L-TARTARIC ACID
L-TARTARIC ACID
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 used as:
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 polyesters obtained by the controlled dehydration of (+)-tartaric acid, together with unchanged (+)-tartaric acid) is permitted in wine in UK Natural tartaric acid isomer.
L-Tartaric acid is found in many foods, some of which are coffee and coffee products, common grape, alcoholic beverages, and fruits.
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.
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.
Application
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 tartaric acid is used for the chiral resolution of amines and also as an asymmetric catalyst.
Chemical Properties
white crystals
Chemical Properties
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.
L-Tartaric acid Uses
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.
L-Tartaric acid 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).
Definition
ChEBI: A tetraric acid that is butanedioic acid substituted by hydroxy groups at positions 2 and 3.
Production Methods
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 tartaric acid and calcium sulfate.
Pharmaceutical Applications
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.
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.
Approved uses
E334 is listed in the group I which means most of its applications are not specific.
The following food may contain with L-tartaric acid:
-Canned or bottled fruit and vegetables
-Jam, jellies and marmalades and sweetened chestnut purée
-Cocoa and Chocolate products
-Fresh (pre-cooked) pasta
-Potato Gnocchi
-Table-top sweeteners in tablets
-Biscuits and rusks and baby foods for infants and young children
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, 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.
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.
Quality Level: 200
grade: ACS reagent
vapor density: 5.18 (vs air)
assay: ≥99.5%
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.
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 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.
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)
Permanent link for this species.
Use this link for bookmarking this species for future reference.
anion traces:
chloride (Cl-): ≤0.001%
oxalate (C2O42-): passes test
phosphate (PO43-): ≤0.001%
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
cation traces:
Fe: ≤5 ppm
heavy metals (as Pb): ≤5 ppm
Tartaric acid has a stronger, sharper taste than citric acid.
Although L-Tartaric acid is renowned for L-Tartaric acids natural occurrence in grapes, L-Tartaric acid 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.
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%
Synonym(s):
L-Threaric acid, (2R,3R)-(+)-Tartaric acid
Linear Formula:
HO2CCH(OH)CH(OH)CO2H
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
USAGE AREA
Gildara is used to give a sour taste.
The tartaric acid E334 is a good antioxidant.
Tartaric acid is the most common area for making soda.
Wool is preferred for painting.
L-Tartaric acid can be used to polish, polish and protect metals.
Oven products are used by releasing carbon dioxide.
Gelatinous desserts are preferred as thickeners in products such as tartaric acid, meringue, lokum and cream whipped cream.
Tartaric acid obtained from grapes is highly preferred in useful pasta production.
For embossing of macaroni, tartaric acid may be preferred to embossed gravy instead.
The production of tartaric acid wine, which has a low density, a piquant and strong taste, is preferred for fermentation of wine.
L-Tartaric acid is used for making marmalade and jams.
WHAT IS L(+) TARTARIC ACID?
L (+) Tartaric Acid is designated as natural tartaric acid. Natural Tartaric is a product of nature.
L (+) Tartaric acid, i.e., natural tartaric acid, is obtained as by-products of wine making after obtaining alcoholic products.
L (+) Tartaric acid should not be mixed with synthetic tartaric acid, starting from synthetic maleic acid.
L (+) Tartaric Acid crystallizer is applied in two stages.
Natural Tartaric Acid has 2 purity.
The raw crystal of L (+) Tartaric Acid, i.e., natural tartaric acid, is re-dissolved and subsequently converted back into crystalline structure.
L (+) Tartaric acid produced in this manner, i.e., natural tartaric acid, abolishes the process residues in the application phase.
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
Tartaric acid (2,3-dihydroxybutanedioic acid) is a naturally occurring dicarboxylic acid containing two stereocenters.
L-Tartaric acid 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.
