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2,3-DIHYDROXYBUTANEDIOIC ACID

2,3-dihydroxybutanedioic acid is an organic acid found in many vegetables and fruits such as bananas, and grapes, but also in bananas, citrus, and tamarinds.
2,3-dihydroxybutanedioic acid is a white, crystalline organic acid that occurs naturally in many fruits, most notably in grapes, but also in tamarinds, bananas, avocados and citrus.
Naturally occurring 2,3-dihydroxybutanedioic acid is a useful raw material in organic chemical synthesis.

CAS Number: 87-69-4
EC Number: 205-695-6
Molecular Formula: C4H6O6
Molecular Weight (g/mol): 150.09

Synonyms: (+)-L-Tartaric acid, (+)-Tartaric acid, 87-69-4, L-(+)-Tartaric acid, L-Tartaric acid, L(+)-Tartaric acid, tartaric acid, (2R,3R)-2,3-dihydroxysuccinic acid, (2R,3R)-2,3-dihydroxybutanedioic acid, (R,R)-Tartaric acid, Threaric acid, L-threaric acid, Dextrotartaric acid, Natural tartaric acid, Acidum tartaricum, DL-Tartaric acid, (2R,3R)-(+)-Tartaric acid, (+)-(R,R)-Tartaric acid, Tartaric acid, L-, Rechtsweinsaeure, Kyselina vinna, (2R,3R)-Tartaric acid, (R,R)-(+)-Tartaric acid, tartrate, Succinic acid, 2,3-dihydroxy, Weinsteinsaeure, L-2,3-Dihydroxybutanedioic acid, 133-37-9, (2R,3R)-rel-2,3-Dihydroxysuccinic acid, 1,2-Dihydroxyethane-1,2-dicarboxylic acid, EINECS 201-766-0, (+)-Weinsaeure, NSC 62778, FEMA No. 3044, INS NO.334, DTXSID8023632, UNII-W4888I119H, CHEBI:15671, Kyselina 2,3-dihydroxybutandiova, AI3-06298, Lamb protein (fungal), INS-334, (+/-)-Tartaric Acid, Butanedioic acid, 2,3-dihydroxy- (2R,3R)-, (R,R)-tartrate, NSC-62778, W4888I119H, Tartaric acid (VAN), Kyselina vinna [Czech], DTXCID203632, E 334, E-334, RR-tartaric acid, (+)-(2R,3R)-Tartaric acid, Tartaric acid, L-(+)-, EC 201-766-0, TARTARIC ACID (L(+)-), Tartaric acid [USAN:JAN], Weinsaeure, BAROS COMPONENT TARTARIC ACID, L-2,3-DIHYDROXYSUCCINIC ACID, MFCD00064207, C4H6O6, L-tartarate, 4J4Z8788N8, 138508-61-9, (2R,3R)-2,3-Dihydroxybernsteinsaeure, TARTARIC ACID COMPONENT OF BAROS, Resolvable tartaric acid, d-alpha,beta-Dihydroxysuccinic acid, TARTARIC ACID (II), TARTARIC ACID [II], 144814-09-5, Kyselina 2,3-dihydroxybutandiova [Czech], REL-(2R,3R)-2,3-DIHYDROXYBUTANEDIOIC ACID, TARTARIC ACID (MART.), TARTARIC ACID [MART.], (1R,2R)-1,2-Dihydroxyethane-1,2-dicarboxylic acid, TARTARIC ACID (USP-RS), TARTARIC ACID [USP-RS], BUTANEDIOIC ACID, 2,3-DIHYDROXY-, (R-(R*,R*))-, Tartaric acid D,L, Butanedioic acid, 2,3-dihydroxy- (R-(R*,R*))-, TARTARIC ACID (EP MONOGRAPH), TARTARIC ACID [EP MONOGRAPH], Tartarate, DL-TARTARICACID, 132517-61-4, L(+) tartaric acid, (2RS,3RS)-Tartaric acid, 2,3-dihydroxy-succinic acid, Traubensaeure, Vogesensaeure, Weinsaure, acide tartrique, acido tartarico, tartaric-acid, para-Weinsaeure, L-Threaric aci, 4ebt, NSC 148314, NSC-148314, (r,r)-tartarate, (+)-tartarate, l(+)tartaric acid, Tartaric acid; L-(+)-Tartaric acid, Tartaric acid (TN), (+-)-Tartaric acid, Butanedioic acid, 2,3-dihydroxy-, (R*,R*)-, L-(+) tartaric acid, (2R,3R)-Tartarate, 1d5r, DL TARTARIC ACID, TARTARICUM ACIDUM, 2,3-dihydroxy-succinate, TARTARIC ACID,DL-, SCHEMBL5762, TARTARIC ACID, DL-, Tartaric acid (JP17/NF), TARTARIC ACID [FCC], TARTARIC ACID [JAN], d-a,b-Dihydroxysuccinic acid, TARTARIC ACID [INCI], MLS001336057, L-TARTARIC ACID [MI], TARTARIC ACID [VANDF], DL-TARTARIC ACID [MI], CCRIS 8978, L-(+)-Tartaric acid, ACS, TARTARIC ACID [WHO-DD], CHEMBL1236315, L-(+)-Tartaric acid, BioXtra, TARTARICUM ACIDUM [HPUS], UNII-4J4Z8788N8, (2R,3R)-2,3-tartaric acid, CHEBI:26849, HMS2270G22, Pharmakon1600-01300044, TARTARIC ACID, DL- [II], TARTARIC ACID, (+/-)-, TARTARIC ACID,DL- [VANDF], HY-Y0293, STR02377, TARTARIC ACID [ORANGE BOOK], EINECS 205-105-7, Tox21_300155, (2R,3R)-2,3-dihydroxysuccinicacid, NSC759609, s6233, AKOS016843282, L-(+)-Tartaric acid, >=99.5%, CS-W020107, DB09459, 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, L-(+)-Tartaric acid, AR, >=99%, (R*,R*)-2,3-dihydroxybutanedioic acid, NCGC00247911-01, NCGC00254043-01, BP-31012, SMR000112492, SBI-0207063.P001, (2R,3R)-rel-2,3-dihydroxybutanedioic acid, NS00074184, T0025, EN300-72271, (R*,R*)-(+-)-2,3-dihydroxybutanedioic acid, C00898, D00103, D70248, L-(+)-Tartaric acid, >=99.7%, FCC, FG, L-(+)-Tartaric acid, ACS reagent, >=99.5%, 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., 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%, Q18226455, F8880-9012, Z1147451717, Butanedioic acid, 2,3-dihydroxy-, (theta,theta)-(+-)-, 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, 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

