79107-71-4

Basic information

• Product Name: 3-Hydroxytetrahydrothiophene
• Synonyms: 3-Hydroxytetrahydrothiophene
• CAS NO: 79107-71-4
• Molecular Formula: C4H8OS
• Molecular Weight: 104.17072
• EINECS: 1533716-785-6
• Mol File: 79107-71-4.mol
• Article Data: 29

Chemical Properties

• Boiling Point: 201.2 °C at 760 mmHg
• Flash Point: 98.7 °C
• Appearance: /
• Density: 1.222 g/cm³
• CAS DataBase Reference: 3-Hydroxytetrahydrothiophene(CAS DataBase Reference)
• NIST Chemistry Reference: 3-Hydroxytetrahydrothiophene(79107-71-4)
• EPA Substance Registry System: 3-Hydroxytetrahydrothiophene(79107-71-4)

Safety Data

• Hazardous Substances Data: 79107-71-4(Hazardous Substances Data)

Usage

General Description

3-Hydroxytetrahydrothiophene is a chemical compound that belongs to the class of organic compounds known as thiophenes. It is a colorless liquid with a strong sulfur-like odor and is used primarily as a flavor and fragrance ingredient in the production of various consumer products. 3-Hydroxytetrahydrothiophene is commonly found in foods such as soy products, cheese, and roasted nuts. It is also used in the synthesis of pharmaceuticals and as a building block in organic chemical synthesis. In addition, it has been studied for its potential biological activities, including antimicrobial and anticancer properties.

InChI:InChI=1S/C4H8OS/c5-4-1-2-6-3-4/h4-5H,1-3H2

Upstream product

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Relevant articles and documents

Enantioselective reduction of heterocyclic ketones with low level of asymmetry using carrots

A whole spectrum of biocatalysts for asymmetric reduction of prochiral ketones is well known including the Daucus carota root. However, this type of reaction is still challenging when pro-chiral ketones present low level of asymmetry, like heterocyclic ketones. In this work, 4,5-dihydro-3(2H)-thiophenone (1), 2-methyltetrahydrofuran-3-one (2), N-Boc-3-pyrrolidinone (3), 1-Z-3-pyrrolidinone (4) and 1-benzyl-3-pyrrolidinone (5) were studied in order to obtain the respective enantioselective heterocyclic secondary alcohols. Except for 5, the corresponding alcohols were obtained in high values of conversion and with high selectivity. In order to circumvent the low isolated yield of the corresponding chiral alcohol from 2, we observed that the use of carrots in the absence of water is feasible. Addition of co-solvents was needed to the water-insoluble ketones 3 and 4. Comparatively, baker’s yeast was used for bio reductions of 1, 3 and 4. And in terms of conversion, selectivity and work-up, the use of carrots were a more efficient biocatalyst, as well as a viable method for obtaining 5-member heterocyclic secondary alcohols.

Methodology Development in Directed Evolution: Exploring Options when Applying Triple-Code Saturation Mutagenesis

Directed evolution of stereo- or regioselective enzymes as catalysts in asymmetric transformations is of particular interest in organic synthesis. Upon evolving these biocatalysts, screening is the bottleneck. To beat the numbers problem most effectively, methods and strategies for building “small but smart” mutant libraries have been developed. Herein, we compared two different strategies regarding the application of triple-code saturation mutagenesis (TCSM) at multiresidue sites of the Thermoanaerobacter brockii alcohol dehydrogenase by using distinct reduced amino-acid alphabets. By using the synthetically difficult-to-reduce prochiral ketone tetrahydrofuran-3-one as a substrate, highly R- and S-selective variants were obtained (92–99 % ee) with minimal screening. The origin of stereoselectivity was provided by molecular dynamics analyses, which is discussed in terms of the Bürgi–Dunitz trajectory.

Origins of stereoselectivity in evolved ketoreductases

Mutants of Lactobacillus kefir short-chain alcohol dehydrogenase, used here as ketoreductases (KREDs), enantioselectively reduce the pharmaceutically relevant substrates 3-thiacyclopentanone and 3-oxacyclopentanone. These substrates differ by only the heteroatom (S or O) in the ring, but the KRED mutants reduce them with different enantioselectivities. Kinetic studies show that these enzymes are more efficient with 3-thiacyclopentanone than with 3-oxacyclopentanone. X-ray crystal structures of apo- and NADP+-bound selected mutants show that the substrate-binding loop conformational preferences are modified by these mutations. Quantum mechanical calculations and molecular dynamics (MD) simulations are used to investigate the mechanism of reduction by the enzyme. We have developed an MD-based method for studying the diastereomeric transition state complexes and rationalize different enantiomeric ratios. This method, which probes the stability of the catalytic arrangement within the theozyme, shows a correlation between the relative fractions of catalytically competent poses for the enantiomeric reductions and the experimental enantiomeric ratio. Some mutations, such as A94F and Y190F, induce conformational changes in the active site that enlarge the small binding pocket, facilitating accommodation of the larger S atom in this region and enhancing S-selectivity with 3-thiacyclopentanone. In contrast, in the E145S mutant and the final variant evolved for large-scale production of the intermediate for the antibiotic sulopenem, R-selectivity is promoted by shrinking the small binding pocket, thereby destabilizing the pro-S orientation.