Pyruvic acid

Pyruvic acid Basic information
Uses Antioxidant effect
Product Name:Pyruvic acid
Synonyms:PYRUVIC ACID, GR 99%;ACID PYRUVATE;PyruvicAcidForSynthesis;PyruvicAcid,FreeAcid;Pyruvic acid, extra pure, 98%;α-ketopropionic acid;PYRUVICACID,REAGENT;PYRUVIC ACID 98%(RG)
CAS:127-17-3
MF:C3H4O3
MW:88.06
EINECS:204-824-3
Product Categories:Nutritional Supplements;PyruvicAcidSeries;bc0001;127-17-3
Mol File:127-17-3.mol
Pyruvic acid Structure
Pyruvic acid Chemical Properties
Melting point 11-12 °C (lit.)
Boiling point 165 °C (lit.)
density 1.267 g/mL at 25 °C (lit.)
vapor pressure 1.72hPa at 25℃
refractive index n20/D 1.428(lit.)
FEMA 2970 | PYRUVIC ACID
Fp 183 °F
storage temp. 2-8°C
solubility Miscible with chloroform and methanol.
pka2.39(at 25℃)
form Liquid
color Clear colorless to light yellow or amber
PH3.11(1 mM solution);2.38(10 mM solution);1.79(100 mM solution);
Odorat 1.00 % in propylene glycol. sharp sour acetic caramellic
Odor Typeacidic
Merck 14,8021
JECFA Number936
BRN 506211
Stability:Stable. Combustible. Incompatible with strong oxidizing agents, strong bases. Refrigerate.
InChIKeyLCTONWCANYUPML-UHFFFAOYSA-N
LogP-1.24
Dissociation constant2.49 at 25℃
CAS DataBase Reference127-17-3(CAS DataBase Reference)
NIST Chemistry ReferencePyruvic acid(127-17-3)
EPA Substance Registry SystemPropanoic acid, 2-oxo- (127-17-3)
Safety Information
Hazard Codes C
Risk Statements 34
Safety Statements 26-36/37/39-45-25-27
RIDADR UN 3265 8/PG 2
WGK Germany 3
RTECS UZ0829800
Autoignition Temperature305 °C
TSCA Yes
HazardClass 8
PackingGroup II
HS Code 29335995
MSDS Information
ProviderLanguage
2-Oxopropanoic acidEnglish
SigmaAldrichEnglish
ACROSEnglish
ALFAEnglish
Pyruvic acid Usage And Synthesis
UsesIntermediate in sugar metabolism and in enzymatic carbohydrate degradation (alcoholic fermentation) where it is converted to acetaldehyde and CO2 by carboxylase. In muscle, Pyruvic acid (derived from glycogen) is reduced to lactic acid during exertion, which is reoxidized and partially retransformed to glycogen during rest. The liver can convert Pyruvic acid to alanine by amination. A diagnostic agent for Parkinson disease.
Antioxidant effectStudies have shown that pyruvic acid can inhibit the oxidation of oxygen free radicals in mice, and as a hydrogen peroxide scavenger, it has the effect of preventing free radical damage, and it has been proved to be protective in cardiac reperfusion injury and acute renal failure. The body resists functional damage. Pyruvic acid can act as an antioxidant through two mechanisms: first, as an α-keto acid, pyruvic acid can directly inhibit hydrogen peroxide through a non-enzymatic decarbonation reaction; second, supplementation of pyruvic acid can enhance In the citric acid cycle, after the production of citric acid increases, the phosphofructokinase is inhibited, thereby entering the pentose phosphate bypass to generate reduced coenzyme II (NADPH), thereby indirectly increasing the ability of the glutathione (GSH) antioxidant system. Pyruvic acid can also increase the ratio of coenzyme I/reduced coenzyme I (NAD+/NADH) and promote the reaction of the tricarboxylic acid cycle.
Chemical PropertiesColorless to light yellow liquid
Chemical PropertiesPyruvic acid has a sour, acetic odor (similar to acetic acid). It has a pleasant, sour taste with a burning, somewhat sweet note. It tends to darken and decompose unless kept free of minor contaminants and in tightly sealed containers
OccurrenceIsolated from cane sugar fermentation broth and from a few plants; also reported found in peppermint, raw asparagus, leaves and stalk of celery, onion, rutabaga, milk, cream, buttermilk, wheaten bread, blue cheeses, cheddar cheese, cottage cheese, provolone cheese, yogurt, beef, Virginia tobacco, beer, white wine, botrytised wine, cocoa and sake.
UsesBiochemical research.
