494-90-6

Basic information

• Product Name: MENTHOFURAN
• Synonyms: 3,6-Dimethyl-4,5,6,7-tetrahydro-1-benzofuran;3,9-Epoxy-p-mentha-3,8-diene;4,5,6,7-tetrahydro-3,6-dimethyl-benzofura;Benzofuran, 4,5,6,7-tetrahydro-3,6-dimethyl-;Menthofurane;p-Mentha-3,8-diene, 3,9-epoxy-;FEMA 3235;MENTHOFURAN
• CAS NO: 494-90-6
• Molecular Formula: C₁₀H₁₄O
• Molecular Weight: 150.22
• EINECS: 207-795-5
• Mol File: 494-90-6.mol
• Article Data: 13

Chemical Properties

• Melting Point: 86°C
• Boiling Point: 80-82 °C13 mm Hg(lit.)
• Flash Point: 168 °F
• Appearance: Clear light yellow/Liquid
• Density: 0.97 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.275mmHg at 25°C
• Refractive Index: n20/D 1.485(lit.)
• Storage Temp.: Room Temperature
• Solubility: Chloroform (Slightly), Ethyl Acetate (Slightly), Methanol (Slightly)
• Stability: Not stable in solution
• CAS DataBase Reference: MENTHOFURAN(CAS DataBase Reference)
• NIST Chemistry Reference: MENTHOFURAN(494-90-6)
• EPA Substance Registry System: MENTHOFURAN(494-90-6)

Safety Data

• Safety Statements: 24/25
• WGK Germany: 2
• RTECS: DF7995750
• TSCA: Yes
• Hazardous Substances Data: 494-90-6(Hazardous Substances Data)

Usage

Description

MENTHOFURAN, also known as 4,5,6,7-Tetrahydro-3,6-dimethylbenzofuran, is a toxin found in a variety of essential oils, including peppermint, corn mint, spearmint, Scotch spearmint, pennyroyal, and buchu oils. It is a colorless liquid with a minty odor and is believed to be the compound responsible for the potentially fatal effects of Pennyroyal. MENTHOFURAN is known to produce hepatotoxic intermediates via an oxidation process. It has a taste threshold value of 10 ppm, with taste characteristics described as musty, nutty, coffee, raw, and legume.

Uses

Used in Chemical Industry:
MENTHOFURAN is used as a chemical compound for its unique properties, such as its minty odor and hepatotoxic effects, which can be utilized in the development of various chemical products and research applications.
Used in Flavor and Fragrance Industry:
MENTHOFURAN is used as a flavoring agent for its musty, nutty, coffee, raw, and legume taste characteristics, adding a distinct flavor profile to various food and beverage products.
Used in Essential Oils Industry:
MENTHOFURAN is used as a component in essential oils, contributing to their unique aroma and properties. It is found in peppermint oil, corn mint oil, spearmint oil, Scotch spearmint oil, pennyroyal oil, and other Mentha oils, as well as buchu oil.
Used in Research and Development:
MENTHOFURAN is used as a research compound for studying its hepatotoxic effects and potential applications in the development of new drugs or treatments for various health conditions.

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.

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.

InChI:InChI=1/C10H14O/c1-7-3-4-9-8(2)6-11-10(9)5-7/h6-7H,3-5H2,1-2H3

Upstream product

• 13341-72-5 menthalactone 
• 89-82-7 pulegone 
• 63549-11-1 4,7-dimethyl-5,6,7,8-tetrahydro-benzo[e][1,2]oxathiine 2,2-dioxide 
• 27579-55-1 2-bromo-4-methylcyclohexanone 
• 24720-64-7 2-(triphenylphosphoranylidene)propionaldehyde 
• 29606-79-9 isopulegone 
• 131475-43-9 6',7'-Dihydro-3',6'-dimethylspiro<1,3-dithiane-2,4'(5'H)benzofuran> 
• 13341-72-5 (+/-)-3,6-dimethyl-5,6,7,7a-tetrahydrobenzofuran-2(4H)-one 
• 84474-76-0 7-Methyl-2-methylen-1,4-dioxaspiro<4,5>decan 
• 134671-00-4 6-Methyl-1-methylene-spiro[2.5]octan-4-one 
• 77878-28-5 (2S,5R)-5-Methyl-2-(2-methyl-oxiranyl)-cyclohexanone 
• 107149-16-6 3,6-dimethyl-4,5-dihydrobenzofuran 
• 73567-99-4 4-methyl-2,3-dimethylene-2,3-dihydrofuran 
• 292638-85-8 acrylic acid methyl ester 

