133447-37-7

Usage

Uses

Used in Flavor Industry:
Propionylpyrroline, 2-propionyl-1-pyrroline is used as a flavor enhancer for its ability to impart a powerful, roasted flavor to foods. Its unique aroma, detectable at extremely low thresholds, makes it a valuable addition to the flavor industry, particularly in the creation of artificial flavors that mimic the taste of roasted or toasted foods.
Used in Food Industry:
In the food industry, propionylpyrroline, 2-propionyl-1-pyrroline is used as a natural flavoring agent to enhance the taste of various products. Its presence in popcorn has been well-documented, and it is likely used to recreate the distinct flavor of this popular snack in other food products. The compound's ability to contribute a rich, roasted flavor makes it a valuable asset in the development of new and innovative food items.
Used in Aroma Chemistry Research:
Propionylpyrroline, 2-propionyl-1-pyrroline is also used in the field of aroma chemistry research, where it serves as a model compound for studying the Maillard reaction and the development of flavors in cooked foods. Understanding the properties and behavior of propionylpyrroline,2-propionyl-1-pyrroline can help researchers develop new methods for creating and enhancing flavors in the food industry, as well as improve our understanding of the complex chemical processes that occur during cooking.

InChI:InChI=1/C7H11NO/c1-2-7(9)6-4-3-5-8-6/h2-5H2,1H3

Upstream product

• 184153-61-5 N-(4,5-Dioxo-heptyl)-2-phenyl-acetamide 
• 2280-44-6 D-Glucose 
• 147-85-3 L-proline 
• 872-81-1 2-Propyl-Δ¹-pyrrolin 
• 925-90-6 ethylmagnesium bromide 
• 108602-79-5 2-cyano-Δ¹-pyrroline 
• 41653-95-6 (Z)-4-heptenoic acid 
• 78078-48-5 (Z)-hept-4-enoyl chloride 
• 57015-08-4 pyrrolidine-2-carbonitrile 
• 184153-59-1 N-Hept-4-ynyl-2-phenyl-acetamide 
• 184153-66-0 1-(N-acetylamino)hept-4-ene 
• 184153-63-7 (Z)-Hept-4-enoic acid amide 
• 184153-57-9 1-aminohept-4-yne 
• 93293-00-6 hept-4-(Z)-ene-1-amine 

Relevant academic research and scientific papers

Flavor Contribution and Formation of the Intense Roast-Smelling Odorants 2-Propionyl-1-pyrroline and 2-Propionyltetrahydropyridine in Maillard-Type Reactions

Application of aroma extract dilution analysis on two different model mixtures of proline and glucose, reacted under aqueous or dry-heating conditions, revealed 2-propionyl-1-pyrroline (PP) and 2-propionyltetrahydropyridine (PTHP; occurring in two tautomers), besides 2-acetyl-1-pyrroline and 2-acetyltetrahydropyridine, as important roast-smelling odorants in both mixtures. A comparison of the isotope distribution in PP and PTHP formed from either 13C6-labeled or unlabeled glucose suggested a formation pathway for both odorants from the same intermediate, 1-pyrroline, when reacted with either 2-oxobutanal (yielding PP) or 1-hydroxy-2-butanone (yielding PTHP). 2-Oxobutanal, a possible precursor of 1-hydroxy-2-butanone, was shown to be formed in high yields (29 mol %) by reacting acetaldehyde and glycolaldehyde, two well-known degradation products of carbohydrates.

A general method for the synthesis of the most powerful naturally?occurring Maillard flavors

The natural flavors 2-acetyl-1-pyrroline 1a, 2-propionyl-1-pyrroline 1b, 2-acetyl-3,4,5,6-tetrahydropyridine 1c, 2-acetyl-2-thiazoline 1d, 2-propionyl-2-thiazoline 1e, and the artificial flavor 2-acetyl-5,6-dihydro-4H-1,3-thiazine 1f have been prepared by catalytic SeO2 oxidation of the corresponding cyclic imines 6a-c and sulfur cyclic imines 7a-c using TBHP as co-oxidant. The oxidation of the pyrrolines 1a and b is completely regioselective. Professional olfactory evaluation together with the odor threshold of the new flavor 1f is reported.

Method for synthesizing 2-propionyl-1-pyrroline

The invention belongs to the technical field of chemical synthesis, in particular to a method for synthesizing 2-propionyl-1-pyrroline, comprising the steps of: 1) dissolving pyrrolidine-2-one in dichloromethane, adding dimethylaminopyridine and triethylamine, adding di-tert-butyl dicarbonate under stirring, and after the reaction is finished, conducting washing with distilled water and saturatedbrine; 2) dissolving the intermediate product obtained in the above step in tetrahydrofuran, dropwise adding tetramethylethylenediamine and a Grignard reagent in a low temperature environment to obtain N-boc-4-oxo-aminoheptane; 3) reacting the N-boc-4-oxo-aminoheptane with trifluoroacetic acid to remove the Boc group to obtain propylpyrroline; and 4) conducting specific oxidation on the propylpyrroline by selenium dioxide to obtain a final product 2-propionyl-1-pyrroline. The method has the advantages of simple operation, low cost, low energy consumption, high yield, high product purity and the like, and is more suitable for industrial production.

Penicillin acylase-mediated synthesis of 2-acetyl-1-pyrroline and of 2-propionyl-1-pyrroline, key roast-smelling odorants in food. Inclusion complexes with i-cyclodextrin and their NMR and MS characterization

The synthesis of the strong natural roast odorants 1 and 2 is achieved from the C-6 isomeric alcohols 16 and 21 via the acetylenic C-6 and C-7 amines 8 and 9. Key step in the process is the hydrolysis of the W-phenylacetamides 12 and 13 by means of immobilized penicillin acylase, which affords the l-amino-4,5-diketones 14 and 15, spontaneously ring closing to 1 and 2. These latter compounds form inclusion complexes with/?-cyclodextrin, as demonstrated by NMR measurements in deuterated water and FAB-MS spectra.

Synthesis of 2-Acetyl-1-pyrroline, the Principal Rice Flavor Component

A new straightforward synthesis of 2-acetyl-1-pyrroline, the principal rice flavor component with a cracker-like flavor, is reported.The reaction sequence involves the conversion of pyrrolidine into tripyrroline, subsequent hydrocyanation of the latter into 2-cyanopyrrolidine, oxidation into 2-cyano-1-pyrroline, and Grignard addition of methylmagnesium iodide, affording an overall yield of 16-19percent from pyrrolidine.In similar way, 2-propionyl-1-pyrroline, a recently discovered flavor component of popcorn, was prepared in addition to several higher analogues, i.e., 2-acyl-1-pyrrolines.Also, the synthesis of 2-(acetyl-d3)-1-pyrroline, a deuterated derivative of the rice flavor compound which is useful for the stable isotope dilution assay, is described.