Propionic acid-d6
Overview
Description
Propionic acid-d6 is a deuterated compound, meaning it contains deuterium, a stable isotope of hydrogen. This compound is a derivative of propanoic acid, where five hydrogen atoms are replaced by deuterium atoms. Deuterated compounds are often used in scientific research due to their unique properties, such as altered vibrational frequencies and kinetic isotope effects.
Scientific Research Applications
Propionic acid-d6 has a wide range of applications in scientific research:
Chemistry: Used as a tracer in reaction mechanisms and kinetic studies due to its unique isotopic properties.
Biology: Employed in metabolic studies to trace the incorporation and transformation of deuterated compounds in biological systems.
Medicine: Investigated for its potential use in drug development, particularly in the design of deuterated drugs with improved pharmacokinetic properties.
Industry: Utilized in the production of deuterated solvents and reagents for various industrial processes.
Preparation Methods
Synthetic Routes and Reaction Conditions
Propionic acid-d6 can be synthesized through several methods. One common approach involves the deuteration of propanoic acid. This can be achieved by reacting propanoic acid with deuterium gas in the presence of a catalyst, such as palladium on carbon. The reaction typically occurs under high pressure and elevated temperatures to ensure complete deuteration.
Another method involves the use of deuterated reagents. For example, propanoic acid can be reacted with deuterated lithium aluminum deuteride to produce this compound. This reaction is typically carried out in an inert atmosphere, such as nitrogen or argon, to prevent unwanted side reactions.
Industrial Production Methods
Industrial production of this compound often involves large-scale deuteration processes. These processes utilize high-pressure reactors and specialized catalysts to achieve high yields of the deuterated compound. The use of deuterated solvents and reagents is also common in industrial settings to ensure the purity and consistency of the final product.
Chemical Reactions Analysis
Types of Reactions
Propionic acid-d6 can undergo various chemical reactions, including:
Oxidation: The compound can be oxidized to produce deuterated carbon dioxide and water.
Reduction: Reduction reactions can convert the compound into deuterated alcohols or alkanes.
Substitution: this compound can participate in substitution reactions, where deuterium atoms are replaced by other atoms or groups.
Common Reagents and Conditions
Oxidation: Common oxidizing agents include potassium permanganate and chromium trioxide. These reactions are typically carried out under acidic or basic conditions.
Reduction: Reducing agents such as lithium aluminum deuteride or sodium borodeuteride are commonly used. These reactions often occur under anhydrous conditions to prevent hydrolysis.
Substitution: Substitution reactions can be facilitated by reagents such as halogens or organometallic compounds. These reactions may require specific solvents and temperatures to proceed efficiently.
Major Products
Oxidation: Deuterated carbon dioxide and water.
Reduction: Deuterated alcohols or alkanes.
Substitution: Various deuterated derivatives, depending on the substituent introduced.
Mechanism of Action
The mechanism of action of Propionic acid-d6 is primarily influenced by the presence of deuterium atoms. Deuterium has a higher mass than hydrogen, which affects the vibrational frequencies of chemical bonds and can alter reaction kinetics. This isotope effect can lead to differences in reaction rates and product distributions compared to non-deuterated compounds. The molecular targets and pathways involved depend on the specific reactions and applications in which the compound is used.
Comparison with Similar Compounds
Propionic acid-d6 can be compared with other deuterated compounds, such as:
Deuterio 2,2,3,3-tetradeuteriopropanoate: Similar structure but with one less deuterium atom.
Deuterio 2,2,3,3,3-pentadeuteriobutanoate: Similar deuteration pattern but with an additional carbon atom in the chain.
Deuterio 2,2,3,3,3-pentadeuteriopropanol: An alcohol derivative with a similar deuteration pattern.
The uniqueness of this compound lies in its specific deuteration pattern and the resulting isotopic effects, which can be leveraged in various scientific and industrial applications.
Properties
IUPAC Name |
deuterio 2,2,3,3,3-pentadeuteriopropanoate |
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)/i1D3,2D2/hD |
Source
|
| Source | PubChem | |
| URL | https://pubchem.ncbi.nlm.nih.gov | |
| Description | Data deposited in or computed by PubChem | |
InChI Key |
XBDQKXXYIPTUBI-WYMDYBCKSA-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 |
[2H]C([2H])([2H])C([2H])([2H])C(=O)O[2H] |
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 |
DTXSID50369134 |
Source
|
| Record name | Propanoic acid-d6 | |
| Source | EPA DSSTox | |
| URL | https://comptox.epa.gov/dashboard/DTXSID50369134 | |
| Description | DSSTox provides a high quality public chemistry resource for supporting improved predictive toxicology. | |
Molecular Weight |
80.12 g/mol |
Source
|
| Source | PubChem | |
| URL | https://pubchem.ncbi.nlm.nih.gov | |
| Description | Data deposited in or computed by PubChem | |
CAS No. |
19448-61-4 |
Source
|
| Record name | Propanoic acid-d6 | |
| Source | EPA DSSTox | |
| URL | https://comptox.epa.gov/dashboard/DTXSID50369134 | |
| Description | DSSTox provides a high quality public chemistry resource for supporting improved predictive toxicology. | |
| Record name | 19448-61-4 | |
| 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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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.
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