D-2,3-Dihydroxysuccinic acid
D(-)-Tartaric acid
CAS: 147-71-7
Molecular Formula: C4H6O6
D-2,3-Dihydroxysuccinic acid - Names and Identifiers
| Name | D(-)-Tartaric acid |
| Synonyms | d-tartaric Tartarieacid TARTARIC ACID D-Tartaric acid D(-)Tartaric acid D(-)-Threaric acid D(-)-Tartaric acid D-(-)-Tartaric acid tartaricacidd-minus (S,S)-TARTARIC ACID TARTARIC ACID, D-(-)- Unnatural tartaric acid TARTARIC ACID UNNATURAL TARTARIC ACID [DEXTRO (+)] (2S,3S)-D-(-)-tartaric acid D(-)-Dihydroxysuccinic acid D-2,3-Dihydroxysuccinic acid (2S,3S)-2,3-dihydroxybutanedioate |
| CAS | 147-71-7 |
| EINECS | 205-695-6 |
| 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 |
| InChIKey | FEWJPZIEWOKRBE-LWMBPPNESA-N |
D-2,3-Dihydroxysuccinic acid - Physico-chemical Properties
| Molecular Formula | C4H6O6 |
| Molar Mass | 150.09 |
| Density | 1,8 g/cm3 |
| Melting Point | 172-174°C(lit.) |
| Boling Point | 191.59°C (rough estimate) |
| Specific Rotation(α) | -12.1 º (c=20, H2O) |
| Flash Point | 210 °C |
| Water Solubility | 1394 g/L (20 ºC) |
| Solubility | Soluble in water |
| Vapor Presure | 4.93E-08mmHg at 25°C |
| Appearance | White powder or crystal |
| Color | White |
| Merck | 14,9068 |
| BRN | 1725145 |
| pKa | 3.0, 4.4(at 25℃) |
| Storage Condition | Store below +30°C. |
| Stability | Stable. Incompatible with oxidizing agents, bases, reducing agents. Combustible. |
| Sensitive | Light Sensitive |
| Refractive Index | -12.5 ° (C=5, H2O) |
| MDL | MFCD00004238 |
| Physical and Chemical Properties | Melting point 166-170°C flash point 210°C specific optical rotation -12.1 ° (c = 20, H2O) water-soluble 1394g/L (20°C) |
| Use | It is used as a pharmaceutical resolving agent, food additive, Biochemical reagent, etc. Purposes: This product is widely used in the food industry, such as as beer foaming agent, food acid, flavor, for cool drinks, candy, fruit juice, sauce, cold dishes, baking powder and so on. This product is in accordance with the Japanese food additive specification. |
D-2,3-Dihydroxysuccinic acid - Risk and Safety
| Hazard Symbols | Xi - Irritant |
| Risk Codes | 36/37/38 - Irritating to eyes, respiratory system and skin. |
| Safety Description | S26 - In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. S36/37 - Wear suitable protective clothing and gloves. S37/39 - Wear suitable gloves and eye/face protection S36 - Wear suitable protective clothing. |
| WGK Germany | 3 |
| RTECS | WW7875000 |
| TSCA | Yes |
| HS Code | 29181200 |
| Hazard Note | Light Sensitive |
D-2,3-Dihydroxysuccinic acid - Upstream Downstream Industry
| Raw Materials | Calcium chloride Sodium hydroxide Hydrochloric acid |
| Downstream Products | Timolol |
D-2,3-Dihydroxysuccinic acid - Reference
| Reference Show more | 1. Li Ningning, Zhang Bo, Niu Jianming, et al. Auxiliary Color Evaluation of Basic Anthocyanins and Protocatechuic Acid in Wine Based on CIELab Parameters [J]. Food and Fermentation Industry, 2019, 45(15). 2. Ren Jiaqi. Study on Physical and Chemical Properties and Stability of Polyphenol/Organic Acid and Apple Pectin Composite System [D]. Southwest University, 2020. 3. Hao Ailing, Feng Li, Qin Yi, et al. Screening of citric acid-degrading yeast and its fermentation performance [J]. Journal of China Food Science, 2018, 018(011):72-80. 4. Wang Jing, Wan Zhibo, Xu Chaoli, et al. Comparative Analysis of Organic Acids in Wine Grape Fruits from Xinjiang Production Areas [J]. Modern Food Science and Technology, 2020, v.36; no.246 (02):75 255-260. 5. Zou Ying, Bu Zhibin, Yu Yuanshan, et al. Enzymatic preparation of purple potato juice and fermentation characteristics of lactic acid bacteria [J]. Food Industry Technology, 2020, v.41;No.442(02):22-26 32. 6. Li Biao, Li Chengjie, Chen Shuangyang, etc. Optimization of Cooking Process of Lentinus edodes Soup and Study on Non-volatile Flavor Substances [J]. Journal of Food Science and Technology, 36(1). 7. Ma Ning, Wang Chaofan, Fang Dong Road, et al. Flavor Changes of Flammulina velutipes Packed with Polyethylene Film during Cold Storage [J]. Chinese Agricultural Sciences, 2019, 52(08):146-159. 8. Yang Chunxia. Analysis of Organic Acid Content in Wine Grape Based on Ion Exchange-Conductivity Detection [J]. Journal of Analysis and Testing, 2016(9):1162-1166 9. Pu Yunfeng, Ding Tian, Zhong Jianjun, et al. Nutritional Quality and Antioxidant Analysis of 12 Dried Fruits in Xinjiang [J]. Chinese Journal of Food Science, 2019, 19(05):293-300. 10. Cui Wenjia, Li Xiao, Wang Yueming, et al. Study on Desalination Technology of Pickled Cucumber [J]. Food Industry, 2018. 