Basic information
- CAS
22047-25-2- Standard SMILES
CC(=O)c1cnccn1- InChIKey
DBZAKQWXICEWNW-UHFFFAOYSA-N- Molecular formula
- C6H6N2O
- Average molar mass
- 122.12 g/mol
- Monoisotopic mass
- 122.04801281
Overview
2-acetylpyrazine is a pyrazine that is substituted by an acetyl group at position 2. It has been identified as one of the volatile flavor constituents in popcorn, bread crust, vinegar, and potato snacks. It has a role as a flavouring agent. It is a member of pyrazines and an aromatic ketone.
Names & identifiers
- Preferred name
- Acetylpyrazine
- IUPAC
- 1-pyrazin-2-ylethanone
- English name
- Acetylpyrazine
- Molecular formula
- C6H6N2O
- Molecular weight
- 122.12
Names & synonyms
Show more names
Database identifiers
- CAS
22047-25-2- PubChem CID
- 30914
- DTXSID
DTXSID5047085- ChEMBL
CHEMBL3188662- ChEBI
CHEBI:145236- UNII
- GR391IBU5C
- EC Number
- 244-753-5
- Nikkaji
- J27.905F
Properties
Computed structural properties
- XLogP
- 0.2
- Topological polar surface area
- 42.9 Ų
- Hydrogen bond donors
- 0
- Hydrogen bond acceptors
- 3
- Rotatable bonds
- 1
- Heavy atoms
- 9
- Formal charge
- 0
- Complexity
- 114
Experimental & physicochemical properties
Solubility
slightly soluble in water; soluble in organic solvents
moderately soluble (in ethanol)
Physical Description
Solid
colourless to pale yellow crystals with a nutty, popcorn, breadcrust odour
Physicochemical properties
- Melting point
- 76 · 76-78 °C (lit.)
- Boiling point
- 78 · 78-79°C 8mm
- Density
- 1.1075 · 1.1075
- refractive index
- 1.535 · 1.5350 (estimate)
- FEMA
- 3126 · 3126 | ACETYLPYRAZINE
- FLAVIS Number
- 14.032 · 14.032 | Acetylpyrazine
- Flash point
- 78 · 78-79°C/8mm
- storage temp.
- Keep in dark place,Sealed in dry,Room Temperature
- solubility
- Chloroform (Slightly), Methanol (Slightly)
- form
- Solid
- pka
- 0.3 · 0.30±0.10(Predicted)
- color
- White to Off-White
- Odor
- popcorn-like odor
- Odor Type
- popcorn
- biological source
- synthetic
- JECFA Number
- 784 · 784
- BRN
- 109630 · 109630
- Major Application
- flavors and fragrances
- Cosmetics Ingredients Functions
- PERFUMING
- InChI
- 1S/C6H6N2O/c1-5(9)6-4-7-2-3-8-6/h2-4H,1H3
- InChIKey
- DBZAKQWXICEWNW-UHFFFAOYSA-N
- SMILES
- CC(=O)c1cnccn1
- LogP
- 0.2 · 0.20
- CAS DataBase Reference
- 22047 · 22047-25-2(CAS DataBase Reference)
- Substances Added to Food (formerly EAFUS)
- ACETYLPYRAZINE
- EWG's Food Scores
- 1 · 1
- FDA UNII
- 391 IBU5C · GR391IBU5C
- NIST Chemistry Reference
- Acetylpyrazine(22047-25-2)
- EPA Substance Registry System
- 1 · Ethanone, 1-pyrazinyl- (22047-25-2)
- UNSPSC Code
- 12352100 · 12352100
- NACRES
- 22 · NA.22
- Symbol(GHS)
- 7 · GHS07
- Signal word
- Warning
- Hazard statements
- 315 · H315-H319-H335
- Precautionary statements
- 261 · P261-P264-P271-P280-P302+P352-P305+P351+P338
- target organs
- Respiratory system
- PPE
- 95 · dust mask type N95 (US), Eyeshields, Gloves
- Hazard Codes
- Xi
- Risk Statements
- 36 · 36/37/38
- Safety Statements
- 26 · 26-36-24/25
- WGK Germany
- 2 · 2
- TSCA
- TSCA listed
- HazardClass
- IRRITANT
- HS Code
- 29339900 · 29339900
- Storage Class
- 11 · 11 - Combustible Solids
- Hazard Classifications
- 2 Skin · Eye Irrit. 2Skin Irrit. 2STOT SE 3
Safety & regulation
GHS classification
GHS Classification
This chemical does not meet GHS hazard criteria for 54.2% (154 of 284) of all reports.
