Propionaldehyde-2,2,3,3,3-d5

Cat. No.: B596258

CAS No.: 198710-93-9

M. Wt: 63.111

InChI Key: NBBJYMSMWIIQGU-ZBJDZAJPSA-N

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Overview

1. Description

8. Comparison with similar compounds

2. Scientific research applications

9. Properties

3. Safety and hazards

10. Synthesis routes and methods I

4. Mechanism of action

11. Synthesis routes and methods II

5. Biochemical analysis

12. Synthesis routes and methods III

6. Preparation methods

13. Synthesis routes and methods IV

7. Chemical reactions analysis

14. Disclaimer

Description

Propionaldehyde-2,2,3,3,3-d5, also known as 2,2,3,3,3-pentadeuteriopropanal, is a deuterium-labeled compound. It is a stable isotope-labeled analog of propionaldehyde, where five hydrogen atoms are replaced by deuterium atoms. This compound is primarily used in scientific research as a tracer in metabolic studies and in the analysis of chemical reactions.

Scientific Research Applications

Propionaldehyde-2,2,3,3,3-d5 is widely used in scientific research due to its stable isotope labeling. Some of its applications include:

Metabolic Studies: Used as a tracer to study metabolic pathways and enzyme kinetics.

NMR Spectroscopy: Utilized in nuclear magnetic resonance (NMR) spectroscopy to study molecular structures and dynamics.

Pharmaceutical Research: Employed in the development of deuterium-labeled drugs to improve their metabolic stability and pharmacokinetics.

Environmental Analysis: Used in the analysis of environmental samples to trace the sources and pathways of pollutants.

Safety and Hazards

Users are advised to avoid contact with skin and eyes, avoid formation of dust and aerosols, and obtain special instructions before use. Appropriate exhaust ventilation should be provided at places where dust is formed.

Mechanism of Action

Biochemical Analysis

Biochemical Properties

It’s hypothesized that it could be used to investigate the metabolic pathways of propionate, a three-carbon fatty acid found in food and produced by gut bacteria. The specific enzymes and proteins it interacts with are yet to be identified.

Molecular Mechanism

It’s hypothesized that it could have binding interactions with biomolecules, potentially leading to enzyme inhibition or activation, and changes in gene expression

Metabolic Pathways

Propionaldehyde-2,2,3,3,3-d5 could potentially be involved in the metabolic pathways of propionate. The specific enzymes or cofactors it interacts with, and its effects on metabolic flux or metabolite levels, are yet to be identified.

Preparation Methods

Synthetic Routes and Reaction Conditions

Propionaldehyde-2,2,3,3,3-d5 can be synthesized through the deuteration of propionaldehyde. One common method involves the exchange of hydrogen atoms with deuterium using deuterium oxide (D2O) in the presence of a catalyst. The reaction typically occurs under mild conditions to ensure the selective incorporation of deuterium atoms.

Industrial Production Methods

Industrial production of this compound involves the hydroformylation of ethylene with deuterium-labeled carbon monoxide and deuterium gas. This process yields deuterium-labeled propionaldehyde, which is then purified to obtain the desired compound .

Chemical Reactions Analysis

Types of Reactions

Propionaldehyde-2,2,3,3,3-d5 undergoes various chemical reactions typical of aldehydes, including:

Oxidation: It can be oxidized to propionic acid-2,2,3,3,3-d5 using oxidizing agents such as potassium permanganate or chromium trioxide.

Reduction: It can be reduced to propanol-2,2,3,3,3-d5 using reducing agents like sodium borohydride or lithium aluminum hydride.

Condensation: It can participate in aldol condensation reactions to form larger molecules.

Common Reagents and Conditions

Oxidation: Potassium permanganate (KMnO4) in an acidic medium.

Reduction: Sodium borohydride (NaBH4) in methanol or lithium aluminum hydride (LiAlH4) in ether.

Condensation: Base catalysts such as sodium hydroxide (NaOH) or acid catalysts like sulfuric acid (H2SO4).

Major Products

Oxidation: Propionic acid-2,2,3,3,3-d5.

Reduction: Propanol-2,2,3,3,3-d5.

Condensation: β-hydroxy aldehydes or ketones, depending on the reactants used.

