Pyruvic acid,(2-Oxopropionic acid)
Pyruvic acid
CAS: 127-17-3
Molecular Formula: C3H4O3
Pyruvic acid,(2-Oxopropionic acid) - Names and Identifiers
| Name | Pyruvic acid |
| Synonyms | CH3COCOOH Pyruvic acid ACID PYRUVATE 2-oxopropanoate 2-oxo-propanoicaci 2-Oxopropanoic acid 2-Oxopropionic acid PyruvicAcid,FreeAcid 2-Ketopropionic acid Propanoic acid, 2-oxo- PyruvicAcidForSynthesis Pyruvic acid,(2-Oxopropionic acid) |
| CAS | 127-17-3 |
| EINECS | 204-824-3 |
| InChI | InChI=1/C3H4O3/c1-2(4)3(5)6/h1H3,(H,5,6)/p-1 |
| InChIKey | LCTONWCANYUPML-UHFFFAOYSA-N |
Pyruvic acid,(2-Oxopropionic acid) - Physico-chemical Properties
| Molecular Formula | C3H4O3 |
| Molar Mass | 88.06 |
| Density | 1.267 g/mL at 25 °C (lit.) |
| Melting Point | 11-12 °C (lit.) |
| Boling Point | 165 °C (lit.) |
| Specific Rotation(α) | n20/D 1.428(lit.) |
| Flash Point | 183°F |
| JECFA Number | 936 |
| Solubility | Can be miscible with water, alcohol and ether. Easy to absorb moisture, easy to polymerize. |
| Vapor Presure | 1.72hPa at 25℃ |
| Appearance | Colorless to light yellow liquid |
| Color | Clear colorless to light yellow or amber |
| Merck | 14,8021 |
| BRN | 506211 |
| pKa | 2.39(at 25℃) |
| PH | 3.11(1 mM solution);2.38(10 mM solution);1.79(100 mM solution); |
| Storage Condition | 2-8°C |
| Stability | Stable. Combustible. Incompatible with strong oxidizing agents, strong bases. Refrigerate. |
| Sensitive | Sensitive to light |
| Refractive Index | n20/D 1.428(lit.) |
| MDL | MFCD00002585 |
| Physical and Chemical Properties | density 1.25 melting point 11.8°C boiling point 165°C refractive index 1.426-1.43 flash point 82°C |
| Use | Used as raw materials for medicine and food additives |
Pyruvic acid,(2-Oxopropionic acid) - Risk and Safety
| Hazard Symbols | C - Corrosive |
| Risk Codes | 34 - Causes burns |
| Safety Description | S26 - In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. S36/37/39 - Wear suitable protective clothing, gloves and eye/face protection. S45 - In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.) S25 - Avoid contact with eyes. S27 - Take off immediately all contaminated clothing. |
| UN IDs | UN 3265 8/PG 2 |
| WGK Germany | 3 |
| RTECS | UZ0829800 |
| TSCA | Yes |
| HS Code | 29335995 |
| Hazard Class | 8 |
| Packing Group | II |
Pyruvic acid,(2-Oxopropionic acid) - Upstream Downstream Industry
| Raw Materials | DL-Tartaric Acid DL-Lactic acid |
| Downstream Products | Pyruvic acid, sodium salt Calcium Pyruvate |
Pyruvic acid,(2-Oxopropionic acid) - Reference
| Reference Show more | 1. Zhang Liping, Ji Shujuan. Effect of Ethephon on Aroma and Key Enzyme Activity in Aroma Synthesis of Nanguo Pear Treated with 1-MCP after Cold Storage [J]. Food Science, 2013, 34(10):294-298. 2. Jiang Peng, Sun Yancai, Cai Ying, etc. Based on ultra-high performance liquid chromatography-high resolution mass spectrometry to study urine metabolome of hepatotoxicity caused by alcohol extract of Sophora flavescens [J]. Journal of Anhui University of Traditional Chinese Medicine, 2018. 3. TUKHVATSHIN MARAT, Zhang Qian, Qu Yanqin, Zheng Deyong, Yang Jiangfan, Ye Naixing. Analysis of Organic Acid Components in White Tea Processing [J]. Fujian Tea, 2019,41(03):11-12. 4. Li Weini, Zhang Yuxiang, Wei Jianping, et al. Optimization of Probiotic Fermentation Apple Juice Process and Changes of Organic Acids [J]. Food Science, 2017(22):80-87. 5. Yan Chao, Hou Lijuan, Qi Xiaoru, etc. Analysis of Changes of Amino Acids and Organic Acids in Fermentation of Jujube Brandy [J]. Food Industry Science and Technology, 2017, 38(014):121-125. 