Menthofuran

Menthofuran

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Names
IUPAC name 3,6-Dimethyl-4,5,6,7-tetrahydro-1-benzofuran
Identifiers
CAS Number	494-90-6 Y 17957-94-7 (R) Y 80183-38-6 (S) Y
ChEBI	CHEBI:50542
ChemSpider	292309
Jmol 3D model	Interactive image
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
Vapor pressure	{{{value}}}
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. After ingestion of menthofuran, it is metabolically activated to chemically reactive intermediates that are hepatotoxic.

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

File:(+)-menthofuran synthase reaction.PNG

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.