CHEBI:67125 - 2-acetyl-1-pyrroline

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ChEBI Name 2-acetyl-1-pyrroline
ChEBI ID CHEBI:67125
Definition A pyrroline that is 1-pyrroline in which the hydrogen at position 2 is replaced by an acetyl group. It is an aroma and flavour compound present in jasmine rice and basmati rice. It is responsible for the 'popcorn' aroma in a large variety of cereal and food products. It is one of the key odourants of the crust of bread and considered to be responsible for the cracker-like odour properties. In bread, it is primarily generated during baking but amounts are influenced by ingredient composition and fermentation conditions.
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information ZINC000008214766
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Formula C6H9NO
Net Charge 0
Average Mass 111.14180
Monoisotopic Mass 111.06841
InChI InChI=1S/C6H9NO/c1-5(8)6-3-2-4-7-6/h2-4H2,1H3
InChIKey DQBQWWSFRPLIAX-UHFFFAOYSA-N
SMILES CC(=O)C1=NCCC1
Roles Classification
Chemical Role(s): Maillard reaction product
Any thermal degradation product obtained as a result of a chemical reaction between an amino acid and a reducing sugar (Maillard reaction, a non-enzymatic browning procedure that usually imparts flavour to starch-based food products).
Biological Role(s): metabolite
Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
flavouring agent
A food additive that is used to added improve the taste or odour of a food.
Application(s): flavouring agent
A food additive that is used to added improve the taste or odour of a food.
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ChEBI Ontology
Outgoing 2-acetyl-1-pyrroline (CHEBI:67125) has role flavouring agent (CHEBI:35617)
2-acetyl-1-pyrroline (CHEBI:67125) has role Maillard reaction product (CHEBI:77523)
2-acetyl-1-pyrroline (CHEBI:67125) has role metabolite (CHEBI:25212)
2-acetyl-1-pyrroline (CHEBI:67125) is a acylimine (CHEBI:51516)
2-acetyl-1-pyrroline (CHEBI:67125) is a methyl ketone (CHEBI:51867)
2-acetyl-1-pyrroline (CHEBI:67125) is a pyrroline (CHEBI:23763)
IUPAC Name
1-(3,4-dihydro-2H-pyrrol-5-yl)ethanone
Synonyms Sources
2-acetyl-4,5-dihydro-3H-pyrrole ChEBI
2AP ChEBI
APR ChEBI
Manual Xrefs Databases
2-Acetyl-1-pyrroline Wikipedia
US4522838 Patent
View more database links
Registry Number Type Source
6321339 Reaxys Registry Number Reaxys
Citations Types Sources
12428963 PubMed citation Europe PMC
12517110 PubMed citation Europe PMC
16356012 PubMed citation Europe PMC
16771451 PubMed citation Europe PMC
20497370 PubMed citation Europe PMC
20800726 PubMed citation Europe PMC
22404867 PubMed citation Europe PMC
IND44456134 Agricola citation Europe PMC
Last Modified
26 February 2014
General Comments
2012-08-14 See also Hee Cho and Devin G. Peterson, Chemistry of bread aroma: A review., Food Science and Biotechnology, 19(3), 575—582. DOI: 10.1007/s10068-010-0081-3 http://www.springerlink.com/content/q31x12hwkg771185/
2012-08-14 See also Vanavichit, A., Areekit, S., Plabpla, A. and Yoshihashi, T. Dissecting the biosynthetic pathway and regulatory switches of 2-acetyl-1-pyrroline, the potent aromatic compound in rice. http://www.intlcss.org/files/congress-proceedings/2008-papers/cs2-s5/cs2-s5-o5-apichart-vanavichit.pdf