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Tartaric acid (L-(+)) belongs to the group of carboxylic acids, and is abundantly found in grapes and wine.
Tartaric acid (L-(+)) is widely used in drugs, food, and beverage industry.
Tartaric acid (L-(+)) is a tetraric acid that is butanedioic acid substituted by hydroxy groups at positions 2 and 3.
CAS: 87-69-4
MF: C4H6O6
MW: 150.09
EINECS: 201-766-0
Synonyms
FEMA 3044;DIHYDROXYSUCCINIC ACID;DEXTROTARTARIC ACID;ACIDUM TARTARICUM;2,3-DIHYDROXYDUTANEDIOIC ACID;(2R,3R)-(+)-TARTARIC ACID;d-alpha,beta-dihydroxysuccinicacid;dextro-rotation-2,3-dihydroxybutanedioicacid
Tartaric acid (L-(+)) is a conjugate acid of a L-tartrate(1-).
Tartaric acid (L-(+)) is an enantiomer of a D-tartaric acid.
Tartaric acid (L-(+)) is a white crystalline powder that is soluble in water.
Tartaric acid (L-(+)) is a model system for the study of calcium and its interactions with other ions, such as sodium and magnesium.
Tartaric acid (L-(+)) has been found to decrease the growth of carcinoma cell lines and increase the activity of certain enzymes, such as sodium salts, in mammalian cells.
Tartaric acid (L-(+)) crystals have been used for biological samples and electrochemical impedance spectroscopy.
Tartaric acid (L-(+)) also inhibits tumor growth in mice by inhibiting the production of proteins vital for cell division.
Tartaric acid (L-(+)) can be toxic at high doses and should not be administered to pregnant women or children.
Tartaric acid (L-(+)) is a white, crystalline organic acid that occurs naturally in many fruits, most notably in grapes but also in tamarinds, bananas, avocados, and citrus.
Tartaric acid (L-(+))'s 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 synthesis.
Tartaric acid (L-(+)), an alpha-hydroxy-carboxylic acid, is diprotic and aldaric in acid characteristics and is a dihydroxyl derivative of succinic acid.
As an antioxidant added to foods, foods can be sour.
The largest use of tartaric acid is in beverage additives.
Tartaric acid (L-(+)) is also a raw material for the pharmaceutical industry.
In the mirror industry, tartaric acid is an important auxiliaries and reducing agents that control the rate of formation of silver mirrors and achieve a very uniform coating.
Pharmaceutical intermediates, resolving agents; metal ion masking agents; anti-dyeing agents; chiral building blocks for natural products, also forming Diels-Alder catalysts with compound TiCl2(O-i-Pr)2
Used as a biochemical reagent, masking agent and beer foaming agent, also used in the tanning industry
Tartaric acid (L-(+)) is widely used as a sour agent in beverages and other foods for wines, soft drinks, confectionery, bread, and some gelatinous confections.
History
Tartaric acid (L-(+)) has been known to winemakers for centuries– its crude crystalline form as found off top of wine barrels were called tartarum (rendered tartre by Chaucer) or "wine stone". However, chemical extraction and purification was developed in 1769 by the Swedish chemist Carl Wilhelm Scheele.
Tartaric acid (L-(+)) 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.
Tartaric acid (L-(+)) Chemical Properties
Melting point: 170-172 °C(lit.)
alpha: 12 º (c=20, H2O)
Boiling point: 191.59°C (rough estimate)
bulk density: 1000kg/m3
density: 1.76
vapor density: 5.18 (vs air)
vapor pressure: <5 Pa (20 °C)
FEMA: 3044 | TARTARIC ACID (D-, L-, DL-, MESO-)
refractive index: 12.5 ° (C=5, H2O)
Fp: 210 °C
storage temp.: Store at +5°C to +30°C.
solubility H2O: soluble1M at 20°C, clear, colorless
form: Solid
pka: 2.98, 4.34(at 25℃)
color: White or colorless
Odor: at 100.00 %. odorless
PH: 3.18(1 mM solution);2.55(10 mM solution);2.01(100 mM solution);
biological source: Vitis vinifera
Optical Rotation: [α]20/D +13.5±0.5°, c = 10% in H2O
Odor Type: odorless
Water Solubility: 1390 g/L (20 ºC)
Merck: 14,9070
JECFA Number: 621
BRN: 1725147
Henry's Law Constant: 4.9×1015 mol/(m3Pa) at 25℃, Burkholder et al. (2019)
Dielectric constant: 35.9（-10℃）
Stability: Stable. Incompatible with oxidizing agents, bases, reducing agents. Combustible.
