22047-25-2

Basic information

• Product Name: Acetylpyrazine
• Synonyms: ACETYLPYRAZINE;ACETYLPYRAZINE, 2-;2-ACETYLPYRAZINE;1-PYRAZIN-2-YLETHAN-1-ONE;1-PYRAZIN-2-YL-ETHANONE;METHYL PYRAZINYL KETONE;METHYL-2-PYRAZINYL KETONE;FEMA 3126
• CAS NO: 22047-25-2
• Molecular Formula: C6H6N2O
• Molecular Weight: 122.12
• EINECS: 244-753-5
• Product Categories: Pharmaceutical Intermediates;ACETYLGROUP;Pyrazines;Pyrazine;Heterocyclic Compounds;Miscellaneous;Chloropyrazines, etc.;pyrazine Flavor;Building Blocks;Heterocyclic Building Blocks;Sulfides flavors;Building Blocks;Chemical Synthesis;Heterocyclic Building Blocks
• Mol File: 22047-25-2.mol
• Article Data: 21

Chemical Properties

• Melting Point: 75-78 °C
• Boiling Point: 78-79°C 8mm
• Flash Point: 78-79°C/8mm
• Appearance: Light yellow to yellow-brownish powder
• Density: 1.1075
• Vapor Pressure: 0.095mmHg at 25°C
• Refractive Index: 1.5350 (estimate)
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• Solubility: Chloroform (Slightly), Methanol (Slightly)
• PKA: 0.30±0.10(Predicted)
• BRN: 109630
• CAS DataBase Reference: Acetylpyrazine(CAS DataBase Reference)
• NIST Chemistry Reference: Acetylpyrazine(22047-25-2)
• EPA Substance Registry System: Acetylpyrazine(22047-25-2)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36-24/25
• WGK Germany: 2
• TSCA: T
• HazardClass: IRRITANT
• Hazardous Substances Data: 22047-25-2(Hazardous Substances Data)

Usage

Description

2-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.

References

[1] https://pubchem.ncbi.nlm.nih.gov/compound/Acetylpyrazine#section=Pharmacology-and-Biochemistry [2] https://en.wikipedia.org/wiki/Acetylpyrazine [3] http://www.chemicalland21.com/specialtychem/perchem/2-ACETYLPYRAZINE.htm

Chemical Properties

Different sources of media describe the Chemical Properties of 22047-25-2 differently. You can refer to the following data:
1. LIGHT YELLOW TO YELLOW-BROWNISH POWDER
2. Acetylpyrazine has a nutty, popcorn, bread crust odor. It is one of the volatile aroma components in popcorn, wheat and rye crusts.

Occurrence

Reported 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.

Uses

Acetylpyrazine has been used in synthesis of:7-heteroaryl-pyrazolo[1,5-a]pyrimidine-3-carboxamidescopper (II) complexes with di-imine ligandsN(4) substituted thiosemicarbazones

Definition

ChEBI: 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.

Application

Acetylpyrazine has been widely used as an intermediate in the organic synthesis of various heterocyclic derivatives and in coupling reactions, alkylation reactions, and sensitizer ligands because of its good biological and reactive activities. For example, it is a significant reaction intermediate for producing drugs for treating malaria, epilepsy, and Parkinson's disease.

Preparation

synthesis 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.

Aroma threshold values

Detection at 62 ppb

Taste threshold values

Taste characteristics at 10 ppm: roasted, nutty, bready, yeasty with popcorn, corn chip nuance

General Description

2-Acetylpyrazine has been identified as one of the volatile flavor constituents in popcorn, wheat and rye bread crust.

