13341-72-5

Basic information

• Product Name: FEMA 3764
• Synonyms: 5,6,7,7a-tetrahydro-3,6-dimethyl-2(4h)-benzofuranon;5,6,7,7a-tetrahydro-3,6-dimethyl-2(4H)-Benzofuranone;MINT LACTONE;MENTHALACTONE;FEMA 3764;5,6,7,7a-tetrahydro-3,6-dimethyl-(4H)-benzofuran-2-one;MENTHALACTONE 99+%;2(4H)-Benzofuranone, 5,6,7,7a-tetrahydro-3,6-dimethyl-
• CAS NO: 13341-72-5
• Molecular Formula: C₁₀H₁₄O₂
• Molecular Weight: 166.22
• EINECS: 236-390-6
• Product Categories: Alphabetical Listings;Flavors and Fragrances;M-N
• Mol File: 13341-72-5.mol
• Article Data: 8

Chemical Properties

• Boiling Point: 87-89 °C25 mm Hg(lit.)
• Flash Point: 176 °F
• Appearance: /
• Density: 1.058 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.000914mmHg at 25°C
• Refractive Index: n20/D 1.5(lit.)
• CAS DataBase Reference: FEMA 3764(CAS DataBase Reference)
• NIST Chemistry Reference: FEMA 3764(13341-72-5)
• EPA Substance Registry System: FEMA 3764(13341-72-5)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 13341-72-5(Hazardous Substances Data)

Usage

Occurrence

Reported found in peppermint and pennyroyal oil, Mentha arvensi

Preparation

By asymmetric dihydroxylation reaction from intrinsically disflavored diastereoface of alkene

Aroma threshold values

Aroma characteristics at 10.0%: sweet, creamy coumarinic, slightly powdery coconut, brown vanilla-like and slightly bready.

Taste threshold values

Taste characteristics at 20 ppm: creamy, coconut, coumarin, milky lactonic with a slight minty and anisic nuance.

Synthesis Reference(s)

Tetrahedron Letters, 31, p. 6789, 1990 DOI: 10.1016/S0040-4039(00)97172-7

General Description

Menthalactone occurs naturally in mint. It may be contributing to its analgesic activity.

Biochem/physiol Actions

Taste at 20 ppm

InChI:InChI=1/C10H14O2/c1-6-3-4-8-7(2)10(11)12-9(8)5-6/h6,9H,3-5H2,1-2H3/t6-,9-/m1/s1

Upstream product

• 37905-03-6 8-hydroxygeranyl acetate 
• 37905-02-5 (2E,6E)-3,7-dimethyl-8-oxoocta-2,6-dien-1-yl acetate 
• 38049-03-5 (+/-)-6-methyl-3-methylene-hexahydrobenzofuran-2(3H)-one 
• 13341-72-5 (+/-) isomintlactone 
• 1334384-66-5 dimethyl 2-(4-methylcyclohexylidene)succinate 
• 589-92-4 1-methylcyclohexan-4-one 
• 31538-47-3 2-(4-Methyl-cyclohex-1-enyl)-propionic acid methyl ester 
• 54263-85-3 (4-methyl-cyclohexyliden)-acetic acid methyl ester 
• 159561-57-6 p-menth-3-en-9-oic acid ethyl ester 
• 96562-29-7 p-menth-3-en-9-oic acid 
• 2570-63-0 thallium(III) acetate 
• 132060-11-8 2-(4-Methyl-7-oxa-bicyclo[4.1.0]hept-1-yl)-propionic acid methyl ester 
• 65817-24-5 3,6-dimethyl-3H-benzo[b]furan-2-one 
• 13537-82-1 ethyl 4-methyl-2-cyclohexanone-1-carboxylate 

Downstream Products

• 13341-72-5 (+/-)-3,6-dimethyl-5,6,7,7a-tetrahydrobenzofuran-2(4H)-one 
• 13674-37-8 2-(4-Methyl-1-cyclohexenyl)-1,2-propanediol 
• 494-90-6 menthofuran 
• 22273-97-8 methyl-4 cyclohexenyl-1 methyle cetone 

Relevant articles and documents

Regio- and stereoselective selenium dioxide allylic oxidation of (E)-dialkyl alkylidenesuccinates to (Z)-allylic alcohols: Synthesis of natural and unnatural butenolides

The first SeO2 induced (Z)-selective allylic alcohol formation of dialkyl alkylidenesuccinates has been demonstrated to accomplish one-step syntheses of several essential butenolides and fused butenolides via an unusual E- to Z- carbon-carbon d

Reaction of β,γ-unsaturated carboxylic acids with Thallium triacetate (TTA): Lactonization vs oxidative decarboxylation

The reaction of six β,γ-unsaturated carboxylic acids with thallium triacetate (TTA) was studied. The nature of the products is highly sensitive to the substitution pattern of the substrates. Aliphatic acids gave mainly lactones, while those bearing an aro

An Efficient Entry Into Butenolides: Synthesis Of (+/-) Mintlactone

Osmylation of β,γ-unsaturated esters and acid catalysed cyclisation of the resultant diols generate butenolides in high yields.