L-Tartaric acid is present in many fruits (fruit acid), and L-Tartaric acids 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 L-Tartaric acid into two enantiomers with a magnifying lens and a pair of tweezers more than 160 years ago.
L-Tartaric acid 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; L-Tartaric acid 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.
Tartaric acid (VAN)
Kyselina vinna [Czech]
(R,R)-(+)-Tartaric acid
FEMA No. 3044
CHEBI:15671
Tartaric acid [USAN:JAN]
Tartaric acid, L-
tartrate
W4888I119H
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.
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 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 [segmented line in picture below].
Tartaric acid in Fehling’s solution binds to copper(II) ions, preventing the formation of insoluble hydroxide salts.
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 [Czech]
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
Production
L-(+)-Tartaric acid
The L-(+)-tartaric acid isomer of tartaric acid is industrially produced in the largest amounts.
L-Tartaric acid 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.
tartaric-acid
Rechtsweinsaeure
NSC-62778
L-Threaric aci
Kyselina 2,3-dihydroxybutandiova
4ebt
NSC 148314
(2R,3R)-2,3-Dihydroxybernsteinsaeure
(+)-Weinsaeure
l(+)tartaric acid
Tartaric acid; L-(+)-Tartaric acid
Tartaric acid (TN)
(+-)-Tartaric acid
Butanedioic acid, 2,3-dihydroxy-, (R*,R*)-
L-(+) tartaric acid
PubChem20078
1d5r
DL TARTARIC ACID
DSSTox_CID_3632
EC 201-766-0
SCHEMBL5762
DSSTox_RID_77120
Tartaric acid (JP17/NF)
DSSTox_GSID_23632
MLS001336057
CCRIS 8978
INS NO.334
L-(+)-Tartaric acid, ACS
CHEMBL1236315
DTXSID8023632
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.
Tartaric acid is a muscle toxin, which works by inhibiting the production of malic acid, and in high doses causes paralysis and death.
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.
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.
L-(+)-Tartaric acid, BioXtra
INS-334
HMS2270G22
Pharmakon1600-01300044
ZINC895301
HY-Y0293
STR02377
EINECS 205-105-7
Tox21_300155
ANW-38882
HTS001779
NSC759609
s6233
AKOS016843282
L-(+)-Tartaric acid, >=99.5%
CS-W020107
DB09459
MCULE-3942804599
MP-2105
NSC-759609
(2R,3R)-2,3-dihydroxy-succinic acid
Butanedioic acid, 2,3-dihydroxy-; Butanedioic acid, 2,3-dihydroxy-, (R-(R*,R*))-
CAS-87-69-4
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.
L-(+)-Tartaric acid, AR, >=99%
NCGC00247911-01
NCGC00254043-01
AK105865
BP-31012
SMR000112492
SBI-0207063.P001
E 334
E-334
T0025
C00898
D00103
Tartaric acid, a naturally occurring organic acid commonly found in grapes and used in winemaking.
L-Tartaric acid has a sour taste and can be used as an acidulant, flavoring agent, antioxidant and chelating agent in food with the European food additive number E334.
Generally, L-Tartaric acid is safe, natural or synthetic, vegan, halal, kosher and gluten-free.
Four types of Tartaric Acid
Tartaric acid is a dihydroxyl derivative of succinic acid.
As there are two asymmetric carbon atoms in its molecule, so L-Tartaric acid exists in four different stereoisomers: L, D, DL and Meso.
The L and DL forms are commonly used as food additives.
1. L-Tartaric Acid
When L-Tartaric acid comes to tartaric acid, we’re mostly talking about L-(+)-tartaric acid, the dextro form which with the CAS number 87-69-4 and E number E334.
L-Tartaric acid is used widely like other acidulants (citric acid and malic acid) for L-Tartaric acids high solubility, strong tart taste (about 1.2 to 1.3 times that of citric acid), and its stable salts.
Natural Source
L tartaric acid is widely present in nature and mostly in the form of potassium, calcium and magnesium salts or free state.
