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108-50-9

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108-50-9 Usage

Description

2,6-Dimethylpyrazine is one of alkylpyrazines. It occurs naturally in cocoa products, coffee, dairy products, meat, peanuts, pecans, filberts, potato products, rum and whisky, soy products. It is used as a flavoring agent in foods such as cereals and products such as cigarettes.

Reference

Glovanni Fenaroli, Fenaroli's Handbook of Flavor Ingredients, 1975, ISBN 0-87819-533-5

Chemical Properties

Different sources of media describe the Chemical Properties of 108-50-9 differently. You can refer to the following data:
1. PALE YELLOW LOW MELTING CRYSTALLINE SOLID
2. 2,6-Dimethylpyrazine has a nutty, coffee-like odor.

Occurrence

Reported found in cocoa products, coffee, diary products, peanuts, pecans, filberts, potato products, rum, whiskey, soy products, tomato puree, baked potato, cooked beef and chicken, mushroom, roasted barley, roasted pecan, tea, and Virginia tobacco; reported found in grilled beef; also a volatile flavor component of potato chips. Also reported found in cheeses, tamarind, coriander seed and corn tortilla

Uses

2,6-Dimethylpyrazine is used Preparation of chocolate, coffee, meat and nuts and other flavors

Preparation

By condensation of 1,2-diaminopropane, followed by column chromatography to separate the 2,6-methylpyrazine from the 2,5-dimethylpyrazine.

Aroma threshold values

Detection: 400 to 1500 ppb. Aroma characteristics at 1.0%: musty, cocoa powdery, tobacco, dry leaf tea, earthy mushroom cap and potato-like, meaty, roasted peanut shell, and coffee.

Taste threshold values

Taste characteristics at 5.0 ppm: musty and earthy, nutty peanut shell, cocoa powdery, earthy coffee, yeasty, woody, milk roasted peanut.

Check Digit Verification of cas no

The CAS Registry Mumber 108-50-9 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 1,0 and 8 respectively; the second part has 2 digits, 5 and 0 respectively.
Calculate Digit Verification of CAS Registry Number 108-50:
(5*1)+(4*0)+(3*8)+(2*5)+(1*0)=39
39 % 10 = 9
So 108-50-9 is a valid CAS Registry Number.
InChI:InChI=1/C6H8N2/c1-5-3-7-4-6(2)8-5/h3-4H,1-2H3

108-50-9 Well-known Company Product Price

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  • (Code)Product description
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  • Alfa Aesar

  • (B24687)  2,6-Dimethylpyrazine, 99%   

  • 108-50-9

  • 5g

  • 528.0CNY

  • Detail
  • Alfa Aesar

  • (B24687)  2,6-Dimethylpyrazine, 99%   

  • 108-50-9

  • 25g

  • 2013.0CNY

  • Detail
  • Alfa Aesar

  • (B24687)  2,6-Dimethylpyrazine, 99%   

  • 108-50-9

  • 100g

  • 7662.0CNY

  • Detail
  • Aldrich

  • (D181803)  2,6-Dimethylpyrazine  98%

  • 108-50-9

  • D181803-5G

  • 503.10CNY

  • Detail
  • Aldrich

  • (D181803)  2,6-Dimethylpyrazine  98%

  • 108-50-9

  • D181803-25G

  • 2,483.91CNY

  • Detail

108-50-9SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 10, 2017

Revision Date: Aug 10, 2017

1.Identification

1.1 GHS Product identifier

Product name 2,6-Dimethylpyrazine

1.2 Other means of identification

Product number -
Other names FEMA No. 3273

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only. Food additives -> Flavoring Agents
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:108-50-9 SDS

108-50-9Related news

Synthesis of 2,6-Dimethylpyrazine (cas 108-50-9) by dehydrocyclization of aqueous glycerol and 1,2-propanediamine over CuCrO catalyst: Rationalization of active sites by pyridine and formic acid adsorbed IR studies08/19/2019

The mixed oxides of CuOCuCr2O4 (CuCrO) with different Cu/Cr mole ratios were examined for synthesis of 2,6-dimethylpyrazine (2,6-DMP) by the utilization of aqueous glycerol in conjunction with 1,2-propanediamine (1,2-PDA). Influence of acid-base (both Bronsted and Lewis) sites on the product dis...detailed

108-50-9Relevant articles and documents

The effects of thermal treatment of ZnO–ZnCr2O4 catalyst on the particle size and product selectivity in dehydrocyclization of crude glycerol and ethylenediamine

Sarkari, Reema,Krishna, Vankudoth,Sudhakar, Medak,Rao, Tumula Venkateshwar,Padmasri, Aytam Hari,Srinivas, Darbha,Venugopal, Akula

, (2016)

The ZnO–ZnCr2O4 (Zn–Cr–O) sample obtained by decomposition of Zn-Cr hydrotalcite precursor was subjected to the thermal treatment at different temperatures and the physico-chemical properties of the Zn–Cr–O system were compared with