6. Ma Yan, Jiang Ming, Liu Zhenyan, et al. Analysis of Changes of Organic Acids and Free Amino Acids in QY-1 Fermentation of Saccharomyces cerevisiae [J]. China Brewing, 2019(10). 7. Dailin, Xu Yuanyuan, xiong Bo, et al. Accumulation Characteristics of Ascorbic Acid, Glutathione and Organic Acids in Huangguoan Fruit [J]. Journal of Zhejiang Agriculture, 2018, v.30;No.189(08):75-82. 8. Wang Siwei, Liu Yanping, Wang Xiaonan, et al. Determination of 10 Organic Acids in Fresh Litchi Pulp Based on High Performance Liquid Chromatography-Triple Quadpole Tandem Mass Spectrometry [J]. Journal of Pesticide Science, 2019(3). 9. Duan Yunfei, Wu Guangbin, Ye Hong, Chen Zhaohua, Zhang Shen, Chen Fahe. Simultaneous Determination of Seven Organic Acids in Postharvest Lotus Fruit by HPLC [J]. Food Science, 2021,42(04):175-180. 10. Jiang, Peng, et al. "Hepatotoxicity induced by Sophora flavescens and hepatic accumulation of kurarinone, a major hepatotoxic constituent of Sophora flavescens in rats." Molecules 22.11 (2017): 1809.https://doi.org/10.3390/molecules22111809 11. Li, Qi, Wei Liu, and Xiashi Zhu. "Green Choline Amino Acid Ionic Liquid Aqueous Two-Phase Extraction Coupled with HPLC for Analysis Sunset Yellow in Beverages." Food Analytical Methods 12.11 (2019): 2527-2534. 12. Li, Qi, Wei Liu, and Xiashi Zhu. "Green Choline Amino Acid Ionic Liquid Aqueous Two-Phase Extraction Coupled with HPLC for Analysis Sunset Yellow in Beverages." Food Analytical Methods 12.11 (2019): 2527-2534. 13. 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. 14. 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 15. 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 16. [IF=4.044] Feng Liu et al."Comparative analysis of proteomic and metabolomic profiles of different species of Paris."J Proteomics. 2019 May;200:11 17. [IF=3.757] Yuchen Wang et al."Metabolic profile of ginkgo kernel juice fermented with lactic aicd bacteria: A potential way to degrade ginkgolic acids and enrich terpene lactones and phenolics."Process Biochem. 2019 Jan;76:25 18. [IF=3.06] Peng Jiang et al."Hepatotoxicity Induced by Sophora flavescens and Hepatic Accumulation of Kurarinone, a Major Hepatotoxic Constituent of Sophora flavescens in Rats."Molecules. 2017 Nov;22(11):1809 19. [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 20. [IF=7.514] Hongcai Li et al."Study on the nutritional characteristics and antioxidant activity of dealcoholized sequentially fermented apple juice with Saccharomyces cerevisiae and Lactobacillus plantarum fermentation."Food Chem. 2021 Nov;363:130351 21. [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 22. [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 23. [IF=3.638] Yingying Han et al."Effect of bentonite and calcium chloride on apple wine."J Sci Food Agr. 2022 Jan;102(1):425-433 24. [IF=6.576] Jie Yang et al."Fermentation and Storage Characteristics of “Fuji” Apple Juice Using Lactobacillus acidophilus, Lactobacillus casei and Lactobacillus plantarum: Microbial Growth, Metabolism of Bioactives and in vitro Bioactivities."Front Nutr. 2022; 9: 83 25. [IF=9.423] Yi Li et al."Blockage of citrate export prevents TCA cycle fragmentation via Irg1 inactivation."Cell Rep. 2022 Feb;38:110391 26. [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 |
Pyruvic acid,(2-Oxopropionic acid) - Nature
Open Data Verified Data
colorless to light yellow liquid with acetic acid odor. Miscible with water, alcohol and ether. Easy moisture absorption, easy polymerization.
