2-Methylpyrazine

2-Methylpyrazine Basic information
Product Name:2-Methylpyrazine
Synonyms:2-METHYL-1,4-DIAZINE;2-methyl-1,4-diazinen;2-METHYLPYRAZINE;FEMA NUMBER 3309;FEMA 3616;FEMA 3309;METHYLPYRAZINE;METHYLPYRAZINE, 2-
CAS:109-08-0
MF:C5H6N2
MW:94.11
EINECS:203-645-8
Product Categories:Pyrazine compounds;Building Blocks;Heterocyclic Building Blocks;Alphabetical Listings;Flavors and Fragrances;M-N;Pyrazine;Pyrazines;Mono- & Polyalkylpyrazines;pyrazine Flavor
Mol File:109-08-0.mol
2-Methylpyrazine Structure
2-Methylpyrazine Chemical Properties
Melting point -29 °C (lit.)
Boiling point 135 °C/761 mmHg (lit.)
density 1.03 g/mL at 25 °C (lit.)
FEMA 3309 | 2-METHYLPYRAZINE
refractive index n20/D 1.504(lit.)
Fp 122 °F
storage temp. 2-8°C
solubility >20.87 mg/mL in EtOH with ultrasonic; >49.9 mg/mL in DMSO;
form Liquid
pka1.45(at 27℃)
color Clear colorless to slightly yellow
Odorat 1.00 % in dipropylene glycol. nutty cocoa roasted chocolate peanut green
Odor Typenutty
Water Solubility Fully miscible in water.
JECFA Number761
BRN 105778
InChIKeyCAWHJQAVHZEVTJ-UHFFFAOYSA-N
LogP0.18
CAS DataBase Reference109-08-0(CAS DataBase Reference)
NIST Chemistry ReferencePyrazine, methyl-(109-08-0)
EPA Substance Registry SystemPyrazine, methyl- (109-08-0)
Safety Information
Hazard Codes Xn,Xi,F
Risk Statements 10-22-36/37/38
Safety Statements 26-36-16
RIDADR UN 1993 3/PG 3
WGK Germany 3
RTECS UQ3675000
TSCA Yes
HazardClass 3
PackingGroup III
HS Code 29339990
Toxicitymouse,LD50,intraperitoneal,1820mg/kg (1820mg/kg),Toxicology and Applied Pharmacology. Vol. 17, Pg. 244, 1970.
MSDS Information
ProviderLanguage
2-Methylpyrazine English
SigmaAldrich English
ACROS English
ALFA English
2-Methylpyrazine Usage And Synthesis
Description2-Methylpyrazine has an odor threshold in water variously reported at 60,000 or 105,000 ppb. May be prepared from the corresponding carboxylic acid; by catalytic dehydrogenation of 2-methyl-piperazine; by condensation of methylglyoxal with ethylenediamine.
Chemical Properties2-Methylpyrazine has a nutty, cocoa, green, roasted, chocolate, meaty odor.
Chemical Propertiesclear colorless to slightly yellow liquid
OccurrenceReported found in bakery products, roasted barley, cocoa products, coffee, dairy products, cooked meats, peanuts, filberts, pecans, popcorn, potato chips, rum and whiskey, soy product, roasted filberts, roasted almonds, guava, papaya, asparagus, kohlrabi, baked and fried potato, milk, boiled egg, smoked fish, beer, coffee, sesame seed, rice, sukiyaki, buckwheat, sweet corn, corn tortillas, malt, wort, wild rice, okra, crayfish, clam, squid and maté.
Uses2-Methylpyrazine is used as flavoring agents in bread fresh bread, butter, chocolate, chocolate cocoa, coffee, meat roasted, nut almond.
UsesThese Secondary Standards are qualified as Certified Reference Materials. These are suitable for use in several analytical applications including but not limited to pharma release testing, pharma method development for qualitative and quantitative analyses, food and beverage quality control testing, and other calibration requirements.
DefinitionChEBI: Methylpyrazine is a member of the class of pyrazines that is pyrazine in which one of the hydrogens is replaced by a methyl group. It is a flavouring agent found in coffee, peanuts and red peppers. It has a role as a flavouring agent, a plant metabolite and a Maillard reaction product.
PreparationFrom corresponding carboxylic acid; by catalytic dehydrogenation of 2-methyl-piperazine; by condensation of methylglyoxal with ethylenediamine
Aroma threshold valuesDetection: 60 ppb to 100 ppm
Taste threshold valuesTaste characteristics at 75 ppm: nutty, brown, musty, roasted and astringent
General Description2-Methylpyrazine is an alkyl-substituted pyrazine used as a key intermediate in the synthesis of pyrazineamide, an anti-tubercular drug.
Safety ProfileModerately toxic by ingestion and intraperitoneal routes. Mutation data reported. Flammable liquid when exposed to heat, sparks, or flame. Can react with oxidizing materials. To fight fire, use water spray, foam, dry chemical, CO2. When heated to decomposition it emits highly toxic fumes of NOx.
Purification MethodsPurify it via the picrate and distil the free base. The picrate has m133-134o(from EtOH). [Wiggins & Wise J Chem Soc 4780 1956, Beilstein 23 III/IV 911, 23/5 V 386.]
Acetylpyrazine Pyrazine 2-METHOXY-3-METHYLPYRAZINE 98+%,2 OR 5 OR 6-METHOXY-3-METHYLPYRAZINE LUMICHROME 2,3-Pyrazinedicarboxylic acid 2-Methoxy-3-isobutyl pyrazine 2-Pyrazinecarboxylic acid Parathion-methyl Tetramethylpyrazine 2,3-PYRAZINEDICARBOXAMIDE 3-AMINO-6-(CHLOROMETHYL)-2-PYRAZINECARBONITRILE 4-OXIDE Thiophanate-methyl 2-Methoxy-3-sec-butyl pyrazine Pirimiphos-methyl 2-Ethyl-3-methoxypyrazine Sulfachoropyrazine sodium 2-Isopropyl-3-methoxypyrazine ALLOXAZINE

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