Menthofuran

Base Information

• Chemical Name: Menthofuran
• CAS No.: 494-90-6
• Deprecated CAS: 59553-66-1
• Molecular Formula: C10H14 O
• Molecular Weight: 150.221
• Hs Code.: 29329990
• European Community (EC) Number: 207-795-5
• NSC Number: 315249
• UNII: LK024V9U3C
• DSSTox Substance ID: DTXSID9025534
• Nikkaji Number: J11.817F
• Wikipedia: Menthofuran
• Wikidata: Q6817554
• Pharos Ligand ID: P7K3S56A129Q
• ChEMBL ID: CHEMBL1522900
• Mol file: 494-90-6.mol

Synonyms:menthofuran;menthofuran, (R)-isomer

Chemical Property of Menthofuran

Chemical Property:

• Vapor Pressure: 0.275mmHg at 25°C
• Melting Point: 86°C
• Refractive Index: n20/D 1.485(lit.)
• Boiling Point: 210.7°Cat760mmHg
• Flash Point: 75.5°C
• PSA: 13.14000
• Density: 0.967g/cm³
• LogP: 2.71280
• Storage Temp.: Room Temperature
• Solubility.: Chloroform (Slightly), Ethyl Acetate (Slightly), Methanol (Slightly)
• XLogP3: 3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 0
• Exact Mass: 150.104465066
• Heavy Atom Count: 11
• Complexity: 144

Purity/Quality:

98% ^*data from raw suppliers

Menthofuran ^*data from reagent suppliers

Safty Information:

• Safety Statements: 24/25

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC1CCC2=C(C1)OC=C2C
• 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 intermedaites via oxidation process. 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.

Technology Process of Menthofuran

There total 66 articles about Menthofuran which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 77.0%

(+/-)-3,6-dimethyl-5,6,7,7a-tetrahydrobenzofuran-2(4H)-one (13341-72-5,16434-36-9,16434-37-0,38049-04-6,51744-94-6,75684-66-1,142759-52-2,142759-53-3) → menthofuran (494-90-6)

Guidance literature:

With diisobutylaluminium hydride; In tetrahydrofuran; for 20h;

Reference yield: 75.0%

menthalactone (13341-72-5,51744-94-6) → menthofuran (494-90-6)

Guidance literature:

With lithium aluminium tetrahydride; isopropyl alcohol; In diethyl ether; at -60 - -50 ℃;

DOI:10.1021/jo01296a037

Reference yield: 72.0%

(6-Methyl-4,5,6,7-tetrahydro-benzofuran-3-ylmethyl)-phenyl-amine → menthofuran (494-90-6)

Guidance literature:

With hydrogen; palladium on activated charcoal; In ethanol; at 60 ℃; for 5h; under 760 Torr;

upstream raw materials:

menthalactone

pulegone

4,7-dimethyl-5,6,7,8-tetrahydro-benzo[e][1,2]oxathiine 2,2-dioxide

2-bromo-4-methylcyclohexanone

Downstream raw materials:

(2R,3R)-2-(3,4-dihydroxyphenyl)-3,4-dihydro-1[2H]-benzopyran-3,5,7-triol

cinnamtannin B-1

Refernces

• 1、 Aso,Ojida,Yang,Cha,Osawa,Kanematsu. "Furannulation strategy for synthesis of the naturally occurring fused 3- methylfurans: Efficient synthesis of evodone and menthofuran and regioselective synthesis of maturone via a Lewis acid catalyzed Diels-Alder reaction. Some comments for its mechanistic aspects". . p. 3960 - 3968. Retrieved 2007/10/02.
• 2、 Aso, Mariko,Sakamoto, Mizue,Urakawa, Narumi,Kanematsu, Ken. "FURANNULATION STRATEGY. AN EFFICIENT SYNTHESIS OF FUSED 3-METHYLFURANS". . p. 1003 - 1006. Retrieved 2007/10/02.