147-71-7 Usage
Description
D-(-)-Tartaric acid, also known as the synthetic enantiomer of L-(+)-Tartaric Acid, is a polycrystalline solid that occurs naturally in grapes and exhibits piezoelectric properties. It is a white crystalline substance that is easily soluble in water and has three stereoisomers: dextrorotatory, levorotatory, and meso tartaric acid. The optical rotation of the mixture of equal amounts of dextrorotatory and levorotatory is mutually offset, known as racemic tartaric acid.
Uses
Used in Pharmaceutical Industry:
D-(-)-Tartaric acid is used as a resolving agent in organic synthesis and as a precursor for the preparation of its ester derivatives, such as D-tartaric acid diethyl ester, D-tartaric acid dimethyl ester, and D-tartaric acid diiso-propyl ester. It finds application in the synthesis of chiral aziridine derivatives, which are common intermediates for the preparation of hydroxyethylamine class HIV protease inhibitors like saquinavir, amprenavir, and nelfinavir.
Used in Food Industry:
D-(-)-Tartaric acid is widely used as an acidifying agent for beverages and other foods, similar to citric acid. It is used as a beer foaming agent, for food acidity regulation, and as a flavoring agent. It is also used in grape and lime-flavored beverages, grape-flavored jellies, and as an acidulant in baking powder. Additionally, it is used as a synergist with antioxidants to prevent rancidity.
Used in Cosmetic Industry:
Although not frequently used due to its difficulty in formulation and potential for skin irritation, tartaric acid is the second-largest AHA in size (glycolic acid being the smallest and citric acid the largest) and can be used in cosmetic or anti-aging preparations.
Used in Photographic Industry:
D-(-)-Tartaric acid can be used as an acid dye mordant when combined with tannin. It is also used for some development and fixing operations in the photographic industry, as its iron salts are photosensitive and can be used to make blueprints.
Used in Electronics Industry:
The crystal form of D-(-)-tartaric acid has piezoelectric properties, making it suitable for use in the electronics industry.
Used as a Cleaning and Polishing Agent:
D-(-)-Tartaric acid can complex with various metal ions, making it useful as a cleaning agent and polishing agent for metal surfaces.
Used in Medicine:
Potassium tartrate (Rochelle salt) can be used to prepare Fehling reagent and is also used as a laxative and diuretic in medicine.
Used as a Chromatographic Reagent and Masking Agent:
D-(-)-Tartaric acid is utilized as a chromatographic reagent and masking agent in various applications.
Used as a Resolving Agent and Biochemical Reagent:
D-(-)-Tartaric acid is used as a resolving agent of medicine and as a biochemical reagent, widely utilized in the food industry for refreshing drinks, candy, fruit juice, sauce, cold dishes, and baking powder. It is in line with the Japanese food additives certificate.
Used as a Chiral Source and Resolving Agent for Chiral Synthesis:
D-(-)-Tartaric acid serves as a chiral source and resolving agent for chiral synthesis in the pharmaceutical and chemical industries.
Preparation
D-(-)-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.
Biotechnological Production
Tartaric 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.
Purification Methods
Crystallise 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.]
Check Digit Verification of cas no
The CAS Registry Mumber 147-71-7 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 1,4 and 7 respectively; the second part has 2 digits, 7 and 1 respectively.
Calculate Digit Verification of CAS Registry Number 147-71:
(5*1)+(4*4)+(3*7)+(2*7)+(1*1)=57
57 % 10 = 7
So 147-71-7 is a valid CAS Registry Number.
InChI:InChI=1/C4H6O6/c5-1(3(7)8)2(6)4(9)10/h1-2,5-6H,(H,7,8)(H,9,10)/p-2/t1-,2-/m0/s1
147-71-7Relevant articles and documents
Preparation method of 2-amino-5-bromopyridine
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Paragraph 0016; 0038-0046, (2020/05/05)
The invention belongs to the technical field of organic synthesis, and specifically relates to a preparation method of 2-amino-5-bromopyridine. The method comprises the following steps: 2-aminopyridine serves as a raw material, dichloromethane or trichloromethane serves as a solvent, 2-aminopyridine and phenyl trimethyl ammonium tribromide carry out reactions for 1-3 hours at the temperature of 20-50 DEG C, and the molar ratio of 2-aminopyridine to phenyl trimethyl ammonium tribromide is 0.7-1.4. The preparation method provided by the invention has the beneficial effects that (1) the generation of a large number of 3-position byproducts in a traditional preparation method is avoided, and the waste of raw materials and the load of subsequent separation are reduced; and (2) the raw materialnamely 2-aminopyridine is easy to obtain and low in cost, the synthesis route has the advantages of high yield and mild conditions, no 3-position byproduct is generated in the whole process, and the preparation method has an industrialization prospect.
Decorated single-enantiomer phosphoramide-based silica/magnetic nanocomposites for direct enantioseparation
Karimi Ahmadabad, Fatemeh,Pourayoubi, Mehrdad,Bakhshi, Hadi
, p. 27147 - 27156 (2019/09/12)
The nano-composites Fe3O4SiO2(-O3Si[(CH2)3NH])P(O)(NH-R(+)CH(CH3)(C6H5))2 (Fe3O4SiO2PTA(+)) and Fe3O4SiO2(-O3Si[(CH2)3NH])P(O)(NH-S(-)CH(CH3)(C6H5))2 (Fe3O4SiO2PTA(-)) were prepared and used for the chiral separation of five racemic mixtures (PTA = phosphoric triamide). The separation results show chiral recognition ability of these materials with respect to racemates belonging to different families of compounds (amine, acid, and amino-acid), which show their feasibility to be potential adsorbents in chiral separation. The nano-composites were characterized by FTIR, TEM, SEM, EDX, XRD, and VSM. The VSM curves of nano-composites indicate their superparamagnetic property, which is stable after their use in the separation process. Fe3O4, Fe3O4SiO2, Fe3O4SiO2PTA(+) and Fe3O4SiO2PTA(-) are regularly spherical with uniform shape and the average sizes of 17-20, 18-23, 36-47 and 43-52 nm, respectively.
Preparation method of (1R,2S)-1-phenyl-2-(1-pyrrolidyl)-1-propanol
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Paragraph 0037, (2016/10/31)
The invention discloses a preparation method of (1R,2S)-1-phenyl-2-(1-pyrrolidyl)-1-propanol. According to the preparation method, DL-1-phenyl-2-(1-pyrrolidyl)-1-acetone is taken as a starting material and subjected to resolution, racemization and reduction, and (1R,2S)-1-phenyl-2-(1-pyrrolidyl)-1-propanol is prepared. The yield of one-time resolution is higher than 35%, a resolving agent is easy to recover, and the recovery rate is higher than 90%; the racemization process is performed under the slightly alkaline condition, and the racemization yield is higher; the yield of (1R,2S)-1-phenyl-2-(1-pyrrolidyl)-1-propanol obtained through reduction is higher than 85%. The preparation method has the advantages of mild reaction conditions, stable process, high product optical purity, low cost, high production safety and the like.