6-acetyl-1,2,3,4-tetrahydropyridine
1-(1,2,3,4-tetrahydropyridin-6-yl)ethanone
 
Notes:
Responsible for mousy taint in wines. Constit. of wheat, popcorn and bread aroma 6-Acetyl-2,3,4,5-tetrahydropyridine is a substituted tetrahydropyridine and a cyclic imine as well as a ketone. The compound exists in a chemical equilibrium with its tautomer 6-acetyl-1,2,3,4-tetrahydropyridine that differs only by the position of the double bond in the tetrahydropyridine ring:; 6-Acetyl-2,3,4,5-tetrahydropyridine, with the IUPAC name 1-(3,4,5,6-tetrahydropyridin-2-yl)ethanone, is an aroma compound and flavor that gives baked goods such as white bread, pop corn, or tortillas their typical smell, together with its structural homolog 2-acetyl-1-pyrroline. Flavouring compound [Flavornet]
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CAS Number: 25343-57-1Picture of molecule3D/inchi
XlogP3-AA: 1.00 (est)
Molecular Weight: 125.17087000
Formula: C7 H11 N O
NMR Predictor: Predict (works with chrome or firefox)
Category: flavoring agents
 
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Physical Properties:
Assay: 95.00 to 100.00 % 
Food Chemicals Codex Listed: No
Boiling Point: 269.00 to  270.00 °C. @ 760.00 mm Hg (est)
Vapor Pressure: 0.007000 mmHg @ 25.00 °C. (est)
Flash Point: 265.00 °F. TCC ( 129.20 °C. ) (est)
logP (o/w): -0.246 (est)
Soluble in:
 alcohol
Insoluble in:
 water
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Organoleptic Properties:
 
Odor Type: caramellic
 
 caramellic  
Odor Description:
caramellic
 
 
Flavor Type: creamy
 
 creamy  bready  bread crust  
Taste Description:
creamy bready
 
Odor and/or flavor descriptions from others (if found).
 
 
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Cosmetic Information:
None found
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Suppliers:
 None found
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Safety Information:
 
Hazards identification
 
Classification of the substance or mixture
GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)
None found.
GHS Label elements, including precautionary statements
 
Pictogram
 
Hazard statement(s)
None found.
Precautionary statement(s)
None found.
Oral/Parenteral Toxicity:
Not determined
Dermal Toxicity:
Not determined
Inhalation Toxicity:
Not determined
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Safety in Use Information:
Category: flavoring agents
Recommendation for 6-acetyl-1,2,3,4-tetrahydropyridine usage levels up to:
 not for fragrance use.
 
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Safety References:
EPI System: View
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EPA ACToR: Toxicology Data
EPA Substance Registry Services (SRS): Registry
Laboratory Chemical Safety Summary : 15775373
National Institute of Allergy and Infectious Diseases: Data
 1-(1,2,3,4-tetrahydropyridin-6-yl)ethanone
Chemidplus: 0025343571
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References:
 1-(1,2,3,4-tetrahydropyridin-6-yl)ethanone
NIST Chemistry WebBook: Search Inchi
Pubchem (cid): 15775373
Pubchem (sid): 135347891
Flavornet: 25343-57-1
Pherobase: View
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Other Information:
(IUPAC): Atomic Weights of the Elements 2011 (pdf)
Videos: The Periodic Table of Videos
tgsc: Atomic Weights use for this web site
(IUPAC): Periodic Table of the Elements
CHEBI: View
HMDB (The Human Metabolome Database): HMDB30345
FooDB: FDB029659
VCF-Online: VCF Volatile Compounds in Food
ChemSpider: View
Wikipedia: View
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Potential Blenders and core components note
 