Synthesis of pyrazinyl compounds from glycerol and 1,2-propanediamine over Cu-TiO2 catalysts supported on γ-Al2O3

Li, Xue,Xu, Cheng-Hua,Liu, Chuan-Qi,Chen, Yu,Liu, Jian-Ying

, p. 751 - 754 (2013)

Cu-TiO2 catalysts supported on γ-Al2O 3 are prepared and used in glycerol cyclization with 1,2-propanediamine to produce pyrazinyl compounds including 6-hydroxymethyl-2- methylpyrazine, 5-hydroxymethyl-2-methylpyrazine, 2,6-dimethylpyrazine and 2,5-dimethylpyrazine in a fixed-bed system. It is found that glycerol cylclization with 1,2-propanediamine gave a high total yield of pyrazinyl compounds (>80%) over Cu-TiO2/γ-Al2O3 catalyst, and cyclization was through the reactions between activated 1,2-propanediamine and the intermediates from glycerol dehydration and oxidation. In addition, the regioselectivity of the pyrazinyl compounds was mainly controlled by the steric hindrance of the substrates during the cyclization process.

-

Tsuchiya et al.

, p. 250 (1976)

-

Regioselective Synthesis of Alkylpyrazines

Buechi, George,Galindo, Jose

, p. 2605 - 2606 (1991)

A new, regioselective synthesis of alkylpyrazines begins with condensation of α-oximido carbonyl compounds with allylamines.The resulting imines are isomerized in the presence of potassium tert-butoxide to the corresponding 1-hydroxy-1,4-diazahexatrienes.Thermal electrocyclization-aromatization to pyrazines is best performed after O-acylation of the oximes with methyl chloroformate.

Mechanisms of Formation of Alkylpyrazines in the Maillard Reaction

Amrani-Hemaimi, Miriam,Cerny, Christoph,Fay, Laurent B.

, p. 2818 - 2822 (1995)

The formation of alkylpyrazines was investigated in the reaction of glucose and fructose with -alanine and glycine.The reaction systems were heated for 7 min at 180 deg C.GC-MS and GC-MS/MS data were used to determine the rate of incorporati

Acceptorless Dehydrogenative Coupling Using Ammonia: Direct Synthesis of N-Heteroaromatics from Diols Catalyzed by Ruthenium

Daw, Prosenjit,Ben-David, Yehoshoa,Milstein, David

supporting information, p. 11931 - 11934 (2018/09/27)

The synthesis of N-heteroaromatic compounds via an acceptorless dehydrogenative coupling process involving direct use of ammonia as the nitrogen source was explored. We report the synthesis of pyrazine derivatives from 1,2-diols and the synthesis of N-substituted pyrroles by a multicomponent dehydrogenative coupling of 1,4-diols and primary alcohols with ammonia. The acridine-based Ru-pincer complex 1 is an effective catalyst for these transformations, in which the acridine backbone is converted to an anionic dearomatized PNP-pincer ligand framework.

CuCr2O4 derived by the sol-gel method as a highly active and selective catalyst for the conversion of glycerol to 2,6-dimethylpyrazine: A benign and eco-friendly process

Vankudoth, Krishna,Gutta, Naresh,Velisoju, Vijay Kumar,Mutyala, Suresh,Aytam, Hari Padmasri,Akula, Venugopal

, p. 3399 - 3407 (2017/08/16)

Vapour phase dehydrocyclization of crude glycerol in conjunction with 1,2-propanediamine (1,2-PDA) was examined over CuCr2O4 obtained by different preparation methods. A high proportion of copper species interacted with Cr2O3 in CuCr2O4 derived from the sol-gel route with a low ratio of Cu2+/Cu0 demonstrating higher dehydrocyclization activity and 2,6-dimethylpyrazine (2,6-DMP) selectivity. X-ray photoelectron spectroscopy analysis of the reduced CuCr2O4 revealed a lower fraction of ionic Cu and a high percentage of metallic Cu in the near surface region. The HCOOH and pyridine adsorbed DRIFT spectra of CuCr2O4 revealed that strong basic and moderate Lewis acid sites are responsible for the selective formation of 2,6-dimethylpyrazine which is consistent with the catalyst poisoning studies on CuCr2O4 co-feeding with pyridine as both Br?nsted and Lewis acid site blocker and 2,6-lutidine as a selective Br?nsted acid site blocker during the dehydrocyclization reaction. The presence of isolated CuO and Cr2O3 species led to a high selectivity for 2,6-dimethylpiperazine. The high intrinsic activity of CuCrsol-gel was also concomitant with the Cu metal surface areas of the catalysts. The fresh, reduced and some of the used catalysts are characterized by BET-surface area, powder XRD, FTIR, XPS, TEM, H2-TPR, TPD of NH3, pyridine, 2,6-dimethylpyridine and HCOOH adsorbed DRIFT spectroscopy.

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