2,3-DIHYDROXYSUCCINIC ACID

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

CAS Number: 133-37-9
EC Number: 205-105-7
IUPAC Name: 2,3-Dihydroxybutanedioic acid
Chemical formula: C4H6O6 

Other names: (±)-tartaric acid, (±)-tartaric acid, (+-)-Tartaric acid, (+-)-tartaric acid, (2R,3R)-2,3-dihydroxybutanedioic acid, (±)-tartaric acid, 2, 3-Dihydroxybutanedioic Acid, 2,3 dihydroxybutanedioic acid, 2,3-Dihydroxybutanedioic acid, 2,3-dihydroxybutanedioic acid, 2,3-Dihydroxysuccinic acid, Acide Tartrique Poudre, Butanedioic acid, 2,3-dihydroxy-, (2R,3R)-rel-, DL-Tartaric Acid, DL-Tartaric acid, DL-tartaric acid, DL-Tartaric acid, Tartaric acid, tartaric acid, 133-37-9, 2,3-Dihydroxysuccinic acid, DL-Tartaric acid, tartaric acid, 2,3-Dihydroxybutanedioic acid, 526-83-0, 133-37-9, Racemic acid, Traubensaure, Racemic tartaric acid, DL-Tartrate, Paratartaric acid, Paratartaric aicd, Uvic acid, Acidum tartaricum, BUTANEDIOIC ACID, 2,3-DIHYDROXY-, Resolvable tartaric acid, NSC62778, Tartaric acid D,L, E-7050 (2S,3S)2,3-Dihydroxysuccinic acid, Tartaric acid, L-(+)-, 2,3-dihydroxy-succinic acid, Baros, CHEBI:15674, dl-2,3-dihydroxybutanedioic acid, (2RS,3RS)-Tartaric acid, tartrate, 1007601-97-9, NSC 148314, Butanedioic acid, 2,3-dihydroxy-, (2R,3R)-rel-, Butanedioic acid, 2,3-dihydroxy-(R*,R*)-(.+/-.)-, Butanedioic acid, 2,3-dihydroxy-, (R*,R*)-, 868-14-4, (.+-.)-Tartaric acid, (2R,3R)-2,3-Dihydroxybernsteinsaeure, Tartaric acid (VAN), Kyselina vinna [Czech], NSC155080, Tartaric acid [USAN:JAN], d-alpha,beta-Dihydroxysuccinic acid, NSC-148314, Kyselina 2,3-dihydroxybutandiova [Czech], (+) tartaric acid, (-) tartaric acid, 1,2-Dihydroxyethane-1,2-dicarboxylic acid, AI3-06298, 1,2-dicarboxylic acid, WLN: QVYQYQVQ, (-) D-Tartaric acid, Sal tartar (Salt/Mix), Tartaric acid, (DL)-, Butanedioic acid, 2,3-dihydroxy- (R-(R*,R*))-, Butanedioic acid, 2,3-dihydroxy-, [S-(R*,R*)]-, Malic acid, 3-hydroxy-, laevo-(+)-tartaric acid, 2,3-Dihydroxysuccinic acidacid, dextro,laevo-tartaric acid, Succinic acid,3-dihydroxy, SCHEMBL848, bmse000167, Succinic acid,3-dihydroxy-, (.+/-.)-Tartaric acid, DSSTox_CID_26986, DSSTox_RID_82036, DSSTox_GSID_46986, Oprea1_827092, TARTARIC ACID, (L), Tartaric acid, (.