InChI:InChI=1/C6H8N2O/c1-6(9)8-4-2-7-3-5-8/h2-5,7H,1H3

Synthetic route

1,4-pyrazine (290-37-9) + 2-oxo-propionic acid (127-17-3) → acetylpyrazine (22047-25-2)

Conditions	Yield
With NH4S2O8; silver nitrate; trifluoroacetic acid In dichloromethane; water at 40℃; for 2.5h;	100%
With ferrous(II) sulfate heptahydrate; ammonium peroxydisulfate; sulfuric acid In dichloromethane; water at 40℃; Reagent/catalyst; Solvent; Minisci Aromatic Substitution;	26%

1-(pyrazin-2-yl)butan-1-one (61892-81-7) → acetylpyrazine (22047-25-2) + 2-Methyl-1-pyrazin-2-yl-cyclopropanol (138836-01-8, 138836-02-9)

Conditions	Yield
In tert-butyl alcohol; benzene for 4h; Irradiation;	A 1% B 95%

3-acetylpyrazine N-oxide (120992-58-7) → acetylpyrazine (22047-25-2)

Conditions	Yield
With Eosin Y; di-tert-butyl 1,4-dihydro-2,6-dimethyl-3,5-pyridine-dicarboxylate In acetonitrile at 20℃; for 3h; Inert atmosphere; Irradiation; chemoselective reaction;	90%

3-methyl-1-(pyrazin-2-yl)butan-1-one (86461-64-5) → acetylpyrazine (22047-25-2) + 2,2-dimethyl-1-(pyrazin-2-yl)cyclopropanol (138836-03-0)

Conditions	Yield
In tert-butyl alcohol; benzene for 4h; Irradiation;	A 2% B 86%

2-pyrazine carbonitrile (19847-12-2) + methylene chloride (74-87-3) → acetylpyrazine (22047-25-2)

Conditions	Yield
Stage #1: methylene chloride With iodine; magnesium In tetrahydrofuran at 60℃; for 2h; Inert atmosphere; Stage #2: 2-pyrazine carbonitrile With copper(l) chloride In tetrahydrofuran at 50℃; for 14h; Inert atmosphere; Stage #3: With water In tetrahydrofuran Temperature; Reagent/catalyst; Solvent; Inert atmosphere;	69%

C6H6Cl2N2 → acetylpyrazine (22047-25-2)

Conditions	Yield
With sodium hydrogencarbonate; dimethyl sulfoxide at 80℃; for 6h;	60%

1,4-pyrazine (290-37-9) + 2-oxo-propionic acid (127-17-3) → acetylpyrazine (22047-25-2) + 1,1′-(pyrazine-2,5-diyl)diethanone (39248-49-2)

Conditions	Yield
With ferrous(II) sulfate heptahydrate; ammonium peroxydisulfate; formic acid; dimethyl sulfoxide In dichloromethane; water at 40℃; Catalytic behavior; Reagent/catalyst; Solvent; Minisci Aromatic Substitution;	A 58% B 10%
With ferrous(II) sulfate heptahydrate; ammonium peroxydisulfate; sulfuric acid In water at 50℃; Minisci Aromatic Substitution;	A 26% B 33%

1,4-pyrazine (290-37-9) + acetaldehyde (75-07-0) → acetylpyrazine (22047-25-2)

Conditions	Yield
With tert.-butylhydroperoxide; di-tert-butyl peroxide; iron(II) sulfate In dichloromethane; sulfuric acid at 5℃; for 1h;	50%

2-pyrazine carbonitrile (19847-12-2) + methyl magnesium iodide (917-64-6) → acetylpyrazine (22047-25-2)

Conditions	Yield
In diethyl ether at 20℃; for 1h; Addition;	42%
In diethyl ether at -10 - 10℃; for 1h;	40%
Stage #1: 2-pyrazine carbonitrile; methyl magnesium iodide In diethyl ether Stage #2: With water

2-(3,3-dimethylbutyryl)pyrazine (138835-87-7) → acetylpyrazine (22047-25-2)

Conditions	Yield
In hexane for 20h; Irradiation;	15%
In tert-butyl alcohol; benzene for 5h; Quantum yield; Irradiation;

2-pyrazine carbonitrile (19847-12-2) + methylmagnesium bromide (75-16-1) → acetylpyrazine (22047-25-2)

Conditions	Yield
With diethyl ether

1,4-pyrazine (290-37-9) + acetaldehyde (75-07-0) → acetylpyrazine (22047-25-2) + 1,1′-(pyrazine-2,5-diyl)diethanone (39248-49-2)

Conditions	Yield
With tert.-butylhydroperoxide; sulfuric acid; iron(II) sulfate In water; benzene Yields of byproduct given;	A 28 % Chromat. B n/a

