Basic information
- Standard SMILES
Cc1cnccn1- InChIKey
CAWHJQAVHZEVTJ-UHFFFAOYSA-N- Molecular formula
- C5H6N2
- Average molar mass
- 94.11 g/mol
- Monoisotopic mass
- 94.05309819
Overview
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.
Names & identifiers
- Preferred name
- 2-Methylpyrazine
- IUPAC
- 2-methylpyrazine
- English name
- 2-Methylpyrazine
- Molecular formula
- C5H6N2
- Molecular weight
- 94.11
Names & synonyms
2-METHYLPYRAZINE109-08-0MethylpyrazinePyrazine, methyl-Pyrazine, 2-methyl-2-Methyl-1,4-diazine2-methyl-pyrazinemethyl-pyrazineFEMA No. 3309DTXSID4047620pyrazine, 2-methylRVC6500U9C
Show more names
FEMA 3309methyl-pyrazin3-MethylpyrazineMETHYLPYRAZINE, 2-MPZFEMA 3616Methylpiazine
NSC-30412NSC-49138CHEBI:89015RefChem:1113273203-645-8methyl pyrazineMFCD000061422-METHYL PYRAZINE
Database identifiers
- CAS
109-08-0- PubChem CID
- 7976
- DTXSID
DTXSID4047620- ChEMBL
CHEMBL479791- ChEBI
CHEBI:89015- UNII
- RVC6500U9C
- EC Number
- 203-645-8
- Nikkaji
- J1.501F
Properties
Computed structural properties
- XLogP
- 0.2
- Topological polar surface area
- 25.8 Ų
- Hydrogen bond donors
- 0
- Hydrogen bond acceptors
- 2
- Rotatable bonds
- 0
- Heavy atoms
- 7
- Formal charge
- 0
- Complexity
- 54
Experimental & physicochemical properties
Chemical ClassesNitrogen Compounds -> Pyrazines
SpringerMaterials Properties15N nuclear magnetic resonance spectrum
FragrancesFragrance Ingredient (2-Methylpyrazine) -> IFRA transparency List
LogP
0.21
0.23
Food AdditivesFLAVORING AGENT OR ADJUVANT -> FDA Substance added to food
Density1.007-1.033
Flavoring AgentsEU Flavoring substances
Solubility
1000 mg/mL at 20 °C
soluble in water and oils
miscible at room temperature (in ethanol)
Boiling Point
135.00 °C. @ 761.00 mm Hg
137 °C
Melting Point-29 °C
Refractive Index1.501-1.509
Physical Description
Colorless liquid; [Alfa Aesar MSDS]
Liquid
colourless to slightly yellow liquid with a nutty, cocoa-like odour
Physicochemical properties
- Melting point
- -29 °C · -29 °C (lit.)
- Boiling point
- 135 °C/761 · 135 °C/761 mmHg (lit.)
- Density
- 1.03 g/mL · 1.03 g/mL at 25 °C (lit.)
- refractive index
- 20 · n20/D 1.504(lit.)
- FEMA
- 3309 · 3309 | 2-METHYLPYRAZINE
- FLAVIS Number
- 14.027 · 14.027 | 2-Methylpyrazine
- Flash point
- 122 °F · 122 °F
- storage temp.
- 2 · 2-8°C
- solubility
- 20.87 mg/mL · >20.87 mg/mL in EtOH with ultrasonic; >49.9 mg/mL in DMSO;
- form
- Liquid
- pka
- 1.45 · 1.45(at 27℃)
- color
- Clear colorless to slightly yellow
- Odor
- 1 % · at 1.00 % in dipropylene glycol. nutty cocoa roasted chocolate peanut green
- Odor Type
- nutty
- biological source
- synthetic
- Water Solubility
- Fully miscible in water.
