Identification of Alkyl Substituted 2H-Furo[2,3-c]pyran-2-ones as Germination Stimulants Present in Smoke

The butenolide, 3-methyl-2H-furo[2,3-c]pyran-2-one (1), is a major compound in smoke responsiblefor promoting the seed germination of a wide range of plant species. We now report the structure offive alkyl substituted variants of 1 that are also present in smoke. The concentrations of theseanalogues, as well as that of 1, in a typical smoke-water solution have been determined using highperformanceliquid chromatography (HPLC) purification followed by gas chromatography-massspectrometry (GC-MS) analysis. The analogue, 3,5-dimethyl-2H-furo[2,3-c]pyran-2-one (3), wasidentified at levels that indicate that it is a contributor to the overall germination-promoting activityof crude smoke extracts.