L-Tartaric acid can be found in a variety of plant fruits such tamarinds, grapes, bananas.
Tartaric acid is another major grape acid, along with malic acid.
But unlike malic acid, L-Tartaric acids concentration does not decline much during the grape ripening process.
How is L-Tartaric acid Made?
Generally, there are three production methods to obtain this ingredient: by-products of winemaking/grape, enzyme process, and microbial fermentation.
The first method is commonly used among European manufacturers for the abundant raw materials – grapes, while China is the biggest manufacturers for the second method.
1. Winemaking byproduct
During the winemaking process, a part of tartaric acid is precipitated in the form of cream of tartar crystals (potassium bitartrate), or more lovingly, “wine diamonds”.
The first step of production is the recrystallization of cream of tartar as its solubility increases along with the rising temperature.
Then reacting L-Tartaric acid with calcium hydroxide and calcium chloride to produce calcium tartrate (insoluble).
And finally, L tartaric acid is obtained by reacting calcium tartrate with sulfuric acid.
L-Tartaric acid can also be extracted from the grape.
For your better understanding, the following are the four steps reaction equations:
Cream of tartar (Recrystallization) → KHC4H4O6
2KHC4H4O6 + Ca(OH)2 → CaC4H4O6 + K2C4H4O6 + 2H2O
K2C4H4O6 + CaCl2 → CaC4H4O6 + 2KCl
CaC4H4O6 + H2SO4 → CaSO4 + C4H6O6
L-Tartaric acid is shown in the European Parliament that the total output quantity in 2016 was around 35, 000MT, and 86% was produced in Europe.
2. Enzyme process
The enzyme method is the mainstream commercial production method of L tartaric acid in China due to the high purity, high conversion efficiency, and safety.
The manufacturing flow chart as follows:
l tartaric acid enzyme production
Maleic anhydride is oxidized to sodium cis-epoxysuccinate by hydrogen peroxide.
Sodium cis-epoxysuccinate is hydrolyzed to tartaric acid using cis-epoxysuccinate hydrolase
3. Fermentation method
Using glucose as raw material, through microbial fermentation, the glucose is oxidized to 5-keto-D-gluconate (5-KGA), and then catalyzed to L- tartaric acid.
l tartaric acid glucose fermentation
2. D-Tartaric Acid
D-Tartaric acid is not the natural form and seldom used in food, also known as D(-)-tartaric acid with the CAS number 147-71-7, it can be obtained by chiral split DL tartaric acid.
3. DL-Tartaric Acid
Racemic tartaric acid is a mixture of equal amounts of L and D, the CAS number 133-37-9.
L-Tartaric acids manufacturing flow chart is similar to that of producing L tartaric acid by enzyme but without the enzyme used in the hydrolysis process.
DL tartaric acid can be used as a PH regulator, chelating agent, and also used to produce tartrates.
4. Meso Tartaric Acid
CAS number 205-696-1.
L-Tartaric acid is optically inactive due to internal molecular symmetry.
Specification
Appearance
Colorless or translucent crystalline granular or powder with a sour taste.
Other names
2,3-dihydroxysuccinic acid
Thearic acid
Uvic acid
Racemic acid
CAS number
13463-67-7
Chemical formula
C4H6O6
Molecular weight
150.09
Melting point
168 °C and 170 °C
Properties
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.
What are the Uses of Tartaric acid?
Tartaric acid, citric acid and malic acid are the most common organic acids used in food.
In general, food grade tartaric acid is used as an acidulant to provide a tart taste for wines, beverages, juices, marmalades, ice cream, sour confectionery, gelatin desserts, jams and jellies.
Why is Tartaric acid used in wine?
Tartaric acid is commonly added in wine making as the natural acidity of grapes is not enough, such as in red, white, and fruit wines.
