stability of the product’s colour and aroma 


The texture of food is altered by the presence of DL-tartaric acid or one of its salts, cream of tartar.
DL-Tartaric acid and cream of tartar are examples of fast-acting baking powders.
Fast-acting baking powders contain acids that release a large amount of gas in a short amount of time during the mixing process or while a batter or other baking mixture is at rest.
DL-Tartaric acid and cream of tartar are important components of the cookie, pancake, and cake mixes and are often sold as ‘double-acting baking powder’ 

DL-tartaric acid in both the nonsynthetic and synthetic forms and its salts (i.e., L(+) potassium acid tartrate, L(+) sodium potassium tartrate acid) have been classified by the FDA as GRAS.


DL-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.
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 the 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.

DL-tartaric acid as an acidity regulator, adjuvant, anticaking agent, antioxidant, bulking agent, emulsifier, flour treatment agent, humectant, preservative, raising agent, sequestrant, stabilizer.

Industry Uses    
Fuels and fuel additives
Laboratory chemicals
Lubricants and lubricant additives
Plating agents and surface treating agents
Processing aids, not otherwise listed
Processing aids, specific to petroleum production

Consumer Uses
Ink, toner, and colorant products
Laboratory Use
Lubricants and greases

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