1H-imidazole (288-32-4) + C6H5N2O(1-)*K(1+) → acetylpyrazine (22047-25-2) + imidazole potassium salt (20671-53-8)

Conditions	Yield
In dimethyl sulfoxide at 24.9℃; Equilibrium constant;

pyrazinamide (98-96-4) → acetylpyrazine (22047-25-2)

Conditions	Yield
Multi-step reaction with 2 steps 1: 85 percent / POCl3 / 1.5 h / 100 °C 2: 40 percent / diethyl ether / 1 h / -10 - 10 °C View Scheme

2-pyrazine carbonitrile (19847-12-2) → acetylpyrazine (22047-25-2)

Conditions	Yield
Multi-step reaction with 2 steps 1: 2.) H+, H2O 2: 2-methyl-propan-2-ol; benzene / 5 h / Irradiation View Scheme

L-serin (56-45-1) + L-lysine (56-87-1) + D-glucose (50-99-7) → 1,4-pyrazine (290-37-9) + 2-Methylpyrazine (109-08-0) + 2,5-dimethyl-pyrazine (123-32-0) + 2,3-dimethylpyrazine (5910-89-4) + acetylpyrazine (22047-25-2) + 2-ethyl-3,6-dimethylpyrazine (13360-65-1) + 2,6-dimethylpyrazine (108-50-9) + 2,3,5-trimethylpyrazine (14667-55-1) + 2-ethyl-6-methylpyrazine (13925-03-6) + 2-ethyl-5-methypyrazine (13360-64-0)

Conditions	Yield
In water at 130℃; for 2h; pH=8; Maillard reaction;

...Expand

L-lysine (56-87-1) + D-glucose (50-99-7) → 1,4-pyrazine (290-37-9) + 2-Methylpyrazine (109-08-0) + 2,5-dimethyl-pyrazine (123-32-0) + 2,3-dimethylpyrazine (5910-89-4) + acetylpyrazine (22047-25-2) + 2-ethyl-3,6-dimethylpyrazine (13360-65-1) + 2,6-dimethylpyrazine (108-50-9) + 2,3,5-trimethylpyrazine (14667-55-1) + 2-ethyl-3,5-dimethylpyrazine (13925-07-0) + 2-ethyl-5-methypyrazine (13360-64-0)

Conditions	Yield
In water at 130℃; for 2h; pH=8; Maillard reaction;

...Expand

2-ethylpyrazine (13925-00-3) → acetylpyrazine (22047-25-2)

Conditions	Yield
With tert.-butylhydroperoxide In water at 60℃; for 12h;	66 %Spectr.

acetylpyrazine (22047-25-2) → 2-bromo-1-pyrazin-2-yl-ethan-1-one hydrobromide (126353-32-0)

Conditions	Yield
With pyridinium hydrobromide perbromide; hydrogen bromide In water; acetic acid at 20℃; for 0.1h;	100%
With hydrogen bromide; bromine In water at 80 - 90℃; for 1h;	82%
With pyridinium hydrobromide perbromide; hydrogen bromide; acetic acid at 20℃; for 1h;
With hydrogen bromide; bromine; acetic acid at 23℃; for 4h; Inert atmosphere;

acetylpyrazine (22047-25-2) + 5-amino isophthaloyl hydrazide → C20H19N9O2

Conditions	Yield
With acetic acid In ethanol Reflux;	100%

acetylpyrazine (22047-25-2) + 1-(1-phenylethyl)-2-methyleneaziridine → 2-pyrazin-2-yl-4-methyl-1-(1-phenylethyl)pyrrole

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0) at 120℃; for 72h;	96%

Dimethyl oxalate (553-90-2) + acetylpyrazine (22047-25-2) → 4-(2-pyrazinyl)-2,4-dioxobutanoic acid methyl ester (858599-85-6)

Conditions	Yield
Stage #1: acetylpyrazine With lithium hexamethyldisilazane In tetrahydrofuran at -78℃; for 0.75h; Stage #2: Dimethyl oxalate In tetrahydrofuran for 0.166667h;	96%

acetylpyrazine (22047-25-2) + thieno[2,3-d]pyrimidin-4-ylhydrazine (14080-58-1) → 4-(2-(1-(pyrazin-2-yl)ethylidene)hydrazinyl)thieno[2,3-d]pyrimidine

