(1,2,3-13C3)propanoic acid
Overview
Description
(1,2,3-13C3)propanoic acid, also known as propanoic acid-13C3, is a stable isotope-labeled compound where all three carbon atoms are replaced with the carbon-13 isotope. This compound is primarily used in scientific research to trace and study metabolic pathways, as well as in various analytical applications. The molecular formula for propionic acid-13C3 is 13CH3-13CH2-13CO2H, and it has a molecular weight of 77.06 g/mol .
Scientific Research Applications
(1,2,3-13C3)propanoic acid has a wide range of applications in scientific research:
Chemistry: Used as a tracer in studying reaction mechanisms and metabolic pathways.
Biology: Employed in metabolic studies to trace the incorporation of carbon atoms into various biomolecules.
Medicine: Utilized in pharmacokinetic studies to understand the metabolism and distribution of drugs.
Industry: Applied in the production of labeled compounds for use in various industrial processes.
Safety and Hazards
Mechanism of Action
Target of Action
Propionic acid-13C3, also known as Propanoic acid-13C3, is a stable isotope of propionic acid . It primarily targets the respiratory system
Mode of Action
Propionic acid, the non-isotopic form, can pass through a cell membrane into the cytoplasm in its non-dissociated form . Due to the alkaline intracellular environment, it can release protons that result in a pH gradient across the cell membrane, causing adverse effects on the transfer of nutrients and growth of mold, yeast, and bacteria .
Result of Action
Propionic acid has been shown to have antimicrobial properties, inhibiting the growth of microorganisms such as salmonella spp, Escherichia coli O157:H7, and Listeria monocytogenes .
Action Environment
It’s important to note that propionic acid is classified as a flammable liquid and vapor, and it may cause respiratory irritation . Therefore, the environment in which Propionic acid-13C3 is used or stored could potentially impact its action and stability.
Biochemical Analysis
Biochemical Properties
Propionic acid-13C3 plays a significant role in biochemical reactions. It is produced via biological pathways using Propionibacterium and some anaerobic bacteria . The compound interacts with various enzymes, proteins, and other biomolecules, influencing their function and activity .
Cellular Effects
Propionic acid-13C3 has profound effects on various types of cells and cellular processes. It influences cell function, including impacts on cell signaling pathways, gene expression, and cellular metabolism . For instance, it has been shown to disrupt endocytosis, the cell cycle, and cellular respiration in yeast cells .
Molecular Mechanism
At the molecular level, Propionic acid-13C3 exerts its effects through binding interactions with biomolecules, enzyme inhibition or activation, and changes in gene expression . It can pass through a cell membrane into the cytoplasm, where it releases protons, resulting in a pH gradient across the cell membrane and consequent adverse effects on the transfer of nutrients and growth of mold, yeast, and bacteria .
Metabolic Pathways
Propionic acid-13C3 is involved in various metabolic pathways. It interacts with enzymes and cofactors, potentially affecting metabolic flux or metabolite levels
Preparation Methods
Synthetic Routes and Reaction Conditions
(1,2,3-13C3)propanoic acid can be synthesized through several methods. One common approach involves the carboxylation of ethylene with carbon-13 labeled carbon dioxide. Another method includes the hydrolysis of carbon-13 labeled propionitrile. The reaction conditions typically involve the use of catalysts such as palladium or nickel to facilitate the carboxylation process .
Industrial Production Methods
In industrial settings, propionic acid-13C3 is produced using isotopically labeled precursors. The production process involves the fermentation of isotopically labeled substrates by specific strains of bacteria, such as Propionibacterium. This biological method is preferred due to its efficiency and the high yield of isotopically labeled propionic acid .
Chemical Reactions Analysis
Types of Reactions
(1,2,3-13C3)propanoic acid undergoes various chemical reactions, including:
Oxidation: this compound can be oxidized to produce acetic acid and carbon dioxide.
Reduction: Reduction of propionic acid-13C3 can yield propanol.
Substitution: this compound can undergo substitution reactions to form esters, amides, and other derivatives.
Common Reagents and Conditions
Oxidation: Potassium permanganate, chromium trioxide, and oxygen.
Reduction: Lithium aluminum hydride, hydrogen gas with a palladium or nickel catalyst.
Substitution: Alcohols, amines, acid chlorides, and bases like sodium hydroxide.
Major Products
Oxidation: Acetic acid and carbon dioxide.
Reduction: Propanol.
Substitution: Esters, amides, and other derivatives.
Comparison with Similar Compounds
Similar Compounds
Propionic acid-1-13C: Only the first carbon atom is labeled with carbon-13.
Propionic acid-2-13C: Only the second carbon atom is labeled with carbon-13.
Propionic acid-1,2-13C2: The first and second carbon atoms are labeled with carbon-13.