L-Tartaric acid is the primary acid that influences the taste, balances color, tannins and sweetness, and maintains chemical stability which are important to the mouthfeel in fermentation, barrel aging process and finished wines.
Also, L-Tartaric acid acts as a preservative which prevents the growth of undesirable spoilage bacteria by lowering PH.
Tartaric acid’s solubility in wine varies according to the temperature.
L-Tartaric acid dissociates into two forms, bitartrate (HT–, mainly present at wine pH) and tartrate (T-2).
So L-Tartaric acid presents three forms in wine together with tartaric acid (H2T).
Different percentages of these three forms in different pHs.
Usually, at room temperature, L-Tartaric acid binds with potassium in wine to form the crystalline tartrate – cream of tartar.
Maybe you have the experience of finding these small crystals on the cork, or bottom in the wine.
The Raw Material for producing Emulsifiers
L-Tartaric acid reacts with fatty acid and glycerol to produce the following three food emulsifiers:
Tartaric acid esters of mono- and diglycerides of fatty acids
Mono- and diacetyl tartaric acid esters of mono- and diglycerides of fatty acids
Mixed acetic and tartaric acid esters of mono- and diglycerides of fatty acids
Cosmetics
L-Tartaric acid functions as a buffering, and masking agent in cosmetic and personal care products.
Pharmaceutical
L-Tartaric acid can be used as an excipient and used to improve the taste of the effervescent tablets.
13948-EP2269986A1
13948-EP2272847A1
13948-EP2281559A1
13948-EP2289887A2
13948-EP2289888A2
13948-EP2295401A2
13948-EP2295423A1
13948-EP2298778A1
13948-EP2308873A1
13948-EP2308875A1
13948-EP2311831A1
13948-EP2316836A1
L-(+)-Tartaric acid, >=99.7%, FCC, FG
L-(+)-Tartaric acid, ACS reagent, >=99.5%
148726-EP2270002A1
148726-EP2289879A1
L-(+)-Tartaric acid, BioUltra, >=99.5% (T)
J-500964
J-520420
L-(+)-Tartaric acid, ReagentPlus(R), >=99.5%
L-(+)-Tartaric acid, SAJ first grade, >=99.5%
L-(+)-Tartaric acid, tested according to Ph.Eur.
(1R,2R)-1,2-Dihydroxyethane-1,2-dicarboxylic acid
Butanedioic acid, 2,3-dihydroxy-, (R*,R*)-(+-)-
L-(+)-Tartaric acid, JIS special grade, >=99.5%
L-(+)-Tartaric acid, natural, >=99.7%, FCC, FG
L-(+)-Tartaric acid, p.a., ACS reagent, 99.0%
L-(+)-Tartaric acid, Vetec(TM) reagent grade, 99%
L-(+)-Tartaric acid, puriss., meets analytical specification of Ph. Eur., NF, 99.7-100.5% (calc. to the dried substance), powder
Tartaric acid is a white crystalline organic acid.
L-Tartaric acid occurs naturally in many plants, particularly grapes and tamarinds, and is one of the main acids found in wine.
L-Tartaric acid is added to other foods to give a sour taste, and is used as an antioxidant.
Salts of tartaric acid are known as tartrates.
L-Tartaric acid is a dihydroxy derivative of dicarboxylic acid.
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, L-Tartaric acid 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.
Naturally-occurring tartaric acid is chiral, meaning that L-Tartaric acid has molecules that are non-superimposable on their mirror-images.
L-Tartaric acid is a useful raw material in organic chemistry for the synthesis of other chiral molecules.
The naturally occurring form of the acid is L-(+)-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.
Tartarate is believed to play a role in inhibiting kidney stone formation.
Most tartarate that is consumed by humans is metabolized by bacteria in the gastrointestinal tract — primarily in the large instestine.