Conditions	Yield
In ethanol for 24h; Reflux;	96%

acetylpyrazine (22047-25-2) → 2-(1-hydroxyethyl)pyrazine (94777-52-3)

Conditions	Yield
Stage #1: acetylpyrazine With C27H43AlClN3Si3; 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane In neat (no solvent) at 20℃; for 16h; Stage #2: With silica gel at 20℃; Catalytic behavior;	95%
With sodium tetrahydroborate In methanol Ambient temperature;
With lithium aluminium tetrahydride In diethyl ether at -78℃; for 1h;

acetylpyrazine (22047-25-2) + isoniazid (54-85-3) → N’-(1-(pyrazin-2-yl)ethylidene)isonicotinohydrazide

Conditions	Yield
With formic acid In ethanol for 4h; Reflux;	95%
With formic acid In ethanol for 5h; Reflux;	90%
In methanol for 4h; Reflux;	64%

acetylpyrazine (22047-25-2) + ethene (74-85-1) + carbon monoxide (201230-82-2) → dihydro-5-methyl-5-(2-pyradinyl)-2(3H)-furanone

Conditions	Yield
dodecacarbonyl-triangulo-triruthenium In toluene at 140℃; for 20h;	94%

acetylpyrazine (22047-25-2) + 2-benzyl-3-hydroxy-2,3-dihydro-isoindol-1-one (17448-14-5) → 2-benzyl-3-(2-oxo-2-(pyrazin-2-yl)ethyl)isoindolin-1-one

Conditions	Yield
With Sn(4+)*4C2F6NO4S2(1-)*8C2H6OS In toluene at 110℃; for 24h; Inert atmosphere; Sealed tube;	94%

acetylpyrazine (22047-25-2) + 4-bromophenylhydrazine hydrochloride (622-88-8) → 2-acetylpyrazine 4-bromophenylhydrazone

Conditions	Yield
With sodium acetate In ethanol; chloroform for 12h; Ambient temperature;	93.5%

acetylpyrazine (22047-25-2) + 1,3-benzothiazol-2-ylhydrazine (615-21-4) → N-Benzothiazol-2-yl-N'-[1-pyrazin-2-yl-eth-(E)-ylidene]-hydrazine

Conditions	Yield
With acetic acid In methanol at 80℃;	93%

acetylpyrazine (22047-25-2) + picolinic acid hydrazide (1452-63-7) → N′-(1-(pyrazin-2-yl)ethylidene)picolinohydrazide

Conditions	Yield
With formic acid In ethanol for 5h; Reflux;	93%
In ethanol

acetylpyrazine (22047-25-2) → C6H8N2O

Conditions	Yield
Stage #1: acetylpyrazine With trimethylaluminum; 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane; 3,3'-bis-(3,5-bis-trifluoromethyl-phenyl)-[1,1']binaphthalenyl-2,2'-diol In toluene at 20℃; for 2h; Glovebox; Inert atmosphere; Stage #2: With methanol for 0.5h; enantioselective reaction;	93%

pent-4-en-2-ynyl-carbamic acid tert-butyl ester + acetylpyrazine (22047-25-2) → [2-(1-hydroxy-1-pyrazin-2-yl-ethyl)-penta-2,4-dienyl]-carbamic acid tert-butyl ester

Conditions	Yield
With (R)-xylyl-WALPHOS; triphenylacetic acid; hydrogen; bis(cycloocta-1,5-diene)rhodium(I) trifluoromethanesulfonate In 1,2-dichloro-ethane at 40℃; under 760 Torr;	92%

acetylpyrazine (22047-25-2) + C9H6F3NO2 → (S)-4,4,4-trifluoro-3-(nitromethyl)-3-phenyl-1-(pyrazin-2-yl)butan-1-one

