What are the various names and identifiers associated with pyruvic acid?

Pyruvic acid is also known by its preferred IUPAC name, 2-Oxopropanoic acid, and its systematic IUPAC name, 2-Oxopropionic acid. Other common names include $\alpha$-Ketopropionic acid, Acetylformic acid, Pyroracemic acid, and Acetylcarboxylic acid. It is abbreviated as Pyr and has a CAS Number of 127-17-3.

What are the key physical and chemical properties of pyruvic acid as listed in the infobox?

Pyruvic acid has the chemical formula C3H4O3 and a molar mass of 88.06 g/mol. Its density is 1.250 g/cm³, its melting point is 11.8 °C (53.2 °F), and its boiling point is 165 °C (329 °F). Its acidity, measured by pKa, is 2.50.

How is pyruvic acid defined in terms of its chemical structure and classification?

Pyruvic acid, with the chemical formula CH3COCOOH, is classified as the simplest of the alpha-keto acids. It features both a carboxylic acid group and a ketone functional group.

What is pyruvate, and what is its significance in cellular metabolism?

Pyruvate is the conjugate base of pyruvic acid, with the chemical formula CH3COCOO-. It serves as a crucial intermediate in numerous metabolic pathways throughout the cell, playing a central role in energy production.

What are the primary metabolic transformations involving pyruvic acid mentioned in the introduction?

Pyruvic acid can be derived from glucose through glycolysis, converted back into carbohydrates like glucose via gluconeogenesis, or transformed into fatty acids after reacting with acetyl-CoA. It is also used in the synthesis of the amino acid alanine and can be converted to ethanol or lactic acid through fermentation.

How does pyruvic acid contribute to cellular energy production under aerobic and anaerobic conditions?

Under aerobic conditions (with oxygen), pyruvic acid supplies energy to cells via the citric acid cycle (Krebs cycle). When oxygen is lacking, it undergoes fermentation to produce lactate.

Who discovered pyruvic acid, and how did it get its name?

Pyruvic acid was first isolated in 1834 by Théophile-Jules Pelouze, who distilled tartaric acid. Jöns Jacob Berzelius characterized the acid the following year and named it pyruvic acid because it was obtained through distillation using heat.

What are some laboratory methods for preparing pyruvic acid?

Pyruvic acid can be prepared in the laboratory by heating tartaric acid with potassium hydrogen sulfate. Other methods include the oxidation of propylene glycol using strong oxidizers like potassium permanganate or bleach, and the hydrolysis of acetyl cyanide, which is formed from acetyl chloride and potassium cyanide.

What is the physical appearance and solubility of pyruvic acid?

Pyruvic acid is described as a colorless liquid that possesses a smell similar to acetic acid. It is also miscible with water, meaning it can dissolve in water in any proportion.

What is the central role of pyruvate in the network of metabolic pathways?

Pyruvate is a key intersection point in metabolic pathways, connecting the breakdown of glucose (glycolysis) to other processes like gluconeogenesis, fatty acid synthesis, and amino acid synthesis. It acts as a central hub in cellular metabolism.

What is the direct product of glycolysis, and how many molecules are produced per glucose molecule?

The direct product of glycolysis is pyruvate. One molecule of glucose is broken down into two molecules of pyruvate during this process.

How is pyruvate typically processed in aerobic respiration?

Under aerobic conditions, pyruvate is converted into acetyl-coenzyme A (acetyl-CoA). Acetyl-CoA then serves as the primary input for the Krebs cycle, also known as the citric acid cycle or tricarboxylic acid cycle, to generate further energy.

Besides conversion to acetyl-CoA, what other important molecule can pyruvate be converted into for aerobic metabolism?

Pyruvate can also be converted into oxaloacetate through an anaplerotic reaction. Oxaloacetate is vital for replenishing intermediates in the Krebs cycle and is also used in gluconeogenesis.

What happens to pyruvate when oxygen is insufficient for aerobic respiration?

