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PYRUVIC ACID

CAS NUMBER: 127-17-3

EC NUMBER: 204-824-3

MOLECULAR FORMULA: C3H4O3

MOLECULAR WEIGHT: 88.06

IUPAC NAME: 2-oxopropanoic acid


Pyruvic Acid (CH3COCOOH) is the simplest of the alpha-keto acids, with a carboxylic acid and a ketone functional group. 
Pyruvate, the conjugate base, CH3COCOO−, is an intermediate in several metabolic pathways throughout the cell.

Pyruvic Acid is a 2-oxo monocarboxylic acid that is the 2-keto derivative of propionic acid. 
Pyruvic Acid is a metabolite obtained during glycolysis. 
Pyruvic Acid has a role as a fundamental metabolite and a cofactor. 
Pyruvic Acid derives from a propionic acid. 
Pyruvic Acid is a conjugate acid of a pyruvate.

Pyruvic Acid is an intermediate compound in the metabolism of carbohydrates, proteins, and fats. 
In thiamine deficiency, its oxidation is retarded and it accumulates in the tissues, especially in nervous structures.

Pyruvic Acid can be made from glucose through glycolysis, converted back to carbohydrates (such as glucose) via gluconeogenesis, or to fatty acids through a reaction with acetyl-CoA.
Pyruvic Acid can also be used to construct the amino acid alanine and can be converted into ethanol or lactic acid via fermentation.
Pyruvic Acid supplies energy to cells through the citric acid cycle (also known as the Krebs cycle) when oxygen is present (aerobic respiration), and alternatively ferments to produce lactate when oxygen is lacking (lactic acid).

Chemistry of Pyruvic Acid:
In 1834, Théophile-Jules Pelouze distilled tartaric acid and isolated glutaric acid and another unknown organic acid. 
Jöns Jacob Berzelius characterized this other acid the following year and named pyruvic acid because it was distilled using heat.
The correct molecular structure was deduced by the 1870s.
Pyruvic Acid is a colorless liquid with a smell similar to that of acetic acid and is miscible with water.
In the laboratory, pyruvic acid may be prepared by heating a mixture of tartaric acid and potassium hydrogen sulfate, by the oxidation of propylene glycol by a strong oxidizer (e.g., potassium permanganate or bleach), or by the hydrolysis of acetyl cyanide, formed by reaction of acetyl chloride with potassium cyanide:

CH3COCl + KCN → CH3COCN + KCl
CH3COCN → CH3COCOOH

Biochemistry of Pyruvic Acid:
Pyruvate is an important chemical compound in biochemistry. 
Pyruvic Acid is the output of the metabolism of glucose known as glycolysis.
One molecule of glucose breaks down into two molecules of pyruvate, which are then used to provide further energy, in one of two ways. 
Pyruvate is converted into acetyl-coenzyme A, which is the main input for a series of reactions known as the Krebs cycle (also known as the citric acid cycle or tricarboxylic acid cycle). 
Pyruvate is also converted to oxaloacetate by an anaplerotic reaction, which replenishes Krebs cycle intermediates; also, the oxaloacetate is used for gluconeogenesis. 
These reactions are named after Hans Adolf Krebs, the biochemist awarded the 1953 Nobel Prize for physiology, jointly with Fritz Lipmann, for research into metabolic processes. 
The cycle is also known as the citric acid cycle or tricarboxylic acid cycle, because citric acid is one of the intermediate compounds formed during the reactions.

If insufficient oxygen is available, the acid is broken down anaerobically, creating lactate in animals and ethanol in plants and microorganisms. 
Pyruvate from glycolysis is converted by fermentation to lactate using the enzyme lactate dehydrogenase and the coenzyme NADH in lactate fermentation, or to acetaldehyde (with the enzyme pyruvate decarboxylase) and then to ethanol in alcoholic fermentation.
Pyruvate is a key intersection in the network of metabolic pathways. 
Pyruvate can be converted into carbohydrates via gluconeogenesis, to fatty acids or energy through acetyl-CoA, to the amino acid alanine, and to ethanol. 
Therefore, it unites several key metabolic processes.

Pyruvic Acid production by glycolysis:
In glycolysis, phosphoenolpyruvate (PEP) is converted to pyruvate by pyruvate kinase. 
This reaction is strongly exergonic and irreversible; in gluconeogenesis, it takes two enzymes, pyruvate carboxylase and PEP carboxykinase, to catalyze the reverse transformation of pyruvate to PEP.

