3-(4-Methylpiperidin-1-yl)propanoic acid: Properties & Uses
3-(4-Methylpiperidin-1-yl)propanoic acid: Properties & Uses
3-(4-Methylpiperidin-1-yl)propanoic acid is a piperidine-containing beta-amino acid analogue that serves as a versatile synthetic intermediate in medicinal chemistry and pharmaceutical research.
- Chemical Name
- 3-(4-Methylpiperidin-1-yl)propanoic acid
- Core Scaffold
- N-substituted piperidine with a propanoic acid side chain
- Functional Groups
- Tertiary amine (piperidine ring), carboxylic acid
- Primary Application
- Pharmaceutical intermediate and building block in drug discovery
- SKU
- P690741
- Supplier
- Aladdin Scientific
Chemical Structure and Properties
3-(4-Methylpiperidin-1-yl)propanoic acid consists of a six-membered piperidine ring bearing a methyl substituent at the 4-position, with a three-carbon propanoic acid chain attached via the ring nitrogen. This arrangement creates a molecule featuring both a tertiary amine and a carboxylic acid functional group, giving it zwitterionic character in aqueous solution.
The piperidine nitrogen is tertiary and non-basic enough to be compatible with many coupling reagents, while the carboxylic acid terminus enables direct participation in amide bond formation, esterification, and other carbonyl-based transformations. The 4-methyl substituent on the ring modulates lipophilicity and can influence binding geometry when incorporated into a target molecule.
These combined structural features make the compound useful as a fragment in structure–activity relationship (SAR) studies, where the piperidine unit is a privileged scaffold in medicinal chemistry owing to its favorable drug-like properties.
Synthesis and Preparation Considerations
N-alkylation of 4-methylpiperidine with a suitable acrylate or beta-halo propanoic acid derivative, followed by hydrolysis of any ester protecting group, represents a straightforward synthetic route to 3-(4-Methylpiperidin-1-yl)propanoic acid. Michael-type addition of the secondary amine of 4-methylpiperidine to acrylic acid under mild conditions can also afford the target compound in a single step, avoiding the need for protecting-group manipulation.
Researchers sourcing the compound as a commercial reagent from Aladdin Scientific (SKU P690741) benefit from pre-characterized material, saving time on synthesis and quality-control analysis. When handling the compound, standard laboratory precautions for organic acids and amines should be observed, including the use of gloves, eye protection, and adequate ventilation.
Purity assessment by HPLC and identity confirmation by NMR or mass spectrometry are recommended before use in sensitive biological assays or downstream pharmaceutical synthesis steps.
Research and Pharmaceutical Applications
The compound's dual functionality—a nucleophilic tertiary amine paired with an electrophilic carboxylic acid—positions it as a bifunctional linker or beta-amino acid surrogate in the synthesis of peptidomimetics and small-molecule drug candidates. Piperidine-containing carboxylic acids of this type are frequently employed to introduce basic nitrogen centers into lead compounds to optimize pharmacokinetic profiles, including membrane permeability and metabolic stability.
In combinatorial chemistry and fragment-based drug discovery (FBDD), 3-(4-Methylpiperidin-1-yl)propanoic acid can be coupled with diverse amine partners via standard peptide coupling reagents (e.g., HATU, EDC/HOBt) to generate focused libraries of amide-containing analogues for biological screening.
The compound may also serve as a synthetic handle for introducing piperidine motifs into proteolysis-targeting chimeras (PROTACs) or other bifunctional degrader molecules, where the carboxylic acid is used to attach the linker component. These broad utilities make it a valuable addition to a medicinal chemistry reagent inventory.
Handling, Storage, and Quality Specifications
As with most piperidine-derived organic acids, 3-(4-Methylpiperidin-1-yl)propanoic acid should be stored in a tightly sealed container under cool, dry conditions away from strong oxidizers and strong acids. Refrigerated storage (2–8 °C) is generally recommended to maintain long-term stability, though specific storage conditions should be confirmed against the certificate of analysis (CoA) provided with each lot.
Researchers should consult the Safety Data Sheet (SDS) supplied by Aladdin Scientific for detailed information on hazard classification, first-aid measures, and disposal procedures. Personal protective equipment including nitrile gloves, safety glasses, and a lab coat is advised during weighing and handling operations.
For Aladdin Scientific product P690741, lot-specific purity data, NMR spectra, and other analytical information are available upon request or via the product page. Procurement teams should confirm current stock availability, packaging options, and pricing directly with Aladdin Scientific.
Frequently asked questions
What is 3-(4-Methylpiperidin-1-yl)propanoic acid used for in drug discovery?
It is primarily used as a synthetic building block and bifunctional linker in medicinal chemistry. Its piperidine nitrogen and carboxylic acid groups allow it to participate in amide coupling reactions to build peptidomimetics, focused compound libraries, and bifunctional molecules such as PROTACs.
How should 3-(4-Methylpiperidin-1-yl)propanoic acid be stored?
The compound should be stored in a tightly sealed container under cool, dry conditions, generally at 2–8 °C. Specific storage requirements should be verified against the certificate of analysis (CoA) supplied with each lot by Aladdin Scientific.
What coupling reagents are compatible with 3-(4-Methylpiperidin-1-yl)propanoic acid?
Standard peptide and amide bond-forming coupling reagents such as HATU, EDC/HOBt, and HBTU are generally compatible with its carboxylic acid functionality. Reaction conditions should be optimized for each specific substrate to ensure high yield and purity.
Where can I purchase 3-(4-Methylpiperidin-1-yl)propanoic acid?
3-(4-Methylpiperidin-1-yl)propanoic acid is available from Aladdin Scientific under SKU P690741. Contact Aladdin Scientific directly or visit the product page to confirm current stock, packaging sizes, and pricing.
References
- Roughley, S. D.; Jordan, A. M. The medicinal chemist's toolbox: An analysis of reactions used in the pursuit of drug candidates. J. Med. Chem. 2011, 54, 3451–3479. doi:10.1021/jm200187y
- Vitaku, E.; Smith, D. T.; Njardarson, J. T. Analysis of the structural diversity, substitution patterns, and frequency of nitrogen heterocycles among U.S. FDA approved pharmaceuticals. J. Med. Chem. 2014, 57, 10257–10274. doi:10.1021/jm501100b
- Aladdin Scientific. Product Page: 3-(4-Methylpiperidin-1-yl)propanoic acid, SKU P690741. Aladdin Scientific, Shanghai.
Products are supplied for research and development use only. Not for use in humans, animals, diagnosis, or therapy.
危险品化学品经营许可证（带存储）