2,3-dihydroxybutanedioic acid is used to generate carbon dioxide.
2,3-dihydroxybutanedioic acid is a diprotic aldaric acid which is crystalline white.
Baking powder is a mixture of 2,3-dihydroxybutanedioic acid with sodium bicarbonate.

2,3-dihydroxybutanedioic acid is widely used in the field of pharmaceuticals.
High doses of 2,3-dihydroxybutanedioic acid can lead to paralysis or death.

2,3-dihydroxybutanedioic 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.

2,3-dihydroxybutanedioic acid is a tetraric acid, which is butanedioic acid substituted with hydroxy groups at the 2 and 3 positions.
2,3-dihydroxybutanedioic acid has a role as a human xenobiotic metabolite and a plant metabolite.
2,3-dihydroxybutanedioic acid is a conjugate acid of 3-carboxy-2,3-dihydroxypropanoate.

2,3-dihydroxybutanedioic acid is a white, crystalline organic acid that occurs naturally in many fruits, most notably in grapes, but also in tamarinds, bananas, avocados and citrus.
2,3-dihydroxybutanedioic acid salt, potassium bitartrate, commonly known as cream of tartar, develops naturally in the process of fermentation.

2,3-dihydroxybutanedioic acid is commonly mixed with sodium bicarbonate and is sold as baking powder used as a leavening agent in food preparation.
2,3-dihydroxybutanedioic acid itself is added to foods as an antioxidant E334 and to impart 2,3-dihydroxybutanedioic acid distinctive sour taste.

2,3-dihydroxybutanedioic acid is an organic acid that naturally occurs in many fruits, most notably in grapes but also in bananas and citrus fruits.
2,3-dihydroxybutanedioic acid is a white, crystalline solid which can easily be dissolved in water.

Approx. 50 % of the produced 2,3-dihydroxybutanedioic acid is subsequently used by the food and pharmaceutical industry, the other half is used in technical applications.
When added to food or beverage products, 2,3-dihydroxybutanedioic acid is denoted by E-number E 334.

Besides that, 2,3-dihydroxybutanedioic acid and its derivatives are often used in the field of pharmaceuticals or as a chelating agent in the farming and metal industry.

Naturally occurring 2,3-dihydroxybutanedioic acid is a useful raw material in organic chemical synthesis.
2,3-dihydroxybutanedioic acid, an alpha-hydroxy-carboxylic acid, is diprotic and aldaric in acid characteristics, and is a dihydroxyl derivative of succinic acid.