In conditions of insufficient oxygen, pyruvate is processed anaerobically. In animals, it is converted to lactate through a process called lactate fermentation, catalyzed by the enzyme lactate dehydrogenase using NADH.

How is pyruvate metabolized anaerobically in plants and microorganisms?

In plants and microorganisms, pyruvate undergoes alcoholic fermentation. It is first converted to acetaldehyde by pyruvate decarboxylase and then to ethanol.

Which enzyme catalyzes the final step of glycolysis, converting phosphoenolpyruvate to pyruvate?

The enzyme pyruvate kinase catalyzes the final step of glycolysis, converting phosphoenolpyruvate into pyruvate. This reaction is highly exergonic and considered irreversible in the context of gluconeogenesis.

How is the conversion of pyruvate back to phosphoenolpyruvate achieved in gluconeogenesis?

The reverse transformation of pyruvate to phosphoenolpyruvate during gluconeogenesis requires two separate enzymatic steps, involving pyruvate carboxylase and PEP carboxykinase. This bypasses the irreversible step catalyzed by pyruvate kinase in glycolysis.

What is the product of pyruvate decarboxylation by the pyruvate dehydrogenase complex?

The decarboxylation of pyruvate by the pyruvate dehydrogenase complex yields acetyl-CoA. This reaction also involves coenzyme A (CoA) and NAD+, producing carbon dioxide (CO2) and NADH + H+.

What enzyme facilitates the carboxylation of pyruvate to oxaloacetate, and what are the required co-substrates?

Pyruvate carboxylase catalyzes the carboxylation of pyruvate to oxaloacetate. This reaction requires ATP and CO2, producing ADP and inorganic phosphate (Pi).

How is the amino acid alanine synthesized from pyruvate?

Pyruvate can be converted into alanine through a transamination reaction catalyzed by alanine transaminase. This process involves the transfer of an amino group, typically from glutamate to pyruvate, producing $\alpha$-ketoglutarate as a byproduct.

What enzyme is responsible for reducing pyruvate to lactate, and what coenzyme is involved?

Lactate dehydrogenase catalyzes the reduction of pyruvate to lactate. This reaction utilizes the coenzyme NADH, which is oxidized to NAD+.

Where is pyruvic acid found in the context of environmental chemistry?

Pyruvic acid is identified as an abundant carboxylic acid present in secondary organic aerosols, which are fine particles found in the atmosphere.

What is one of the purported uses of pyruvate, and what does the scientific evidence suggest?

Pyruvate is marketed as a weight-loss supplement, but credible scientific evidence to support this claim is limited. A systematic review found a small, statistically significant difference in weight loss compared to placebo, but noted methodological weaknesses in the studies and potential adverse effects.

What adverse events have been associated with pyruvate supplementation?

Adverse events reported with pyruvate supplementation include gastrointestinal issues such as diarrhea, bloating, and gas. Additionally, an increase in low-density lipoprotein (LDL) cholesterol has been observed.

In what context has pyruvate shown potential benefits related to cardiac function?

Research suggests that pyruvate may improve cardiac metabolism by stimulating NADH production, potentially enhancing cardiac function. This has been observed in studies on isolated hearts and in patients with congestive heart failure.

What is the chemical formula for pyruvic acid?

The chemical formula for pyruvic acid is C3H4O3. This formula indicates that each molecule contains three carbon atoms, four hydrogen atoms, and three oxygen atoms.

What is the molar mass of pyruvic acid?

The molar mass of pyruvic acid is 88.06 grams per mole (g/mol). This value is calculated by summing the atomic masses of all atoms in its chemical formula.

What is the pKa value of pyruvic acid, indicating its acidity?

Pyruvic acid has an acidity value (pKa) of 2.50. This relatively low pKa indicates that it is a moderately strong organic acid.

What is the primary anion related to pyruvic acid?

The primary anion related to pyruvic acid is pyruvate (CH3COCOO-). Pyruvate is the deprotonated form of pyruvic acid and is a key molecule in metabolic pathways.

