MENTHOFURAN Chemical Properties

Melting point:

86°C

Boiling point:

80-82 °C13 mm Hg(lit.)

Density 

0.97 g/mL at 25 °C(lit.)

refractive index 

n20/D 1.485(lit.)

FEMA 

3235 | 4,5,6,7-TETRAHYDRO-3,6-DIMETHYLBENZOFURAN

Flash point:

168 °F

storage temp. 

Room Temperature

solubility 

Chloroform (Slightly), Ethyl Acetate (Slightly), Methanol (Slightly)

form 

Liquid

color 

Clear light yellow

Odor

at 1.00 % in dipropylene glycol. pungent musty nutty earthy coffee

Odor Type

musty

optical activity

[α]25/D +90°, c = 10 in methanol

JECFA Number

758

Stability:

Not stable in solution

LogP

4.02

CAS DataBase Reference

494-90-6(CAS DataBase Reference)

EPA Substance Registry System

Benzofuran, 4,5,6,7-tetrahydro-3,6-dimethyl- (494-90-6)

Safety Information

Safety Statements 

24/25

WGK Germany 

2

RTECS 

DF7995750

TSCA 

Yes

HS Code 

29329990

MSDS

• Language:English Provider:ACROS
• Language:English Provider:SigmaAldrich
• Language:English Provider:ALFA

MENTHOFURAN Usage And Synthesis

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

CLEAR LIGHT YELLOW LIQUID

Chemical Properties

Menthofuran occurs as the (+) isomer, in peppermint essential oils. It is a colorless liquid with a minty odor.

Chemical Properties

4,5,6,7-Tetrahydro-3,6-dimethylbenzofuran has an odor very similar to that of menthol.

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.

MENTHOFURAN(494-90-6)Related Product Information

• Geneticin
• Ethanol
• Citric acid
• Salicylic acid
• Furazolidone
• Carbofuran
• FURFURYL ALCOHOL RESIN
• Edible essence
• 2(4H)-Benzofuranone, 5,6-dihydro-3,6-dimethyl-, (6R)-
• MENTHOFURAN
• 3,6,6-TRIMETHYL-4-OXO-4,5,6,7-TETRAHYDRO-BENZOFURAN-2-CARBOXYLIC ACID
• (2,6,6-TRIMETHYL-4-OXO-4,5,6,7-TETRAHYDRO-BENZOFURAN-3-YL)-ACETIC ACID
• 3-ACETYL-2,6,6-TRIMETHYL-5,6,7-TRIHYDROOXAINDEN-4-ONE
• (R)-(+)-MENTHOFURAN,(+)-MENTHOFURAN,(+)-MENTHOFURAN, TERPENE STANDARD
• 4-HYDROXY-3,6,6-TRIMETHYL-4,5,6,7-TETRAHYDRO-1-BENZOFURAN-2-CARBOXYLIC ACID
• 6,6-DIMETHYL-4-OXO-4,5,6,7-TETRAHYDRO-1-BENZOFURAN-3-CARBOXYLIC ACID
• menthofuran synthase
• MENTHOFURAN(4,5,6,7-TETRAHYDRO-3,6-DIMETHYLBENZOFURAN)