13341-72-5

Usage

Uses

Used in Flavor and Fragrance Industry:
FEMA 3764 is used as a flavoring agent for its creamy, coconut, and coumarin-like taste characteristics, adding a unique flavor profile to food and beverage products.
FEMA 3764 is also used as a fragrance ingredient for its sweet, creamy, and slightly powdery coconut aroma, contributing to the overall scent of personal care and cosmetic products.
Used in Pharmaceutical Industry:
Menthalactone, as a component of mint, may contribute to its analgesic activity. Therefore, FEMA 3764 can be used in the development of pain-relief medications and topical analgesic formulations.

Preparation

By asymmetric dihydroxylation reaction from intrinsically disflavored diastereoface of alkene

Synthesis Reference(s)

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

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

• 72952-61-5 Ethyl 2-<1-(ethoxycarbonyl)-4-methyl-2-oxocyclohexyl>propionate 
• 589-92-4 1-methylcyclohexan-4-one 
• 132060-11-8 2-(4-Methyl-7-oxa-bicyclo[4.1.0]hept-1-yl)-propionic acid methyl ester 
• 96562-29-7 p-menth-3-en-9-oic acid 
• 2570-63-0 thallium(III) acetate 
• 1334384-66-5 dimethyl 2-(4-methylcyclohexylidene)succinate 
• 38049-03-5 (+/-)-6-methyl-3-methylene-hexahydrobenzofuran-2(3H)-one 
• 106-25-2 Nerol 
• 106-24-1 Geraniol 
• 2565-83-5 geraniol methyl ether 
• 2565-83-5 (2Z)-1-methoxy-3,7-dimethylocta-2,6-diene 
• 139372-89-7 E,E-2-formyl-8-methoxy-6-methyl-2,6-octadiene 
• 13341-72-5 (+/-) isomintlactone 
• 118759-44-7 2-hydroxy-4-methylcyclohexanone 

Downstream Products

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

Relevant academic research and scientific papers

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

Use of 3,6-dimethyl-2(3H)-benzofuranone as flavor material and new process for its preparation

3,6-Dimethyl-2(3H)-benzofuranone is a new, valuable flavor material. A process for its industrial-scale preparation was developed.

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

A facile synthesis of (±)-mintlactone

(±)-Mintlactone has been synthesized by applying a novel effective synthetic sequence. 4-Methylcyclohexanone was subjected to acetoxylation with Pb(OAc)4. Hydrolysis followed by reaction with 2-chloropropionyl chloride, then treatment with trie

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.

A versatile synthesis of butenolides: Total synthesis of (+/-)-mintlactone

The butenolide monoterpenes, mintlactone and isomintlactone, have been synthesized by a new method for the preparation of butenolides from α,β-unsaturated esters by deconjugation, epoxidation and rearrangement.

Chemical Tranformation of Terpenoids. V. Acidic Conversions of 10-Hydroxygeraniol and 10-Hydroxynerol Derivatives Leading to Cyclic Monoterpenoids

Acid treatment of 1-O-acetyl-10-hydroxygeraniol (5a), 1-O-methyl-10-hydroxygeraniol (5b), 1-O-acetyl-10-hydroxynerol (6a), and 1-O-methyl-10-hydroxynerol (6b) was investigated under various conditions.It was found that treatment of 5a and 6a with HCOOH gave menth-1-ene-8,9-diol (7), while treatment of 5a, 5b, 6a, or 6b with BF3-etherate in CH2Cl2 furnished two menthofuran-type compounds (9, 10) and two bicyclooct-2-ene derivatives (17, 24).Both 9 and 10 were successfully converted to menthofuran (16) and 17 was converted to a bicyclooctenone derivative (23) which was a key intermediate for a synthesis of juvabione (27).Keywords - geraniol; nerol; 10-hydroxygeraniol; 10-hydroxynerol; 10-hydroxygeraniol derivative; 10-hydroxynerol derivative; uroterpenol; menthofuran; bicyclooct-2-ene derivative