2.3- Dihydroxybutanedioic acid

Tartaric acid [526-83-0] (2,3-dihydroxybutanedioic acid, 2,3-dihydroxysuccinic acid), C H O, is a dihydroxy dicarboxyhc acid with two chiral centers. It exists as the dextro- and levorotatory acid the meso form (which is inactive owing to internal compensation), and the racemic mixture (which is commonly known as racemic acid). The commercial product in the United States is the natural, dextrorotatory form, (R-R, R )-tartaric acid (L(+)-tartaric acid) [87-69-4]. This enantiomer occurs in grapes as its acid potassium salt (cream of tartar). In the fermentation of wine (qv), this salt forms deposits in the vats free crystallized tartaric acid was first obtained from such fermentation residues by Scheele in 1769. 

Since chirality is a property of a molecule as a whole, the specific juxtaposition of two or more stereogenic centers in a molecule may result in an achiral molecule. For example, there are three stereoisomers of tartaric acid (2,3-dihydroxybutanedioic acid). Two of these are chiral and optically active but the third is not. 

Proceeding as we did for threonine, we can write four projection formulas for tartaric acid, 2,3-dihydroxybutanedioic acid, as shown by 23-26 ... 

Dihydroxybutanedioic acid, see Tartaric acid, 1540 Dihydroxybutenedioic acid, see Dihydroxymaleic acid, 1443... 

CN (17/ ,21a)-17,21-dihydroxy-4-propylajmalanium salt with [R-(R, / )l-2,3-dihydroxybutanedioic acid... 

The two butenedioic acids are called fumaric acid (trans) and maleic acid (cis). 2,3-Dihydroxybutanedioic acid is called... 

Dihydroxybutanedioic acid) Averrhoa carambola (Oxalidaceae), Vitis activity of ilextro-... 

SYNS AMMONIUM TARTRATE pOT) AMMONIUM-d-TARTRATE 2,3-DIHYDROXYBUTANEDIOIC ACID, DIAMMONIUM SALT 1-TARTARIC ACID, AMMONIUM SALT TARTARIC ACID, DIAMMONIUM SALT... 

DIHYDROXYBUTANEDIOIC ACID, DIAMMONIUM SALT see DCHOOO DIHYDROXYCHLOROTHIAZIDUiM see CFYOOO DIHYDROXY 3-12 CHOEANATE de Na (FRENCH) see SGEOOO... 

L-(+)-2,3-Dihydroxybutanedioic acid (2R,3R)-2,3-dihydroxy-butane-l,4-dioic acid 2,3-dibydroxysuccinic acid E334 d-tartaric acid L-(+)-tartaric acid. 

As a prototype molecule, tartaric acid (2 2,3-dihydroxybutanedioic acid), shown here without stereochemical specification, is chosen. Tartaric acid is a compound of considerable historical importance (Section 3.6), and derivatives of tartaric acid are still compounds of contemporary research interest (see Seebach et al.1). (2i ,3i )-(+)-Tartaric acid is shown in sawhorse projection in 3. 

Tartaric acid pkia. = 3.02 pfC,2 = 4.54 HOOC.CH(OH).CH(OH).COOH (+)-2,3-dihydroxybutanedioic acid d-2,3-dihydroxysuccinic acid (only the dextrorotatory (+, or d) form is active) [dicarboxy dialpba-bydroxy acid]... 

DIHYDROXYBUTANEDIOIC ACID (87-69-4) C4H6O6 Combustible solid (flash point 410°F/210°C Fire Rating 1). Reacts violently with strong oxidizers, bromine, 90% hydrogen peroxide, phosphorus trichloride, silver powders or dust silver compounds. Mixture with some silver compounds forms explosive salts of silver oxalate. Aqueous solution reacts with bases, ammonia, amines, amides, inorganic hydroxides isocyanates, alkylene oxides, epichlorohydrin. Attacks some metals in the presence of moisture. 

Calcium Tartrate, 2,3.Dihydroxybutanedioic acid calcium salt. C4H4Ca06 mol wt 188.15. C 25.53%, H 2.147c, Ca 21.30%, O 51.02%. CaC4H404. A byproduct of the wine industry. Prepn from wine dregs Dabul, U.S. pat. 3,114,770 (1963 to Orandi Massera). See also the processes mentioned under L-tartaric acid. 

AntiweinsSure Butanedioic acid, 2,3-dihydroxy-, (2R,3S)-rel- (R, S )-2,3-Dihydroxybutanedioic acid L-( )-Dihydroxysuccinic acid EINECS 205-696-1 internally compensated tartaric acid meso-Tartaric acid unresolvable tartaric acid. Prepared by raoemization of L-tartaric acid. Crystals mp = 140° 1,66 soluble in H2O (125... 

The monoaminomonophosphonic acids, either in the free state or, very often, as their diethyl esters, have been resolved by the usual techniques of repeated crystallization of appropriate salts those of L-(+)-tartaric acid (2,3-dihydroxybutanedioic acid) or its mono-or di-benzoyl derivativesor of D-(-)-mandelic acid, have been widely employed the use of di-O-benzoylated L-tartaric anhydride, which is based on the separation of diastereoisomeric amides (111), has also been employed to a limited extent. In selected cases, such as the monoaminomonophosphonocarboxylic acids or A -acylated (aminoalkyl)phosphonic acids, resolution following salt formation with organic bases has also been carried out ephedrine, quinine and both enantiomers of l-phenylethylamine have all been used. In many cases, only one enantiomer of the (aminoalkyl)phosphonic acid (or diester) has been isolated in optically pure form. Sometimes, the acidity of the substrate, and hence choice of base for resolution, can be modified by using a mono- (as opposed to di-) ester or (or even in addition to) protection of the amino group as, for example, the phthalimido, benzyloxycarbonyl (cbz) or r r -butyloxycarbonyl (boc) derivative. Resolved di- and mono-esters can be hydrolysed to the free acids under acidic conditions, and A -protection can also be removed through the customary procedures. 

Tartaric acid serves as the stereochemical connection between the carbohydrates and glyceraldehyde, and is a chiral butanediol that exists in three forms. L-( + )-Tartaric acid, (27, 3/ )-2,3-dihydroxybutanedioic acid 1 (R=H), is referred to as the natural form, and it is widely distributed in nature and classified as a fruit acid. D-( —)-(2 S, 35)-2,3-dihydroxy-butanedioic acid 2 (R=H) is often called unnatural , although it does occur in nature as well. It has the same absolute configuration as D-glyceraldehyde. A third form, called meso-tartaric acid, possess an internal plane of symmetry and is thus inherently racemic and unresolvable. The name tartaric acid is derived from Tartarus, and is probably of medieval and alchemical origin. 

Tartaric acid (2,3-dihydroxybutanedioic acid, grape acid). 

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