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133447-37-7

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133447-37-7 Usage

Chemical Properties

2-Propionylpyrroline has an intense roasted, fishy odor.

Occurrence

Reportedly present in popcorn and has been characterized in a proline/glucose Maillard system.

Uses

The most powerful naturally occurring Maillard flavors.

Aroma threshold values

Detection in air at 0.00002 mg/m3.

Check Digit Verification of cas no

The CAS Registry Mumber 133447-37-7 includes 9 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 6 digits, 1,3,3,4,4 and 7 respectively; the second part has 2 digits, 3 and 7 respectively.
Calculate Digit Verification of CAS Registry Number 133447-37:
(8*1)+(7*3)+(6*3)+(5*4)+(4*4)+(3*7)+(2*3)+(1*7)=117
117 % 10 = 7
So 133447-37-7 is a valid CAS Registry Number.
InChI:InChI=1/C7H11NO/c1-2-7(9)6-4-3-5-8-6/h2-5H2,1H3

133447-37-7SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 17, 2017

Revision Date: Aug 17, 2017

1.Identification

1.1 GHS Product identifier

Product name 1-(3,4-dihydro-2H-pyrrol-5-yl)propan-1-one

1.2 Other means of identification

Product number -
Other names FEMA No. 4063

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:133447-37-7 SDS

133447-37-7Downstream Products

133447-37-7Relevant articles and documents

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

Hofmann, Thomas,Schieberle, Peter

, p. 2721 - 2726 (1998)

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.

Method for synthesizing 2-propionyl-1-pyrroline

-

Paragraph 0017; 0020, (2019/04/26)

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.

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

Kimpe, Norbert G. De,Stevens, Christian V.,Keppens, Marian A.

, p. 1458 - 1461 (2007/10/02)

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.

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