Uses of Pyruvic Acid:
Pyruvate is sold as a weight-loss supplement, though credible science has yet to back this claim.
A systematic review of six trials found a statistically significant difference in body weight with pyruvate compared to placebo. 
However, all of the trials had methodological weaknesses and the magnitude of the effect was small. 
The review also identified adverse events associated with pyruvate such as diarrhea, bloating, gas, and increase in low-density lipoprotein (LDL) cholesterol. 
The authors concluded that there was insufficient evidence to support the use of pyruvate for weight loss.

There is also in vitro as well as in vivo evidence in hearts that pyruvate improves metabolism by NADH production stimulation and increases cardiac function
Pyruvic Acid, (CH3COCOOH), is an organic acid that probably occurs in all living cells. It ionizes to give a hydrogen ion and an anion, termed pyruvate. 
Biochemists use the terms pyruvate and pyruvic acid almost interchangeably.

Pyruvic Acid is a key product at the crossroads between the catabolism (breaking down) and anabolism (synthesizing) of carbohydrates, fats, and proteins. 
Pyruvic Acid is a complex sequence of enzyme reactions leading from sugar (or carbohydrate, in the form of glucose or fructose) to pyruvate is common to five metabolic processes. 
These are: 
-the fermentation of sugar to ethyl alcohol by yeast; 
-the fermentation of sugar to lactic acid in muscle; 
-the oxidation of sugar to carbon dioxide and water by way of the Krebs cycle; 
-the conversion of sugar to fatty acids; and 
-the conversion of sugar to amino acids, such as alanine, which are the building blocks of proteins.

Pyruvic Acid, formerly called pyroracemic acid, was first obtained by Jöns Jacob Berzelius in 1835 by the dry distillation of tartaric acid. 
The preparation of pyruvic acid in bulk amounts is similar: tartaric acid is heated with fused potassium hydrogen sulfate at 210–220 °C. 
The product is purified by fractional distillation under reduced pressure. 
At room temperature, pure pyruvic acid is a colourless liquid with a pungent odour resembling that of acetic acid. 
On cooling, it forms crystals that melt at 13.6 °C. The boiling point is 165 °C.

Pharmacology:
Pyruvic Acid or pyruvate is a key intermediate in the glycolytic and pyruvate dehydrogenase pathways, which are involved in biological energy production. 
Pyruvate is widely found in living organisms. 
Pyruvic Acid is not an essential nutrient since it can be synthesized in the cells of the body. Certain fruits and vegetables are rich in pyruvate. 
For example, an average-size red apple contains approximately 450 milligrams. 
Dark beer and red wine are also rich sources of pyruvate. 
Recent research suggests that pyruvate in high concentrations may have a role in cardiovascular therapy, as an inotropic agent. 
Supplements of this dietary substance may also have bariatric and ergogenic applications.

Pyruvate is absorbed from the gastrointestinal tract from whence it is transported to the liver via the portal circulation.
In the liver, pyruvate is metabolized via several pathways.

Mechanism of Action:
Pyruvate serves as a biological fuel by being converted to acetyl coenzyme A, which enters the tricarboxylic acid or Krebs cycle where it is metabolized to produce ATP aerobically. 
Energy can also be obtained anaerobically from pyruvate via its conversion to lactate. 
Pyruvate injections or perfusions increase contractile function of hearts when metabolizing glucose or fatty acids. 
This inotropic effect is striking in hearts stunned by ischemia/reperfusion. 
The inotropic effect of pyruvate requires intracoronary infusion. 

Among possible mechanisms for this effect are increased generation of ATP and an increase in ATP phosphorylation potential. 
Another is activation of pyruvate dehydrogenase, promoting its own oxidation by inhibiting pyruvate dehydrogenase kinase. 
Pyruvate dehydrogenase is inactivated in ischemia myocardium. 
Yet another is reduction of cytosolic inorganic phosphate concentration. 
Pyruvate, as an antioxidant, is known to scavenge such reactive oxygen species as hydrogen peroxide and lipid peroxides. 
Indirectly, supraphysiological levels of pyruvate may increase cellular reduced glutathione.

Tissue Locations:
-Adipose Tissue
-Brain
-Fibroblasts
-Heart
-Kidney
-Liver
-Neuron
-Pancreas
-Placenta
-Skeletal Muscle
-Spleen
-Testis
-Thyroid Gland

Cellular Locations:
-Extracellular
-Mitochondria
-Peroxisome

It is a colorless, water-soluble, organic liquid produced by the breakdown of carbohydrates and sugars during glycolysis, and with a chemical formula of: CH3COCO2H. 
If oxygen is available, Pyruvic Acid is converted to acetyl coenzyme A that enters the energy-producing pathway, the Krebs cycle. 
If oxygen is lacking, pyruvic acid is converted to lactic acid.
This compound is also used in the body to synthesize alanine.

