3334-05-2

Basic information

• Product Name: TETRAHYDRO-THIOPHEN-3-OL
• Synonyms: TETRAHYDRO-THIOPHEN-3-OL;THIOPHENE-3-OL, TETRAHYDRO-;tetrahydro-3-thiopheneol(SALTDATA: FREE);(R)-tetrahydrothiophen-3-ol;3(S)-hydroxytetrahydrothiophene;Tetrahydro-Thiophen-3-Ol(WX642050)
• CAS NO: 3334-05-2
• Molecular Formula: C₄H₈OS
• Molecular Weight: 104.17
• Mol File: 3334-05-2.mol

Chemical Properties

• Boiling Point: 201.2 °C at 760 mmHg
• Flash Point: 98.7 °C
• Appearance: /
• Density: 1.222g/cm³
• Vapor Pressure: 0.0771mmHg at 25°C
• Refractive Index: 1.576
• Storage Temp.: 2-8°C
• CAS DataBase Reference: TETRAHYDRO-THIOPHEN-3-OL(CAS DataBase Reference)
• NIST Chemistry Reference: TETRAHYDRO-THIOPHEN-3-OL(3334-05-2)
• EPA Substance Registry System: TETRAHYDRO-THIOPHEN-3-OL(3334-05-2)

Safety Data

• Hazardous Substances Data: 3334-05-2(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
Tetrahydro-thiophen-3-ol is used as a key intermediate in the synthesis of various pharmaceuticals. Its chemical structure allows for the development of new drugs with potential therapeutic applications.
Used in Agrochemical Industry:
In the agrochemical sector, Tetrahydro-thiophen-3-ol is utilized as a building block for the creation of compounds with pesticidal properties, contributing to the development of effective crop protection solutions.
Used in Fragrance Industry:
Tetrahydro-thiophen-3-ol is employed as a component in the formulation of fragrances due to its strong, distinctive odor, adding depth and complexity to scent profiles in perfumes and other aromatic products.
Used in Food and Beverage Industry:
As a flavoring agent, Tetrahydro-thiophen-3-ol is used to impart unique taste and aroma characteristics to food and beverage products, enhancing the sensory experience for consumers.

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

Upstream product

• 1120-59-8 2,3-dihydrothiophene 
• 1003-04-9 Tetrahydrothiophen-3-one 
• 19398-47-1 1,4-dibromo-2-butanol 
• 50-99-7 D-glucose 

Downstream Products

• 3334-00-7 tetrahydrothiophen-3-yl benzenesulfonate 
• 1003-04-9 Tetrahydrothiophen-3-one 
• 13031-76-0 3-hydroxytetrahydrothiophene-1,1-dioxide 
• 3334-01-8 3-(4-toluenesulfonyl)thiolane 

Relevant articles and documents

Enantiomeric purity enrichment of (R)-tetrahydrothiophene-3-ol sulfonyl derivatives by crystallization

(R)-Tetrahydrothiophene-3-ol sulfonyl derivatives 3-19 were prepared by introduction of various sulfonyl groups at the hydroxyl group of (R)-tetrahydrothiophene-3-ol 1 with low enantiomeric purity (68-74% ee). Crystallization was applied to improve their

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.

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.

Ketoreductase polypeptides for the production of (R)-3-hydroxythiolane

The present disclosure provides engineered ketoreductase enzymes having improved properties as compared to a naturally occurring wild-type ketoreductase enzyme. Also provided are polynucleotides encoding the engineered ketoreductase enzymes, host cells capable of expressing the engineered ketoreductase enzymes, and methods of using the engineered ketoreductase enzymes to synthesize chiral compounds.

Ketoreductase polypeptides for the production of (R)-3-hydroxythiolane

The present disclosure provides engineered ketoreductase enzymes having improved properties as compared to a naturally occurring wild-type ketoreductase enzyme. Also provided are polynucleotides encoding the engineered ketoreductase enzymes, host cells capable of expressing the engineered ketoreductase enzymes, and methods of using the engineered ketoreductase enzymes to synthesize chiral compounds.