2,3-dihydroxybutanedioic acid is a white crystalline organic acid that occurs naturally in many plants, most notably in grapes.
2,3-dihydroxybutanedioic is an alpha-hydroxy-carboxylic acid, is diprotic and aldaric in acid characteristics, and is a dihydroxyl derivative of succinic acid.

2,3-dihydroxybutanedioic acid is a white crystalline diprotic organic acid.
2,3-dihydroxybutanedioic acid occurs naturally in many plants, particularly in grapes, bananas, and tamarinds.
2,3-dihydroxybutanedioic acid is also one of the main acids found in wine.

2,3-dihydroxybutanedioic acid can be added to food when a sour taste is desired.
2,3-dihydroxybutanedioic acid is also used as an antioxidant.

Salts of 2,3-dihydroxybutanedioic acid are known as tartarates.
2,3-dihydroxybutanedioic acid is a dihydroxy derivative of succinic acid.

2,3-dihydroxybutanedioic acid is found in cream of tartar and baking powder.
2,3-dihydroxybutanedioic acid is used in silvering mirrors, tanning leather, and in Rochelle Salt.
In medical analysis, 2,3-dihydroxybutanedioic acid is used to make solutions for the determination of glucose.

2,3-dihydroxybutanedioic acid is a naturally occurring dicarboxylic acid containing two stereocenters.
2,3-dihydroxybutanedioic acid exists as a pair of enantiomers and an achiral meso compound.

2,3-dihydroxybutanedioic acid is present in many fruits (fruit acid), and 2,3-dihydroxybutanedioic acid monopotassium salt is found as a deposit during the fermentation of grape juice.

2,3-dihydroxybutanedioic acid is a historical compound, dating back to when Louis Pasteur separated 2,3-dihydroxybutanedioic acid into two enantiomers with a magnifying lens and a pair of tweezers more than 160 years ago.

2,3-dihydroxybutanedioic acid has a stronger, sharper taste than citric acid.
Although 2,3-dihydroxybutanedioic acid is renowned for its natural occurrence in grapes, 2,3-dihydroxybutanedioic acid also occurs in apples, cherries, papaya, peach, pear, pineapple, strawberries, mangos, and citrus fruits.

2,3-dihydroxybutanedioic acid is used preferentially in foods containing cranberries or grapes, notably wines, jellies, and confectioneries.
Commercially, 2,3-dihydroxybutanedioic acid is prepared from the waste products of the wine industry and is more expensive than most acidulants, including citric and malic acids.

2,3-dihydroxybutanedioic acid is an abundant constituent of many fruits such as grapes and bananas and exhibits a slightly astringent and refreshing sour taste.
2,3-dihydroxybutanedioic acid is one of the main acids found in wine.

2,3-dihydroxybutanedioic 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.
2,3-dihydroxybutanedioic 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 2,3-dihydroxybutanedioic acid is used for the chiral resolution of amines and also as an asymmetric catalyst.

2,3-dihydroxybutanedioic acid is the most water-soluble of the solid acidulants.
2,3-dihydroxybutanedioic acid contributes a strong tart taste that enhances fruit flavors, particularly grape and lime.

2,3-dihydroxybutanedioic acid is often used as an acidulant in grape- and lime-flavored beverages, gelatin desserts, jams, jellies, and hard sour confectionery.

2,3-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 2,3-dihydroxybutanedioic acid salts, cream of tartar (potassium hydrogen tartrate) and Rochelle salt (potassium sodium tartrate), 2,3-dihydroxybutanedioic acid is obtained from by-products of wine fermentation.

Study of the crystallographic, chemical, and optical properties of the 2,3-dihydroxybutanedioic acids by French chemist and microbiologist Louis Pasteur laid the basis for modern ideas of stereoisomerism.

2,3-dihydroxybutanedioic acid is widely used as an acidulant in carbonated drinks, effervescent tablets, gelatin desserts, and fruit jellies.
2,3-dihydroxybutanedioic acid has many industrial applications—e.g., in cleaning and polishing metals, in calico printing, in wool dyeing, and in certain photographic printing and development processes.
2,3-dihydroxybutanedioic acid is used in silvering mirrors, in processing cheese, and in compounding mild cathartics.

2,3-dihydroxybutanedioic acid is incorporated into baking powders, hard candies, and taffies; and 2,3-dihydroxybutanedioic acid is employed in the cleaning of brass, the electrolytic tinning of iron and steel, and the coating of other metals with gold and silver.

2,3-dihydroxybutanedioic acid is an organic acid.
2,3-dihydroxybutanedioic acid is also known as 2,3-dihydroxysuccinic acid or Racemic acid.
2,3-dihydroxybutanedioic acid is in use to generate carbon dioxide.