For Odor
No odor group found for these
(R)-strawberry furanoneFL/FR
(S)-strawberry furanoneFL/FR
acidic
 cyclohexyl acetic acidFL/FR
balsamic
2-acetyl furanFL/FR
isoamyl pyruvateFL/FR
bready
 coffee furanoneFL/FR
 furfuralFL/FR
 rum etherFL/FR
buttery
 acetoinFL/FR
 acetyl butyrylFL/FR
 acetyl propionylFL/FR
3,4-hexane dioneFL/FR
isoamyl levulinateFL/FR
2-oxobutyric acidFL/FR
 caramel furanone solutionFL/FR
 caramel pentadioneFL/FR
 cycloteneFL/FR
 cyclotene hydrateFL/FR
alpha,alpha-dimethyl anisyl acetoneFL/FR
 ethyl 2-hydroxy-2-methyl butyrateFL/FR
 ethyl cyclopentenoloneFL/FR
 ethyl furaneolFL/FR
 ethyl maltolFL/FR
5-ethyl-2,3,4,5-tetramethyl-2-cyclohexen-1-oneFL/FR
3-ethyl-4-methyl cycloteneFL/FR
 fenugreek absoluteFL/FR
 fenugreek oleoresinFL/FR
 immortelle absoluteFL/FR
 levulinic acidFL/FR
 maltolFL/FR
 maltyl isobutyrateFL/FR
 maltyl propionateFL/FR
 maple furanoneFL/FR
 menthone lactoneFL/FR
5-methyl furfuralFL/FR
isopropenyl pyrazineFL/FR
 rosefuranFL/FR
 shoyu furanoneFL/FR
 strawberry furanoneFL/FR
 strawberry furanone acetateFL/FR
 strawberry furanone solutionFL/FR
 toffee furanoneFL/FR
2,6-dimethyl pyrazineFL/FR
2-methyl butyraldehydeFL/FR
coconut
gamma-heptalactoneFL/FR
creamy
gamma-butyrolactoneFL/FR
ethereal
 ethyl 4-pentenoateFL/FR
 ethyl pyruvateFL/FR
fermented
 amyl alcoholFL/FR
 butyl laevo-lactateFL/FR
 ethyl (E)-2-crotonateFL/FR
 ethyl crotonateFL/FR
 valeraldehydeFL/FR
floral
 phenethyl alcoholFL/FR
fruity
isobutyl 2-butenoateFL/FR
 cherry propanolFL/FR
 ethyl lactateFL/FR
(E)-ethyl tiglateFL/FR
 hexyl (E)-tiglateFL/FR
 maltyl acetateFL/FR
 methyl nonane dioneFL/FR
2-pentyl furanFL/FR
 tetrahydrofurfuryl acetateFL/FR
green
isoamyl 3-(2-furan) propionateFL/FR
herbal
 butyl levulinateFL/FR
white cognac oilFL/FR
meaty
 sulfurolFL/FR
 sulfuryl acetateFL/FR
minty
dextro-carvoneFL/FR
musty
2-acetyl pyrroleFL/FR
3-acetyl-2,5-dimethyl furanFL/FR
nutty
2-acetyl-3,5(or 6)-dimethyl pyrazineFL/FR
2-acetyl-5-methyl furanFL/FR
3,5-cocoa pyrazineFL/FR
1,2-cyclohexane dioneFL/FR
2,3-dimethyl pyrazineFL/FR
 filbert pyrazineFL/FR
2,6-lutidineFL/FR
2-methyl thio-3,5 or 6-methyl pyrazineFL/FR
 nutty cyclohexenoneFL/FR
phenolic
4-methyl-2,6-dimethoxyphenolFL/FR
popcorn
2-acetyl pyrazineFL/FR
2-acetyl pyridineFL/FR
spicy
 caraway seed oleoresinFL/FR
(E)-propyl 2-furan acrylateFL/FR
 spicy acetoacetateFL/FR
(E)-tiglic acidFL/FR
sweet
 vanilla oleoresin baliFL/FR
vanilla
 ethyl vanillinFL/FR
 vanilla oleoresin bourbonFL/FR
 vanillinFL/FR
 vanillyl isobutyrateFL/FR
 tetrahydrofurfuryl alcoholFL/FR
 
