Open main menu

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]

Menthofuran
Menthofuran.svg
Names
IUPAC name
3,6-Dimethyl-4,5,6,7-tetrahydro-1-benzofuran
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.007.087
Properties
C10H14O
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).
Infobox references

Methofuran is produced biosynthetically from pulegone by the enzyme menthofuran synthase.

Menthofuran synthase converts pulegone to menthofuran

SynthesisEdit

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]

ReferencesEdit

  1. ^ 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)
  2. ^ 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.
  3. ^ 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.