Cosmetics Ingredients Functions: FRAGRANCE
BUFFERING
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
InChIKey: FEWJPZIEWOKRBE-JCYAYHJZSA-N
LogP: -1.43
CAS DataBase Reference: 87-69-4(CAS DataBase Reference)
NIST Chemistry Reference: Tartaric acid (L-(+)) (87-69-4)
EPA Substance Registry System: Tartaric acid (L-(+))(87-69-4)
Tartaric acid (L-(+)) occurs as colorless monoclinic crystals, or a white or almost white crystalline powder.
Tartaric acid (L-(+)) is odorless, with an extremely tart taste.
Tartaric acid (L-(+)) is a naturally occurring chemical compound found in berries, grapes and various wines.
Tartaric acid (L-(+)) provides antioxidant properties and contributes to the sour taste within these products.
Uses
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).
Tartaric acid (L-(+)) is widely utilized in pharmaceutical industries.
Tartaric acid (L-(+)) is used in soft drinks, confectionaries, food products, gelatin desserts and as a buffering agent.
Tartaric acid (L-(+)) forms a compound, TiCl2(O-i-Pr)2 with Diels-Alder catalyst and acta as a chelate agent in metal industries.
Owing to its efficient chelating property towards metal ions, Tartaric acid (L-(+)) is used in farming and metal industries for complexing micronutrients and for cleaning metal surfaces, respectively.
Tartaric acid (L-(+)) and its derivatives have a plethora of uses in the field of pharmaceuticals.
For example, Tartaric acid (L-(+)) 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 (L-(+)) 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.
Pharmaceutical Applications
Tartaric acid (L-(+)) is used in beverages, confectionery, food products, and pharmaceutical formulations as an acidulant.
Tartaric acid (L-(+)) may also be used as a sequestering agent and as an antioxidant synergist.
In pharmaceutical formulations, Tartaric acid (L-(+)) is widely used in combination with bicarbonates, as the acid component of effervescent granules, powders, and tablets.
Tartaric acid (L-(+)) is also used to form molecular compounds (salts and cocrystals) with active pharmaceutical ingredients to improve physicochemical properties such as dissolution rate and solubility.
Production Methods
Tartaric acid (L-(+)) occurs naturally in many fruits as the free acid or in combination with calcium, magnesium, and potassium.
Commercially, Tartaric acid (L-(+)) is manufactured from potassium tartrate (cream of tartar), a by-product of wine making.
Tartaric acid (L-(+)) 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 tartaric acid and calcium sulfate.
Biochem/physiol Actions
Tartaric acid (L-(+)) serves as a donor ligand for biological processes.
Tartaric acid (L-(+)) is used as a food additive in candies and soft drinks to impart a sour taste.
Production
Tartaric acid (L-(+))
The Tartaric acid (L-(+)) isomer of tartaric acid is industrially produced in the largest amounts.
Tartaric acid (L-(+)) 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 (Ca(OH)2):
KH(C4H4O6) + Ca(OH)2 → Ca(C4H4O6) + KOH + H2O
In practice, higher yields of calcium tartrate are obtained with the addition of calcium sulfate.
Tartaric acid (L-(+)) is then converted to tartaric acid by treating the salt with aqueous sulfuric acid:
Ca(C4H4O6) + H2SO4 → H2(C4H4O6) + CaSO4
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 [de] as a catalyst.
HO2CCH=CHCO2H + H2O2 → HO2C(CHCH)(O)CO2H + H2O
In the next step, the epoxide is hydrolyzed.
HO2C(CHCH)(O)CO2H + H2O → HO2CCH(OH)CH(OH)CO2H
meso-Tartaric acid
A mixture of racemic acid and meso-tartaric acid is formed when dextro-tartaric acid is heated in water at 165 °C for about 2 days.
meso-Tartaric acid can also be prepared from dibromosuccinic acid using silver hydroxide:
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
Tartaric acid (L-(+)), can participate in several reactions.
As shown the reaction scheme below, dihydroxymalonic acid is produced upon treatment of Tartaric acid (L-(+)) 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.