Besides pyruvic acid, what other keto-acids are listed as related compounds?

Other related keto-acids mentioned include glyoxylic acid and acetoacetic acid. These compounds also feature a ketone group alongside a carboxylic acid group, though at different positions or with additional functional groups.

What are some other compounds listed as related to pyruvic acid?

Related compounds include propionaldehyde, methylglyoxal, and sodium pyruvate. Propionaldehyde is an aldehyde, methylglyoxal is another alpha-ketoaldehyde, and sodium pyruvate is the sodium salt of pyruvic acid.

What specific organic acid did Pelouze isolate when distilling tartaric acid, besides glutaric acid?

When Théophile-Jules Pelouze distilled tartaric acid in 1834, he isolated glutaric acid and another unknown organic acid, which was later identified as pyruvic acid by Jöns Jacob Berzelius.

Why is pyruvate referred to as a 'crossroads compound' in biochemistry?

Pyruvate is called a 'crossroads compound' because it connects several major metabolic pathways. It can be converted into carbohydrates, fatty acids, amino acids, or further oxidized for energy, making it a central hub in cellular metabolism.

How does the conversion of pyruvate back to phosphoenolpyruvate in gluconeogenesis highlight the irreversibility of the final step of glycolysis?

The final step of glycolysis, catalyzed by pyruvate kinase, is irreversible under cellular conditions. Reversing this reaction in gluconeogenesis requires two separate enzymatic steps, involving pyruvate carboxylase and PEP carboxykinase, to overcome the energy barrier.

What are the alternative names for the citric acid cycle, which pyruvate enters after conversion to acetyl-CoA?

The citric acid cycle is also known as the Krebs cycle or the tricarboxylic acid (TCA) cycle. These names refer to the same series of biochemical reactions that oxidize acetyl-CoA to generate energy.

Which Nobel laureate's work is mentioned in relation to the citric acid cycle?

Hans Adolf Krebs, who was awarded the 1953 Nobel Prize in Physiology or Medicine for his research into metabolic processes, is mentioned in connection with the citric acid cycle. He shared the prize with Fritz Lipmann.

What was the conclusion of the systematic review regarding pyruvate for weight loss?

The systematic review concluded that there was insufficient evidence to support the use of pyruvate for weight loss. While a small statistically significant difference in weight loss was noted compared to placebo, the trials had methodological weaknesses and the effect size was minor.

What is the CAS Registry Number for pyruvic acid?

The CAS Registry Number for pyruvic acid is 127-17-3. This unique identifier is used globally to identify chemical substances.

What is the SMILES (Simplified Molecular Input Line Entry System) notation for pyruvic acid?

The SMILES notation for pyruvic acid is O=C(C(=O)C)C. This string represents the chemical structure in a linear format that can be parsed by computer software.

What is the InChI (International Chemical Identifier) for pyruvic acid?

The InChI for pyruvic acid is InChI=1S/C3H4O3/c1-2(4)3(5)6/h1H3,(H,5,6). The associated InChIKey is LCTONWCANYUPML-UHFFFAOYSA-N.

What is produced alongside alanine when pyruvate undergoes transamination?

When pyruvate is transaminated to alanine, $\alpha$-ketoglutarate is produced alongside alanine, typically from the amino donor glutamate. This reaction is reversible.

What molecules are produced during the conversion of pyruvate to acetyl-CoA?

The conversion of pyruvate to acetyl-CoA produces carbon dioxide (CO2), NADH, and H+. It also requires coenzyme A (CoA).

What molecules are consumed and produced during the carboxylation of pyruvate to oxaloacetate?

The carboxylation of pyruvate to oxaloacetate consumes ATP and CO2, and produces ADP and inorganic phosphate (Pi). This reaction is catalyzed by pyruvate carboxylase.

What are the reactants and products involved in the reduction of pyruvate to lactate?

