171230-53-8

Basic information

• Product Name: 2(3H)-Furanone, dihydro-4-[(3-methoxyphenyl)methyl]-, (4S)-
• CAS NO: 171230-53-8
• Molecular Formula: C12H14O3
• Molecular Weight: 206.241
• Mol File: 171230-53-8.mol
• Article Data: 9

Chemical Properties

• CAS DataBase Reference: 2(3H)-Furanone, dihydro-4-[(3-methoxyphenyl)methyl]-, (4S)-(CAS DataBase Reference)
• NIST Chemistry Reference: 2(3H)-Furanone, dihydro-4-[(3-methoxyphenyl)methyl]-, (4S)-(171230-53-8)
• EPA Substance Registry System: 2(3H)-Furanone, dihydro-4-[(3-methoxyphenyl)methyl]-, (4S)-(171230-53-8)

Safety Data

• Hazardous Substances Data: 171230-53-8(Hazardous Substances Data)

Usage

General Description

2(3H)-Furanone, dihydro-4-[(3-methoxyphenyl)methyl]-, (4S)-, also known as S-(+)-sotolone, is a chemical compound that is commonly found in natural products and is used in a variety of commercial applications. It has a sweet, caramel-like odor and is used as a flavoring agent in food and beverages. It is also used in the production of perfumes and fragrances due to its unique scent. Additionally, it has been studied for its potential medicinal properties, including its ability to act as an antioxidant and its potential anti-inflammatory effects. Overall, 2(3H)-Furanone, dihydro-4-[(3-methoxyphenyl)methyl]-, (4S)- is a versatile chemical compound with a range of applications in various industries.

Upstream product

• 213553-70-9 3-[(3-methoxyphenyl)methyl]cyclobutanone 
• 24743-14-4 1-allyl-3-methoxybenzene 
• 1402081-39-3 C₁₂H₁₂Cl₂O₂ 
• 626-20-0 3-methoxystyrene 
• 1260675-20-4 3-(3-methoxyphenyl)cyclobutan-1-one 
• 263716-54-7 (4R)-4-(diphenylmethyl)-3-[[(2S)-2-(tert-butyloxycarbonyl)methyl-3-(3'-methoxyphenyl)]propanoyl]-2-oxazolidinone 
• 263716-53-6 (4R)-4-(diphenylmethyl)-3-[3-(3'-methoxyphenyl)propanoyl]-2-oxazolidinone 
• 40478-49-7 3-(3-methoxyphenyl)propanoyl chloride 
• 791096-44-1 (2S,4S)-2-(tert-Butyl-dimethyl-silanyloxy)-4-(3-methoxy-benzyl)-pentane-1,5-diol 
• 791096-43-0 tert-Butyl-[(1S,4S)-4-(3-methoxy-benzyl)-cyclopent-2-enyloxy]-dimethyl-silane 
• 791096-42-9 (1S,4S)-4-(3-Methoxy-benzyl)-cyclopent-2-enol 
• 26905-40-8 3-methoxybenzylmagnesium chloride 
• 791096-46-3 (S)-4-(3-Methoxy-benzyl)-tetrahydro-furan-2-ol 
• 263716-55-8 tert-butyloxycarbonyl (2S)-2-(carboxymethyl)-3-(3'-methoxyphenyl)propionic acid 

Downstream Products

• 185254-91-5 (3S,4S)-3,4-bis[(3-methoxyphenyl)methyl]dihydro-2(3H)-furanone 

Relevant articles and documents

First chemo-enzymatic synthesis of the (R)-Taniguchi lactone and substrate profiles of CAMO and OTEMO, two new Baeyer–Villiger monooxygenases

Abstract: This study investigates the substrate profile of cycloalkanone monooxygenase and 2-oxo-Δ3-4,5,5-trimethylcyclopentenylacetyl-coenzyme A monooxygenase, two recently discovered enzymes of the Baeyer–Villiger monooxygenase family, used as whole-cell biocatalysts. Biooxidations of a diverse set of ketones were performed on analytical scale: desymmetrization of substituted prochiral cyclobutanones and cyclohexanones, regiodivergent oxidation of terpenones and bicyclic ketones, as well as kinetic resolution of racemic cycloketones. We demonstrated the applicability of the title enzymes in the enantioselective synthesis of (R)-(?)-Taniguchi lactone, a building block for the preparation of various natural product analogs such as ent-quinine. Graphical abstract: [Figure not available: see fulltext.]

Enantioselective baeyer-villiger oxidation: Desymmetrization of meso cyclic ketones and kinetic resolution of racemic 2-arylcyclohexanones

Catalytic enantioselective Baeyer-Villiger (BV) oxidations of racemic and meso cyclic ketones were achieved in the presence of chiral N,N'-dioxide-Sc III complex catalysts. The BV oxidations of prochiral cyclohexanones and cyclobutanones afforded series of optically active μ- and γ-lactones, respectively, in up to 99% yield and 95% ee. Meanwhile, the kinetic resolution of racemic 2-arylcyclohexanones was also realized via an abnormal BV oxidation. Enantioenriched 3-aryloxepan-2-ones, whose formation is counter to the migratory aptitude, were obtained preferentially. Both the lactones and the unreacted ketones were obtained with high ee values.

Comparing the stereoselective biooxidation of cyclobutanones by recombinant strains expressing bacterial baeyer - Villiger monooxygenases

Microbial Baeyer - Villiger oxidation of representative prochiral ketones with a cyclobutanone structural motif was investigated using a collection of eight monooxygenases of different bacterial origin. This platform of enzymes is able to perform stereoselective biotransformations on an array of structurally diverse substrates. With several ketone precursors, biooxidations yielded enantiocomplementary butyrolactones as key intermediates for the synthesis of natural products and bioactive compounds. The microbial Baeyer - Villiger oxidation allows a facile and rapid entry to several compound classes in a desymmetrization reaction upon de novo generation of chirality.