Pyruvic Acid (CH3COCOOH; is an organic acid, a ketone, and the simplest of the alpha-keto acids. 
The carboxylate (COO−) anion of pyruvic acid. 
The Brønsted–Lowry conjugate base, CH3COCOO−, is known as pyruvate, and is a key intersection in several metabolic pathways.

Pyruvic Acid can be made from glucose through glycolysis, converted back to carbohydrates (such as glucose) via gluconeogenesis, or to fatty acids through acetyl-CoA. 
Pyruvic Acid can also be used to construct the amino acid alanine and be converted into ethanol. 
Pyruvic acid supplies energy to living cells through the citric acid cycle (also known as the Krebs cycle) when oxygen is present (aerobic respiration), and alternatively ferments to produce lactic acid when oxygen is lacking (fermentation).

Pyruvic acid can be made from glucose through glycolysis, converted back to carbohydrates (such as glucose) via gluconeogenesis, or to fatty acids through acetyl-CoA. 
Pyruvic Acid can also be used to construct the amino acid alanine
And it can be converted into ethanol.

Pyruvic Acid supplies energy to living cells through the citric acid cycle (also known as the Krebs cycle) when oxygen is present (aerobic respiration); when oxygen is lacking, it ferments to produce lactic acid. 
Pyruvate is an important chemical compound in biochemistry. 
Pyruvic Acid is the output of the anaerobic metabolism of glucose known as glycolysis. 
One molecule of glucose breaks down into two molecules of pyruvate, which are then used to provide further energy in one of two ways. 
Pyruvate is converted into acetyl- coenzyme A, which is the main input for a series of reactions known as the Krebs cycle. 
Pyruvate is also converted to oxaloacetate by an anaplerotic reaction, which replenishes Krebs cycle intermediates; also, oxaloacetate is used for gluconeogenesis. 
These reactions are named after Hans Adolf Krebs, the biochemist awarded the 1953 Nobel Prize for physiology, jointly with Fritz Lipmann, for research into metabolic processes. 
The cycle is also known as the citric acid cycle or tri-carboxylic acid cycle, because citric acid is one of the intermediate compounds formed during the reactions.

If insufficient oxygen is available, the acid is broken down anaerobically, creating lactate in animals and ethanol in plants and microorganisms. 
Pyruvate from glycolysis is converted by fermentation to lactate using the enzyme lactate dehydrogenase and the coenzyme NADH in lactate fermentation. 
Alternatively it is converted to acetaldehyde and then to ethanol in alcoholic fermentation.

Pyruvate is a key intersection in the network of metabolic pathways. 
Pyruvate can be converted into carbohydrates via gluconeogenesis, to fatty acids or energy through acetyl-CoA, to the amino acid alanine, and to ethanol. 
Therefore, Pyruvic Acid unites several key metabolic processes.

-Pyruvic Acid can be made from glucose through glycolysis, converted back to carbohydrates (such as glucose) via gluconeogenesis, or to fatty acids through acetyl-CoA.
-Pyruvic Acid supplies energy to living cells through the citric acid cycle (also known as the Krebs cycle ) when oxygen is present (aerobic respiration); it ferments to produce lactic acid when oxygen is lacking ( fermentation ).
-Pyruvate is the output of the anaerobic metabolism of glucose known as glycolysis.
-Pyruvate can be converted into carbohydrates via gluconeogenesis, to fatty acids or energy through acetyl-CoA, to the amino acid alanine, and to ethanol.

Pyruvic Acid, the simplest α-ketoacid, plays a central role in sugar metabolism. 
Pyruvic Acid is the product of glycolysis, the anaerobic decomposition of glucose. 
In muscle, Pyruvic Acid is reduced to lactic acid during exertion.

With a carboxylic acid and a ketone functional group, pyruvic acid (CH3COCOOH) is the most basic of the alpha-keto acids. 
Pyruvic Acid (CH3COCOOH) is an organic acid found in almost all living organisms. 
Pyruvic Acid ionizes to form hydrogen ions and an anion. 
This anion is known as pyruvate. 
Pyruvate and Pyruvic Acid are almost interchangeable terms among biochemists. 
This article will study the pyruvate definition, pyruvate chemical formula, the chemical formula of pyruvic acid, pyruvic acid to lactic acid and the difference between pyruvate and pyruvic acid.