The reduction of pyruvate to lactate involves pyruvate and NADH. The products are lactate and NAD+. This reaction is catalyzed by lactate dehydrogenase.

What information does the image comparing blood values convey regarding pyruvate?

The image displays reference ranges for blood tests, showing the relative levels of various blood constituents, with pyruvate indicated in violet near the middle of the chart. This visual comparison helps contextualize pyruvate levels within a broader physiological context.

What biochemical processes are illustrated in the interactive pathway map mentioned in the text?

The interactive pathway map illustrates the processes of glycolysis and gluconeogenesis. It visually depicts the sequence of reactions and the molecules involved in both the breakdown and synthesis of glucose.

How can propylene glycol be converted to pyruvic acid through oxidation?

Propylene glycol can be oxidized to pyruvic acid using strong oxidizing agents such as potassium permanganate or bleach. This chemical reaction transforms the alcohol groups into ketone and carboxylic acid functionalities.

Which amino acid can be synthesized directly from pyruvate?

The amino acid alanine can be synthesized directly from pyruvate through a process called transamination. This is a common metabolic pathway for amino acid production.

How is pyruvate linked to the synthesis of fatty acids?

Pyruvate can be converted into fatty acids through a reaction with acetyl-CoA. Acetyl-CoA is a key intermediate that serves as the building block for fatty acid synthesis.

In what year was pyruvic acid first characterized by Jöns Jacob Berzelius?

Jöns Jacob Berzelius characterized pyruvic acid in 1835, the year following its initial isolation by Théophile-Jules Pelouze.

What role does pyruvate play in gluconeogenesis?

In gluconeogenesis, pyruvate serves as a precursor molecule that can be converted back into glucose. This process is essential for maintaining blood glucose levels when dietary intake is insufficient.

Pyruvic Acid Wiki: Pyruvic Acid: The Metabolic Crossroads

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What is Pyruvic Acid?

Chemical Identity

Pyruvic acid, chemically represented as CH₃COCOOH, is the simplest alpha-keto acid. It features both a carboxylic acid group and a ketone functional group. Its conjugate base, pyruvate (CH₃COCOO^-), is a crucial intermediate in numerous cellular metabolic pathways.

Metabolic Hub

Pyruvate serves as a central junction in metabolism. It is derived from glucose via glycolysis, can be converted back into carbohydrates through gluconeogenesis, or transformed into fatty acids via acetyl-CoA. It also participates in the synthesis of the amino acid alanine and can be converted to ethanol or lactic acid through fermentation.

Energy Production

Pyruvic acid provides energy to cells through the citric acid cycle (Krebs cycle) under aerobic conditions. In the absence of sufficient oxygen (anaerobic conditions), it undergoes fermentation, yielding lactate in animals or ethanol in plants and microorganisms.

Chemical Properties

Historical Context

First isolated in 1834 by Théophile-Jules Pelouze through the distillation of tartaric acid, its structure was elucidated by Jöns Jacob Berzelius the following year. The name "pyruvic acid" originates from the German "Brenztraubensäure," reflecting its distillation from tartaric acid.

Physical Characteristics

Pyruvic acid is a colorless liquid, miscible with water, and possesses an odor reminiscent of acetic acid. Its key chemical properties include:

Chemical Formula: C₃H₄O₃
Molar Mass: 88.06 g/mol
Density: 1.250 g/cm³
Melting Point: 11.8 °C
Boiling Point: 165 °C
Acidity (pKa): 2.50

Key identifiers include:

CAS Number: 127-17-3
ChEBI: CHEBI:32816
PubChem CID: 1060
InChI: 1S/C3H4O3/c1-2(4)3(5)6/h1H3,(H,5,6)
SMILES: O=C(C(=O)O)C

Biochemical Significance

Glycolysis Output

Glycolysis, the breakdown of glucose, concludes with the formation of two pyruvate molecules from one glucose molecule. Pyruvate then enters one of two primary metabolic routes: conversion to acetyl-CoA for the citric acid cycle (aerobic respiration) or fermentation to lactate or ethanol (anaerobic conditions).