11. Li Weini, Zhang Yuxiang, Wei Jianping, et al. Optimization of Probiotic Fermented Apple Juice Process and Changes of Organic Acids [J]. Food Science, 2017(22):80-87. 12. Wang Siwei, Liu Yanping, wang Xiaonan, et al. Determination of 10 Organic Acids in Fresh Litchi Pulp Based on High Performance Liquid Chromatography-Triple Quadrupole Tandem Mass Spectrometry [J]. Journal of Pesticide Science, 2019(3). 13. Wu Yingchun. Comparative Study on Main NADPH Supply Genes in Fatty Acid Synthesis of Mortierella alpine [D]. Hebei University of Engineering, 2021. 14. Liu Xinye, Li Yunshu, Ma Qi, Wu Zijian, Xu Huaide, Li Mei. Effects of Different Drying Methods on Taste Components of Pleurotus eryngii [J]. Food Research and Development, 2020,41(16):8-13. 15. Xue Xiaomin, Han Xueping, Wang Jinzheng, Dong Fang. Analysis of Sugar and Acid Components in Plum Fruits at Different Harvest Periods [J]. Jiangsu Agricultural Sciences, 2020,48(21):220-224. 16. Peng, Wanying, et al. "Effect of the apple cultivar on cloudy apple juice fermented by a mixture of Lactobacillus acidophilus, Lactobacillus plantarum, and Lactobacillus fermentum." Food Chemistry 340 (2021): 127922.https://doi.org/10.1016/j.foodchem. 2020. 17. Xu, Xinxing, et al. "Correlation between autochthonous microbial communities and key odorants during the fermentation of red pepper (Capsicum annuum L.)." Food Microbiology 91 (2020): 103510.https://doi.org/10.1016/j.fm. 2020.103510 18. Wei, Jianping, et al. "Chemical composition, sensorial properties, and aroma-active compounds of ciders fermented with Hanseniaspora osmophila and Torulaspora quercuum in co-and sequential fermentations." Food chemistry 306 (2020): 125623.https://doi.org/1 19. Wei, Jianping, et al. "Chemical composition, sensorial properties, and aroma-active compounds of ciders fermented with Hanseniaspora osmophila and Torulaspora quercuum in co-and sequential fermentations." Food chemistry 306 (2020): 125623.https://doi.org/1 20. [IF=3.935] Meilian Wang et al."Natural deep eutectic solvents as eco-friendly and sustainable dilution medium for the determination of residual organic solvents in pharmaceuticals with static headspace-gas chromatography."J Pharmaceut Biomed. 2018 Sep;158:262 21. [IF=7.514] Jianping Wei et al."Chemical composition, sensorial properties, and aroma-active compounds of ciders fermented with Hanseniaspora osmophila and Torulaspora quercuum in co- and sequential fermentations."Food Chem. 2020 Feb;306:125623 22. [IF=6.429] Limei Wang et al."Changes in cell wall metabolism and flavor qualities of mushrooms (Agaricus bernardii) under EMAP treatments during storage."Food Packaging Shelf. 2021 Sep;29:100732 23. [IF=5.64] Li Jie et al."Investigation of the Lactic Acid Bacteria in Kazak Cheese and Their Contributions to Cheese Fermentation."Front Microbiol. 2020 Mar;0:228 24. [IF=5.277] Jianping Wei et al."Assessment of chemical composition and sensorial properties of ciders fermented with different non-Saccharomyces yeasts in pure and mixed fermentations."Int J Food Microbiol. 2020 Apr;318:108471 25. [IF=4.556] Dandan Zhao et al."Physico-chemical properties and free amino acids profiles of six wolfberry cultivars in Zhongning."J Food Compos Anal. 2020 May;88:103460 26. [IF=2.044] Zhang Wei et al."Determination of Residual Solvents in Pharmaceuticals by Static Headspace Gas Chromatography Using Natural Deep Eutectic Solvents as Mediums: A Partition Coefficients Study."Chromatographia. 2019 Oct;82(10):1523-1529 27. [IF=4.952] Wenyue Yu et al."Insight into the characteristics of cider fermented by single and co-culture with Saccharomyces cerevisiae and Schizosaccharomyces pombe based on metabolomic and transcriptomic approaches."LWT-FOOD SCIENCE AND TECHNOLOGY. 2022 Jun;163:1135 |
D-2,3-Dihydroxysuccinic acid - Introduction
There are two asymmetric carbon atoms and four stereoisomers, namely: right-handed (D-type, L-type), left-handed (L-type, D-type), meso-racemic, and racemic. Usually, racemic tartaric acid is also called gluconic acid. D-type tartaric acid is widely distributed in higher plants in the form of free or K salt, Ca salt, and Mg salt, especially in fruits and leaves. The optical rotation of the mixture of the same amount of right-handed body and left-handed body cancels each other and is called racemic tartaric acid. The racemate does not exist in nature and can be synthesized by chemistry. All kinds of tartaric acid are colorless crystals that are easily soluble in water.
