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D-Tartaric acid

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  • D-Tartaric acid
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  • D-Tartaric Acid
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  • CAS:147-71-7
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D-Tartaric acid Basic information
Chemical properties Application Preparation
Product Name:D-Tartaric acid
Synonyms:Tartarieacid;TARTARIC ACID, D-(-)-;TARTARIC ACID [DEXTRO (+)];TARTARIC ACID UNNATURAL;TARTARIC(D-) ACID;UNNATURAL TARTARIC ACID;TARTARIC ACID, D-(-)-(P);D-Tartaric acid C4H6O6
CAS:147-71-7
MF:C4H6O6
MW:150.09
EINECS:205-695-6
Product Categories:Chiral chemicals;Carboxylic Acids (Chiral);Chiral Building Blocks;for Resolution of Bases;Optical Resolution;Synthetic Organic Chemistry;FINE Chemical & INTERMEDIATES;Chiral Compounds;Food additive and acidulant;amino;147-71-7;bc0001
Mol File:147-71-7.mol
D-Tartaric acid Structure
D-Tartaric acid Chemical Properties
Melting point 172-174 °C(lit.)
alpha -12.1 º (c=20, H2O)
Boiling point 191.59°C (rough estimate)
density 1,8 g/cm3
refractive index -12.5 ° (C=5, H2O)
Fp 210 °C
storage temp. Store below +30°C.
solubility water: soluble100mg/mL, clear, colorless
form Crystals or Crystalline Powder
pka3.0, 4.4(at 25℃)
color White
Odorodorless
optical activity[α]20/D 13.5±0.5°, c = 10% in H2O
Water Solubility 1394 g/L (20 ºC)
Sensitive Light Sensitive
Merck 14,9068
BRN 1725145
Dielectric constant35.9(-10℃)
Stability:Stable. Incompatible with oxidizing agents, bases, reducing agents. Combustible.
InChIKeyFEWJPZIEWOKRBE-LWMBPPNESA-N
LogP-1.081 (est)
CAS DataBase Reference147-71-7(CAS DataBase Reference)
NIST Chemistry ReferenceD-Tartaric acid(147-71-7)
EPA Substance Registry SystemButanedioic acid, 2,3-dihydroxy-, (2S,3S)- (147-71-7)
Safety Information
Hazard Codes Xi
Risk Statements 36/37/38
Safety Statements 26-36/37-37/39-36
WGK Germany 3
RTECS WW7875000
Autoignition Temperature425 °C
Hazard Note Light Sensitive
TSCA Yes
HS Code 29181200
MSDS Information
ProviderLanguage
(2S,3S)-(-)-Tartaric acid English
SigmaAldrich English
ACROS English
ALFA English
D-Tartaric acid Usage And Synthesis
Chemical propertiesThere are three stereoisomers of tartaric acid: dextrose tartaric acid, levophyllic acid and meso tartaric acid. The optical rotation of the mixture of the same amount of dextrorotatory and levorotism is mutually offset, known as racemic tartaric acid. The mesomer does not exist in nature and can be synthesized chemically. Various tartaric acids are colorless crystals that are easily soluble in water.
ApplicationD-(-)-tartaric acid is widely used as an acidifier in beverages and food, similar to citric acid. It can also be used as a mordant for acid dye when combined with tannin. In the photographic industry, tartaric acid is used for some development and fixing processes. Its iron salts are photosensitive, making them suitable for blueprint production. Tartaric acid has the ability to form complexes with various metal ions, making it effective as a cleaning and polishing agent for metal surfaces. Potassium tartrate, known as Rochelle salt, is used to prepare Fehling reagent and is also employed as a laxative and diuretic in medicine. It is used as an intermediate for the synthesis of quinophan. Due to its piezoelectric properties, tartaric acid crystals find application in the electronics industry.
PreparationD-(-)-tartaric acid is mainly present in the form of potassium salt in the fruit of a variety of plants, and a small amount of it exists in free form. We produce dextrose tartaric acid through glucose fermentation industrially. The racemate can be prepared by fumaric acid with potassium permanganate as oxidant. The mesomer can be prepared by maleic acid with potassium permanganate as oxidant. L-lactic acid can be obtained by resolution of racemates. In the practical application of tartaric acid, the main application is dextrose tartaric acid or its complex salt. The by-product tartra of brewing grape is the main raw material of actual production of tartaric acid, and the all tartaric acids are dextrose tartaric acids.
Chemical PropertiesD-Tartaric acid is a white crystalline dicarboxylic acid found in many plants, particularly tamarinds and grapes. It is an acidulant that occurs naturally in grapes. It is hygroscopic and rapidly soluble, with a solubility of 150 g in 100 ml of distilled water at 25°c. It has a slightly tarter taste than citric acid, with a tartness equivalent of 0.8–0.9. It augments the flavor of fruits in which it is a natural constituent. It is used in grapeand limeflavored beverages and grape-flavored jellies. It is used as an acidulant in baking powder and as a synergist with antioxidants to prevent rancidity.
UsesD-(-)-Tartaric acid is commonly used as a resolving agent in organic synthesis. It is the synthetic enantiomer of L-(+)-Tartaric acid and is utilized in the production of synthetic analgesics. Tartaric acid is the second largest alpha hydroxy acid (AHA) in terms of size, with glycolic acid being the smallest and citric acid being the largest. It serves as a precursor for the synthesis of ester derivatives such as D-tartaric acid diethyl ester, D-tartaric acid dimethyl ester, and D-tartaric acid diiso-propyl ester. Moreover, it is employed in the creation of chiral aziridine derivative, which is a common intermediate for manufacturing hydroxyethylamine class HIV protease inhibitors like saquinavir, amprenavir, and nelfinavir. In the food industry, it is extensively used as a beer foaming agent, for regulating food acidity, and as a flavoring agent. However, due to its challenging workability and potential skin irritation, it is not frequently utilized in cosmetic or anti-aging preparations.
DefinitionChEBI: D-tartaric acid is the D-enantiomer of tartaric acid. It has a role as an Escherichia coli metabolite. It is a conjugate acid of a D-tartrate(1-). It is an enantiomer of a L-tartaric acid.
Biotechnological ProductionTartaric acid is generally produced from crude tartar and lees, which are byproducts of wine production. However, there are a few reports of fermentative production of tartaric acid by Gluconobacter suboxydans growing on Glucose or sorbitol. Vanadate plays a central role in this process. The microorganism forms 5-keto-D-gluconic acid, which is oxidized to tartaric acid. The vanadium catalyzes this reaction. Product concentrations up to 2.96 g.L-1 have been observed after 3 days of fermentation.
General DescriptionD-(-)-Tartaric acid is a polycrystalline solid, widely used as food additive. It has been reported to exhibit piezoelectric effect.
Purification MethodsCrystallise the acid from distilled H2O or *benzene/diethyl ether containing 5% of pet ether (b 60-80o) (1:1). Soxhlet extraction with diethyl ether has been used to remove an impurity absorbing at 265nm. It has also been crystallised from absolute EtOH/hexane and dried in a vacuum for 18hours [Kornblum & Wade J Org Chem 52 5301 1987]. [Beilstein 3 IV 1229.]
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