What is Pyruvic Acid?
Pyruvic Acid is a central substance at the crossroads of carbohydrate, fat, and protein catabolism (breaking down) and anabolism (synthesis).
Pyruvic Acid may be made from glucose, converted back to carbohydrates (such as glucose) through gluconeogenesis, or converted to fatty acids via an acetyl-CoA reaction. 
It can also be used to make the amino acid alanine, and it can be fermented to produce ethanol or lactic acid.
Five metabolic processes share a complex sequence of enzyme reactions that lead from sugar (or carbohydrate, in the form of glucose or fructose) to pyruvate. 
They are:yeast fermentation of sugar to ethyl alcohol; muscle fermentation of sugar to lactic acid; the Krebs cycle's oxidation of sugar to carbon dioxide and water; sugar conversion to fatty acids; and sugar conversion to amino acids, such as alanine, which are the building blocks of proteins.

Pyruvic  cid (CH3COCOOH) is the simplest of the alpha-keto acids, with a carboxylic acid and a ketone functional group. 
Pyruvate, the conjugate base, CH3COCOO−, is an intermediate in several metabolic pathways throughout the cell. 
Pyruvic  cid can be made from glucose through glycolysis, converted back to carbohydrates (such as glucose) via gluconeogenesis, or to fatty acids through a reaction with acetyl-CoA. 
Pyruvic Acid can also be used to construct the amino acid alanine and can be converted into ethanol or lactic acid via fermentation. 
Pyruvic Acid supplies energy to cells through the citric acid cycle (also known as the Krebs cycle) when oxygen is present (aerobic respiration), and alternatively ferments to produce lactate when oxygen is lacking.

Pyruvic Acid is an ingredient of a blood cell processing solution used to rejuvenate a unit of red blood cells (RBC) in preparation for transfusion.
Pyruvic Acid is an intermediate compound in the metabolism of carbohydrates, proteins, and fats. In thiamine deficiency, its oxidation is retarded and it accumulates in the tissues, especially in nervous structures. 

Pyruvic Acid or pyruvate is a key intermediate in the glycolytic and pyruvate dehydrogenase pathways, which are involved in biological energy production. 
Pyruvate is widely found in living organisms. 
Pyruvic Acid is not an essential nutrient since it can be synthesized in the cells of the body. Certain fruits and vegetables are rich in pyruvate. 
For example, an average-size red apple contains approximately 450 milligrams. Dark beer and red wine are also rich sources of pyruvate. 
Recent research suggests that pyruvate in high concentrations may have a role in cardiovascular therapy, as an inotropic agent. 
Supplements of this dietary substance may also have bariatric and ergogenic applications.

pyruvic acid A 3-carbon keto acid that occupies a central position in cell metabolism. 
It represents the final product of glycolysis in aerobic respiration, and subsequently undergoes oxidation to carbon dioxide and acetyl coenzyme A. 
During anaerobic respiration it is irreversibly converted to ethyl alcohol and carbon dioxide in plant cells (and reversibly to lactic acid in animal cells). 
It may also be variously converted into alanine, malic acid, and oxaloacetic acid.

pyruvic acid is an intermediate in the metabolism of carbohydrates, formed by the anaerobic metabolism of glucose. 
It may then either be converted to acetyl CoA, and oxidized through the citric acid cycle, or be reduced to lactic acid. 
The oxidation to acetyl CoA is thiamin dependent, and blood concentrations of pyruvate and lactate rise in thiamin deficiency.

pyruvic Acid (2-oxopropanoic acid) a colourless liquid organic acid, CH3COCOOH. 
Pyruvate is an important intermediate compound in metabolism, being produced during glycolysis and converted to acetyl coenzyme A, required for the Krebs cycle. 
Under anaerobic conditions pyruvate is converted to lactate or ethanol.
Pyruvic Acid (C3H4O3 (CH3COCO2H)) is a three-carbon, keto acid that plays an important role in biochemical processes. 
At the pH levels of the human body, pyruvic acid is usually ionized to pyruvate; the two terms are used essentially synonymously.

Pyruvic Acid is formed as an end product of glycolysis, a process that breaks down glucose (a six-carbon molecule) into two molecules of pyruvate (a three-carbon molecule) and simultaneously yields a small net gain of the universal energy storage molecule adenosine triphosphate (ATP), used to power cellular function. 
The pyruvate is then further processed in a variety of ways, depending on conditions, especially the oxygen level, within the cell.