Conditions	Yield
Stage #1: acetylpyrazine With bis(acetylacetonate)nickel(II); (S,S)-2,2'-isopropylidenebis(4-phenyl-2-oxazoline) In isopropyl alcohol at 0℃; for 0.5h; Michael Addition; Schlenk technique; Inert atmosphere; Stage #2: C9H6F3NO2 In isopropyl alcohol at 0℃; for 96h; Michael Addition; Schlenk technique; Inert atmosphere; enantioselective reaction;	92%

acetylpyrazine (22047-25-2) + C18H12ClF3N2O4S → (S)-3-(5-chloro-1-tosyl-1H-indol-3-yl)-4,4,4-trifluoro-3-(nitromethyl)-1-(pyrazin-2-yl)butan-1-one

Conditions	Yield
With C28H29N3O; cobalt(II) aceylacetonate In tert-butyl methyl ether at 20℃; Michael Addition; Schlenk technique; Inert atmosphere; enantioselective reaction;	92%

acetylpyrazine (22047-25-2) + 5-Iodoisophthalic dihydrazide (193614-92-5) → C20H17IN8O2

Conditions	Yield
With acetic acid In ethanol Reflux;	92%

acetylpyrazine (22047-25-2) + N,N-dimethyl-formamide dimethyl acetal (4637-24-5) → 3-(N,N-dimethylamino)-1-(pyrazin-2-yl)prop-2-en-1-one (866000-17-1)

Conditions	Yield
With guanidineacetic acid at 100℃; for 1h;	91%
With L-proline In neat (no solvent) at 80℃; for 1.5h;	90%
With triethylamine at 110℃; for 16h;	81%

acetylpyrazine (22047-25-2) + trans-1-(4-fluorophenyl)-2-nitro-ethene (706-08-1, 5153-69-5) → (R)-3-(4-fluorophenyl)-4-nitro-1-(pyrazin-2-yl)butan-1-one (1433955-80-6)

Conditions	Yield
With nickel(II) acetate tetrahydrate; (4R,4'R,5S,5'S)-2,2'-(propane-2,2-diyl)bis(4,5-diphenyl-4,5-dihydrooxazole) In isopropyl alcohol at 20℃; for 3h; Michael Addition; Inert atmosphere; enantioselective reaction;	91%

2-Aminonicotinaldehyde (7521-41-7) + acetylpyrazine (22047-25-2) → 2-(pyrazin-2-yl)-1,8-naphthyridine (1338090-17-7)

Conditions	Yield
With potassium hydroxide In methanol; water at 60℃;	91%
With potassium hydroxide In methanol at 60℃; Inert atmosphere; Schlenk technique; Reflux;	85%

acetylpyrazine (22047-25-2) + 2,5-dihydroxybenzohydrazide (15791-90-9) → N1-(2,5-dihydroxybenzoyl)-N2-[1-(2-pyrazinyl)ethylidene]hydrazine

Conditions	Yield
With acetic acid In ethanol for 1h; Reflux;	91%

acetylpyrazine (22047-25-2) + 3,4-dimethoxy-benzaldehyde (120-14-9) + malononitrile (109-77-3) → 2-amino-4-(3,4-dimethoxyphenyl)-6-(pyrazin-2-yl)nicotinonitrile

Conditions	Yield
With ammonium acetate In ethanol Reflux;	91%

acetylpyrazine (22047-25-2) + 5-methoxy isophthaloyl hydrazide (23341-07-3) → C21H20N8O3

Conditions	Yield
With acetic acid In ethanol Reflux;	91%

acetylpyrazine (22047-25-2) + N,N-dimethyl-formamide dimethyl acetal (4637-24-5) → 3-dimethylamino-1-(3-pyrazinyl)-2-propene-1-one (111781-53-4)

Conditions	Yield
In 5,5-dimethyl-1,3-cyclohexadiene at 140℃; for 20h; Inert atmosphere; Schlenk technique;	90.2%
In xylene Heating;	73%
In methanol for 10h; Reflux;	38%
for 19h; Heating / reflux;
Reflux;

acetylpyrazine (22047-25-2) + C10H5F6NO2 → (S)-4,4,4-trifluoro-3-(4-(trifluoromethyl)phenyl)-3-(nitromethyl)-1-(pyrazin-2-yl)butan-1-one