For Flavor
 
No flavor group found for these
4-acetyl-2,5-dimethyl-3(2H)-furanoneFL
2-acetyl-3,4,5,6-tetrahydropyridineFL
(E)-aconitic acidFL
 allyl 2-furoateFL
isoamyl levulinateFL/FR
isoamyl pyruvateFL/FR
 benzyl disulfideFL
1,2-cyclohexane dioneFL/FR
2,5-diethyl tetrahydrofuranFL
alpha,alpha-dimethyl anisyl acetoneFL/FR
 ethyl 2-hydroxy-2-methyl butyrateFL/FR
 ethyl 4-pentenoateFL/FR
5-ethyl-2,3,4,5-tetramethyl-2-cyclohexen-1-oneFL/FR
3-ethyl-4-methyl cycloteneFL/FR
 furfuryl acetoneFL
 menthone lactoneFL/FR
 methyl nonane dioneFL/FR
 rosefuranFL/FR
(R)-strawberry furanoneFL/FR
(S)-strawberry furanoneFL/FR
 strawberry furanone ethyl etherFL
isoamyl 3-(2-furan) propionateFL/FR
acetic
 formic acidFL
acidic
 levulinic acidFL/FR
dextro,laevo-tartaric acidFL
berry
 maltyl acetateFL/FR
bready
 bread crust distillateFL
 mango furanoneFL
2-propionyl thiazoleFL
brown
2-oxobutyric acidFL/FR
 fenugreek oleoresinFL/FR
 furfuralFL/FR
5-methyl furfuralFL/FR
 tetrahydrofurfuryl acetateFL/FR
(E)-tiglic acidFL/FR
burnt
 furfuryl alcoholFL
isopropenyl pyrazineFL/FR
 rum etherFL/FR
buttery
 butyl laevo-lactateFL/FR
 diacetylFL
3,4-hexane dioneFL/FR
caramellic
 caramel furanoneFL
 caramel furanone solutionFL/FR
 caramel pentadioneFL/FR
 cycloteneFL/FR
 cyclotene hydrateFL/FR
 ethyl furaneolFL/FR
 ethyl maltolFL/FR
5-ethyl-3,4,5,6-tetramethyl cyclohexen-2-oneFL
 fenugreek absoluteFL/FR
 maltolFL/FR
 maltyl propionateFL/FR
 maple furanoneFL/FR
3-methyl butyl 2-furyl butyrateFL
 pyruvaldehydeFL
 shoyu furanoneFL/FR
 strawberry furanoneFL/FR
 strawberry furanone acetateFL/FR
 strawberry furanone solutionFL/FR
 toffee furanoneFL/FR
cocoa
 butyraldehydeFL
coffee
 coffee distillatesFL
 diisoamyl thiomalateFL
2-thiophene thiolFL
corn
2-acetyl pyridineFL/FR
2-acetyl-2-thiazolineFL
creamy
 acetoinFL/FR
 acetyl butyrylFL/FR
2-propanoyl thiopheneFL
fatty
 diacetyl trimerFL
(E,E)-2,4-undecadienalFL
2,4-undecadienalFL
floral
 phenethyl alcoholFL/FR
 rosa canina seed extractFL
fruity
 cherry propanolFL/FR
 ethyl lactateFL/FR
(E)-ethyl tiglateFL/FR
 furfuryl valerateFL
2-pentanoyl furanFL
banana cream pie flavorFL
(E)-propyl 2-furan acrylateFL/FR
fusel
 amyl alcoholFL/FR
white cognac oilFL/FR
2-methyl butyraldehydeFL/FR
green
isobutyl 2-butenoateFL/FR
 hexyl (E)-tiglateFL/FR
 immortelle absoluteFL/FR
2-pentyl furanFL/FR
herbal
 butyl levulinateFL/FR
5-hydroxymethyl furfuralFL
jammy
 ethyl cyclopentenoloneFL/FR
 maltyl isobutyrateFL/FR
lactonic
gamma-heptalactoneFL/FR
malty
 hordeum vulgare extract (cereal grass)FL
 malt distillatesFL
meaty
 sulfurolFL/FR
 sulfuryl acetateFL/FR
metallic
2,5-dihydroxy-1,4-dithianeFL
milky
gamma-butyrolactoneFL/FR
minty
dextro-carvoneFL/FR
molasses
 molasses blackstrapFL
musty
 ethyl (E)-2-crotonateFL/FR
nutty
2-acetyl furanFL/FR
2-acetyl pyrroleFL/FR
3-acetyl-2,5-dimethyl furanFL/FR
2-acetyl-3,5(or 6)-dimethyl pyrazineFL/FR
2-acetyl-5-methyl furanFL/FR
 aconitic acidFL
3,5-cocoa pyrazineFL/FR
 coffee furanoneFL/FR
2,6-dimethyl pyrazineFL/FR
2,3-dimethyl pyrazineFL/FR
 filbert pyrazineFL/FR
2,6-lutidineFL/FR
2-methyl thio-3,5 or 6-methyl pyrazineFL/FR
 nutty cyclohexenoneFL/FR
 peanut oxazoleFL
 tetrahydrofurfuryl alcoholFL/FR
phenolic
4-methyl-2,6-dimethoxyphenolFL/FR
roasted
 acer spicatum bark extractFL
2-acetyl pyrazineFL/FR
rummy
 ethyl crotonateFL/FR
 ethyl pyruvateFL/FR
smoky
dextro-xyloseFL
spicy
 caraway seed oleoresinFL/FR
 spicy acetoacetateFL/FR
sweet
 acetone alcoholFL
 caramel dioneFL
 cyclohexyl acetic acidFL/FR
 honey distillatesFL
dextro-sorbitolFL
 sugar distillatesFL
 vanilla oleoresin baliFL/FR
toasted
 acetyl propionylFL/FR
vanilla
 ethyl vanillinFL/FR
 vanilla oleoresin bourbonFL/FR
 vanillinFL/FR
 vanillyl isobutyrateFL/FR
waxy
 furfuryl octanoateFL
 octyl 2-furoateFL
winey
 valeraldehydeFL/FR
yeasty
 faex extractsFL
 
