(2R,3R)-2,3-Dihydroxybernsteinsaeure
(2R,3R)-2,3-Dihydroxybernsteinsaeure
CAS: 526-83-0
Molecular Formula: C4H6O6
(2R,3R)-2,3-Dihydroxybernsteinsaeure - Names and Identifiers
| Name | (2R,3R)-2,3-Dihydroxybernsteinsaeure |
| Synonyms | L-tartaricaci Tartaric Acid D(-)-Tartaric acid D-2,3-Dihydroxysuccinic acid 2,3-Dihydroxybutanedioic acid (2R,3R)-2,3-Dihydroxybernsteinsaeure (2R,3S)-2,3-Dihydroxybernsteinsaeure |
| CAS | 526-83-0 |
| EINECS | 200-533-0 |
| InChI | InChI=1/C4H6O6/c5-1(3(7)8)2(6)4(9)10/h1-2,5-6H,(H,7,8)(H,9,10) |
(2R,3R)-2,3-Dihydroxybernsteinsaeure - Physico-chemical Properties
| Molecular Formula | C4H6O6 |
| Molar Mass | 150.09 |
| Density | 1.886±0.06 g/cm3(Predicted) |
| Melting Point | 159-171°C |
| Boling Point | 399.3±42.0 °C(Predicted) |
| Solubility | DMSO (Slightly, Heated), Methanol (Slightly), Water (Sparingly, Sonicated) |
| Appearance | Solid |
| Color | White to Off-White |
| pKa | 3.07±0.34(Predicted) |
| Storage Condition | Sealed in dry,Room Temperature |
(2R,3R)-2,3-Dihydroxybernsteinsaeure - Risk and Safety
| HS Code | 29181200 |
(2R,3R)-2,3-Dihydroxybernsteinsaeure - Reference
| Reference Show more | 1. Yang Chunxia, Gu Chunlin, Shan Qiaoling. Study on the changes of organic acids in wine-making process [J]. China Brewing, 2017(4). 2. Liu Ping, Wang Xuemei, xiang qin, Sun Wenjia, Li Yalong, Li jiayeng, Chen Zhiwei, Che Zhenming. Optimization of intelligent post-fermentation process and quality analysis of Pixian douban [J]. Food Science, 2020,41(22):166-176. 3. Wu Yuxia, Liu Yulian, Ma Chaoling, Mao Juan, Yang Jiangshan, Wang Yanxiu, Chang Yongyi. Quality Analysis of delayed cultivation grape in alpine desert area [J]. Food and Fermentation Industry, 2021,47(01):88-96. 4. Ma Yanli, Ding Yufeng, Li Suping, Liang Jingjing, Xi Xiaoli, Liu Yaqiong, Wang Xie. Comparison of quality of different grape varieties in Huailai of China [J]. Food Research and Development, 2020,41(15):137-142. 5. Qiang Chang et al. [IF = 2.478]. "Physiico chemical Properties and Antioxidant Capacity of Chinese Olive (Canarium album L.) cultivars." J Food Sci. 2017 Jun;82(6):1369-1377 6. [IF = 4.952] Fangting Bai et al."Caffeoyl substitution changes the inhibition mode of tartaric acid against alpha-amylase: Analysis of the enzyme inhibition by four caffeic and tartaric acid derivates."Lwt Food Sci Technol. 2020 Nov;133:109942 7. [IF=4.35] Yajing Li et al.Effects of Genetic Background and Altitude on Sugars, Malic Acid and Ascorbic Acid in Fruits of Wild and Cultivated Apples (Malus sp.).Foods. 2021 Dec;10(12):2950 8. [IF=2.998] Zan Shengyue et al."Composition analysis of rootstock cherry (Prunus mahaleb L.), a potential source of human nutrition and dietary supplements."Eur Food Res Technol. 2022 Feb;:1-15 |
(2R,3R)-2,3-Dihydroxybernsteinsaeure - Reference Information
| EPA chemical information | Information provided by: ofmpub.epa.gov (external link) |
| use | tartaric acid (tartaric acid) is a carboxylic acid, which exists in many plants, such as grapes and tamarind, and is also one of the main organic acids in wine. Tartaric acid, as an antioxidant added to food, can make food sour. Tartaric acid is similar to citric acid and can be used in the food industry, such as making beverages. The combination of tartaric acid and tannin can be used as a mordant for acid dyes. Tartaric acid can be complexed with a variety of metal ions and can be used as a cleaning agent and polishing agent for metal surfaces. |
| product characteristics and functions | tartaric acid aliases 2, 3-dihydroxysuccinic acid, dihydroxysuccinic acid, and grape acid. because tartaric acid contains two identical asymmetric carbon atoms, there are three optical isomers. tartaric acid is D-tartaric acid, L-tartaric acid and DL-tartaric acid. Tartaric acid is a colorless transparent prismatic crystal or powder. It has a strong sour taste and a slight taste. It is soluble in water. In nature, it is widely found in a variety of plants in the form of potassium or calcium salt, with more grape content. Tartaric acid is made from the yellow crystals deposited on the bottom of the barrel when making wine, so it is called tartaric acid. Its sour taste is about 1.3 times that of citric acid, its use is similar to citric acid, and it is soluble in water, so it is suitable for making foaming beverages. tartaric acid crystal contains 1 molecule of crystal water, odorless, stable in the air, sour taste, sour taste threshold 0.0025%, sour taste strength is about 1.2~1.3 times of citric acid, taste slightly astringent, smell of roasted granulated sugar when burning, with metal ion chelating effect. 1g is dissolved in 0.8mL of water (25 ℃),0.5mL of boiling water and 3mL of ethanol. The pH of the 0.3% aqueous solution is 2.4. DL tartaric acid is widely used as food additive, vitamin C effervescent tablets, salt-forming acidifier (choline bicartrate) of organic alkali drugs, etc. Tartaric acid can form acid salt and neutral salt with alkali. For example, potassium hydrogen tartrate is used in potassium hydroxide. The latter can also be further made into potassium antimony tartrate (ie * tartrate) and * potassium sodium tartrate. It can also be used to make salts such as sodium hydrogen tartrate, sodium tartrate and ammonium tartrate. according to the GB2760-86 regulations of our country, tartaric acid can be used as sour agent for food additives, such as refreshing drinks, jams, beverages, jelly, canned food and candy. Due to its low hygroscopicity and good