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CAS Number: 87-69-4
EC Number: 201-766-0
Molecular Weight: 150.09
L-Tartaric acid is present in many fruits, wines and coffee.
L-Tartaric acid is used as acidulant for beverages, foods and pharmaceuticals,used to enhance natural and synthetic fruit flavours, especies in grape- and lime-flavoured drinks and candies.
L-Tartaric acid is used as Firming agent, humectant.
L-Tartaric acid is used in leavening systems including baking powders.
L-Tartaric acid is the most water-soluble of the solid acidulants.
L-Tartaric acid contributes a strong tart taste that enhances fruit flavors, particularly grape and lime.
This dibasic acid is produced from potassium acid tartrate, which has been recovered from various by-products of the wine industry, including press cakes from fermented and partially fermented grape juice, lees (the dried, slimy sediments in wine fermentation vats), and argols (the crystalline crusts formed in vats during the second fermentation step of wine making).
The major European wine-producing countries, Spain, Germany, Italy, and France, use more of the acid than the United States.
L-Tartaric acid is often used as an acidulant in grape- and lime-flavored beverages, gelatin desserts, jams, jellies, and hard sour confectionery.
The acidic monopotassium salt, more commonly known as ‘cream of tartar,’ is used in baking powders and leavening systems.
Because L-Tartaric acid has limited solubility at lower temperatures, cream of tartar does not react with bicarbonate until the baking temperatures are reached.
This ensures maximum development of volume in the finished product.
l(+)-Tartaric acid (l-2R,3R-dihydrobutanedioic acid, C4H6O6) derives L-Tartaric acids name from the medieval, alchemical term tartarus.
L-Tartaric acid is a white, crystalline powder, odorless, and with an acidic taste.
L-Tartaric acid is a strong organic acid, widely distributed in nature, and classified as a fruit acid (it is the most expensive fruit acid).
The acid has two stereogenic atoms and it exists in three stereoisomeric forms – l(+), d(−), and the dl-racemic L-Tartaric acid, which is distinct from the meso-tartaric acid.
Although the dextrorotatory d(−)-isomer is the ‘unnatural’ form of the acid, its occurrence in small amounts in nature has been demonstrated.
L-Tartaric acid is present in its free form or combined with potassium, calcium, and magnesium.
L-Tartaric acid is highly soluble in water, methanol, ethanol, and glycerol but is insoluble in chloroform.
Uses of L-Tartaric acid:
Stabiliising agent for ground spices and cheeses to prevent discoloration.
Chelating agent in fatty foods.
Synergist with antioxidants, pH control agent in milk, jams and jellies, moisture-control agent.
Metatartaric acid (a mixture of polyith unchanged (+)-tartaric acid) is permitted in wine in UK Natural tartaresters obtained by the controlled dehydration of (+)-tartaric acid, together wic acid isomer.
L-Tartaric acid is found in many foods, some of which are coffee and coffee products, common grape, alcoholic beverages, and fruits.
L-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.
L-Tartaric acids salt, potassium bitartrate, commonly known as cream of tartar, develops naturally in the process of fermentation.
L-Tartaric acid 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 L-Tartaric acids distinctive sour taste.
L-Tartaric acid is an alpha-hydroxy-carboxylic acid, is diprotic and aldaric in acid characteristics, and is a dihydroxyl derivative of succinic acid.
L-(+)-Tartaric acid, or "natural" tartaric acid, is abundant in nature, especially in fruits.
L-Tartaric acids primary commercial source is as a byproduct of the wine industry.
L-Tartaric acid is used as an additive in many foods, such as soft drinks, bakery products, and candies.
Industrial uses include tanning, ceramics manufacture, and the production of tartrate esters for lacquers and textile printing.
L-(+)-Tartaric Acid is a naturally occurring chemical compound found in berries, grapes and various wines.
L-Tartaric acid provides antioxidant properties and contributes to the sour taste within these products.
In the soft drink industry, confectionery products, bakery products, gelatin desserts, as an acidulant.
In photography, tanning, ceramics, manufacture of tartrates.
The common commercial esters are the diethyl and dibutyl derivatives used for lacquers and in textile printing.
Pharmaceutic aid (buffering agent).
Applications of L-Tartaric acid:
L-(+)-Tartaric acid may be used in the synthesis of (R,R)-1,2-diammoniumcyclohexane mono-(+)-tartrate, an intermediate to prepare an enantioselective epoxidation catalyst.
L-Tartaric acid may also be used as a starting material in the multi-step synthesis of 1,4-di-O-benzyl-L-threitol.
L-Tartaric acid can be used a chiral resolving agent for the resolution of 2,2′-bispyrrolidine.
Chiral building block for natural products.