Only about 15-20% of consumed tartaric acid is secreted in the urine unchanged.
form:
crystalline powder
crystals
optical activity: [α]20/D +12.4°, c = 20 in H2O
optical purity: ee: 99% (GLC)
autoignition temp.: 797 °F
impurities:
≤0.002% S compounds
≤0.005% insolubles
ign. residue: ≤0.02%
mp: 170-172 °C (lit.)
The biosynthetic pathway of L-tartaric acid, the form most commonly encountered in nature, and its catabolic ties to vitamin C, remain a challenge to plant scientists. Vitamin C and L-tartaric acid are plant-derived metabolites with intrinsic human value.
In contrast to most fruits during development, grapes accumulate L-tartaric acid, which remains within the berry throughout ripening.
Berry taste and the organoleptic properties and aging potential of wines are intimately linked to levels of L-tartaric acid present in the fruit, and those added during vinification.
Elucidation of the reactions relating L-tartaric acid to vitamin C catabolism in the Vitaceae showed that they proceed via the oxidation of L-idonic acid, the proposed rate-limiting step in the pathway.
Here we report the use of transcript and metabolite profiling to identify candidate cDNAs from genes expressed at developmental times and in tissues appropriate for L-tartaric acid biosynthesis in grape berries.
Enzymological analyses of one candidate confirmed its activity in the proposed rate-limiting step of the direct pathway from vitamin C to tartaric acid in higher plants.
Surveying organic acid content in Vitis and related genera, we have identified a non-tartrate-forming species in which this gene is deleted.
This species accumulates in excess of three times the levels of vitamin C than comparably ripe berries of tartrate-accumulating species, suggesting that modulation of tartaric acid biosynthesis may provide a rational basis for the production of grapes rich in vitamin C.
Q18226455
F8880-9012
Z1262250859
Butanedioic acid, 2,3-dihydroxy-, (theta,theta)-(+-)-
UNII-4J4Z8788N8 component FEWJPZIEWOKRBE-JCYAYHJZSA-N
000189E3-11D0-4B0A-8C7B-31E02A48A51F
L-(+)-Tartaric acid, puriss. p.a., ACS reagent, >=99.5%
L-(+)-Tartaric acid, certified reference material, TraceCERT(R)
Tartaric acid, United States Pharmacopeia (USP) Reference Standard
L(+)-Tartaric acid, specified according to the requirements of Ph.Eur.
L-(+)-Tartaric acid, anhydrous, free-flowing, Redi-Dri(TM), ACS reagent, >=99.5%
L-(+)-Tartaric acid, p.a., ACS reagent, reag. ISO, reag. Ph. Eur., 99.5%
Tartaric Acid, Pharmaceutical Secondary Standard; Certified Reference Material
L-(+)-Tartaric acid, puriss. p.a., reag. ISO, reag. Ph. Eur., 99.5-101.0% (calc. to the dried substance)
L-(+)-Tartaric acid, puriss., meets analytical specification of Ph. Eur., BP, NF, FCC, E334, 99.7-100.5% (calc. to the dried substance), grit
CAS Number: 87-69-4
Molecular Weight: 150.09
Beilstein/REAXYS Number: 1725147
EC Number: 201-766-0
MDL number: MFCD00064207
PubChem Substance ID: 24855129
L-(+)-Tartaric acid
(+)-(2R,3R)-Tartaric acid
(+)-(R,R)-tartaric acid
(+)-L-tartaric acid
(+)-tartaric acid
(2R,3R)-(+)-Tartaric acid
(2R,3R)-2,3-Dihydroxybernsteinsäure [German] [ACD/IUPAC Name]
(2R,3R)-2,3-dihydroxybutanedioic acid
(2R,3R)-2,3-Dihydroxysuccinic acid [ACD/IUPAC Name]
(2R,3R)-tartaric acid
(R,R)-(+)-tartaric acid
(R,R)-tartaric acid
[R-(R*,R*)]-2,3-Dihydroxybutanedioic Acid
133-37-9 [RN]
1725147 [Beilstein]
201-766-0 [EINECS]
205-105-7 [EINECS]
87-69-4 [RN]
L-Tartaric acid, also called dihydroxybutanedioic acid, a dicarboxylic acid, one of the most widely distributed of plant acids, with a number of food and industrial uses.
