17957-94-7

Basic information

• Product Name: (+)-MENTHOFURAN
• Synonyms: (R)-3,6-DIMETHYL-4,5,6,7-TETRAHYDROBENZOFURAN;(+)-MENTHOFURAN;(+)-MENTHOFURAN, TERPENE STANDARD;(R)-(+)-MENTHOFURAN
• CAS NO: 17957-94-7
• Molecular Formula: C₁₀H₁₄O
• Molecular Weight: 150.22
• Mol File: 17957-94-7.mol
• Article Data: 9

Chemical Properties

• Boiling Point: 204-206 °C(lit.)
• Flash Point: 75.5°C
• Appearance: /
• Density: 0.97 g/mL at 20 °C(lit.)
• Vapor Pressure: 0.275mmHg at 25°C
• Refractive Index: n20/D 1.484
• Storage Temp.: 2-8°C
• Solubility: Chloroform (Slightly), Methanol (Slightly)
• BRN: 2729
• CAS DataBase Reference: (+)-MENTHOFURAN(CAS DataBase Reference)
• NIST Chemistry Reference: (+)-MENTHOFURAN(17957-94-7)
• EPA Substance Registry System: (+)-MENTHOFURAN(17957-94-7)

Safety Data

• WGK Germany: 3
• F: 10-23
• Hazardous Substances Data: 17957-94-7(Hazardous Substances Data)

Usage

Description

(+)-MENTHOFURAN, also known as (R)-(+)-menthofuran, is a 4,5,6,7-tetrahydro-1-benzofuran with methyl groups substituted at positions 3 and 6 (the 6R-enantiomer). It is a monoterpene found in mint plants and is known for its potential role in the formation of p-menthane lactone in red wines.

Uses

Used in Wine Industry:
(+)-MENTHOFURAN is used as a precursor for p-menthane lactone, which contributes to the aroma and flavor profile of red wines. The presence of (+)-MENTHOFURAN in the wine production process can enhance the overall sensory experience of the final product.
Used in Pharmaceutical Industry:
(+)-MENTHOFURAN is used as a chemical intermediate for the synthesis of various pharmaceutical compounds. Its unique chemical structure allows it to be a valuable building block in the development of new drugs.
Used in Toxicology Research:
(+)-MENTHOFURAN is used as a research compound to study the oxidation process by mammalian cytochrome P450 (CYP) enzymes, specifically CYP1, which can lead to the formation of hepatotoxic metabolites. Understanding this process can help in the development of safer drugs and the study of drug metabolism in the body.

InChI:InChI=1/C10H14O/c1-7-3-4-9-8(2)6-11-10(9)5-7/h6-7H,3-5H2,1-2H3/t7-/m0/s1

Upstream product

• 17882-43-8 (?)-trans-isopulegone 
• 1600-27-7 mercury(II) diacetate 
• 77878-28-5 isopulegone epoxide 
• 63159-77-3 3,5,6,7,8,8a-hexahydro-4,7-dimethyl-1,2-benzodioxin 
• 13368-65-5 (3R)-3-methylcyclohexanone 
• 13834-13-4 isopulegol epoxide 
• 97345-71-6 (+)-(6R)-8-tert-butyldimethylsilyloxy-2,6-dimethyloct-2-ene 
• 147594-70-5 (-)-(6R)-(2E)-1-acetoxy-8-iodo-2,6-dimethyloct-2-ene 
• 141208-69-7 (+)-(6R)-(2E)-1-acetoxy-8-hydroxy-2,6-dimethyloct-2-ene 
• 141208-73-3 (+)-(6R)-(2E)-8-tert-butyldimethylsilyloxy-2,6-dimethyloct-2-en-1-ol 
• 141208-70-0 (-)-(6R)-(2E)-1-acetoxy-7-hydroxyimino-2,6-dimethylhept-2-ene 
• 141208-72-2 (+)-(6R)-(2E)-1-acetoxy-8-nitro-2,6-dimethyloct-2-ene 
• 147594-67-0 (+)-(6R)-(2E)-1-acetoxy-8-tert-butyldimethylsilyloxy-2,6-dimethyloct-2-ene 
• 147594-69-2 Acetic acid (E)-(R)-8-methanesulfonyloxy-2,6-dimethyl-oct-2-enyl ester 

Downstream Products

• 132106-32-2 1,4-Oxido-2,3-dicaraethoxy-5,9-dimethyl-2,3-diaza-bicyclo<0.4.4>decen-(5) 
• 75640-26-5 (R)-3,6-dimethyl-5,6-dihydrobenzofuran-2(4H)-one 
• 132183-58-5 2(Z)-(2'-Keto-4'-methylcyclohexylidene)propanal 

Relevant articles and documents

Molecular response of Musca domestica L. to Mintostachys verticillata essential oil, (4R)(+)-pulegone and menthone

Intense applications of synthetic insecticides for the control of adult Musca domestica have led to the insects developing resistance to most of them. In consequence, there is interest in new active ingredients as alternatives to conventional insecticides. Essential oils (EO) are potential tools for controlling M. domestica because of their effectiveness and their minimal environmental effects. In a fumigant assay, M. domestica adults treated with Minthostachys verticillata EO [LC50 = 0.5 mg/dm3; majority components by SPME-GC: (4R)(+)-pulegone (67.5%), menthone (22.3%) and (4R)(+)-limonene (3.8%)], died within 15 min or less. The terpenes absorbed by the flies and their metabolites, analyzed using SPME fiber, were (4R)(+)-limonene (LC50 = 6.2 mg/dm3), menthone (LC 50 = 1.9 mg/dm3), (4R)(+)-pulegone (LC50 = 1.7 mg/dm3) and a new component, menthofuran (LC50 = 0.3 mg/dm3), in a relative proportion of 12.4, 6.5, 35.9 and 44.2% respectively. Menthofuran was formed by oxidation of either (4R)(+)-pulegone or menthone mediated by cytochrome P450, as demonstrated by a fumigation assay on flies previously treated with piperonyl butoxide, a P450 inhibitor, which showed a decrease in toxicity of the EO, (4R)(+)-pulegone and of menthone, supporting the participation of the P450 oxidizing system in the formation of menthofuran. The enzymatic reaction of isolated fly microsomes with the EO or the (4R)(+)-pulegone produced menthofuran in both cases. Contrary to expectations, the insect detoxification system contributed to enhance the toxicity of the M. verticillata EO. Consequently, resistant strains overexpressing P450 genes will be more susceptible to either M. verticillata EO or (4R)(+)-pulegone and menthone.

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Furanoterpene synthesis via intramolecular nitrile oxide cycloaddition reaction: a total synthesis of (+)-menthofuran

A fused furan assembling strategy based on an intramolecular dipolar cycloaddition reaction of nitrile oxide has been applied to a total synthesis of perfumy furanomonoterpene (+)-menthofuran (1).The key cycloaddition substrates (9) and (12) are easily prepared via straightforward routes starting from (+)-citronellal and these are treated with sodium hypochlorite and p-chlorophenyl isocyanate, respectively.The cycloaddition reactions generate 10 : 1 mixture of diastereoisomeric isoxazolines (2a) and (2b) in good to excellent yields.The isoxazolines (2a,b)thus obtained are converted to (+)-menthofuran (1) by sequential reductive hydrolysis and alkaline hydrolysis (or vice versa) followed by acid treatment of the resulting β,γ-dihydroxy ketone (14).