Menthofuran

Menthofuran

Names
IUPAC name 3,6-Dimethyl-4,5,6,7-tetrahydro-1-benzofuran
Identifiers
CAS Number	494-90-6 17957-94-7 (R) 80183-38-6 (S)
3D model (Jmol)	Interactive image
ChEBI	CHEBI:50542
ChemSpider	292309
ECHA InfoCard	100.007.087
PubChem	329983
InChI InChI=1S/C10H14O/c1-7-3-4-9-8(2)6-11-10(9)5-7/h6-7H,3-5H2,1-2H3 Key: YGWKXXYGDYYFJU-UHFFFAOYSA-N InChI=1/C10H14O/c1-7-3-4-9-8(2)6-11-10(9)5-7/h6-7H,3-5H2,1-2H3 Key: YGWKXXYGDYYFJU-UHFFFAOYAW
SMILES o1c2c(c(c1)C)CCC(C2)C
Properties
Chemical formula	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

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.

Menthofuran synthase converts pulegone to menthofuran

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

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.