+-.)-, Butanedioic acid,3-dihydroxy-, CHEMBL333714, Dihydroxysuccinic acid, (DL)-, Tartaric acid, (.+/-.)-, L+Tartaric Acid FCC, NF, USP, DTXSID501031477, HMS3370M15, (+)-2,3-dihydroxybutanedioic acid, BCP14303, Tox21_302052, BBL011588, MFCD00064206, NSC133735, NSC148314, NSC608773, s2997, STK387106, 2,3-Dihydroxysuccinic acid, (DL)-, 3-carboxy-2,3-dihydroxypropanoic acid, AKOS000120086, AKOS016844048, NSC-133735, NSC-608773, SB44180, SB44181, SMP2_000051, d-.alpha.,.beta.-Dihydroxysuccinic acid, NCGC00256063-01, NCGC00347131-03, AS-10983, CAS-133-37-9, NCI60_001102, (+)-2,3-dihydroxy-1,4-butanedioic acid, DB-016129, DB-016159, DB-042899, AM20110247, CS-0022654, FT-0624346, FT-0625514, FT-0628018, FT-0628243, FT-0656080, FT-0772946, FT-0773804, T0001, (+/-)-2,3-dihydroxy-1,4-butanedioic acid, A22866, Butanedioic acid,3-dihydroxy- [R-(R*,R*)]-, 133D379, A829202, Q194322, Butanedioic acid,3-dihydroxy-, (R*,R*)-(.+-.)-, F2191-0230, Z1258943354, 1,2-Dihydroxyethane-1,2-dicarboxylic acid;2,3-Dihydrosuccinic acid, (2S,3S)-(-)-Tartaric acid; D(-)-Threaric acid;D(-)-Dihydroxysuccinic acid, Copper, mixt. with [R-(R*,R*)]-2,3-dihydroxybutanedioic acid monopotassium salt, 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], 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, 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)-rel2,3-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], 56959-20-7 [RN], 69-72-7 [RN], 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, l-酒石酸 [Chinese], Metatartaric acid, MFCD00071626 [MDL number], R,R-tartaric acid, Rechtsweinsaeure, STR02377, TAR, Tartaric acid (TN), THREARIC ACID, TLA, Weinsteinsaeure, 3044 [DBID], 4J4Z8788N8 [DBID], UNII:4J4Z8788N8 [DBID], W4888I119H [DBID], 1725147; 4231301 [DBID], 251380_SIAL [DBID], 27504_RIEDEL [DBID], 27506_RIEDEL [DBID], 33801_RIEDEL [DBID], 50824_FLUKA [DBID], 526-83-087-69-4 [DBID], 95308_FLUKA [DBID], AIDS072996 [DBID], AIDS-072996 [DBID], CHEBI:15671 [DBID], D00103 [DBID], NSC155080 [DBID], Pharmakon1600-01300044 [DBID], T109_ALDRICH [DBID], T1807_SIAL [DBID], UNII:W4888I119H [DBID], UNII-4J4Z8788N8 [DBID], UNII-W4888I119H [DBID], W304409_ALDRICH [DBID], WW 7874_ALDRICH [DBID], 133737-60-2