Warning
H315 (45.8%): Causes skin irritation [Warning Skin corrosion/irritation]
P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 284 reports by companies from 16 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Hazard information
Regulatory Information
Chemical: Ethanone, 1-pyrazinyl-
Regulation (EC) No 1831/2003 (amended)
Ethanone, 1-pyrazinyl-: Does not have an individual approval but may be used under an appropriate group standard
Safety data
- PPE
- dust mask type N95 (US), Eyeshields, Gloves
- wgk
- 2
- tsca
- TSCA listed
- hs_code
- 29339900
- risk_code
- 36/37/38
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- hazard_code
- Xi
- safety_code
- 26-36-24/25
- hazard_class
- IRRITANT
- Storage Class
- 11 - Combustible Solids
- target organs
- Respiratory system
- Hazard statements
- H315-H319-H335
- Hazard Classifications
- Eye Irrit. 2Skin Irrit. 2STOT SE 3
- Precautionary statements
- P261-P264-P271-P280-P302+P352-P305+P351+P338
Chemistry & industry
Pharmacology
Uses & manufacturing
Use Classification
Fragrance Ingredients
Flavouring Agent -> FLAVOURING_AGENT -> JECFA Functional Classes
Flavoring Agents -> JECFA Flavorings Index
Flavouring Agent -> FLAVOURING_AGENT -> JECFA Functional Classes
Flavouring Agent -> FLAVOURING_AGENT -> JECFA Functional Classes
Applications
Description2-acetylpyrazine is white to pale yellow crystalline powder with a nutty, popcorn, bread-crust odor. It is soluble in water and stable under ordinary conditions. It is used to manufacture many polycyclic compounds and used as useful structures in pharmaceuticals and perfumes. It is a component of the folates (vitamin B compounds) and of the isoalloxazine ring nucleus of flavins. Numerous pyrazine derivatives such as pyrazine polycyclic compounds, alkyl-, alicyclic-, and alkylaryl-substituted compounds, derivatives containing oxygenated functional groups and thio-functional groups in the side-chains are used in biological, drug, flavoring and perfumery industry. 2-acetylpyrazine is used as food additive, commonly used in chocolate and baked goods.
OccurrenceReported found in guava fruit (Psidium guajava L.), wheaten bread, other types of breads, boiled and cooked beef, grilled/roasted uncured pork, pork liver, cocoa, coffee, black tea, roasted barley, roasted filbert (Corylus avellano), roasted peanut (Arachis hypogea), roasted almond (Prunus amygdalus), scallop, filberts, popcorn and sesame oil.
UsesAcetylpyrazine has been used in synthesis of:7-heteroaryl-pyrazolo[1,5-a]pyrimidine-3-carboxamidescopper (II) complexes with di-imine ligandsN(4) substituted thiosemicarbazones
General Description2-Acetylpyrazine has been identified as one of the volatile flavor constituents in popcorn, wheat and rye bread crust.
Preparation methods
Preparationsynthesis of acetylpyrazine: By the ester condensation of EtO2 C-pyrazine; by dehydrating pyrazynamide with POCI3 and then reacting the resulting 2-cyano-pyrazine with methyl magnesium bromide.
Upstream & downstream products
Upstream raw materials
Downstream products
Suppliers100 total
Additional notes
DefinitionChEBI: 2-acetylpyrazine is a pyrazine that is substituted by an acetyl group at position 2. It has been identified as one of the volatile flavor constituents in popcorn, bread crust, vinegar, and potato snacks. It has a role as a flavouring agent. It is an aromatic ketone and a member of pyrazines.
Related reactions
Compound notes
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