Along with several of L-Tartaric acids salts, cream of tartar (potassium hydrogen tartrate) and Rochelle salt (potassium sodium tartrate), L-Tartaric acid is obtained from by-products of wine fermentation.
CAS number: 87-69-4
EC number: 201-766-0
Grade: Ph Eur,BP,JP,NF,E 334
Hill Formula: C₄H₆O₆
Chemical formula: HOOCCH(OH)CH(OH)COOH
Molar Mass: 150.09 g/mol
HS Code: 2918 12 00
Acide (2R,3R)-2,3-dihydroxysuccinique [French] [ACD/IUPAC Name]
Acidum tartaricum
Butanedioic acid, 2,3-dihydroxy-, (2R,3R)- [ACD/Index Name]
Butanedioic acid, 2,3-dihydroxy-, (2R,3R)-rel-
L-(+)-Tartarate
L(+)-Tartaric acid
L-(+)-Tartrate
L-2,3-Dihydroxybutanedioic Acid
L-tartaric acid
L-threaric acid
MFCD00064207 [MDL number]
Ordinary Tartaric Acid
Tartarate [ACD/IUPAC Name]
Tartaric acid [ACD/IUPAC Name] [JP15] [NF] [Trade name] [Wiki]
Weinsaure [German]
Weinsteinsaure [German]
(+)-tartarate
(2R,3R)-Tartarate
(R,R)-tartarate
(R,R)-tartrate
The interaction of L-tartrate with alkaline metal ions was studied by potentiometry and ultraviolet circular dichroism (UV/CD), and the formation of L-tartrate–polyammonium cation species was also studied by calorimetry.
The ultraviolet circular dichroism technique was also used in order to clarify some aspects of the ion pair formation process between L-tartrate anion and alkaline (various ionic strength values were employed) or polyammonium cations.
As in potentiometry, tetraethylammonium chloride has been considered as a reference ionic medium (that is, used as a non-interactive salt) for each comparison of the CD spectra recorded in different solutions.
The spectropolarimetric technique was shown to be an efficient means of establishing the capacity of the ions considered for mutual conformational adaptability.
Some differences clearly appear between the ion pairs formed by L-malate, studied in a previous paper, and L-tartrate anions.
In the systems L-tartrate–polyammonium cations the species ALHr are formed [L = tartrate, A = amine, r = 1, 2, …, (n + 1), n = maximum protonation degree of amine] with stability depending on the charges involved in the formation reaction.
Comparisons are made with other carboxylic ligands previously investigated.
2,3-dihydroxybutanedioate
2,3-dihydroxy-succinate
2,3-dihydroxysuccinic acid
2,3-Dihydroxy-succinic acid
L-tartarate
tartrate [ACD/IUPAC Name] [Wiki]
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 [RN]
144814-09-5 [RN]
147-71-7 [RN]
2,3-dihydrosuccinic acid
2,3-dihydroxybutanedioic acid
205-695-6 [EINECS]
3164-29-2 [RN]
39469-81-3 [RN]
3-hydroxymalic acid
41014-96-4 [RN]
4231301 [Beilstein]
526-83-0 [RN]
526-83-087-69-4
56959-20-7 [RN]
69-72-7 [RN]
ACS
D(-)-TARTARIC ACID
D-(-)-Tartaric Acid (en)
Dl-dihydroxysuccinic acid
https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:15671
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
l-酒石酸
Metatartaric acid
MFCD00071626 [MDL number]
R,R-tartaric acid
Rechtsweinsaeure
STR02377
TAR
Tartaric acid (TN)
THREARIC ACID
TLA
Weinsteinsaeure