2-acetyl-1-pyrroline (CHEBI:67125)

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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.

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Formula

C6H9NO

Net Charge

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.

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

Registry Number	Type	Source
6321339	Reaxys Registry Number	Reaxys

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