Menthofuran
Names | |
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IUPAC name
3,6-Dimethyl-4,5,6,7-tetrahydro-1-benzofuran | |
Identifiers | |
494-90-6 17957-94-7 (R) 80183-38-6 (S) | |
ChEBI | CHEBI:50542 |
ChemSpider | 292309 |
| |
Jmol-3D images | Image |
PubChem | 329983 |
| |
Properties | |
Molecular formula |
C10H14O |
Molar mass | 150.22 g·mol−1 |
Except where noted otherwise, data is given for materials in their standard state (at 25 °C (77 °F), 100 kPa) | |
Infobox references | |
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.[1] After ingestion of menthofuran, it is metabolically activated to chemically reactive intermediates that are hepatotoxic.[2]
Methofuran is produced biosynthetically from pulegone by the enzyme menthofuran synthase.
Synthesis
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.[3]
References
- ↑ 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.