2,3,5,6-tetramethylpyrazine

Structural formula
General
Surname	2,3,5,6-tetramethylpyrazine
other names	Ligustrazine; Tetrapyrazine;
Molecular formula	C 8 H 12 N 2
Brief description	white solid with a pleasant odor
External identifiers / databases
ECHA InfoCard	100.013.084
PubChem	14296
ChemSpider	13658
Wikidata	Q11319317
properties
Molar mass	136.19 g mol −1
Physical state	firmly
density	1.08 g cm −3
Melting point	77-80 ° C
boiling point	190 ° C
solubility	soluble in water (4 g l −1 at 20 ° C)
safety instructions
GHS labeling of hazardous substances Caution
H and P phrases	H: 302
	P: 301 + 312 + 330
Toxicological data	1910 mg kg −1 ( LD 50 , rat , oral )
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

2,3,5,6-Tetramethylpyrazine is a chemical compound from the group of pyrazines .

Occurrence

Camembert

2,3,5,6-Tetramethylpyrazine is one of the major volatile flavorings in roasted cocoa beans and maple syrup . It was also used in French fries, paprika, wheat bread, Emmental cheese, Swiss cheese, Camembert cheese, Gruyere cheese, boiled, grilled and roasted beef, grilled and roasted pork, beer, black and green tea, coffee, dairy products, oatmeal, galbanum oil, Roasted peanuts, soybeans, beans, mushrooms, trassi, coriander seeds, rice bran, sukiyaki , soy sauce, malt, licorice , dried bonito, wild rice, prawns , crabs, clams, scallops, filberts, rum , sake , wine , whiskey , burley tobacco and soy products .

Extraction and presentation

2,3,5,6-tetramethyl may be made of 2,5-dimethylpyrazine by ring alkylation with methyllithium or by condensation of 2,3-butanedione with 2,3-butanediamine can be obtained.

properties

2,3,5,6-Tetramethylpyrazine is a white solid with a pleasant odor that is soluble in water. It has a musty, fermented, coffee-like odor.

use

2,3,5,6-Tetramethylpyrazine is an anti-inflammatory compound that was isolated from the fermented food natto . It showed nootropic activity in rats in vivo . It is useful in treating various diseases such as asthma, heart failure, rhinitis, and urinary incontinence. It is a flavor ingredient in tobacco . The compound is also used as a flavoring agent.

Individual evidence

↑ ^a ^b ^c ^d ^e data sheet 2,3,5,6-tetramethylpyrazine, 98 +% from AlfaAesar, accessed on January 2, 2019 ( PDF )(JavaScript required) .
↑ ^a ^b ^c ^d ^e ^f ^g data sheet 2,3,5,6-tetramethylpyrazine, natural, ≥98%, FG from Sigma-Aldrich , accessed on January 2, 2019 ( PDF ).
↑ ^a ^b ^c ^d George A. Burdock: Fenaroli's Handbook of Flavor Ingredients . CRC Press, 2004, ISBN 978-1-4200-3787-6 , pp. 1786 ( limited preview in Google Book search).

[Alfa-1] ↑ ^a ^b ^c ^d ^e data sheet 2,3,5,6-tetramethylpyrazine, 98 +% from AlfaAesar, accessed on January 2, 2019 ( PDF )(JavaScript required) .

[Sigma-2] ↑ ^a ^b ^c ^d ^e ^f ^g data sheet 2,3,5,6-tetramethylpyrazine, natural, ≥98%, FG from Sigma-Aldrich , accessed on January 2, 2019 ( PDF ).

[George_A._Burdock-3] George A. Burdock: Fenaroli's Handbook of Flavor Ingredients . CRC Press, 2004, ISBN 978-1-4200-3787-6 , pp. 1786 ( limited preview in Google Book search).