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J Agric Food Chem. 2009 Oct 28;57(20):9475-80. doi: 10.1021/jf9028128.

Identification of alkyl substituted 2H-furo[2,3-c]pyran-2-ones as germination stimulants present in smoke.

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School of Biomedical, Biomolecular and Chemical Sciences, The University of Western Australia, Crawley, WA 6009, Australia.


The butenolide, 3-methyl-2H-furo[2,3-c]pyran-2-one (1), is a major compound in smoke responsible for promoting the seed germination of a wide range of plant species. We now report the structure of five alkyl substituted variants of 1 that are also present in smoke. The concentrations of these analogues, as well as that of 1, in a typical smoke-water solution have been determined using high-performance liquid chromatography (HPLC) purification followed by gas chromatography-mass spectrometry (GC-MS) analysis. The analogue, 3,5-dimethyl-2H-furo[2,3-c]pyran-2-one (3), was identified at levels that indicate that it is a contributor to the overall germination-promoting activity of crude smoke extracts.

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