stability, it is especially suitable for fruit juice and solid beverages. It is also used as food emulsifier and chelating agent, antioxidant synergist; metal surface cleaning agent and polishing agent; pharmaceutical raw materials, mordant, etc. It is mostly used in combination with citric acid, malic acid, etc. The limit of sweets is 2% (Japan) and 4% (United States). Precautions for use: This product has strong sour taste and slightly astringent taste. It is often used in combination with other acids. It is mostly used to prepare beverages and other foods with grape flavor. scope of use and usage: it can be used in all kinds of food according to production needs. Practical reference: when used in jam and jelly, it is better to keep the pH of the product at 2.8~3.5; It is mostly combined with citric acid, malic acid, etc. This product can also be used in appropriate amounts for candy and baked goods. |
| Use history | Tartaric acid has two identical chiral carbon atoms, and there are three three-dimensional foreign bodies (left-handed body (D-tartaric acid), right-handed body (L-tartaric acid), racemate). L-tartaric acid and D-tartaric acid are enantiomers. The naturally occurring tartaric acid is dextrorotatory. A mixture of equal amounts of left-handed and right-handed bodies constitutes a racemate. In the process of fermentation of grape juice or other pulp juice, the acid potassium salt of dextran tartaric acid, which is insoluble in ethanol and water, is deposited on the wall of the barrel, called tartaric acid, and the name of tartaric acid comes from this. Tartaric acid mainly exists in various plants and fruits in the form of potassium salt, and a small amount exists in a free state. In 1769, Scheler first obtained free colorless tartaric acid crystals from the fermentation broth of grape juice. Its various stereoisomers and racemates have different physical properties. There are mostly dextrorotatory bodies in nature, especially grape juice and other pulp juices, so it is also called fruit acid. If the oxidation is controlled with butenedioic acid, the racemate is obtained. The tartarite produced in the above reaction process is treated with lime milk to produce calcium tartrate, and then acidified to obtain racemate. Tartrate has played a role in the establishment of organic stereochemistry in history. In 1848, when the French chemist Pasteur was engaged in the research of sodium ammonium tartrate crystallography, he saw an interesting phenomenon that had not been noticed by predecessors: the non-optical sodium ammonium tartrate is a mixture of two different crystals. Their shapes are mirror images of each other, and they are actually racemates. He carefully divided the mixture into small piles with a magnifying glass and tweezers. A pile of right-handed body crystals, a pile of left-handed body crystals, they are like a pile of right gloves, a pile of left gloves. Both piles of crystals are optically active when dissolved in water. He first discovered the relationship between molecular stereoisomerism and optical rotation, and proposed the concept of enantiomerism, which laid the foundation for the development of organic stereochemistry. Tartaric acid is commonly used in pharmaceuticals, mordants and tanning agents, and is also commonly used as a reagent for splitting racemic basic compounds. It is also a sour agent in food additives, and the sour feeling is better than malic acid and lactic acid. Several of its salts have important applications. For example, the Fehring reagent is formulated with potassium sodium tartrate in the laboratory to identify aldehyde functional groups in organic molecular structures. Its potassium sodium salt is also called Rochelle salt. Its crystal is polarized under pressure to generate a potential difference (piezoelectric effect) on the two surfaces, which can be made into piezoelectric elements for radio and radio. The receiver and pickup of electric broadcasting. Antimony potassium tartrate (commonly known as tartrate) is used in medical treatment to treat schistosomiasis. |
| Preparation method | 1. The preparation of dl-tartaric acid is obtained by oxidation of fumaric acid or maleic acid. 2, obtained from the reaction of glyoxal and hydrocyanic acid and then acid hydrolysis. d-tartaric acid, found in many fruits or other parts of many plants, exists in a free state, and also exists in a combined state with potassium, calcium, and magnesium. 3, tartaric acid is prepared from crude tartarite precipitate generated during the production of wine, potassium hydrogen tartrate is extracted, and then converted into calcium tartrate, acidified with dilute sulfuric acid, and d-glucose can also be oxidized with nitric acid. The preparation of dl-tartaric acid is to azeotropic d-tartaric acid with NaOH aqueous solution, or oxidize fumaric acid. 1-and meso-tartaric acid are well known, they are not very important. 49 grams of maleic anhydride, 0.25 grams of tungstic acid, 130 grams of 30% hydrogen peroxide and 50 ml of water are mixed evenly, stirred and reacted at 70 ℃ for 8 hours, and then flowed for 1 hour. The reaction solution is cooled, 5 ml of concentrated sulfuric acid is added, and heated and boiled for 1 hour. Cooling, precipitating crystallization. Filter, wash the filter cake 3 times, drain and dry to obtain 5 grams of tartaric acid. the preparation process of tartaric acid is as follows: |
Last Update：2024-04-09 21:01:54
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