Menthofuran is an organic compound found in a variety of essential oils including that of Pennyroyal. It is highly toxic and believed to be the primary toxin in Pennyroyal responsible for its potentially fatal effects. After ingestion of menthofuran, it is metabolically activated to chemically reactive intermediates that are hepatotoxic.
3D model (JSmol)
|Molar mass||150.22 g·mol−1|
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Menthofuran was synthesized from 5-methylcyclohexane-1,3-dione and allenyldimethylsulfonium bromide in two steps via a novel furannulation strategy consisting of enolate addition and rearrangement.
- Anderson, IB; Mullen, WH; Meeker, JE; Oishi, S; Nelson, SD; Blanc, PD (1996). "Pennyroyal toxicity: Measurement of toxic metabolite levels in two cases and review of the literature". Annals of Internal Medicine. 124 (8): 726–34. doi:10.7326/0003-4819-124-8-199604150-00004. PMID 8633832. Missing
|last4=in Authors list (help)
- Thomassen, D; Knebel, N; Slattery, JT; McClanahan, RH; Nelson, SD (1992). "Reactive intermediates in the oxidation of menthofuran by cytochromes P-450". Chemical research in toxicology. 5 (1): 123–30. doi:10.1021/tx00025a021. PMID 1581528.
- Mariko Aso; Sakamoto, Mizue; Urakawa, Narumi; Kanematsu, Ken (1990). "Furannulation strategy. An efficient synthesis of fused 3-methylfurans". Heterocycles. 31 (6): 1003–6. doi:10.3987/com-90-5392.