2,3-dihydroxybutanedioic acid is a diprotic aldaric acid.
2,3-dihydroxybutanedioic acid is an alpha-hydroxy-carboxylic acid and is a dihydroxyl derivative of succinic acid.

2,3-dihydroxybutanedioic acid is widely in use in the field of pharmaceuticals.
A High dose of 2,3-dihydroxybutanedioic acid can affect our body to a great extent.

2,3-dihydroxybutanedioic acid is a white and crystalline that occurs naturally in many fruits and vegetables and most notably in grapes.
2,3-dihydroxybutanedioic acid is also present in bananas, tamarinds, and citrus.

2,3-dihydroxybutanedioic acid is commonly mixed with sodium bicarbonate and is sold as a baking powder that is in use as a leavening agent in food preparation.
The 2,3-dihydroxybutanedioic acid is added to foods being an antioxidant i.e., E334 and to impart 2,3-dihydroxybutanedioic acid distinctive sour taste.

2,3-dihydroxybutanedioic acid, sometimes called racemic acid, is an organic compound that naturally occurs in plants, wine, and many fruits, such as grapes, tamarinds, citrus, and bananas.
The acid is available as a white solid that’s soluble in water.
2,3-dihydroxybutanedioic acid salt, commonly referred to as cream of tartar, is created naturally through fermentation.

2,3-dihydroxybutanedioic acid is made from potassium acid tartrate obtained from different by-products of the wine industry, such as lees, argol, and press cakes from fermented grape juice.
This dibasic acid is usually mixed with sodium bicarbonate and is available as baking powder commonly used as a food additive.

Uses of 2,3-dihydroxybutanedioic acid:
2,3-dihydroxybutanedioic acid is Levo form of dextrorotatory 2,3-dihydroxybutanedioic acid.
2,3-dihydroxybutanedioic acid is found throughout nature and classified as a fruit acid.

2,3-dihydroxybutanedioic acid is used in soft drinks and foods, as an acidulant, complexing agent, pharmaceutic aid (buffering agent), in photography, tanning, ceramics, and to make tartrates.
Diethyl and dibutyl ester derivatives are commercially significant for use in lacquers and in textile printing.

2,3-dihydroxybutanedioic acid is used as an intermediate, in construction and ceramics applications, in cleaning products, cosmetics/personal care products, and metal surface treatments (including galvanic and electroplating products).
2,3-dihydroxybutanedioic acid is used as a flavoring agent, anticaking agent, drying agent, firming agent, humectant, leavening agent, and pH control agent for foods.

2,3-dihydroxybutanedioic acid is used to improve the taste of oral medications.
2,3-dihydroxybutanedioic acid is used to chelate metal ions such as magnesium and calcium.

2,3-dihydroxybutanedioic acid is used in recipes as a leavening agent along with baking soda.
2,3-dihydroxybutanedioic acid is used as an antioxidant.

2,3-dihydroxybutanedioic acid is as one of the important acids in wine.
2,3-dihydroxybutanedioic acid is used in foods to give a sour taste.

2,3-dihydroxybutanedioic acid is sometimes used to induce vomiting.
2,3-dihydroxybutanedioic acid is used to make silver mirrors.

In its ester form, 2,3-dihydroxybutanedioic acid is used in the dyeing of textiles.
2,3-dihydroxybutanedioic acid is used in the tanning of leather.

2,3-dihydroxybutanedioic acid is used in candies.
In its cream form, 2,3-dihydroxybutanedioic acid is used as a stabilizer in food.

Food industry:
2,3-dihydroxybutanedioic acid is used as acidifier and natural preservative for marmalades, ice cream, jellies, juices, preserves, and beverages.
2,3-dihydroxybutanedioic acid is used as effervescent for carbonated water.
2,3-dihydroxybutanedioic acid is used as emulsifier and preservative in the bread-making industry and in the preparation of candies and sweets.

Oenology:
2,3-dihydroxybutanedioic acid is used as an acidifier.
2,3-dihydroxybutanedioic acid is used in musts and wines to prepare wines that are more balanced from the point of view of taste, the result being an increase in their degree of acidity and a decrease in their pH content.

Pharmaceuticals industry:
2,3-dihydroxybutanedioic acid is used as an excipient for the preparation of effervescent tablets.

Construction industry:
2,3-dihydroxybutanedioic acid is used in cement, plaster, and plaster of Paris to retard drying and facilitate the handling of these materials.

Cosmetics industry:
2,3-dihydroxybutanedioic acid is used as a basic component of many natural body crèmes.