- JECFA Number
- 761 · 761
- BRN
- 105778 · 105778
- Henry's Law Constant
- 4.5 · 4.5×100 mol/(m3Pa) at 25℃, Buttery et al. (1971)
- Major Application
- flavors and fragrances
- InChI
- 1S/C5H6N2/c1-5-4-6-2-3-7-5/h2-4H,1H3
- InChIKey
- CAWHJQAVHZEVTJ-UHFFFAOYSA-N
- SMILES
- Cc1cnccn1
- LogP
- 0.18 · 0.18
- CAS DataBase Reference
- 109 · 109-08-0(CAS DataBase Reference)
- Substances Added to Food (formerly EAFUS)
- 2 · 2-METHYLPYRAZINE
- EWG's Food Scores
- 1 · 1
- FDA UNII
- 6500 U9C · RVC6500U9C
- NIST Chemistry Reference
- Pyrazine, methyl-(109-08-0)
- EPA Substance Registry System
- Pyrazine, methyl- (109-08-0)
- UNSPSC Code
- 41116107 · 41116107
- NACRES
- 24 · NA.24
- Symbol(GHS)
- 2 · GHS02,GHS07
- Signal word
- Warning
- Hazard statements
- 226 · H226-H302
- Precautionary statements
- 210 · P210-P233-P240-P241-P242-P301+P312
- PPE
- Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter
- Hazard Codes
- Xn,Xi,F
- Risk Statements
- 10 · 10-22-36/37/38
- Safety Statements
- 26 · 26-36-16
- RIDADR
- 1993 · UN 1993 3/PG 3
- WGK Germany
- 3 · 3
- RTECS
- 3675000 · UQ3675000
- TSCA
- TSCA listed
- HazardClass
- 3 · 3
- PackingGroup
- III
- HS Code
- 29339990 · 29339990
- Storage Class
- 3 · 3 - Flammable liquids
- Hazard Classifications
- 4 OralFlam · Acute Tox. 4 OralFlam. Liq. 3
- Toxicity
- 50 · mouse,LD50,intraperitoneal,1820mg/kg (1820mg/kg),Toxicology and Applied Pharmacology. Vol. 17, Pg. 244, 1970.
- Limited Quantities
- 5 L · 5.0 L (1.3 gallons) (liquid)
- Excepted Quantities
- Max Inner Pack (30g or 30ml) and Max Outer Pack (1Kg or 1L)
Safety & regulation
GHS classification
GHS Classification
Warning
H226 (100%): Flammable liquid and vapor [Warning Flammable liquids]
P210, P233, P240, P241, P242, P243, P264, P270, P280, P301+P317, P303+P361+P353, P330, P370+P378, P403+P235, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 1659 reports by companies from 10 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, methyl-
Regulation (EC) No 1831/2003 (amended)
2-Methylpyrazine: Does not have an individual approval but may be used under an appropriate group standard
Hazards SummarySafe when used as a flavoring agent in food; [JECFA] An irritant; Harmful by ingestion; [Alfa Aesar MSDS]
Hazard Classes and Categories
Flam. Liq. 3 (100%)
Flammable liquids - Category 3
Safety data
- PPE
- Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter
- wgk
- 3
- tsca
- TSCA listed
- rtecs
- UQ3675000
- ridadr
- UN 1993 3/PG 3
- hs_code
- 29339990
- Toxicity
- mouse,LD50,intraperitoneal,1820mg/kg (1820mg/kg),Toxicology and Applied Pharmacology. Vol. 17, Pg. 244, 1970.
- risk_code
- 10-22-36/37/38
- Signal word
- Warning
- Symbol(GHS)
- GHS02,GHS07
- hazard_code
- Xn,Xi,F
- safety_code
- 26-36-16
- hazard_class
- 3
- Storage Class
- 3 - Flammable liquids
- packing_group
- III
- Hazard statements
- H226-H302
- Limited Quantities
- 5.0 L (1.3 gallons) (liquid)
- Excepted Quantities
- Max Inner Pack (30g or 30ml) and Max Outer Pack (1Kg or 1L)
- Hazard Classifications
- Acute Tox. 4 OralFlam. Liq. 3
- Precautionary statements
- P210-P233-P240-P241-P242-P301+P312
Chemistry & industry
Pharmacology
Cellular LocationsCytoplasm
Uses & manufacturing
UsesUsed as flavoring agent or adjuvant; [FDA]
Use Classification
Fragrance Ingredients
Flavouring Agent -> FLAVOURING_AGENT -> JECFA Functional Classes
Flavoring Agents -> JECFA Flavorings Index
Flavouring Agent -> FLAVOURING_AGENT -> JECFA Functional Classes
General Manufacturing InformationPyrazine, 2-methyl-: ACTIVE
Applications
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.
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.
General Description2-Methylpyrazine is an alkyl-substituted pyrazine used as a key intermediate in the synthesis of pyrazineamide, an anti-tubercular drug.
Preparation methods
PreparationFrom corresponding carboxylic acid; by catalytic dehydrogenation of 2-methyl-piperazine; by condensation of methylglyoxal with ethylenediamine
Upstream & downstream products
Upstream raw materials
Downstream products
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Additional notes
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.
Related reactions
36 records
Linked notes
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