Comparison with Similar Compounds

Similar Compounds

Propionaldehyde: The non-deuterated analog of Propionaldehyde-2,2,3,3,3-d5.

Acetaldehyde-d4: A deuterium-labeled analog of acetaldehyde.

Butyraldehyde-d7: A deuterium-labeled analog of butyraldehyde.

Uniqueness

This compound is unique due to its specific deuterium labeling, which provides distinct advantages in research applications. The presence of five deuterium atoms allows for precise tracking and analysis in metabolic studies and NMR spectroscopy, making it a valuable tool in scientific research .

Properties

IUPAC Name	2,2,3,3,3-pentadeuteriopropanal	Source
Source	PubChem
URL	https://pubchem.ncbi.nlm.nih.gov
Description	Data deposited in or computed by PubChem

InChI	InChI=1S/C3H6O/c1-2-3-4/h3H,2H2,1H3/i1D3,2D2	Source
Source	PubChem
URL	https://pubchem.ncbi.nlm.nih.gov
Description	Data deposited in or computed by PubChem

InChI Key	NBBJYMSMWIIQGU-ZBJDZAJPSA-N	Source
Source	PubChem
URL	https://pubchem.ncbi.nlm.nih.gov
Description	Data deposited in or computed by PubChem

Canonical SMILES	CCC=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	Source
Source	PubChem
URL	https://pubchem.ncbi.nlm.nih.gov
Description	Data deposited in or computed by PubChem

Molecular Formula	C3H6O	Source
Source	PubChem
URL	https://pubchem.ncbi.nlm.nih.gov
Description	Data deposited in or computed by PubChem

Molecular Weight	63.11 g/mol	Source
Source	PubChem
URL	https://pubchem.ncbi.nlm.nih.gov
Description	Data deposited in or computed by PubChem

CAS No.	198710-93-9	Source
Record name	Propionaldehyde-2,2,3,3,3-D5
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.

Synthesis routes and methods I

Procedure details

Compounds of formula III where n is zero and B is an oxo group can be prepared, for example, by oxidatively cleaving an optionally esterified tartaric acid; for example, using lead tetraacetate at room temperature in an organic solvent such as benzene. The resulting glyoxalic acid derivative is subsequently condensed in a conventional manner, e.g., conveniently in the presence of an amine, with propionaldehyde at an elevated temperature, e.g., at a temperature between 60° C. and 110° C. with water cleavage to yield the corresponding 3-formyl-crotonic acid derivative.

Name

water

Quantity

0 (± 1) mol

Type

solvent

Reaction Step One

[Compound]

Name

formula III

Quantity

0 (± 1) mol

Type

reactant

Reaction Step Two

[Compound]

Name

esterified tartaric acid

Quantity

0 (± 1) mol

Type

reactant

Reaction Step Three

Name

lead tetraacetate

Quantity

0 (± 1) mol

Type

reactant

Reaction Step Four

Name

benzene

Quantity

0 (± 1) mol

Type

reactant

Reaction Step Five

Name

glyoxalic acid

Quantity

0 (± 1) mol

Type

reactant

Reaction Step Six

[Compound]

Name

amine

Name

propionaldehyde

Name

3-formyl-crotonic acid

Details

Synthesis routes and methods II

Procedure details

When the reaction is a two-stage partial oxidation of propylene to acrylic acid, some or even all of the fresh propane may also be supplied into the starting reaction gas mixture for the second stage of the partial oxidation (however, this starting reaction gas mixture is sometimes not explosive even when this qualification was actually true for the starting reaction gas mixture for the first stage of the partial oxidation). This is advantageous in particular because the undesired side reaction of propane to give propionaldehyde and/or propionic acid starts in particular from the first partial oxidation stage (propylene→acrolein) under the conditions thereof. It is also advantageous to divide a fresh propane supply substantially uniformly between the first and the second partial oxidation stage.

