471-87-4

Basic information

• Product Name: N,N-Dimethyl-L-proline
• Synonyms: (2s)-1,1-dimethylpyrrolidinium-2-carboxylate;1,1-dimethylpyrrolidinium-2-carboxylate;(Pyrrolidinium, 2-carboxy-1,1-dimethyl-, innersalt, (2S)-;Methyl hygrate betaine;(S)-2-Carboxy-1,1-dimethylpyrrolidinium hydroxide inner salt;1-Methylproline methylbetaine;Cadabine;(2S)-1,1-Dimethyl-2-carboxylatopyrrolidin-1-ium
• CAS NO: 471-87-4
• Molecular Formula: C₇H₁₃NO₂
• Molecular Weight: 144.19
• EINECS: 207-445-1
• Product Categories: Alkaloids;Natural Plant Extract
• Mol File: 471-87-4.mol
• Article Data: 2

Chemical Properties

• Melting Point: 235°C
• Boiling Point: 261.28°C (rough estimate)
• Appearance: /
• Density: 1.1095 (rough estimate)
• Refractive Index: 1.4150 (estimate)
• Storage Temp.: 2-8°C
• CAS DataBase Reference: N,N-Dimethyl-L-proline(CAS DataBase Reference)
• NIST Chemistry Reference: N,N-Dimethyl-L-proline(471-87-4)
• EPA Substance Registry System: N,N-Dimethyl-L-proline(471-87-4)

Safety Data

• Hazardous Substances Data: 471-87-4(Hazardous Substances Data)

Usage

Description

N,N-Dimethyl-L-proline is an amino acid derivative that is structurally similar to the naturally occurring L-proline. It is characterized by the presence of two methyl groups attached to the nitrogen atom, which distinguishes it from its natural counterpart. This modification may lead to altered properties and potential applications in various fields.

Uses

Used in Pharmaceutical Industry:
N,N-Dimethyl-L-proline is used as a building block for the synthesis of various pharmaceutical compounds, such as peptidomimetics and peptidic drugs. Its unique structural features allow for the development of novel bioactive molecules with improved stability, selectivity, and bioavailability.
Used in Chemical Research:
N,N-Dimethyl-L-proline is utilized as a chiral auxiliary in asymmetric synthesis, providing a source of chirality to help control the stereochemistry of the target molecules. This application is valuable in the development of enantiomerically pure compounds with potential applications in various industries.
Used in Nutritional Supplements:
N,N-Dimethyl-L-proline may be used as an ingredient in nutritional supplements, potentially offering benefits related to cognitive function, mood regulation, and overall well-being. Its role in these applications is still under investigation, and further research is needed to establish its efficacy and safety.
Used in Cosmetics Industry:
In the cosmetics industry, N,N-Dimethyl-L-proline could be employed as an active ingredient in skincare products, potentially providing anti-aging, moisturizing, or soothing effects. Its incorporation into cosmetic formulations may be based on its ability to interact with proteins and other biomolecules in the skin.
Please note that the provided materials do not contain specific information about the uses of N,N-Dimethyl-L-proline. The uses listed above are inferred based on the general knowledge of similar compounds and their applications in various industries.

References

Ahmad, Basha, Atta-ur-Rahman, Pak. J. Sci. Ind. Res., 17, 109 (1975)

InChI:InChI=1/C7H13NO2/c1-8(2)5-3-4-6(8)7(9)10/h6H,3-5H2,1-2H3/t6-/m0/s1

Upstream product

• 147-85-3 L-proline 
• 475-11-6 N-methyl-L-proline 
• 74-88-4 methyl iodide 

Downstream Products

• 475-11-6 N-methyl-L-proline 

Relevant articles and documents

Quaternary ammonium oxidative demethylation: X-ray crystallographic, resonance raman, and uv-visible spectroscopic analysis of a Rieske-type demethylase

Herein, the structure resulting from in situ turnover in a chemically challenging quaternary ammonium oxidative demethylation reaction was captured via crystallographic analysis and analyzed via single-crystal spectroscopy. Crystal structures were determined for the Rieske-type monooxygenase, stachydrine demethylase, in the unliganded state (at 1.6 A resolution) and in the product complex (at 2.2 A resolution). The ligand complex was obtained from enzyme aerobically cocrystallized with the substrate stachydrine (N,N-dimethylproline). The ligand electron density in the complex was interpreted as proline, generated within the active site at 100 K by the absorption of X-ray photon energy and two consecutive demethylation cycles. The oxidation state of the Rieske iron-sulfur cluster was characterized by UV-visible spectroscopy throughout X-ray data collection in conjunction with resonance Raman spectra collected before and after diffraction data. Shifts in the absorption band wavelength and intensity as a function of absorbed X-ray dose demonstrated that the Rieske center was reduced by solvated electrons generated by X-ray photons; the kinetics of the reduction process differed dramatically for the liganded complex compared to unliganded demethylase, which may correspond to the observed turnover in the crystal.