Last Update：2024-01-02 23:10:35
Pyruvic acid,(2-Oxopropionic acid) - Preparation Method
Open Data Verified Data
prepared from tartaric acid and potassium pyrosulfate.
Last Update：2022-01-01 09:27:23
Pyruvic acid,(2-Oxopropionic acid) - Introduction
It smells like acetic acid. Easy to absorb moisture, easy to polymerize. See the light color darker. In addition to pure quality and sealed preservation from light, it is easy to produce polymerization and decomposition during storage. Can be miscible with water, alcohol and ether. It's corrosive.
Last Update：2022-10-16 17:13:03
Pyruvic acid,(2-Oxopropionic acid) - Use
Open Data Verified Data
can be used in biotechnology diagnostic reagents, detection reagents, as primary and secondary alcohol assay, biochemical transaminase determination, can also be used as aliphatic amine display agent. Pyruvate is a very versatile organic acid. In the chemical industry, pharmaceutical and agricultural chemicals and other industries have a wide range of applications.
Last Update：2022-01-01 09:27:24
Pyruvic acid,(2-Oxopropionic acid) - Safety
Open Data Verified Data
The eyes, skin, respiratory tract irritation, staff should be protected.
Last Update：2022-01-01 09:27:24
Pyruvic acid,(2-Oxopropionic acid) - Reference Information
| FEMA | 2970 | PYRUVIC ACID |
| dissociation constant | 2.49 at 25 ℃ |
| NIST chemical information | Information provided by: webbook.nist.gov (external link) |
| EPA chemical information | Information provided by: ofmpub.epa.gov (external link) |
| overview | pyruvate is a component of the human body. it is mainly involved in the metabolism of sugar and fat in the human body, and is also one of the intermediate products of carbohydrate metabolism. Pyruvate and the salt it produces are widely used in the field of medicine, used in the production of sedatives, antioxidants, antiviral agents, synthetic drugs for the treatment of hypertension, etc. Pyruvic acid is also called acetoformic acid, pyrogluconic acid, 2-oxopropionic acid. Light yellow to yellow transparent liquid. It smells like acetic acid. It has a sour taste. Natural products are found in mint and sucrose fermentation broth. Relative molecular mass 88.06. Relative density 1.2271. Melting point 13.8 ℃. Boiling point 165 ℃ (decomposition), 106.5 ℃(13.332 × 103Pa), 85.3 ℃(5.333 × 103 Pa), 70.8 ℃(2.666 × 103Pa), 57.9 ℃(1.333 × 103 Pa), 45.8 ℃(0.667 × 103Pa), 21.4 ℃(0.133 × 103 Pa). Flash point 82 ℃. 1.4280 refractive index. Miscible with water, ethanol, ether, etc. The color darkens in the air. It polymerizes slowly when heated, is full of reactivity, and is easy to react with nitrides, aldehydes, halides, phosphides, etc., and participates in the biochemical synthesis and metabolism of sugar metabolism, colloids, amino acids, proteins, etc., and alcohol fermentation. When applied, it is reduced to lactic acid in the muscle, oxidized again at rest and partially converted to glycogen. Rat oral LD502100mg/kg. Uses: It is used in the synthesis of medicines, amino acids (L-tyrosine substrates), etc., which can improve efficiency, especially in the pharmaceutical industry, which can shorten the process and simplify the process, such as the 2-Phenylocynic acid made of this product is an antipyretic, analgesic, diuretic drug. Using this product as a raw material can greatly reduce production costs; in addition, it is also used as an anti-tuberculosis drug, isoniazid calcium pyruvate, hormone synthesis, the raw material of insect repellent pamote (Pyrunium pamote); it is also used as a raw material for pesticides; pyruvate, indole and ammonia are used as raw materials for biochemical reactions to produce tryptophan; the production of monosodium glutamate is to improve L-threonine This product can be used in the yield; spices are edible spices allowed in my country's GB2760-1996 regulations. preparation method: 1, using lactate as raw material for gas phase or liquid phase oxidation to obtain acetone ester, further hydrolysis can be obtained. 2, using tartaric acid as raw material, adding potassium bisulfate and sodium bisulfate, heating to 210~220 ℃, dehydrogenation, crude pyruvic acid can be obtained, and then refined by vacuum distillation. 3.2, 2-dichloropropionic acid is used as raw material, sodium hydroxide is used, pH = 6 is adjusted, and hydrolysis is carried out. |
