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

Description

Isoaltholactone is a chemical compound belonging to the lactone family, characterized by a cyclic ester with a five-membered ring. It is predominantly found in natural products, particularly in marine organisms and plants, and has been recognized for its diverse biological activities, including anti-inflammatory, anticancer, antimicrobial, antioxidant, and antifungal properties. These attributes render isoaltholactone a promising candidate for pharmaceutical and medical applications, with potential therapeutic uses in various areas of health and wellness.

Uses

Used in Pharmaceutical Development:
Isoaltholactone is used as a pharmaceutical candidate for its anti-inflammatory, anticancer, and antimicrobial properties. It is particularly promising for the development of treatments targeting inflammation and cancer, given its ability to inhibit the growth of cancer cells and reduce inflammation.
Used in Anticancer Applications:
Isoaltholactone is used as an anticancer agent, showing potential in inhibiting the growth of various types of cancer cells. Its effectiveness in reducing inflammation and demonstrating antioxidant activities further supports its role in cancer treatment and prevention.
Used in Antimicrobial Applications:
Isoaltholactone is used as an antimicrobial agent, leveraging its ability to combat microbial infections. Its broad-spectrum activity against various pathogens makes it a valuable asset in the development of new antimicrobial drugs.
Used in Antioxidant Formulations:
Isoaltholactone is used as an antioxidant in formulations designed to protect against oxidative stress and related diseases. Its antioxidant properties can help in the development of health supplements and skincare products that promote overall well-being and skin health.
Used in Antifungal Applications:
Isoaltholactone is used as an antifungal agent, effective against various fungal species. This makes it a potential ingredient in the development of antifungal medications and treatments for fungal infections.
Used in Marine and Plant-based Industries:
Isoaltholactone, being commonly found in marine organisms and plants, is used in these industries for the extraction and development of natural products with therapeutic potential. Its presence in these sources underscores the importance of biodiversity in discovering new compounds with medicinal properties.

Upstream product

• 474126-20-0 (2S,3S,6S)-3-tert-butyldimethylsilanyloxy-6-(1-ethoxyethoxy)-2-[(E)-styryl]-3,6-dihydro-2H-pyran 
• 474126-24-4 (3S,6S)-3-acetyl-6-(1-ethoxyethoxy)-isoaltholactone 
• 474126-22-2 (2S,3S,6S)-6-(1-ethoxyethoxy)-2-[(3R)-3-phenyloxiranyl]-3,6-dihydro-2H-pyran-3-ol 
• 474126-23-3 6S-6-(1-ethoxyethoxy)-isoaltholactone 
• 474126-19-7 (2S,3S,6S)-6-(1-ethoxyethoxy)-2-[(E)-styryl]-3,6-dihydro-2H-pyran-3-ol 
• 129694-46-8 (2S,6S)-6-(1-Ethoxyethoxy)-2-<(E)-styryl>-6H-pyran-3(2H)-one 
• 129694-47-9 (2S,3R,6S)-6-(1-Ethoxyethoxy)-2-<(E)-styryl>-3,6-dihydro-2H-pyran-3-ol 
• 129694-45-7 (2S)-6-Hydroxy-2-<(E)-styryl>-6H-pyran-3(2H)-one 
• 607376-02-3 ethyl 2,2-dimethyl-6-phenyl-(3aS,4R,6S,6aS)-perhydrofuro[3,4-d][1,3]dioxole-4-carboxylate 
• 474126-25-5 3-acetyl-isoaltholactone 
• 302348-81-8 (5S)-5-hydroxy-(6S)-6-((2S,3R)-3-phenyloxiranyl)-5,6-dihydro-pyran-2-one 
• 160699-77-4 (5S,6S)-5-hydroxy-6-[(E)-styryl]-5,6-dihydro-2H-pyran-2-one 
• 302348-88-5 (5S)-5-hydroxy-(6S)-6-((2S,3S)-3-phenyloxiranyl)-5,6-dihydro-pyran-2-one 
• 124868-05-9 (2S,3R,4S,5S)-2-<(Z)-2-(ethoxycarbonyl)-ethenyl>-3,4-bis(methoxymethoxy)-5-phenyltetrahydrofuran 

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.