Acetylpyrazine

HCID 30914

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

Acetylpyrazine2-ACETYLPYRAZINE22047-25-2Ethanone, 1-pyrazinyl-1-(pyrazin-2-yl)ethan-1-one1-pyrazin-2-ylethanone1-PyrazinylethanonePyrazin-1-ylethan-1-oneEthanone, l-pyrazinyl-FEMA No. 3126DTXSID5047085GR391IBU5C
Show more names
FEMA 31262-Acetyl1-PYRAZIN-2-YL-ETHANONE9H-12-AcylpyrazineFEMA NUMBER 3126ACETYL-2-PYRAZIN
DTXCID3027085NSC-72374CHEBI:145236RefChem:85006244-753-5Methyl pyrazinyl ketone1-(pyrazin-2-yl)ethanoneKetone, methyl pyrazinyl

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

Experimental & physicochemical properties

FragrancesFragrance Ingredient (Acetylpyrazine) -> IFRA transparency List
LogP0.20
Food AdditivesFLAVORING AGENT OR ADJUVANT -> FDA Substance added to food
Flavoring AgentsEU Flavoring substances
Solubility · 2 items

slightly soluble in water; soluble in organic solvents

moderately soluble (in ethanol)

Boiling Point188 °C

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

Safety & regulation

GHS classification

GHS Classification · 5 items

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 · 3 items

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

Hazard Classes and CategoriesSkin Irrit. 2 (45.8%)

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

Chemistry & industry

Pharmacology

Cellular LocationsCytoplasm

Uses & manufacturing

Use Classification · 5 items

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

General Manufacturing InformationEthanone, 1-(2-pyrazinyl)-: ACTIVE
Applications · 4 items

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.

Suppliers100 total

国药集团化学试剂有限公司86-21-63210123 · [email protected]
梯希爱(上海)化成工业发展有限公司021-67121386 · [email protected]
衢州润东化工有限公司0570-8789886 18892685668 · [email protected]
上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]
枣庄九星生物科技有限公司0632-3759569 13589608009
Additional notes · 1 item

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

55 records

Compound notes

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