Also forms a Diels-Alder catalyst with TiCl2(O-i-Pr)2.
L-Tartaric acid is an abundant constituent of many fruits such as grapes and bananas and exhibits a slightly astringent and refreshing sour taste.
L-Tartaric acid is one of the main acids found in wine.
L-Tartaric acid 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.
L-Tartaric acid is produced by acid hydrolysis of calcium tartrate, which is prepared from potassium tartrate obtained as a by-product during wine production.
Optically active L-Tartaric acid is used for the chiral resolution of amines and also as an asymmetric catalyst.
Pharmaceutical Applications of L-Tartaric acid:
L-Tartaric acid is used in beverages, confectionery, food products, and pharmaceutical formulations as an acidulant.
L-Tartaric acid may also be used as a sequestering agent and as an antioxidant synergist.
In pharmaceutical formulations, L-Tartaric acid is widely used in combination with bicarbonates, as the acid component of effervescent granules, powders, and tablets.
L-Tartaric acid is also used to form molecular compounds (salts and cocrystals) with active pharmaceutical ingredients to improve physicochemical properties such as dissolution rate and solubility.
L-Tartaric acid and its derivatives have a plethora of uses in the field of pharmaceuticals.
For example, L-Tartaric acid 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.
L-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.
Chemical Properties of L-Tartaric acid:
L-Tartaric acid occurs as colorless monoclinic crystals, or a white or almost white crystalline powder.
L-Tartaric acid is odorless, with an extremely tart taste.
Production Methods of L-Tartaric acid:
L-Tartaric acid occurs naturally in many fruits as the free acid or in combination with calcium, magnesium, and potassium.
Commercially, L-(＋)-tartaric acid is manufactured from potassium tartrate (cream of tartar), a by-product of wine making.
Potassium tartrate is treated with hydrochloric acid, followed by the addition of a calcium salt to produce insoluble calcium tartrate.
This precipitate is then removed by filtration and reacted with 70% sulfuric acid to yield L-Tartaric acid and calcium sulfate.
Stereochemistry of L-Tartaric acid:
L-Tartaric acid crystals drawn as if seen through an optical microscope
Naturally occurring L-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 L-Tartaric acid is available naturally, L-Tartaric acid 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.
L-Tartaric acid in Fehling's solution binds to copper(II) ions, preventing the formation of insoluble hydroxide salts.
History of L-Tartaric acid:
L-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.
L-Tartaric acid played an important role in the discovery of chemical chirality.
This property of L-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.
Identifiers of L-Tartaric acid:
CAS Number: 87-69-4
Formula Weight: 150.09
Formula: C4H6O6
Density (g/mL): 1.76
Freezing Point (°C): 169-172
Solubility: Alcohol and Water
Synonyms: 2,3-Dihydroxybutanedioic Acid
Shelf Life (months): 36
Storage: Green
Properties of L-Tartaric acid:
Quality Level: 200
grade: ACS reagent
vapor density: 5.18 (vs air)
assay: ≥99.5%
Appearance: Powder
Physical State: Solid
Solubility: Soluble in water
Storage: Store at room temperature
Melting Point: 170-172° C (lit.)
Optical Activity: α20/D +12.4°, c = 20 in water; α20/D +12°±5°, c = 2 in water
SMILES string: O[C@H]([C@@H](O)C(O)=O)C(O)=O
InChI: 1S/C4H6O6/c5-1(3(7)8)2(6)4(9)10/h1-2,5-6H,(H,7,8)(H,9,10)/t1-,2-/m1/s1
InChI key: FEWJPZIEWOKRBE-JCYAYHJZSA-N
ACS reagent, ≥99.5%
Chemical formula: C4H6O6
Molecular weight: 150.09
Melting point: 168 °C and 170 °C
Solubility:
In water: L-Tartaric acid is polar and highly water-soluble, 20°C, 139g/100ml (L form) and 18.4g/100ml (DL form)
In organic solvents: 33g/100ml (L form), sparingly soluble (DL form) in ethanol.
PKa:
L-Tartaric acid is a weak dicarboxylic acid, but stronger than malic and citric acid.
L form has two PKa, PKa1 2.98 and PKa2 4.40 at 25°C, respectively.
PH: PH value 3.18 with the concentration 1 mmol/L at 25°C and 2.55 with the concentration of 10 mmol/L.