Chemical sector:
2,3-dihydroxybutanedioic acid is used in galvanic baths.
2,3-dihydroxybutanedioic acid is used in electronics industry.

2,3-dihydroxybutanedioic acid is used as mordant in the textile industry.
2,3-dihydroxybutanedioic acid is used as an anti-oxidant in industrial greases.

Industry Uses:
Processing aids not otherwise specified

Consumer Uses:
Processing aids not otherwise specified

Industrial Processes with risk of exposure:
Electroplating
Painting (Pigments, Binders, and Biocides)
Leather Tanning and Processing
Photographic Processing
Textiles (Printing, Dyeing, or Finishing)

Usage Areas of 2,3-dihydroxybutanedioic acid:
2,3-dihydroxybutanedioic acid, this crystalline acid, is commonly seen in plants and fruits.
The chemical formula of 2,3-dihydroxybutanedioic acid, an organic acid, is C4H6O6 and its density is 1.788g/cm.

2,3-dihydroxybutanedioic acid is used in different branches of industry, especially industry.
2,3-dihydroxybutanedioic acid is generally preferred for the fermentation of wine and is formed as a byproduct of potassium during fermentation.

2,3-dihydroxybutanedioic acid is frequently used in wool dyeing, polishing, gelatin, desserts and sodas.
2,3-dihydroxybutanedioic acid, which is mostly found in grape fruits, also occurs in some fruits other than grapes.

2,3-dihydroxybutanedioic acid, which is formed from the mixture of raceme, is called levo.
2,3-dihydroxybutanedioic acids are among the water-soluble dicarboxylic acids.

2,3-dihydroxybutanedioic acid is used to give a sour taste to foods.
2,3-dihydroxybutanedioic acid, E334, is a good antioxidant.

The most common use of 2,3-dihydroxybutanedioic acid is in soda production.
2,3-dihydroxybutanedioic acid, which is used to flavor soda, is an indispensable component of soda.

2,3-dihydroxybutanedioic acid is preferred for dyeing wool.
2,3-dihydroxybutanedioic acid can be used for polishing, polishing and cleaning metals.

2,3-dihydroxybutanedioic acid is used to release carbon dioxide in bakery products.
2,3-dihydroxybutanedioic acid, an indispensable ingredient in gelatin desserts, is generally preferred as a thickener in products such as meringue, Turkish delight and whipped cream.

The form of 2,3-dihydroxybutanedioic acid obtained from grapes is generally preferred in pastry.
2,3-dihydroxybutanedioic acid can be preferred over baking powder for rising cakes.

2,3-dihydroxybutanedioic acid, which is frequently found in fruits and has a tart and strong taste, is preferred for winemaking and fermentation of wine.
2,3-dihydroxybutanedioic acid is used in making marmalade and jams.

Applications of 2,3-dihydroxybutanedioic acid:
2,3-dihydroxybutanedioic acid and its derivatives have a plethora of uses in the field of pharmaceuticals.
For example, 2,3-dihydroxybutanedioic acid has been used in the production of effervescent salts, in combination with citric acid, to improve the taste of oral medications.

2,3-dihydroxybutanedioic 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.

2,3-dihydroxybutanedioic acid is used in fuels and fuel additives, laboratory chemicals, lubricants and lubricant additives, coating agents and surface treatment agents.
2,3-dihydroxybutanedioic acid is used in processing aids and petroleum production specific processing aids.

2,3-dihydroxybutanedioic acid is used in ink, toner and coloring products, laboratory use, lubricants and greases.
2,3-dihydroxybutanedioic acid is found in cream of tartar, which is used in making candies and frostings for cakes.

2,3-dihydroxybutanedioic acid is also used in baking powder where 2,3-dihydroxybutanedioic acid serves as the source of acid that reacts with sodium bicarbonate (baking soda).
This reaction produces carbon dioxide gas and lets products “rise,” but 2,3-dihydroxybutanedioic acid does so without the “yeast” taste that can result from using active yeast cultures as a source of the carbon dioxide gas.

2,3-dihydroxybutanedioic acid is used in silvering mirrors, tanning leather, and in the making of Rochelle Salt, which is sometimes used as a laxative.
Blue prints are made with ferric tartarte as the source of the blue ink.

In medical analysis, 2,3-dihydroxybutanedioic acid is used to make solutions for the determination of glucose.
Common esters of 2,3-dihydroxybutanedioic acid are diethyl tartarate and dibutyl tartrate.
Both are made by reacting 2,3-dihydroxybutanedioic acid with the appropriate alcohol, ethanol or n-butanol.

2,3-dihydroxybutanedioic acid in wine:
2,3-dihydroxybutanedioic 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.

