Menthofuran

Chemical compound From Wikipedia, the free encyclopedia

Menthofuran is an organic compound found in a variety of essential oils including that of pennyroyal (Mentha pulegium). 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]

Quick facts Names, Identifiers ...
Menthofuran
Names
IUPAC name
3,6-Dimethyl-4,5,6,7-tetrahydro-1-benzofuran
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.007.087 Edit this at Wikidata
UNII
  • 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
  • o1c2c(c(c1)C)CCC(C2)C
Properties
C10H14O
Molar mass 150.221 g·mol−1
Boiling point 208
Hazards
Flash point 86
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Biosynthesis

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

Menthofuran synthase converts pulegone to menthofuran

Chemistry

Synthesis

Menthofuran can be synthesized from 5-methylcyclohexane-1,3-dione and allenyldimethylsulfonium bromide in two steps via a furannulation strategy consisting of enolate addition and rearrangement.[3]

Pharmacology

Menthofuran is a metabolite of pulegone. Both in vitro and in vivo studies have found the pulegone metabolite menthofuran to be an inhibitor of CYP2A6.[4][5][6][7]

Menthofuran may deplete glutathione levels, leaving hepatocytes vulnerable to free radical damage.[5]

References

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