Basic information
- CAS
14667-55-1- Standard SMILES
Cc1cnc(C)c(C)n1- InChIKey
IAEGWXHKWJGQAZ-UHFFFAOYSA-N- Molecular formula
- C7H10N2
- Average molar mass
- 122.17 g/mol
- Monoisotopic mass
- 122.08439832
Overview
Trimethylpyrazine is a member of the class of pyrazines that is pyrazine in which three hydrogens at positions 2, 3 and 5 have been replaced by methyl groups. It has a role as a pheromone, a flavouring agent, an animal metabolite, a plant metabolite and a bacterial metabolite.
Names & identifiers
- Preferred name
- Trimethylpyrazine
- IUPAC
- 2,3,5-trimethylpyrazine
- English name
- 2,3,5-Trimethylpyrazine
- Molecular formula
- C7H10N2
- Molecular weight
- 122.17
Names & synonyms
2,3,5-Trimethylpyrazine14667-55-1TRIMETHYLPYRAZINEPyrazine, trimethyl-2,3,5-Trimethyl pyrazine2,3,6-TrimethylpyrazineFEMA No. 3244DTXSID1047075Q8PR0W8TITDTXCID9027075CHEBI:190131RefChem:441845
Show more names
FEMA 32442,3,5-TriMethylpyrazine 99%FEMA NUMBER 3244Compound Fr14500trimethyl-pyrazin2.3.5-Methyl pyrazine
238-712-0Pyrazine, 2,3,5-trimethyl-Trimethyl-pyrazinetrimethyl pyrazineMFCD00006145Pyrazine, 2,3,5-trimethylCCRIS 2932EINECS 238-712-0
Database identifiers
- CAS
14667-55-1- PubChem CID
- 26808
- DTXSID
DTXSID1047075- ChEMBL
CHEMBL320146- ChEBI
CHEBI:190131- UNII
- Q8PR0W8TIT
- EC Number
- 238-712-0
- Nikkaji
- J27.872F
Properties
Computed structural properties
- XLogP
- 1
- Topological polar surface area
- 25.8 Ų
- Hydrogen bond donors
- 0
- Hydrogen bond acceptors
- 2
- Rotatable bonds
- 0
- Heavy atoms
- 9
- Formal charge
- 0
- Complexity
- 92.9
Experimental & physicochemical properties
FragrancesFragrance Ingredient (2,3,5-Trimethylpyrazine) -> IFRA transparency List
LogP
0.95
0.95
Food AdditivesFLAVORING AGENT OR ADJUVANT -> FDA Substance added to food
Density0.960-0.990
Flavoring AgentsEU Flavoring substances
Solubility
soluble in water, oils, organic solvents
miscible at room temperature (in ethanol)
Boiling Point171 °C
Refractive Index1.500-1.509
Physical Description
Liquid
colourless to slightly yellow liquid with a roasted nut, baked potato odour
Physicochemical properties
Safety & regulation
GHS classification
GHS Classification
Warning
H226 (99.7%): Flammable liquid and vapor [Warning Flammable liquids]
P210, P233, P240, P241, P242, P243, P264, P264+P265, P270, P280, P301+P317, P303+P361+P353, P305+P351+P338, P330, P337+P317, P370+P378, P403+P235, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 1880 reports by companies from 13 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Warning
H226: Flammable liquid and vapor [Warning Flammable liquids]
Hazard information
Regulatory Information
Chemical: Pyrazine, trimethyl-
Regulation (EC) No 1831/2003 (amended)
Pyrazine, 2,3,5-trimethyl- is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of Pyrazine, 2,3,5-trimethyl- are required to report information about their production and use of this chemical to the EPA under the Toxic Substances Control Act (TSCA). (40 eCFR Part 711)
Pyrazine, trimethyl-: Does not have an individual approval but may be used under an appropriate group standard
Hazard Classes and Categories
Flam. Liq. 3 (99.7%)
Flammable liquids - Category 3
Safety data
- PPE
- Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter
- wgk
- 3
- tsca
- TSCA listed
- rtecs
- UQ3907000
- ridadr
- UN 1993 3/PG 3
- hs_code
- 29339900
- Toxicity
- rat,LD50,oral,806mg/kg (806mg/kg),Drug and Chemical Toxicology. Vol. 3, Pg. 249, 1980.
- risk_code
Chemistry & industry
Pharmacology
Cellular LocationsCytoplasm
Uses & manufacturing
U.S. Production2021: 26 lb
Consumer UsesFragrance
Household ProductsInformation on 1 consumer products that contain Trimethylpyrazine in the following categories is provided:
Use Classification
Fragrance Ingredients
Flavoring Agents -> JECFA Flavorings Index
Flavouring Agent -> FLAVOURING_AGENT -> JECFA Functional Classes
General Manufacturing InformationPyrazine, 2,3,5-trimethyl-: ACTIVE
Applications
OccurrenceReported present in bakery products, roasted barley, cocoa products, coffee, dairy products, meat, peanuts, filberts, pecans, popcorn, potato products, rum and whiskey, soy products, raw asparagus, baked potato, wheaten bread, crispbread, Swiss cheese, coffee, black tea, green tea, roasted barley, roasted filbert, heated beef, roasted peanut, soybean, raw beans, coriander seed, scallop, guava, kohlrabi, bell pepper, blue, Swiss and Gruyere cheese, boiled egg, fatty fish, beer, sherry, barley, peanut, oat products, coconut, beans, mushroom, trassi, almond, macadamia nut, sesame seed, coriander seed, rice, licorice, sweet corn, malt, peated malt, wort, krill, fermented shrimp, crab, okra, crayfish, clam, scallop and squid.
UsesTrimethylpyrazine is a key aroma compound of dark chocolates differing in organoleptic properties.
Uses2,3,5-Trimethylpyrazine can be used as a flavor ingredient in food industries.
2,3,5-Trimethylpyrazine is present in brown cheese.
Related reactions
6 records
Compound notes
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