2,3-dihydroxybutanedioic 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, 2,3-dihydroxybutanedioic acid provides some of the tartness in the wine, although citric and malic acids also play a role.

2,3-dihydroxybutanedioic acid in fruits:
Grapes and tamarinds have the highest levels of 2,3-dihydroxybutanedioic acid concentration.
Other fruits with 2,3-dihydroxybutanedioic acid are bananas, avocados, prickly pear fruit, apples, cherries, papayas, peaches, pears, pineapples, strawberries, mangoes and citrus fruits.

Results from a study showed that in citrus (oranges, lemons and mandarins), fruits produced in organic farming contain higher levels of 2,3-dihydroxybutanedioic acid than fruits produced in conventional agriculture.

Trace amounts of 2,3-dihydroxybutanedioic acid have been found in cranberries and other berries.
2,3-dihydroxybutanedioic acid is also present in the leaves and pods of Pelargonium plants and beans.

Retarding Agent:
2,3-dihydroxybutanedioic acid is widely used as a retarding agent in oilfield applications as well as in cementitious-based systems.
2,3-dihydroxybutanedioic acid works by slowing the setting of cement by impeding certain reactions during the hydration of the cement process.
2,3-dihydroxybutanedioic acid retards various steps, including ettringite formation and C3A hydration.

Food Additive:
2,3-dihydroxybutanedioic acid also has many uses in the food industry.
As an acidulant, 2,3-dihydroxybutanedioic acid offers a pleasant sour taste and gives food a sharp flavor.

2,3-dihydroxybutanedioic acid also serves as a preservative food agent and can help set gels.
2,3-dihydroxybutanedioic acid is usually added to most products, including carbonated beverages, gelatin, fruit jellies, and effervescent tablets.
This acid is also used as an ingredient in candy and various brands of baking powders and leavening systems to make goods rise.

Industrial Applications:
2,3-dihydroxybutanedioic acid has many industrial applications.
2,3-dihydroxybutanedioic acid’s used in gold and silver plating, making blue ink for blueprints, tanning leather, and cleaning and polishing metals.
2,3-dihydroxybutanedioic acid’s also one of the ingredients in Rochelle Salt, which is luxuriant and reacts with silver nitrate to form the silvering in mirrors.

Commercial Application:
The by-products obtained from the fermentation of wine during the production of 2,3-dihydroxybutanedioic acid are heated with calcium hydroxide.
This causes calcium tartrate to develop a residue, which is further treated with sulfuric acid to form a mixture of 2,3-dihydroxybutanedioic acid and calcium sulfate.
Once the mixture is separated, 2,3-dihydroxybutanedioic acid is purified and used for commercial production.

Other 2,3-dihydroxybutanedioic acid uses include pharmaceutical applications to produce effervescent salt that helps enhance the taste of oral medications.
2,3-dihydroxybutanedioic acid’s also used in the metals and farming industry as a chelating agent for cleaning metal surfaces and adding nutrients to the soil.

Derivatives of 2,3-dihydroxybutanedioic acid:

Important derivatives of 2,3-dihydroxybutanedioic acid include:
Sodium ammonium tartrate, the first material separated into 2,3-dihydroxybutanedioic acid enantiomers
Cream of tartar (potassium bitartrate), used in cooking
Rochelle salt (potassium sodium tartrate), which has unusual optical properties
Tartar emetic (antimony potassium tartrate), a resolving agent.
Diisopropyl tartrate is used as a co-catalyst in asymmetric synthesis.

2,3-dihydroxybutanedioic acid is a muscle toxin, which works by inhibiting the production of malic acid, and in high doses causes paralysis and death.
As a food additive, 2,3-dihydroxybutanedioic acid is used as an antioxidant with E number E334; 2,3-dihydroxybutanedioic acids are other additives serving as antioxidants or emulsifiers.

Production of 2,3-dihydroxybutanedioic acid:
2,3-dihydroxybutanedioic acid is industrially produced in the largest amounts.
2,3-dihydroxybutanedioic 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 calcium hydroxide "milk of lime" (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 chloride.

Calcium tartrate is then converted to 2,3-dihydroxybutanedioic acid by treating the salt with aqueous sulfuric acid:
Ca(C4H4O6) + H2SO4 -> H2(C4H4O6) + CaSO4

Racemic 2,3-dihydroxybutanedioic acid:
Racemic 2,3-dihydroxybutanedioic 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-2,3-dihydroxybutanedioic acid:
A mixture of racemic acid and meso-2,3-dihydroxybutanedioic acid is formed when dextro-2,3-dihydroxybutanedioic acid is heated in water at 165 °C for about 2 days.

meso-2,3-dihydroxybutanedioic acid can also be prepared from dibromosuccinic acid using silver hydroxide:
HO2CCHBrCHBrCO2H + 2 AgOH → HO2CCH(OH)CH(OH)CO2H + 2 AgBr

meso-2,3-dihydroxybutanedioic acid can be separated from residual racemic acid by crystallization, the racemate being less soluble.

