124868-11-7

Basic information

• Product Name: Isoaltholactone
• Synonyms: Isoaltholactone
• CAS NO: 124868-11-7
• Molecular Formula: C₁₃H₁₂O₄
• Molecular Weight: 232.23
• Mol File: 124868-11-7.mol
• Article Data: 8

Chemical Properties

• Appearance: /
• CAS DataBase Reference: Isoaltholactone(CAS DataBase Reference)
• NIST Chemistry Reference: Isoaltholactone(124868-11-7)
• EPA Substance Registry System: Isoaltholactone(124868-11-7)

Safety Data

• Hazardous Substances Data: 124868-11-7(Hazardous Substances Data)

Usage

General Description

Isoaltholactone is a chemical compound that belongs to the lactone family and is composed of a cyclic ester with a five-membered ring. It is commonly found in natural products, specifically in marine organisms and plants, and has been identified for its potential biological activities. Isoaltholactone has been reported to possess anti-inflammatory, anticancer, and antimicrobial properties, making it a promising candidate for the development of pharmaceuticals and other medical applications. Studies have shown its ability to inhibit the growth of cancer cells and reduce inflammation, making it an area of interest for further research and potential therapeutic uses. Additionally, isoaltholactone has demonstrated antioxidant and antifungal activities, further highlighting its potential as a valuable natural compound with diverse biological effects.

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Relevant articles and documents

Stereospecificity in the Au-catalysed cyclisation of monoallylic diols. Synthesis of (+)-isoaltholactone

We describe a concise synthesis of (+)-isoaltholactone via a Au-catalysed cyclisation of a monoallylic diol to form the tetrahydrofuranyl ring. Analogous cyclisations show that the stereochemical outcome is dictated by the stereochemistry of the diol substrate.

A concise and stereoselective synthesis of both enantiomers of altholactone and isoaltholactone

A concise and flexible stereoselective route to synthesize both enantiomers of the highly functionalized α,β-unsaturated-δ-lactones, altholactone and isoaltholactone, from readily available cinnamyl alcohol is described. This approach derived its asymmetry from Sharpless catalytic asymmetric epoxidation and Sharpless asymmetric dihydroxylation reactions. The resulting diols were produced in high enantiomeric excess and were cyclized in a stereoselective manner in the presence of a catalytic amount of camphor sulphonic acid.

An olefination approach to the enantioselective syntheses of several styryllactones

A flexible enantioselective route to highly functionalized α,β-unsaturated δ-lactones, has allowed for the syntheses of the styryllactones: altholactone, isoaltholactone, 3-epi-altholactone, 2-epi-altholactone and 5-hydroxy goniothalamin in 2.5, 10, 5, 1 and 13% overall yields from furfural, respectively. This approach derives its asymmetry by applying the Sharpless catalytic asymmetric dihydroxylation to vinylfuran. The resulting diols are produced in high enantioexcess and can be stereoselectively transformed into α,β-unsaturated-δ-lactones via a short highly diastereoselective oxidation and reduction sequence. Wittig olefination or Julia olefination reactions were used to introduce the phenyl group side chain either cis or trans selectively and these intermediates were further elaborated into the altholactone isomers via selective epoxidation reactions.