28227-36-3

Basic information

• Product Name: 2(3H)-Furanone,3-(acetyloxy)dihydro-4,4-dimethyl-, (3R)-
• Synonyms: 2(3H)-Furanone,3-(acetyloxy)dihydro-4,4-dimethyl-, (R)-; 2(3H)-Furanone,dihydro-3-hydroxy-4,4-dimethyl-, acetate, D-(-)- (8CI); (R)-(-)-Pantolactoneacetate; D-O-Acetylpantolactone; D-Pantolactone acetate
• CAS NO: 28227-36-3
• Molecular Formula: C₈H₁₂O₄
• Molecular Weight: 172.1785
• Mol File: 28227-36-3.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 263.9°Cat760mmHg
• Flash Point: 130.4°C
• Density: 1.14g/cm³
• CAS DataBase Reference: 2(3H)-Furanone,3-(acetyloxy)dihydro-4,4-dimethyl-, (3R)-(CAS DataBase Reference)
• NIST Chemistry Reference: 2(3H)-Furanone,3-(acetyloxy)dihydro-4,4-dimethyl-, (3R)-(28227-36-3)
• EPA Substance Registry System: 2(3H)-Furanone,3-(acetyloxy)dihydro-4,4-dimethyl-, (3R)-(28227-36-3)

Safety Data

• Hazardous Substances Data: 28227-36-3(Hazardous Substances Data)

Usage

Class

Organic compound, Furanone derivative

Structure

Cyclic chemical structure with a furan ring

Stereochemistry

(3R)configuration

Potential applications

Pharmaceuticals, fragrances, flavors (requires further research)

Upstream product

• 75-36-5 acetyl chloride 
• 599-04-2 (R)-Pantolacton 
• 79-50-5 pantolactone 
• 108-24-7 acetic anhydride 

Downstream Products

• 599-04-2 (R)-Pantolacton 

Relevant articles and documents

Synthesis, biological activities, and docking studies of D-pantolactone derivatives as novel FAS inhibitors

A novel series of fatty acid synthase (FAS) inhibitors with D-(?)-pantolactone moiety and potential utility for the treatment of obesity were designed, synthesized and characterized, in which the structure of compound 3k was further confirmed by single X-

Rapid screening of hydrolases for the enantioselective conversion of 'difficult-to-resolve' substrates

Hydrolases showing high enantioselectivity towards three racemic alcohols (1-methoxy-2-propanol, 3-hydroxy-tetrahydrofuran, 3-butyn-2-ol) and pantolactone were identified by a step-wise screening procedure. Initially, those biocatalysts, which exhibited hydrolytic activity towards the corresponding acetates or butyrates, were selected out of >100 enzymes. Here, rapid screening was performed in a pH-indicator-based format in microtiter plates. Subsequently, enantioselectivity of active hydrolases was determined in small scale reactions (～1 mg substrate per reaction) by means of gas chromatography using chiral columns. Enzymes exhibiting highest enantioselectivities were then chosen for preparative scale resolution. Using this strategy, at least one suitable hydrolase was found for 3 out of the 4 model compounds examined, allowing efficient kinetic resolution. Moreover, in all cases enantiocomplementary enzymes were identified thus enabling access to both enantiomers of all substrates.

145. Analytic and Preparative Resolution on Racemic γ- and δ-Lactones by Chromatography on Cellulose Triacetate. Relationship between Elution Order and Absolute Configuration

Enantiomers of various chiral five- and six-membered-ring lactones, which are important classes of cpmpounds (flavour and pheromone components, key intermediates in the synthesis of biologically active substrates) have been separated chromatographically on the chiral phase cellulose triacetate, crystallographic form I (CTA I).Four different series of five-membered-ring lactones, relationships have been found between the elution order of the enantiomers and their absolute configuration.Preparative resolutions of γ-phenyl-γ-butyrolactone (1) and of the pheromone component 5b have been carried out to demonstrate the applicability of the method to g-scale separations.