Downstream Products

• 490-46-0 (2R,3R)-2-(3,4-dihydroxyphenyl)-3,4-dihydro-1[2H]-benzopyran-3,5,7-triol 
• 88082-60-4 cinnamtannin B-1 
• 94673-31-1 3,6-dimethyl-1-phenyl-4,5,6,7-tetrahydro-indole 

Relevant articles and documents

In Vivo Studies on the Metabolism of the Monoterpene Pulegone in Humans Using the Metabolism of Ingestion-Correlated Amounts (MICA) Approach: Explanation for the Toxicity Differences between (S)-(-)- and (R)-(+)-Pulegone

The major in vivo metabolites of (S)-(-)-pulegone in humans using a metabolism of ingestion-correlated amounts (MICA) experiment were newly identified as 2-(2-hydroxy-1-methylethyl)-5-methylcyclohexanone (8-hydroxymenthone, M1), 3-hydroxy-3-methyl-6-(1-methylethyl)cyclohexanone (1-hydroxymenthone, M2), 3-methyl-6-(1-methylethyl)cyclohexanol (menthol), and E-2-(2-hydroxy-1-methylethylidene)-5-methylcyclohexanone (10-hydroxypulegone, M4) on the basis of mass spectrometric analysis in combination with syntheses and NMR experiments. Minor metabolites were be identified as 3-methyl-6-(1-methylethyl)-2-cyclohexenone (piperitone, M5) and α,α,4-trimethyl-1-cyclohexene-1-methanol (3-p-menthen-8-ol, M6). Menthofuran was not a major metabolite of pulegone and is most probably an artifact formed during workup from known (M4) and/or unknown precursors. The differences in toxicity between (S)-(-)- and (R)-(+)-pulegone can be explained by the strongly diminished ability for enzymatic reduction of the double bond in (R)-(+)-pulegone. This might lead to further oxidative metabolism of 10-hydroxypulegone (M4) and the formation of further currently undetected metabolites that might account for the observed hepatotoxic and pneumotoxic activity in humans.

A Novel Synthesis of Methylenecyclopropane Spiro-Linked with Cycloalkanes via a Cyclization of Allylic Epoxides and Its Application to a Synthesis of Fused 3-Methylfurans

Ring closure of allylic epoxides derived from 1-chloroalkyl phenyl sulfoxides and cyclic ketones with lithium diisopropylamide (LDA) in 3-Exo-Tet mode gave spiro-linked methylenecyclopropanes having a hydroxyl group in good yields.Oxidation of these compounds gave ketones, which were then treated with p-toluenesulfonic acid in 1,4-dioxane or DMSO at 100 deg C to give fused 3-methylfurans in good overall yields.This procedure was applied to a synthesis of menthofuran from 4-methylcyclohexanone.

TOTAL SYNTHESIS OF VARIOUS ELEMANOLIDES

Starting with a suitable substituted divinyl cyclohexanone, eleven naturally occurring 12.8-elemanolides bearing exo-methylene or methyl groups at C-11 and differing in substitution as well as in relative configuration, have been synthesized in racemic form.An approach to elemanolides with additional oxygen functionalities is principally possible by modification of the basic concept.Methods for the oxidative generation of terpenoid exo-methylene lactone and furan units are exemplified by synthesis of menthofuran and the p-menthenolides from isopulegols.