General Manufacturing Information of 2,3-dihydroxybutanedioic acid:

Industry Processing Sectors:
Computer and Electronic Product Manufacturing
Construction
Not Known or Reasonably Ascertainable

Stereochemistry of 2,3-dihydroxybutanedioic acid:
Naturally occurring form of the acid is dextro 2,3-dihydroxybutanedioic acid.
Because 2,3-dihydroxybutanedioic acid is available naturally, 2,3-dihydroxybutanedioic acid is cheaper than its enantiomer and the meso isomer.

Dextro and levo form monoclinic sphenoidal crystals and orthorhombic crystals.
Racemic 2,3-dihydroxybutanedioic acid forms monoclinic and triclinic crystals (space group P1).

Anhydrous meso 2,3-dihydroxybutanedioic acid form two anhydrous polymorphs: triclinic and orthorhombic.
Monohydrated meso 2,3-dihydroxybutanedioic acid crystallizes as monoclinic and triclinic polymorphys depending on the temperature at which crystallization from aqueous solution occurs.
2,3-dihydroxybutanedioic acid in Fehling's solution binds to copper(II) ions, preventing the formation of insoluble hydroxide salts.

History of 2,3-dihydroxybutanedioic acid:
2,3-dihydroxybutanedioic 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.

2,3-dihydroxybutanedioic acid played an important role in the discovery of chemical chirality.
This property of 2,3-dihydroxybutanedioic acid was first observed in 1832 by Jean Baptiste Biot, who observed 2,3-dihydroxybutanedioic acid 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 levo2,3-dihydroxybutanedioic acid.

Pharmacology and Biochemistry of 2,3-dihydroxybutanedioic acid:

Pharmacodynamics:
2,3-dihydroxybutanedioic 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.
In high doses, this agent acts as a muscle toxin by inhibiting the production of malic acid, which could cause paralysis and maybe death.

Route of Elimination:
Only about 15-20% of consumed 2,3-dihydroxybutanedioic acid is secreted in the urine unchanged.

Metabolism / Metabolites:
Most tartarate that is consumed by humans is metabolized by bacteria in the gastrointestinal tract, primarily in the large instestine.

Human Metabolite Information of 2,3-dihydroxybutanedioic acid:

Tissue Locations:
Adipose Tissue
Platelet
Prostate

Cellular Locations:
Cytoplasm

Reactivity of 2,3-dihydroxybutanedioic acid:
2,3-dihydroxybutanedioic acid, can participate in several reactions.

As shown the reaction scheme below, dihydroxymaleic acid is produced upon treatment of 2,3-dihydroxybutanedioic 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 2,3-dihydroxybutanedioic acid with nitric acid.

Accidental Release Measures of 2,3-dihydroxybutanedioic acid:

Spillage Disposal:

Personal protection:
Particulate filter respirator adapted to the airborne concentration of 2,3-dihydroxybutanedioic acid.
Sweep spilled substance into covered containers.

If appropriate, moisten first to prevent dusting.
Store and dispose of according to local regulations.

Identifiers of 2,3-dihydroxybutanedioic acid:
CAS Number:
R,R-isomer: 87-69-4
S,S-isomer: 147-71-7
racemic: 133-37-9
meso-isomer: 147-73-9
ChEBI: CHEBI:15674

ChEMBL:
ChEMBL333714
ChEMBL1200861

ChemSpider: 852
DrugBank: DB01694
ECHA InfoCard: 100.121.903
E number: E334 (antioxidants, ...)
KEGG: C00898
MeSH: tartaric+acid
PubChem CID: 875 unspecified isomer
UNII: W4888I119H
CompTox Dashboard (EPA): DTXSID5046986
InChI: InChI=1S/C4H6O6/c5-1(3(7)8)2(6)4(9)10/h1-2,5-6H,(H,7,8)(H,9,10)
Key: FEWJPZIEWOKRBE-UHFFFAOYSA-N
InChI=1/C4H6O6/c5-1(3(7)8)2(6)4(9)10/h1-2,5-6H,(H,7,8)(H,9,10)
Key: FEWJPZIEWOKRBE-UHFFFAOYAZ
SMILES: O=C(O)C(O)C(O)C(=O)O