Last Update：2022-10-16 17:14:01
D-2,3-Dihydroxysuccinic acid - Reference Information
| NIST chemical information | Information provided by: webbook.nist.gov (external link) |
| EPA chemical information | Information provided by: ofmpub.epa.gov (external link) |
| traits | white crystalline powder |
| Properties | There are three stereoisomers of tartaric acid: stone-spin tartaric acid, L-tartaric acid and meso-tartaric acid. The optical rotation of the mixture of the same amount of right-handed body and left-handed body cancels each other and is called racemic tartaric acid. The racemate does not exist in nature and can be synthesized by chemistry. All kinds of tartaric acid are colorless crystals that are easily soluble in water. |
| use | widely used in food industry, such as as beer foaming agent, food sour agent, flavoring agent, used in cool drinks, candy, fruit juice, sauce, cold vegetables, baking powder, etc. tartaric acid is widely used as an acidifier for beverages and other foods, this use is similar to citric acid. The combination of tartaric acid and tannin can be used as a mordant for acid dyes. It is also used in some development and fixing operations in the photographic industry. Its iron salt is photosensitive, so it can be used to make blueprints. 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. Potassium sodium tartrate (Rochelle salt) can be used to prepare Feilin reagent, can also be used as a laxative and diuretic in medicine, and can also be used as an intermediate of occinfen. Its crystal has piezoelectric properties and can be used in the electronics industry. used as chromatographic analysis reagent and masking agent used as medical resolution agent, food additive, biochemical reagent, etc. Uses: This product is widely used in food industry, such as as beer foaming agent, food sour agent, flavoring agent, used in cool drinks, candy, fruit juice, sauce, cold vegetables, baking powder, etc. This product complies with the Japanese Food Additives. Chiral source and resolution agent for chiral synthesis |
| application | tartaric acid is widely used as an acidifying agent for beverages and other foods, and this use is similar to citric acid. The combination of tartaric acid and tannin can be used as a mordant for acid dyes. It is also used in some development and fixing operations in the photographic industry. Its iron salt is photosensitive, so it can be used to make blueprints. 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. Potassium sodium tartrate (Rochelle salt) can be used to prepare Feilin reagent, can also be used as a laxative and diuretic in medicine, and can also be used as an intermediate of occinfen. Its crystal has piezoelectric properties and can be used in the electronics industry. Mainly used in beverages, candy, bread, gelatin as sour agent, biochemical reagents, racemate splitting agent, pharmaceutical splitting agent. It is also used in photography, can manufacturing, printing and dyeing, pottery industry and preparation of other splitting agents and salts, |
| Production method | Tartaric acid mainly exists in the form of potassium salt in the fruits of various plants, and a small amount also exists in a free state. Glucose fermentation is commonly used in industry to produce dextrotaric acid; racemate can be made by oxidation of fumaric acid with potassium permanganate; racemate can be made by oxidation of maleic acid with potassium permanganate; L-alcohol acid can be obtained by splitting racemate. In the practical application field of tartaric acid, dextrorotatory tartaric acid or its double salt is mainly used. The by-product of grape brewing tartaric acid is currently the main raw material for the actual production of tartaric acid, and the tartaric acid produced is dextrorotatory. |
| spontaneous combustion temperature | 425°C |
Last Update：2024-04-09 21:01:54
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Raw Materials for D-2,3-Dihydroxysuccinic acid
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