Conditions	Yield
Stage #1: acetylpyrazine With bis(acetylacetonate)nickel(II); (S,S)-2,2'-isopropylidenebis(4-phenyl-2-oxazoline) In isopropyl alcohol at 0℃; for 0.5h; Michael Addition; Schlenk technique; Inert atmosphere; Stage #2: C10H5F6NO2 In isopropyl alcohol at 0℃; Michael Addition; Schlenk technique; Inert atmosphere; enantioselective reaction;	90%

pyridine (110-86-1) + acetylpyrazine (22047-25-2) → N-{1-pyrazinyl-1-oxo-2-ethyl}pyridinium iodide

Conditions	Yield
With iodine at 110℃; for 3h;	88%
With iodine for 1h; Reflux;	82%
With iodine at 90℃; for 1.5h;	48%

acetylpyrazine (22047-25-2) + benzil dihydrazone (4702-78-7) → N',N'-bis[1-(pyrazine-2-yl)ethylidene]benzil dihydrazone

Conditions	Yield
for 5h; Heating;	87%

Upstream product

• 127-17-3 Pyruvic acid 
• 8032-32-4 PETROLEUM ETHER 
• 290-37-9 Pyrazine 
• 76-05-1 Trifluoroacetic acid 
• 60-29-7 Diethyl ether 
• 141-78-6 Ethyl acetate 
• 7727-54-0 Ammonium persulfate 

Downstream Products

• 22047-26-3 Ethanone, 1-(6-methylpyrazinyl)- 
• 22047-27-4 Ethanone, 1-(5-methylpyrazinyl)- 
• 22047-29-6 butanedioic acid, bis[2-[(1-oxooctadecyl)oxy]-1-[[(1-oxooctadecyl)oxy]methyl]ethyl] ester 
• 220473-94-9 1-Butanethiol, 4-[4-[(1E)-phenylazo]phenoxy]- (9CI) 
• 22047-43-4 peroxymonosulfate 
• 22047-49-0 2-ETHYLHEXYL STEARATE 
• 220476-15-3 1-CYANOMETHYLIMIDAZOLE HYDROCHLORIDE 
• 220476-38-0 2,4,6-tris(hexyloxy)benzenediazoniuM-5-benzoyl-4-hydroxy-2-Methoxybenzenesulfonate (ON-5) 
• 2204-76-4 4-nitrophenyl (3,4-dichlorophenyl)carbamate 
• 2204-77-5 4-cyanophenyl (3,4-dichlorophenyl)carbamate 
• 22047-86-5 4,6-DIMETHYLNICOTINIC ACID 
• 22047-88-7 2-BENZYLOXYPHENYLACETIC ACID 
• 22048-12-0 3-Ethyl-4-hydroxy-7-methoxyquinolin-2(1H)-one 
• 22048-13-1 3-Ethyl-4,7-dimethoxy-2(1H)-quinolone 

Recommend Products

• 290-37-9  1,4-pyrazine 
• 75-07-0  acetaldehyde 
• 39248-49-2  1,1′-(pyrazine-2,5-diyl)diethanone 
• 127-17-3  2-oxo-propionic acid 
• 74476-22-5  (E)-3-(3-Hydroxy-4-methoxy-phenyl)-1-pyrazin-2-yl-propenone 
• 621-59-0  isovanillin 
• 74476-18-9  (E)-3-(3-Ethoxy-4-hydroxy-phenyl)-1-pyrazin-2-yl-propenone 
• 121-32-4  4-hydroxy-3-ethoxybenzaldehyde 
• 24677-78-9  2,3-dihydroxybenzaldehyde 
• 74476-16-7  (E)-3-(3-Ethoxy-2-hydroxy-phenyl)-1-pyrazin-2-yl-propenone 
• 492-88-6  3-ethoxysalicylaldehyde 
• 74475-98-2  (E)-3-(4-Chloro-phenyl)-1-pyrazin-2-yl-propenone 
• 104-88-1  4-chlorobenzaldehyde 
• 74475-94-8  (2E)-3-(2-chlorophenyl)-1-(pyrazin-2-yl)prop-2-en-1-one