| The simplest α-keto acid | Pyruvate is the simplest and most important α-keto acid, which has the general properties of ketones and carboxylic acids. It is more acidic than propionic acid and hydroxypropionic acid, and can react with silver mirrors. Pyruvic acid has active chemical properties and can undergo decarbonylation and oxidation reactions: Pyruvic acid is an intermediate product of carbohydrate fermentation and metabolism. It can be converted into amino acids in animals, which is of great physiological significance. It can be used for biochemical research, verification of primary and secondary alcohols, as a developer for verification of aliphatic amines, and determination of transaminases. |
| pyruvate metabolism | pyruvate metabolism refers to the synthesis and decomposition process of pyruvate in animals. Pyruvate is an intermediate product of carbohydrates in fermentation and metabolism. It can be converted into amino acids in animals, which is of great physiological significance. Pyruvate in the body mainly comes from glycolysis, and a small amount comes from the metabolism of certain amino acids and glycerol. The decomposition products of pyruvate vary depending on the conditions. When the animal is anoxic and the glycolysis is accelerated, the lactic acid dehydrogenase catalyzes the conversion of pyruvate to lactic acid, and the reduced nicotinamide adenine dinucleotide (NADH) regenerates oxidized nicotinamide adenine dinucleotide (NAD ), so that the glycolysis can continue. When aerobic, pyruvate is catalyzed by pyruvate dehydrogenase system to generate acetyl-CoA (acetyl-CoA) in mitochondria. Acetyl-CoA can enter the tricarboxylic acid cycle to completely oxidize or convert into other substances. The overall reaction is: Pyruvate dehydrogenase system |
| Phosphoenolpyruvate carboxykinase | The process of converting pyruvate into phosphoenolpyruvate is more complicated and cannot be achieved through a simple substrate circulation pathway. It needs to be completed by two energy-consuming reactions catalyzed by pyruvate carboxylase and phosphoenolpyruvate carboxykinase. This process is called pyruvate carboxylation branch. Pyruvate carboxylation branch: Pyruvate is first carboxylated into oxaloacetate, oxaloacetate is then decarboxylated and acidified into phosphoenolpyruvate. The enzyme that catalyzes the first step of the reaction is the pyruvate carboxylase in the mitochondria, and the second step of the reaction is the phosphoenolpyruvate carboxykinase in the cytosol. For this reason, pyruvate must enter the mitochondria, transform into oxaloacetic acid and then return to the cytosol, but oxaloacetic acid cannot freely pass through the inner mitochondrial membrane, so it needs to be reduced to malic acid first, and then dehydrogenated in the cytosol to regenerate oxaloacetic acid, which is catalyzed by phosphoenolpyruvate carboxykinase, and finally generates phosphoenolpyruvate. References: Handbook of Bed Practitioners> Biochemistry> Glucose Metabolism> Gluconeogenesis |
| calcium pyruvate | calcium pyruvate is the calcium salt of pyruvate, very stable, white crystalline powder, odorless, almost neutral, slightly soluble in water. Pyruvate is extremely unstable and easily oxidized. Weak oxidants Fe and H2O2 can oxidize pyruvate to acetic acid and release carbon dioxide. Pyruvate is an intermediate product in the process of carbohydrate metabolism in the organic body. It is also a necessary transit station for the metabolism of proteins and lipids. It is a colorless and pungent liquid under natural conditions, with a boiling point of 165 ℃ (decomposition), It is easily soluble in water. In addition to the typical properties of hydroxy acid and ketones, it also has the characteristics of a-keto acid. Pyruvate is the simplest a-keto acid (belonging to hydroxy acid). At present, calcium pyruvate can only be chemically synthesized in our country, and all the calcium pyruvate produced is industrial raw material grade. The calcium pyruvate obtained in this way is a racemate (that is, calcium pyruvate and