97344-05-3

Usage

Uses

Used in Fragrance and Flavor Industries:
Isoapiole is used as a key ingredient in perfumes, soaps, and other cosmetic products due to its aromatic and spicy odor. It contributes to the unique and distinctive scent of these products.
Used in Food Products:
Isoapiole is used as a flavoring agent in food products, enhancing their taste and providing a distinctive flavor profile.
Used in Medicinal Applications:
Isoapiole has been studied for its potential medicinal properties, including its antimicrobial and antioxidant effects. These properties make it a promising candidate for various therapeutic applications.
Used in Antimicrobial Applications:
Isoapiole exhibits antimicrobial properties, making it useful in the development of treatments for bacterial infections and other related conditions.
Used in Antioxidant Applications:
As an antioxidant, isoapiole can help protect cells from damage caused by free radicals and oxidative stress, contributing to overall health and well-being.

Upstream product

• 103522-55-0 (2E,8E,10E)-(S)-(+)-tert-butyl 2,6-dimethyl-12-hydroxy-dodeca-2,8,10-trienoate 
• 168131-81-5 tert-Butyl (2E,4E,10E)-(R)-(+)-2,6-dimethyl-12-hydroxyundeca-2,8,10-trienoate 

Relevant academic research and scientific papers

Oblongolide: Synthesis and Absolute Configuration

The absolute configuration of oblongolide is shown to be (1) by an unambiguous synthesis from (+)-citronellol involving an intramolecular Diels-Alder reaction.

A Synthesis of (+)-Oblongolide

The absolute configuration of natural oblongolide is reassigned as (3aS,5aR,7S,9aS,9bS)-3a,5a,6,7,8,9,9a,9b-octahydro-7,9b-dimethylnaphthofuran-1(3H)-one 2 by a 7-stage synthesis of its enantiomer 1 from (+)-citronellol involving a regioselective reduction and an intramolecular Diels-Alder reaction (IMDA) as the key steps. (+)-Citronellol was converted into methyl (2E,4E,10E)-(S)-(+)-11-tert-butoxycarbonyl-7-methyl-undeca-2,4,10-trienoate 7 by sequential Lemieux-Johnson oxidation, Wittig reaction, pyridinium chlorochromate oxidation, and Wadsworth-Emmons-Horner alkenation.A regioselective reduction of the methoxycarbonyl group in 7 afforded tert-butyl (2E,8E,10E)-(S)-(+)-2,6-dimethyl-12-hydroxy-dodeca-2,8,10-trienoate 8 from which (+)-oblongolide was readily obtained via an IMDA reaction.Key Words; Oblongolide; Absolute configuration; Citronellol; Intramolecular Diels-Alder reaction.

A Short Synthesis of Natural (-)-Oblongolide via an Intramolecular or a Transannular Diels-Alder Reaction

The absolute configuration on naturally occurring oblongolide is confirmed as (3aS,5aR,7S,9aS,9bS)-3a,5a,6,7,8,9,9a,9b-octahydro-7,9b-dimethylnaphthofuran-1(3H)-one (1) on the basis of a six-stage or an eight-stage synthesis from (-)-citronellol involving a steric-controlled, regioselective reduction and an intramolecular Diels-Alder (IMDA) reaction or a transannular Diels-Alder (TDA) reaction as the key steps. (-)-Citronellol (5) was converted into methyl (2E,4E,10E)-(S)-(+)-11-(tert-butoxycarbonyl)-7-methylundeca-2,4,10-trienoate (7) by sequential Lemiuex-Johnson oxidation, Wittig olefination, pyridinium dichromate oxidation, and Wadsworth-Emmons-Horner alkenation.A regioselective reduction of the methoxycarbonyl group in 7 afforded tert-butyl (2E,8E,10E)-(S)-(+)-2,6-dimethyl-12-hydroxydodeca-2,8,10-trienoate (8) from which oblongolide (1) was obtained via an IMDA reaction.The macrocyclic (2E,8E,10E)-(S)-(+)-2,6-dimethyldodeca-2,8,10-trieno-1,12-lactone derived from 8 underwent a highly stereoselective TDA reaction to give 1 at a lower reaction temperature, in a shorter reaction time and in a better yield than the analogous IMDA reaction.