CAS number: 147-71-7
EC number: 205-695-6
Hill Formula: C₄H₆O₆
Chemical formula: HOOCCH(OH)CH(OH)COOH
Molar Mass: 150.09 g/mol
HS Code: 2918 12 00

CAS: 87-69-4
Molecular Formula: C4H6O6
Molecular Weight (g/mol): 150.09
MDL Number: MFCD00064207
InChI Key: FEWJPZIEWOKRBE-UHFFFAOYNA-N
PubChem CID: 444305
ChEBI: CHEBI:15671
SMILES: OC(C(O)C(O)=O)C(O)=O

Properties of 2,3-dihydroxybutanedioic acid:
Chemical formula:
C4H6O6 (basic formula)
HO2CCH(OH)CH(OH)CO2H (structural formula)

Molar mass: 150.087 g/mol
Appearance: White powder

Density:
1.737 g/cm3 (R,R- and S,S-)
1.79 g/cm3 (racemate)
1.886 g/cm3 (meso)

Melting point:
169, 172 °C (R,R- and S,S-)
206 °C (racemate)
165-6 °C (meso)

Solubility in water:
1.33 kg/L (L or D-tartaric)
0.21 kg/L (DL, racemic)
1.25 kg/L ("meso")

Acidity (pKa): L(+) 25 °C: pKa1= 2.89, pKa2= 4.40
meso 25 °C: pKa1= 3.22, pKa2= 4.85
Conjugate base: Bitartrate
Magnetic susceptibility (χ): −67.5·10−6 cm3/mol

Density: 1.8 g/cm3 (20 °C)
Flash point: 210 °C
Ignition temperature: 425 °C
Melting Point: 172 - 174 °C
Solubility: 1394 g/l

grade: ACS reagent
Quality Level: 200
vapor density: 5.18 (vs air)
Assay: ≥99.5%

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.)

anion traces:
chloride (Cl-): ≤0.001%
oxalate (C2O42-): passes test
phosphate (PO43-): ≤0.001%

cation traces:
Fe: ≤5 ppm
heavy metals (as Pb): ≤5 ppm

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

Molecular Weight: 150.09 g/mol
XLogP3-AA: -1.9
Hydrogen Bond Donor Count: 4
Hydrogen Bond Acceptor Count: 6
Rotatable Bond Count: 3
Exact Mass: 150.01643791 g/mol
Monoisotopic Mass: 150.01643791 g/mol
Topological Polar Surface Area: 115Å²
Heavy Atom Count: 10
Complexity: 134
Isotope Atom Count: 0
Defined Atom Stereocenter Count: 2
Undefined Atom Stereocenter Count: 0
Defined Bond Stereocenter Count: 0
Undefined Bond Stereocenter Count: 0
Covalently-Bonded Unit Count: 1
Compound Is Canonicalized: Yes

Specifications of 2,3-dihydroxybutanedioic acid:
Assay (acidimetric): ≥ 99.0 %
Melting range (lower value): ≥ 166 °C
Melting range (upper value): ≤ 169 °C
Spec. rotation [α²0/D (c=10 in water): -14.0 - -12.0 °
Identity (IR): passes test

Melting Point: 168.0°C to 172.0°C
Color: White or Colorless
Assay Percent Range: 99+%
Linear Formula: HO2CCH(OH)CH(OH)CO2H
Solubility Information: Solubility in water: 1390g/L (20°C).
Other solubilities: soluble in methanol, ethanol, propanol and, glycerol, 4g/L ether, insoluble in chloroform
IUPAC Name: 2,3-dihydroxybutanedioic acid
Formula Weight: 150.09
Percent Purity: ≥99%
Quantity: 500 g
Flash Point: 210°C
Infrared Spectrum: Authentic
Loss on Drying: 0.5% (1g, 105°C) max.
Packaging: Plastic bottle
Physical Form: Crystals or Crystalline Powder
Chemical Name or Material: L(+)-Tartaric acid

Related compounds of 2,3-dihydroxybutanedioic acid:
2,3-Butanediol
Cichoric acid

Other cations:
Monosodium tartrate
Disodium tartrate
Monopotassium tartrate
Dipotassium tartrate

Related carboxylic acids:
Butyric acid
Succinic acid
Dimercaptosuccinic acid
Malic acid
Maleic acid
Fumaric acid

Names of 2,3-dihydroxybutanedioic acid:

Preferred IUPAC name:
2,3-Dihydroxybutanedioic acid

Other names:
Tartaric acid
2,3-Dihydroxysuccinic acid
Threaric acid
Racemic acid
Uvic acid
Paratartaric acid
Winestone