Metabolic Interconnections

Pyruvate acts as a critical link between various metabolic pathways:

Gluconeogenesis: Pyruvate can be converted back to glucose.
Citric Acid Cycle: Decarboxylation yields acetyl-CoA, the primary fuel for this cycle.
Anaplerosis: Carboxylation forms oxaloacetate, replenishing citric acid cycle intermediates.
Amino Acid Synthesis: Pyruvate can be transaminated to form alanine.
Fermentation: Reduction yields lactate or acetaldehyde (leading to ethanol).

Pyruvate's central role is illustrated in metabolic pathway maps like Glycolysis and Gluconeogenesis. These diagrams show how pyruvate connects glucose metabolism to energy production (via acetyl-CoA and the citric acid cycle) and anaerobic pathways (lactate fermentation).

Applications & Research

Weight Management Supplements

Pyruvate is marketed as a weight-loss supplement. While some clinical trials suggest a statistically significant, albeit small, effect on body weight compared to placebo, these studies often have methodological limitations. Potential adverse effects include gastrointestinal issues and increased LDL cholesterol. The scientific consensus indicates insufficient evidence to support its efficacy for weight loss.

Cardiac Function Research

Research, including *in vitro* and *in vivo* studies on heart tissue, suggests that pyruvate may improve cardiac metabolism and function by stimulating NADH production. This area is under investigation for potential therapeutic applications.

Environmental Chemistry

Pyruvic acid is also found as a component in secondary organic aerosols within the atmosphere, contributing to atmospheric chemistry processes.

Related Compounds

Conjugate Base

The primary related compound is pyruvate (CH₃COCOO^-), the deprotonated form of pyruvic acid, which is the active species in most biological reactions.

Metabolic Partners

Key metabolic partners include:

Acetyl-CoA: Formed from pyruvate, entering the citric acid cycle.
Oxaloacetate: Formed via pyruvate carboxylation, crucial for gluconeogenesis and the citric acid cycle.
Lactate: Formed via pyruvate reduction under anaerobic conditions.
Alanine: An amino acid synthesized from pyruvate via transamination.
Glucose: The precursor molecule in glycolysis.

Other Keto-acids

Pyruvic acid belongs to the class of alpha-keto acids, which also includes compounds like glyoxylic acid and acetoacetic acid, each playing distinct roles in metabolism.

Notes

Data Verification

Unless otherwise specified, data presented are for materials in their standard state (25 °C, 100 kPa). Verification of these values may be required.

Citations

Information is sourced from established scientific literature and databases. Specific details regarding chemical nomenclature and properties are often derived from IUPAC recommendations and standard biochemical references.

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Pyruvic Acid: The Metabolic Crossroads

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What is Pyruvic Acid? ℹ️

🧪 Chemical Identity

🔄 Metabolic Hub

⚡ Energy Production

Chemical Properties ⚛️

📜 Historical Context

💧 Physical Characteristics

Biochemical Significance 🧬

➡️ Glycolysis Output

🔄 Metabolic Interconnections

Applications & Research 💡

⚖️ Weight Management Supplements

❤️ Cardiac Function Research

💨 Environmental Chemistry

Related Compounds 🔗

➡️ Conjugate Base

🧬 Metabolic Partners

🧪 Other Keto-acids

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Dive in with Flashcard Learning!

What is Pyruvic Acid?

Chemical Identity

Metabolic Hub

Energy Production

Chemical Properties

Historical Context

Physical Characteristics

Biochemical Significance

Glycolysis Output

Metabolic Interconnections

Applications & Research

Weight Management Supplements

Cardiac Function Research

Environmental Chemistry

Related Compounds

Conjugate Base

Metabolic Partners

Other Keto-acids

Notes

Data Verification

Citations

Teacher's Corner

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References

Feedback & Support

Disclaimer

Important Notice