dextrorotatory calcium pyruvate are as many), while only pyruvate with left-handed structure can be absorbed by the human body. At present, most of the acetone acid products used in medicine and weight loss in our country need to be imported from abroad. Japan's production technology in this area is in an international leading position, and it can produce L-pyruvate products through biological fermentation. Used as raw materials and food additives for medicine. As a dietary supplement, calcium pyruvate has the effects of accelerating fat consumption, reducing weight, enhancing human endurance, and improving competitive performance; it has a special protective effect on the heart, which can enhance the efficacy of heart muscles and reduce heart disease or heart ischemia. Damage caused; at the same time, calcium pyruvate has significant effects such as phagocytosis of free radicals in the body and inhibiting the generation of free radicals. Calcium pyruvate is also a calcium nutritional supplement. Although its calcium content is not 20% enough, unlike other calcium supplements, acid ions will increase the burden on the liver and kidney and have side effects. Pyruvate ions can enter cells to participate in organic matter metabolism and lose weight without affecting protein storage. |
| toxicity | can be safely used in food (FDA, 172.51 5,2000). |
| usage limit | FEMA(mg/kg): soft drink 0.25; Cold drinks 0.25~20; Candy 27; Baked food 30; Gum sugar 110. |
| use | GB 2760-1996 specified as allowed food spices. Pyruvate is an intermediate of the fungicide thiabendazole. Used in organic synthesis and biochemical research. Used as raw materials and food additives for medicine Biochemical research. Verification of primary and secondary alcohols. Color developing agent for verification of aliphatic amines. Determination of transaminase. It is the main raw material for the production of tryptophan, phenylalanine and vitamin B, the raw material for the biosynthesis of L-dopa, and the initiator of ethylene polymer |
| Production method | is obtained by the reaction of tartaric acid and potassium pyrosulfate. First, mix tartaric acid and potassium pyrosulfate thoroughly, put them into a glass-lined reaction pot, heat them to about 180 ℃ in an oil bath, the solid starts to melt, and a large amount of foam rises. Start the agitator to break up the foam to prevent overflow, and then raise the temperature to 220 ℃, I .e. pyruvic acid is steamed out, and the oil temperature is kept at 245 ℃ until pyruvic acid is steamed out. There are several preparation methods. Preparation of tartaric acid from tartaric acid is prepared by dehydration and carbon dioxide in the presence of potassium disulfate. Prepared from dichloropropionic acid, 2, 2-dichloropropionic acid and 10% NaOH solution are refluxed, and finally the pH of the reactant is 2.5, cooling is carried out, water is evaporated, dilute H2SO4 is added to form a viscous acidic substance, and the product is distilled under reduced pressure. Oxidation with ethyl lactate and then hydrolysis ethyl lactate oxidation can be carried out gas phase oxidation or liquid phase oxidation to produce pyruvate, and manganese dioxide and hydrogen peroxide can also be used as oxidants for oxidation, and the obtained ethyl pyruvate is hydrolyzed to obtain the product. Acrylate oxidation followed by hydrolysis of acrylic acid or its ester in the presence of catalyst Cr or V compound oxidation with H2O2 to produce products. Glucose is used as a raw material for fermentation of acetone aldehyde oxidation of acetone aldehyde can be obtained by gas phase oxidation of 1, 2-propanediol, and then further with methanol in the presence of nickel phosphate catalyst with oxygen gas phase oxidation to prepare the product. Among them, method (3) and method (5) can be industrialized. It is obtained by distillation of tartaric acid in the presence of dehydrating agent potassium bisulfate and then vacuum distillation. The nitrile is formed from acetyl chloride and potassium cyanide, which is obtained by acid hydrolysis. |
| spontaneous combustion temperature | 305°C |
Last Update：2024-04-10 22:29:15
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