Names of L-Tartaric acid:
2,3-dihydroxysuccinic acid
Thearic acid
Uvic acid
Racemic acid
Synonyms of L-Tartaric acid:
Other names of L-Tartaric acid:
Tartaric Acid
Butanedioic acid, 2,3-dihydroxy- [R-(R*,R*)]-
Tartaric acid, L-(+)-
(+)-Tartaric acid
(R,R)-(+)-Tartaric acid
(2R,3R)-Tartaric acid
Butanedioic acid, 2,3-dihydroxy-
L-(+)-Tartaric acid
L-Tartaric acid
Natural tartaric acid
Succinic acid, 2,3-dihydroxy
Threaric acid
1,2-Dihydroxyethane-1,2-dicarboxylic acid
(2R,3R)-(+)-Tartaric acid
(+)-(2R,3R)-Tartaric acid
Dextrotartaric acid
Malic acid, 3-hydroxy-, (L)-
Tartaric acid, (L)-
2,3-Dihydroxysuccinic acid, (2R,3R)-
2,3-Dihydroxybutanedioic acid
Kyselina 2,3-dihydroxybutandiova
Kyselina vinna
(+)-(R,R)-Tartaric acid
(+)-L-Tartaric acid
Butanedioic acid, 2,3-dihydroxy- (2R,3R)-
d-Tartaric acid
NSC 62778
Baros (Salt/Mix)
L-tartaric acid
87-69-4
L-(+)-Tartaric acid
L(+)-Tartaric acid
(2R,3R)-2,3-dihydroxysuccinic acid
(+)-L-Tartaric acid
(R,R)-Tartaric acid
(2R,3R)-2,3-dihydroxybutanedioic acid
L-threaric acid
(+)-Tartaric acid
(+)-(R,R)-Tartaric acid
(2R,3R)-(+)-Tartaric acid
Dextrotartaric acid
Acidum tartaricum
UNII-W4888I119H
(2R,3R)-Tartaric acid
MFCD00064207
Butanedioic acid, 2,3-dihydroxy-, (2R,3R)-rel-
(2R,3R)-rel-2,3-Dihydroxysuccinic acid
d-alpha,beta-Dihydroxysuccinic acid
Butanedioic acid, 2,3-dihydroxy- (2R,3R)-
(R,R)-tartrate
L-(+)-tartrate
Kyselina 2,3-dihydroxybutandiova
1,2-Dihydroxyethane-1,2-dicarboxylic acid
AI3-06298
C4H6O6
2, 3-Dihydroxybutanedioic Acid
L(+)-Tartaric acid, 99+%
L(+)-Tartaric acid, ACS reagent
Kyselina vinna
Tartaric acid D,L
Butanedioic acid, 2,3-dihydroxy- (R-(R*,R*))-
Succinic acid, 2,3-dihydroxy
L(+) tartaric acid
(2RS,3RS)-Tartaric acid
EINECS 201-766-0
NSC 62778
(+)-(2R,3R)-Tartaric acid
Weinsteinsaeure
Weinsaure
2,3-dihydroxybutanedioate
2,3-dihydroxy-succinate
2,3-dihydroxysuccinic acid
2,3-Dihydroxy-succinic acid
L-tartarate
tartrate
Weinsaeure
(+)-Weinsaeure
(1R,2R)-1,2-Dihydroxyethane-1,2-dicarboxylic acid
(2R,3R)-(+)-2,3-Dihydroxybutane-1,4-dioic acid
(2R,3R)-(+)-2,3-Dihydroxybutane-1,4-dioic acid, (2R,3R)-(+)-2,3-Dihydroxysuccinic acid
(2R,3R)-(+)-2,3-Dihydroxysuccinic acid
(2R,3R)-2,3-Dihydroxybernsteinsaeure
(2R,3R)-2,3-dihydroxybutanedioate
(2R,3R)-2,3-tartaric acid
(2R,3R)-rel-2,3-Dihydroxybutanedioic acid
(2R,3R)-rel-2,3-Dihydroxysuccinic acid
(R,R)-(+)-tartatic acid
1,2-DIHYDROXYETHANE-1,2-DICARBOXYLIC ACID
138508-61-9
144814-09-5
147-71-7
2,3-dihydrosuccinic acid
2,3-dihydroxybutanedioic acid
205-695-6
3164-29-2
39469-81-3
3-hydroxymalic acid
41014-96-4
4231301
526-83-0
526-83-087-69-4
56959-20-7
69-72-7
ACS
D(-)-TARTARIC ACID
D-(-)-Tartaric Acid (en)
Dl-dihydroxysuccinic acid
hydrogen (2R,3R)-tartrate
l-(+)-tartaric acid
l-( )-tartaric acid
L-(+) tartaric acid
L-(+)-Tartaric acid, ACS
l-(+)-tartaric acid, anhydrous
L(+)-Tartaricacid
L-(+)-Tartaricacid
lamB protein (fungal)
l-tartaricacid
Metatartaric acid
MFCD00071626
R,R-tartaric acid
Rechtsweinsaeure
STR02377
TAR
Tartaric acid (TN)
THREARIC ACID
TLA
Weinsteinsaeure