UsesPyruvic acid is used as a component in culture broths and media as commercial red seaweed polysaccharide. It is involved in the construction of amino acid alanine as well as supplies energy to living cells via citric acid cycle (Krebs cycle). It reacts with N-acetyl mannosamine by an aldol-type condensation to prepare sialic acid. It is employed to study the cultivation of soil bacteria as micro colonies using soil substrate membrane system. It finds application in liquid chromatography and in the determination of organic acids in red wine.
Usespyruvic acid is an alpha hydroxy acid that can be irritating and is considered difficult to work with. It has a larger molecular size than the most commonly used AHAs. Sodium pyruvate is more commonly used, and is an organic salt.
DefinitionA fundamen- tal intermediate in protein and carbohydrate metabolism in the cell.
PreparationBy distillation of tartaric acid in the presence of potassium acid sulfate as a dehydrating agent; from acetyl chloride and potassium cyanide to yield the nitrile, which is subsequently acid hydrolyzed to the acid; pyruvic acid must be rectified under vacuum.
Aroma threshold valuesAroma characteristics at 1.0%: acidic, sweet, caramellic and sour.
Taste threshold valuesTaste characteristics at 5 ppm: sharp acidic, sour fruity, with sour creamy and caramellic nuances.
General DescriptionPyruvic acid is the key component formed during the hydrolysis of flavor-precursors called S-alk(en)yl-L-cysteine-sulfoxides in onion tissues by allinase during maceration or chopping. The amount of pyruvic acid formed is used as a measure for onion pungency.
Biochem/physiol ActionsTaste at 5 ppm
Biotechnological ApplicationsPyruvic acid is a key position in cell metabolism and is involved in many catabolic and anabolic pathways, including glycolysis, gluconeogenesis, amino acid, and protein metabolism. Pyruvic acid is employed for the production of L-tryptophan, L-tyrosine, and 3,4-dihydroxyphenyl alanine in various industries. The diet supplementation with pyruvic acid increased fat loss and minimized the associated loss of body protein. Pyruvic acid is also used in biochemical researches and medicine as a substrate for assaying activities of such enzymes as pyruvate dehydrogenase, pyruvate carboxylase, and pyruvate decarboxylase (Nakazawa et al. 1972; Yamada et al. 1972; Stanko et al. 1992).
Y. lipolytica oxidize glucose and form pyruvic acid (75–80 %) and a-ketoglutaric acid (20–25 %) under thiamine deficiency conditions. The synthesis of the acid was triggered by a decrease in intracellular thiamine concentration to 3.0 lg per 1 g biomass. An approximately 3-fold increase in the amount of the biomass was associated with a subsequent decrease in thiamine content to the level of 1.0 lg per 1 g biomass, whose maximum production of pyruvic acid was 50 g/L in this condition. In addition to glucose, thiamine-auxotrophic yeasts are capable of synthesizing pyruvic acid when grown on glycerol and propionic acid. Technicalgrade glycerol is the most promising raw material for pyruvic acid production. Pyruvic acid was obtained at a concentration of 61 g/L with a yield of 71 % from glycerol (Morgunov et al. 2004; Finogenova et al. 2005).
Purification MethodsDistil it twice, then fractionally crystallise it by partial freezing. [Beilstein 3 IV 1505.]
Pyruvic acid Preparation Products And Raw materials
Raw materialsHydrogen peroxide–>CARBON DIOXIDE–>POTASSIUM CYANIDE–>Manganese dioxide–>Oxygen–>Ethyl pyruvate–>6-Benzylaminopurine–>Potassium sulfate–>Propylene glycol–>Lactic acid–>D(-)-Tartaric acid–>Potassium bisulfate–>Dehydrolyzing agent–>DL-Tartaric acid–>Ethyl lactate–>Methylglyoxal–>Sodium pyruvate–>Potassium pyrosulfate–>(R)-Lactate–>NICKEL (II) PHOSPHATE–>ALDRIN–>2,2-Dichloropropionic acid
Preparation ProductsEthyl pyruvate–>DL-Tryptophan–>Ethyl (R)-2-hydroxy-4-phenylbutyrate–>SULFENTRAZONE–>Thiabendazole–>2-AMINO-3-METHYLQUINOXALINE–>3-Bromopyruvic acid–>3-Mercaptopropionic acid–>Gestrinone–>Acetylpyrazine–>Sodium pyruvate–>carfentrazone-ethyl–>3-METHYL-2-QUINOXALINOL–>2-CHLORO-3-METHYL-QUINOXALINE–>1,2,3-THIADIAZOLE-4-CARBOXYLIC ACID–>4-Thiazolecarboxylic acid–>6-AZATHYMINE–>1,2,3-Thiadiazole-4-carbonyl chloride (6CI,7CI,8CI,9CI)–>Methyl pyruvate–>Calcium pyruvate

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