Pyruvic Acid was used to study the cultivation of previously undescribed soil bacteria as micro colonies using soil substrate membrane system. 
Pyruvic Acid was used to develop a new method for simultaneous determination of organic acids in red wine and must using liquid chromatography.

Pyruvic Acid is an α-hydroxy acid that has various keratolytic, antimicrobial, antioxidant, depigmenting and sebostatic properties. 
In addition, it has a moisturizing effect and a great capacity to stimulate the formation of new collagen and elastic fibers; reaching very deep layers of the dermis.

What are Pyruvic Acid's Benefits?
Due to Pyruvic Acid's antimicrobial and sebostatic properties, it has been used in patients with inflammatory acne, moderate acne scars, actinic keratosis, and warts.
Pyruvic Acid has also shown antioxidant capacity, thus significantly reducing the damage caused by UV radiation.
The chemical peel with pyruvic acid is very effective for skins that require deep exfoliation, minimizing spots, scars, and other skin imperfections.
Pyruvic Acid's effectiveness as an anti-aging agent has also been demonstrated, with a great reduction in skin wrinkles after its application, as it causes separation of the dermis and epidermis, and increases the production of collagen, elastic fibers, and glycoproteins.

PHYSICAL PROPERTIES OF PYRUVIC ACID:

-Molecular Weight: 88.06    

-XLogP3-AA: -0.3    

-Exact Mass: 88.016043985

-Monoisotopic Mass: 88.016043985    

-Topological Polar Surface Area: 54.4 Ų    

-Compound Is Canonicalized: Yes

-Physical Description: colourless to amber viscous liquid with a sour vinegar-like odour

-Color: colourless

-Form: liquid

-Odor: sour vinegar-like odour

-Boiling Point: 54 °C

-Melting Point: 13.8 °C

-Solubility: 11.36 M

-Density: 1.260-1.281

-Vapor Pressure: 1.29 mmHg

-Refractive Index: 1.424-1.435

-Dissociation Constants: pKa=2.45

Pyruvic Acid is a 2-oxo monocarboxylic acid that is the 2-keto derivative of propionic acid. 
Pyruvic Acid is a metabolite obtained during glycolysis. 
Pyruvic Acid has a role as a fundamental metabolite and a cofactor. 

Pyruvic Acid can be made from glucose through glycolysis, converted back to carbohydrates (such as glucose) via gluconeogenesis, or to fatty acids through a reaction with acetyl-CoA.
Pyruvic Acid can also be used to construct the amino acid alanine and can be converted into ethanol or lactic acid via fermentation.
Pyruvic Acid supplies energy to cells through the citric acid cycle (also known as the Krebs cycle) when oxygen is present (aerobic respiration), and alternatively ferments to produce lactate when oxygen is lacking (lactic acid).

CHEMICAL PROPERTIES OF PYRUVIC ACID:

-Hydrogen Bond Donor Count: 1    

-Hydrogen Bond Acceptor Count: 3    

-Rotatable Bond Count: 1    

-Heavy Atom Count: 6    

-Formal Charge: 0    

-Complexity: 84    

-Isotope Atom Count: 0    

-Defined Atom Stereocenter Count: 0    

-Undefined Atom Stereocenter Count: 0    

-Defined Bond Stereocenter Count: 0    

-Undefined Bond Stereocenter Count: 0    

-Covalently-Bonded Unit Count: 1    

-LogP: -0.5

-Henrys Law Constant: 3.23e-09 atm-m3/mole


SYNONYMS:

2-Oxopropanoic acid
2-Oxopropionic acid
acetylformic acid
Pyroracemic acid
alpha-ketopropionic acid
2-Ketopropionic acid
Propanoic acid, 2-oxo-
2-Oxopropanoate
2-oxo-propionic acid
2-Oxopropansaeure
2-Oxopropionsaeure
alpha-Oxopropionsaeure
Pyruvic acid (natural)
acide pyruvique
a-Ketopropionic acid
Propanoic acid, oxo-
pyruvicacid
alpha-keto propionic acid
2-KETOPROPANOIC ACID
.alpha.-Ketopropionic acid
2-oxo-Propanoic acid
Brenztraubensaeure
Pyruvic acid (8CI)
Acetylformate
Pyroracemate
Acid pyruvate
a-Ketopropionate
2-Oxopropionate
acetyl formic acid
alpha-Ketopropionate
2-Oxopropanoic'acid
2-oxo propanoic acid
Pyruvic acid, 95%
bmse000112
Pyruvic-2-[13C] acid
Pyruvic acid, natural, >=80%
Propanoic acid, 2-oxo- (9CI)

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