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

History of 2,3-Dihydroxysuccinic acid
2,3-Dihydroxysuccinic 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-Dihydroxysuccinic acid played an important role in the discovery of chemical chirality. 

This property of 2,3-Dihydroxysuccinic 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 of 2,3-Dihydroxysuccinic acid
Naturally occurring form of the acid is dextro tartaric acid or 2,3-Dihydroxysuccinic acid (obsolete name d-tartaric acid). 
Because 2,3-Dihydroxysuccinic acid is available naturally, 2,3-Dihydroxysuccinic acid is cheaper than its enantiomer and the meso isomer. 

The dextro and levo prefixes are archaic terms.
Modern textbooks refer to the natural form as 2,3-Dihydroxysuccinic acid (2,3-Dihydroxysuccinic acid), and its enantiomer as (2S,3S)-tartaric acid (D-(-)-tartaric acid). 
The meso diastereomer is referred to as (2R,3S)-tartaric acid or (2S,3R)-tartaric acid.

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

Applications of 2,3-Dihydroxysuccinic acid
2,3-Dihydroxysuccinic acid and its derivatives have a plethora of uses in the field of pharmaceuticals. 
For example, 2,3-Dihydroxysuccinic 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.

2,3-Dihydroxysuccinic 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-Dihydroxysuccinic acid, also called tartaric 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 its salts, cream of tartar (potassium hydrogen tartrate) and Rochelle salt (potassium sodium tartrate), it is obtained from by-products of wine fermentation. 

In a partially purified form, tartar was known to the ancient Greeks and Romans; the free acid was first isolated in 1769 by Swedish chemist Carl Wilhelm Scheele. 
The lees, or sediments, and other waste products from fermentation are heated and neutralized with calcium hydroxide; the precipitated calcium tartrate is then treated with sulfuric acid to produce free 2,3-Dihydroxysuccinic acid. 

Rochelle salt is prepared from the crude crystalline potassium acid salt, called argol, by neutralization with sodium carbonate. 
Purified cream of tartar comes chiefly from the filtrates from production of the acid and Rochelle salt. 
A third salt, tartar emetic (antimony potassium tartrate), is made from the potassium acid salt and antimony oxide.

Three stereoisomeric forms of 2,3-Dihydroxysuccinic acid exist:  dextrorotatory 2,3-Dihydroxysuccinic acid (D-tartaric acid) found in grapes and several other fruits, (2) levorotatory tartaric acid (L-tartaric acid) obtained chiefly by resolution of racemic tartaric acid, and (3) a meso or achiral form. 
Racemic tartaric acid (an equal mixture of D- and L-tartaric acid) is prepared commercially by the molybdenum- or tungsten-catalyzed oxidation of maleic anhydride with hydrogen peroxide.

Usage areas of 2,3-Dihydroxysuccinic acid:
2,3-Dihydroxysuccinic acid, this crystalline acid, is commonly seen in plants and fruits in general. 
The chemical formula of 2,3-Dihydroxysuccinic acid, which is an organic acid, is C4H6O6 and its density is 1.788g/cm. 
2,3-Dihydroxysuccinic acid is also used in different industries, especially in industry. 
This acid is generally preferred for the fermentation of wine and is formed as a byproduct of potassium during fermentation.

2,3-Dihydroxysuccinic acid is frequently used in wool dyeing, polishing, gelatin, desserts and sodas. 
Apart from this, antimony potassium tartars are generally preferred and used as mordant with pesticides. 
2,3-Dihydroxysuccinic acid, which is found in the majority of grape fruits, also occurs in some fruits other than grapes. 
However, 2,3-Dihydroxysuccinic acids seen in these fruits are called dextrotartaric acid. 
2,3-Dihydroxysuccinic acid, which consists of a mixture of racemine, is called levo. 
2,3-Dihydroxysuccinic acids are among the water-soluble dicarboxylic acids.

Usage areas 
2,3-Dihydroxysuccinic acid is used to give a sour taste to foods.
2,3-Dihydroxysuccinic acid, E334, is a good antioxidant.
The most common use of 2,3-Dihydroxysuccinic acid is in soda production. 
2,3-Dihydroxysuccinic acid, which is almost used to flavor the soda, is an indispensable component of soda.
2,3-Dihydroxysuccinic acid is preferred for dyeing wool.

2,3-Dihydroxysuccinic acid can be used for polishing, polishing and cleaning metals.
2,3-Dihydroxysuccinic acid is used in bakery products to release carbon dioxide.
2,3-Dihydroxysuccinic acid, which is indispensable for gelatinous desserts, is generally preferred as a thickener in products such as meringue, Turkish delight and whipped cream.

The form of 2,3-Dihydroxysuccinic acid obtained from grapes is generally preferred in pastry. Tartaric acid can be preferred instead of baking powder for rising cakes.
2,3-Dihydroxysuccinic acid, which is frequently found in fruits and has a sour and strong taste, is preferred for fermentation of wine in winemaking.
2,3-Dihydroxysuccinic acid is used in making marmalade and jams.