Heterocyclic lithium amides as chiral ligands for an enantioselective hydroxyalkylation with n-BuLi

(Chemical Equation Presented) Chiral heterocyclic structures based on 3-aminopyrrolidines (3APs), 3-aminotetrahydrothiophens (3ATTs), and 3-aminotetrahydrofurans (3ATFs) have been synthesized. The corresponding lithium amides have been evaluated as chiral ligands in the condensation of n-BuLi on o-tolualdehyde. The returned levels of induction were in the 46-80% ee range. The cheap and easily prepared 3ATFLi's turned out to be also the best ligands, giving access to the expected R or S alcohols in a same 80% level of induction at -78°C in THF. In all cases, the sense of induction depends on the absolute configuration of C8 on the 3-amino appendage. A general concept is proposed to rationalize the process of induction in the presence of organolithium species.

A Novel heterospirocyclic 2H-azirin-3-amine as synthon for 3-aminothiolane-3-carboxylic acid

The heterospirocyclic 2H-azirin-3-amine (9), i.e., N-methyl-N-phenyl-5-thia-1-azaspiro[2.4]hept-1-en-2-amine, was prepared from the commercially available thiolane-3-one (10) via the corresponding 3-carbonitrile (11) and 3-thiocarboxamide (14). This aziri

Pyrano, piperidino, and thiopyrano compounds and methods of use

The present invention provides novel compounds of formula I which may be useful in hyperpolarizing cell membranes, opening potassium channels, relaxing smooth muscle cells, and inhibiting bladder contractions.

Pyrano, piperidino, and thiopyrano compounds and methods of use

The present invention provides novel compounds of formula I which may be useful in hyperpolarizing cell membranes, opening potassium channels, relaxing smooth muscle cells, and inhibiting bladder contractions.

Enhancement of Bacterial Mutagenicity of Bifunctional Alkylating Agents by Expression of Mammalian Glutathione S-Transferase

Recently, we inserted the plasmid vector pKK233-2 containing rat GSH S-transferase (GST) 5-5 cDNA into Salmonella typhimurium TA1535 and found that these bacteria [GST 5-5(+)] expressed the protein and produced mutations whrn ethylene or methylene dihalides were added [Thier, R., Taylor, J. B., Pemble, S. E., Ketterer, B., Persmark, M., Humphreys, W. G., and Guengerich, F. P. (1993) Proc. Natl. Acad. Sci. U.S.A. 90, 8576-8580]. After exposure to the known GST 5-5 substrate 1,2-epoxy-3-(4'-nitrophenoxy)propane, the GST 5-5(+) strain showed fewer mutants than the bacteria transfected with the cDNA clone in a reverse orientation [GST 5-5(-)], suggesting a protective role of GST 5-5. However, mutations were considerably enhanced in the GST 5-5(+) strain [as compared to GST 5-5(-)] when 1,2,3,4-diepoxybutane (butadiene diepoxide) or 1,2-epoxy-4-bromobutane was added. The GST 5-5(+) and GST 5-5(-) bacterial stains showed similar responses to 1,2-epoxypropane, 3,4-epoxy-1-butene, and 1,4-dibromobutane. The results suggest that some bifunctional activated butanes are transformed to mutagenic products through GSH conjugation. We also found that the GST 5-5(+) strain showed enhanced mutagenicity with 1,4-dibromo-2,3-epoxybutane, 1,2-epoxy-3-bromopropane, (epibromohydrin), and (+/-)-1,4-dibromo-2,3-dihydroxybutane. The possibility was considered that a 5-membered thialonium ion may be involved in the mutagenicity. Model thialonium compounds were rather stable to hydrolysis in aqueous solution at pH 7.4 and slowly alkylated 4-(4-nitrobenzyl)pyridine. The presence of a hydroxyl group β to the sulfur did not enhance reactivity. Mechanisms involving episulfonium ions are considered more likely. Potential oxidation products of the toxic pesticide 1,2-dibromo-3-chloropropane (DBCP) were also considered in this system. DBCP itself gave rather similar results in the two strains. Others have reported that oxidation of DBCP is required for mutagenicity, along with GST-catalyzed GSH conjugation [Simula, T. P., Glancey, M. J., Soederlund, E. J., Dybing, E., and Wolf, C. R. (1993) Carcinogenesis, 14, 2303-2307]. The putative oxidation product 1,2-dibromopropional did not show a difference between the two strains. However, 1,3-dichloroacetone, a model for the putative oxidation product 1-bromo-3-chloroacetone, was considerably more mutagenic in the GST 5-5(+) strain.