Odor
Sweet, haylike-minty odor, sometimes referred to as "Lactone"-odor. Moderate to poor tenacity. The initial impression is that of a very pungent and sharp odor. The taste - in dilutions lower than 10 ppm -is slightly bitter, almost tarry and not very pleasant.
Chemical Properties
4,5,6,7-Tetrahydro-3,6-dimethylbenzofuran has an odor very similar to that of menthol.
Chemical Properties
CLEAR LIGHT YELLOW LIQUID
Chemical Properties
Menthofuran occurs as the (+) isomer, in peppermint essential oils. It is a colorless liquid with
a minty odor.
Occurrence
Reported found in peppermint oil, corn mint oil, spearmint oil, Scotch spearmint oil, pennyroyal oil and other Mentha oils and buchu oil.
Uses
Menthofuran is a toxin found in vairety of essential oils and is believed to be the compound responsible for the potentially fatal effects of Pennyroyal. Menthofuran is known to produce hepatotoxic intermediates via oxidation process.
Definition
ChEBI: Menthofuran is a monoterpenoid that is 4,5,6,7-tetrahydro-1-benzofuran substituted by methyl groups at positions 3 and 6. It has a role as a nematicide and a plant metabolite. It is a member of 1-benzofurans and a monoterpenoid.
Preparation
(+)-Menthofuran [17957-94-7] is isolated fromMentha oils or is prepared synthetically,
for example, by treatment of (+)-pulegone with fuming sulfuric acid in
acetic anhydride and pyrolysis of the resulting sultone.
Taste threshold values
Taste characteristics at 10 ppm: musty, nutty, coffee, raw and legume
Synthesis Reference(s)
The Journal of Organic Chemistry, 48, p. 2442, 1983
DOI: 10.1021/jo00162a037
Synthesis
By thermal decomposition of the sulfone of 3-hydroxy-3,8(9)-methadiene-9-sulfonic acid; the latter is obtained by sulfonapulegone in acetic anhydride.