Uniqueness
(1,2,3-13C3)propanoic acid is unique because all three carbon atoms are labeled with carbon-13, providing a more comprehensive tracing capability in metabolic studies compared to compounds with fewer labeled carbon atoms. This makes it particularly valuable in detailed metabolic and pharmacokinetic studies .
Properties
IUPAC Name |
(1,2,3-13C3)propanoic acid |
Source
|
|---|---|---|
| Source | PubChem | |
| URL | https://pubchem.ncbi.nlm.nih.gov | |
| Description | Data deposited in or computed by PubChem | |
InChI |
InChI=1S/C3H6O2/c1-2-3(4)5/h2H2,1H3,(H,4,5)/i1+1,2+1,3+1 |
Source
|
| Source | PubChem | |
| URL | https://pubchem.ncbi.nlm.nih.gov | |
| Description | Data deposited in or computed by PubChem | |
InChI Key |
XBDQKXXYIPTUBI-VMIGTVKRSA-N |
Source
|
| Source | PubChem | |
| URL | https://pubchem.ncbi.nlm.nih.gov | |
| Description | Data deposited in or computed by PubChem | |
Canonical SMILES |
CCC(=O)O |
Source
|
| Source | PubChem | |
| URL | https://pubchem.ncbi.nlm.nih.gov | |
| Description | Data deposited in or computed by PubChem | |
Isomeric SMILES |
[13CH3][13CH2][13C](=O)O |
Source
|
| Source | PubChem | |
| URL | https://pubchem.ncbi.nlm.nih.gov | |
| Description | Data deposited in or computed by PubChem | |
Molecular Formula |
C3H6O2 |
Source
|
| Source | PubChem | |
| URL | https://pubchem.ncbi.nlm.nih.gov | |
| Description | Data deposited in or computed by PubChem | |
DSSTOX Substance ID |
DTXSID20432142 |
Source
|
| Record name | Propionic acid-13C3 | |
| Source | EPA DSSTox | |
| URL | https://comptox.epa.gov/dashboard/DTXSID20432142 | |
| Description | DSSTox provides a high quality public chemistry resource for supporting improved predictive toxicology. | |
Molecular Weight |
77.057 g/mol |
Source
|
| Source | PubChem | |
| URL | https://pubchem.ncbi.nlm.nih.gov | |
| Description | Data deposited in or computed by PubChem | |
CAS No. |
153474-35-2 |
Source
|
| Record name | Propionic acid-13C3 | |
| Source | EPA DSSTox | |
| URL | https://comptox.epa.gov/dashboard/DTXSID20432142 | |
| Description | DSSTox provides a high quality public chemistry resource for supporting improved predictive toxicology. | |
| Record name | 153474-35-2 | |
| Source | European Chemicals Agency (ECHA) | |
| URL | https://echa.europa.eu/information-on-chemicals | |
| Description | The European Chemicals Agency (ECHA) is an agency of the European Union which is the driving force among regulatory authorities in implementing the EU's groundbreaking chemicals legislation for the benefit of human health and the environment as well as for innovation and competitiveness. | |
| Explanation | Use of the information, documents and data from the ECHA website is subject to the terms and conditions of this Legal Notice, and subject to other binding limitations provided for under applicable law, the information, documents and data made available on the ECHA website may be reproduced, distributed and/or used, totally or in part, for non-commercial purposes provided that ECHA is acknowledged as the source: "Source: European Chemicals Agency, http://echa.europa.eu/". Such acknowledgement must be included in each copy of the material. ECHA permits and encourages organisations and individuals to create links to the ECHA website under the following cumulative conditions: Links can only be made to webpages that provide a link to the Legal Notice page. | |
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Retrosynthesis Analysis
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Strategy Settings
| Precursor scoring | Relevance Heuristic |
|---|---|
| Min. plausibility | 0.01 |
| Model | Template_relevance |
| Template Set | Pistachio/Bkms_metabolic/Pistachio_ringbreaker/Reaxys/Reaxys_biocatalysis |
| Top-N result to add to graph | 6 |
Feasible Synthetic Routes
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Please be aware that all articles and product information presented on BenchChem are intended solely for informational purposes. The products available for purchase on BenchChem are specifically designed for in-vitro studies, which are conducted outside of living organisms. In-vitro studies, derived from the Latin term "in glass," involve experiments performed in controlled laboratory settings using cells or tissues. It is important to note that these products are not categorized as medicines or drugs, and they have not received approval from the FDA for the prevention, treatment, or cure of any medical condition, ailment, or disease. We must emphasize that any form of bodily introduction of these products into humans or animals is strictly prohibited by law. It is essential to adhere to these guidelines to ensure compliance with legal and ethical standards in research and experimentation.