Name

propylene

Quantity

0 (± 1) mol

Type

reactant

Reaction Step One

Name

acrylic acid

Quantity

0 (± 1) mol

Type

reactant

Reaction Step Two

Name

propane

Quantity

0 (± 1) mol

Type

reactant

Reaction Step Three

Name

propane

Quantity

0 (± 1) mol

Type

reactant

Reaction Step Four

Name

propionaldehyde

Name

propionic acid

Name

propylene

Details

Synthesis routes and methods III

Procedure details

4-(4-{[(S)-2-(4-methanesulfonyl-phenyl)-1-methyl-ethyl]-propyl-amino}-butyl)-5-oxo-[1,4]diazepane-1-carboxylic acid tert-butyl ester A mixture of sodium borohydride (0.55 g) and tetrahydrofuran (40 ml) was stirred and a mixture of acetic acid (2.62 g) and tetrohydrofuran (10 ml) slowly added with cooling to maintain the temperature below ambient. The mixture was stirred for several hours. A solution of the 4-{4-[2-(4-methanesulfonyl-phenyl)-1-methyl-ethylamino]-butyl}-5-oxo-[1,4]diazepane-1-carboxylic acid tert-butyl ester (7.0 g) and propionaldehyde (0.85 g) in tetrahydrofuran (25 ml) was prepared. The solution was slowly added to the borohydride mixture with stirring. The mixture stirred several hours followed by slow addition of 25% sodium hydroxide solution (14 g).The upper organic layer was distilled under vacuum. The residue was dissolved in toluene and washed with water. The organic layer vacuum distilled to yield 7.5g of 4-(4-{[(S)-2-(4-methanesulfonyl-phenyl)-1-methyl-ethyl]-propyl-amino}-butyl)-5-oxo-[1,4]diazepane-1-carboxylic acid tert-butyl ester as an oil.

Name

tetrahydrofuran

Quantity

25 mL

Type

solvent

Reaction Step One

Name

4-(4-{[(S)-2-(4-methanesulfonyl-phenyl)-1-methyl-ethyl]-propyl-amino}-butyl)-5-oxo-[1,4]diazepane-1-carboxylic acid tert-butyl ester

Quantity

0 (± 1) mol

Type

reactant

Reaction Step Two

Name

sodium borohydride

Quantity

0.55 g

Type

reactant

Reaction Step Two

Name

tetrahydrofuran

Quantity

40 mL

Type

solvent

Reaction Step Two

Name

borohydride

Quantity

0 (± 1) mol

Type

reactant

Reaction Step Three

Name

sodium hydroxide

Quantity

14 g

Type

reactant

Reaction Step Four

Name

acetic acid

Quantity

2.62 g

Type

solvent

Reaction Step Five

Name

propionaldehyde

Name

4-(4-{[(S)-2-(4-methanesulfonyl-phenyl)-1-methyl-ethyl]-propyl-amino}-butyl)-5-oxo-[1,4]diazepane-1-carboxylic acid tert-butyl ester

Details

Synthesis routes and methods IV

Procedure details

1.60 g (5.6 mmol) of 2-(quinuclidin-3-yl)amino-8-methoxy-1,2,3,4-tetrahydronaphthalene (obtained from 8-methoxy-2-tetralone and 3-aminoquinuclidine by reductive amination in the conventional fashion), 3.20 g (56 mmol) of propionaldehyde and 1.70 g (28 mmol) of glacial acetic acid were stirred for 30 minutes at 0° C. 0.80 g (11 mmol) of sodium cyanoborohydride was then added, and the mixture was stirred for 15 hours at room temperature. The reaction mixture was concentrated, taken up in toluene and reconcentrated, taken up in tert.-butyl methyl ether, and stirred vigorously for 30 minutes with 20% strength sodium hydroxide solution. The aqueous phase was extracted carefully with tert.-butyl methyl ether. Washing the combined organic phases with water and saturated sodium chloride solution, drying over potassium carbonate, and concentrating in a rotary evaporator yielded the crude product as an oil (2.0 g). Chromatography on silica gel (toluene/ethanol 3:1) supplied the title compound as a syrup.

Name

8-methoxy-2-tetralone

Quantity

0 (± 1) mol

Type

reactant

Reaction Step One

Name

3-aminoquinuclidine

Quantity

0 (± 1) mol

Type

reactant

Reaction Step One

Name

acetic acid

Quantity

1.7 g

Type

reactant

Reaction Step One

Name

2-(quinuclidin-3-yl)amino-8-methoxy-1,2,3,4-tetrahydronaphthalene

Name

propionaldehyde

Details

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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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