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Names | |
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IUPAC name 3,6-Dimethyl-4,5,6,7-tetrahydro-1-benzofuran | |
Identifiers | |
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3D model (JSmol) | |
ChEBI | |
ChemSpider | |
ECHA InfoCard | 100.007.087 |
PubChem CID | |
UNII |
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CompTox Dashboard (EPA) | |
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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). |
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]
Menthofuran is produced biosynthetically from pulegone by the enzyme menthofuran synthase.
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]
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]