FOOD INDUSTRY
As acidifier and natural preservative for marmalades, ice cream, jellies, juices, preserves, and beverages.
As effervescent for carbonated water.
As emulsifier and preservative in the bread-making industry and in the preparation of candies and sweets.

OENOLOGY
Used as an acidifier. 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.

CONSTRUCTION INDUSTRY
Used in cement, plaster, and plaster of Paris to retard drying and facilitate the handling of these materials.

COSMETICS INDUSTRY
Used as a basic component of many natural body crèmes.

CHEMICAL SECTOR
Galvanic baths
Electronics industry
As mordant in the textile industry
As an anti-oxidant in industrial greases

2,3-Dihydroxysuccinic 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-Dihydroxysuccinic acid is also known as tartaric acid or Racemic acid. 
2,3-Dihydroxysuccinic acid is used to generate carbon dioxide. 

2,3-Dihydroxysuccinic acid is a diprotic aldaric acid which is crystalline white. 
Baking powder is a mixture of tartaric acid with sodium bicarbonate.
2,3-Dihydroxysuccinic acid is widely used in the field of pharmaceuticals. 
High doses of 2,3-Dihydroxysuccinic acid can lead to paralysis or death.

2,3-Dihydroxysuccinic acid is used to improve the taste of oral medications
2,3-Dihydroxysuccinic acid is used to chelate metal ions such as magnesium and calcium
2,3-Dihydroxysuccinic acid is used in recipes as a leavening agent along with baking soda
2,3-Dihydroxysuccinic acid is used as an antioxidant
2,3-Dihydroxysuccinic acid is as one of the important acids in wine

2,3-Dihydroxysuccinic acid is used in foods to give a sour taste
2,3-Dihydroxysuccinic acid is sometimes used to induce vomiting
2,3-Dihydroxysuccinic acid is used to make silver mirrors

-In its ester form, it is used in the dyeing of textiles
2,3-Dihydroxysuccinic acid is used in the tanning of leather
2,3-Dihydroxysuccinic acid is used in candies
In its cream form, 2,3-Dihydroxysuccinic acid is used as a stabilizer in food

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

2,3-Dihydroxysuccinic acid can be added to food when a sour taste is desired. 
2,3-Dihydroxysuccinic acid is also used as an antioxidant. 
Salts of 2,3-Dihydroxysuccinic acid are known as tartarates. 
The chemical is a dihydroxy derivative of succinic acid.

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

First aid measures of 2,3-Dihydroxysuccinic acid
After inhalation: 
Loosen clothing as necessary and position individual in a comfortable position.
Move exposed to fresh air. 
Give artificial respiration if necessary. 
If breathing is difficult give oxygen.
Get medical assistance if cough or other symptoms appear

After skin contact: 
Rinse/flush exposed skin gently using soap and water for 15-20 minutes.
Seek medical advice if discomfort or irritation persists.

After eye contact: 
Protect unexposed eye. 
Rinse/flush exposed eye(s) gently using water for 15-20 minutes.
Remove contact lens(es) if able to do so during rinsing. 
Seek medical attention if irritation persists or if concerned.

After swallowing: 
Rinse mouth thoroughly. 
Do not induce vomiting. 
Have exposed individual drink sips of water. 
Seek medical attention if irritation, discomfort or vomiting persists.
Never give anything by mouth to an unconscious person.

Hazard classification & labelling of 2,3-Dihydroxysuccinic acid
Danger! According to the classification provided by companies to ECHA in REACH registrations this substance causes serious eye damage.

About 2,3-Dihydroxysuccinic acid
2,3-Dihydroxysuccinic acid is registered under the REACH Regulation and is manufactured in and / or imported to the European Economic Area, for intermediate use only.
2,3-Dihydroxysuccinic acid is used at industrial sites.
2,3-Dihydroxysuccinic acid is used for the manufacture of: chemicals.