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Potential Uses:
 breadFL
 cheese cheddar cheeseFL
 lycheeFR
 popcornFR
 riceFL
 tea green teaFR
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Occurrence (nature, food, other): note
 bread rye bread crust
Search  PMC Picture
 bread wheat bread crust
Search  PMC Picture
 popcorn
Search  PMC Picture
 wine
Search  Picture
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Synonyms:
2-acetyl-1,4,5,6-tetrahydropyridine
 ethanone, 1-(1,4,5,6-tetrahydro-2-pyridinyl)-
 pyridine, 2-acetyl-1,4,5,6-tetrahydro-
1-(1,4,5,6-tetrahydro-2-pyridinyl) ethanone
1-(1,4,5,6-tetrahydropyridin-2-yl)ethanone
1-(1,2,3,4-tetrahydropyridin-6-yl)ethanone
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Articles:
PubMed: New short and general synthesis of three key Maillard flavour compounds: 2-Acetyl-1-pyrroline, 6-acetyl-1,2,3,4-tetrahydropyridine and 5-acetyl-2,3-dihydro-4H-1,4-thiazine.
PubMed: Stabilization of the potent odorant 2-acetyl-1-pyrroline and structural analogues by complexation with zinc halides.
PubMed: Chemistry of 2-acetyl-1-pyrroline, 6-acetyl-1,2,3,4-tetrahydropyridine, 2-acetyl-2-thiazoline, and 5-acetyl-2,3-dihydro-4H-thiazine: extraordinary Maillard flavor compounds.
PubMed: An expeditious, high-yielding construction of the food aroma compounds 6-acetyl-1,2,3,4-tetrahydropyridine and 2-acetyl-1-pyrroline.
PubMed: Elucidation of tautomer structures of 2-acetyltetrahydropyridine using gas chromatography/mass spectrometry and gas chromatography/infrared spectroscopy.
PubMed: Detailed investigation of the production of the bread flavor component 6-acetyl-1,2,3,4-tetrahydropyridine in proline/1,3-dihydroxyacetone model systems.
PubMed: Formation of odorants in Maillard model systems based on l-proline as affected by pH.
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