Category: esters-buliding-blocks

Improvement of enantioselectivity and stability of Klebsiella oxytoca hydrolase immobilized on Eupergit C 250L was written by Wang, Pei-Yun;Tsai, Shau-Wei;Chen, Teh-Liang. And the article was included in Journal of Chemical Technology and Biotechnology in 2008.Recommanded Product: Ethyl 2-hydroxy-3-phenylpropanoate This article mentions the following:

A simple procedure was employed to covalently immobilize a Klebsiella oxytoca hydrolase (SNSM-87) onto epoxy-activated supports of Eupergit C 250L via multipoint covalent attachment. The resultant biocatalyst was explored for the hydrolytic resolution of a variety of (R,S)-2-hydroxycarboxylic acid Et esters. Results: With the hydrolytic resolution of (R,S)-Et mandelate in biphasic media as the model system, optimal conditions of 55°, pH 6 buffer and isooctane as the organic phase were selected for improving the enzyme stability (activity retained from 10% to 50% at 96 h) and enantioselectivity (V_SV_R^-1 value enhanced from 44 to 319) in comparison to the performance of free enzyme. Moreover, the immobilized enzyme retained its activity and enantioselectivity after eight cycles of hydrolysis at 55°. When applying the resolution process to other (R,S)-2-hydroxycarboxylic acid Et esters, 2.4- to 4.0-fold enhancements of the enantioselectivity in general were obtainable. The enantioselectivity enhancement, good reusability and easy recovery after reaction indicate that the immobilized SNSM-87 may have the potential as an industrial biocatalyst for the preparation of optically pure 2-hydroxycarboxylic acids. In the experiment, the researchers used many compounds, for example, Ethyl 2-hydroxy-3-phenylpropanoate (cas: 15399-05-0Recommanded Product: Ethyl 2-hydroxy-3-phenylpropanoate).

Ethyl 2-hydroxy-3-phenylpropanoate (cas: 15399-05-0) belongs to esters. Esters perform as high-grade solvents for a broad array of plastics, plasticizers, resins, and lacquers, and are one of the largest classes of synthetic lubricants on the commercial market. Esterification is the general name for a chemical reaction in which two reactants (typically an alcohol and an acid) form an ester as the reaction product. Esters are common in organic chemistry and biological materials.Recommanded Product: Ethyl 2-hydroxy-3-phenylpropanoate

Referemce:
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Using a bio-inspired surface resonance plasmon electronic nose for fundamental research on human olfaction was written by Mantel, Marylou;Fournel, Arnaud;Staedle, Ines;Oelschlagel, Annegret;Carro, Jeanne;Dubreuil, Romain;Herrier, Cyril;Livache, Thierry;Haehner, Antje;Hummel, Thomas;Roy, Jean-Michel;Bensafi, Moustafa. And the article was included in Sensors and Actuators, B: Chemical in 2022.Formula: C9H10O3 This article mentions the following:

Electronic noses are artificial devices designed to detect and classify odors, used for many industrial applications but they can also be a tool for fundamental research on the chem. senses. Indeed, one major issue in research on olfaction is that the relationship between the structure of volatile olfactory compounds and the perception they evoke is still little understood. Acknowledging the importance of biol. in the equation, the present study offers a new way to approach to stimulus-percept problem in olfaction, 1/ by considering as stimulus the interaction between odorants and olfactory receptors and 2/ by extending the measure of percept and considering the issue of interindividual diversity. To this end, we used a bio-inspired surface resonance plasmon electronic nose (e-nose) and acquired response patterns for 20 representative odorants. We also collected perceptual ratings (on intensity, pleasantness, familiarity, edibility and irritation) and verbal description of the perceptual experience associated to these odorants in a sample of 74 individuals. Combining Principal Component Anal. and Dissimilarity Matrix Anal., we showed a relationship between the e-nose space and both measures of perception, but only for odorants eliciting homogenous responses among the subjects. This study thus shows the relevance of a bio-inspired e-nose as a model of olfactory receptors interactions for the study of natural olfaction. In the experiment, the researchers used many compounds, for example, Ethyl 2-hydroxybenzoate (cas: 118-61-6Formula: C9H10O3).

Ethyl 2-hydroxybenzoate (cas: 118-61-6) belongs to esters. Esters are also usually derived from carboxylic acids. It may also be obtained by reaction of acid anhydride or acid halides with alcohols or by the reaction of salts of carboxylic acids with alkyl halides. Esters are more polar than ethers but less polar than alcohols. They participate in hydrogen bonds as hydrogen-bond acceptors, but cannot act as hydrogen-bond donors, unlike their parent alcohols. This ability to participate in hydrogen bonding confers some water-solubility.Formula: C9H10O3

Referemce:
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Screening and characteristic aroma analysis of aroma-producing yeasts in high-temperature Daqu was written by Lu, Yan-xiang;Liang, Hui-zhen;Chen, Peng;Liu, Zheng;Zhong, Cheng. And the article was included in Shipin Yanjiu Yu Kaifa in 2021.Safety of Isopentyl 3-methylbutanoate This article mentions the following:

Two yeast strains characterized by high aroma production, namely Y3 and Y5, were obtained from the high-temperature Daqu. After separation and purification, primary screening for aroma production using liquid fermentation, and secondary screening using solid fermentation were performed. Headspace solid-phase microextraction-gas chromatog.-mass spectrometry (HS-SPME-GC-MS) was employed to detect and analyze the products obtained after solid-state fermentation of Y3 and Y5. As a result, 43 and 37 volatile aroma compounds were recovered from Y3 and Y5, resp. The main aroma producing compounds among the products obtained after Y3 solid-state fermentation were β-phenethyl alc., isoamyl alc., isovaleric acid, and Et butyrate, and those obtained after Y5 solid-state fermentation were β-phenylethanol, 4-vinylguaiacol, and isoamyl alc. acid. Based on the morphol., physiol., and biochem. examinations, and mol. identification, Y3 was identified as Saccharomycopsis fibuligera, and Y5 was identified as Wickerhamomyces anomalus. Thereafter, Y3 and Y5 were mixed in equal proportions, and added to the Maotai-flavored liquor fermented grains to simulate the production and fermentation, and then the distilled liquor samples were examined using gas chromatog. (GC) for skeleton composition The results revealed that both Y3 and Y5 significantly increased the levels of Et acetate, Et lactate, and β-phenylethanol in liquor. In the experiment, the researchers used many compounds, for example, Isopentyl 3-methylbutanoate (cas: 659-70-1Safety of Isopentyl 3-methylbutanoate).

Isopentyl 3-methylbutanoate (cas: 659-70-1) belongs to esters. Esters are widespread in nature and are widely used in industry. In nature, fats are in general triesters derived from glycerol and fatty acids. Esters are responsible for the aroma of many fruits. Because of their lack of hydrogen-bond-donating ability, esters do not self-associate. Consequently, esters are more volatile than carboxylic acids of similar molecular weight.Safety of Isopentyl 3-methylbutanoate

Referemce:
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Discovery and Characterization of R/S-N-3-Cyanophenyl-N’-(6-tert-butoxycarbonylamino-3,4-dihydro-2,2-dimethyl-2H-1-benzopyran-4-yl)urea, a New Histone Deacetylase Class III Inhibitor Exerting Antiproliferative Activity against Cancer Cell Lines was written by Schnekenburger, Michael;Goffin, Eric;Lee, Jin-Young;Jang, Jun Young;Mazumder, Aloran;Ji, Seungwon;Rogister, Bernard;Bouider, Nafila;Lefranc, Florence;Miklos, Walter;Mathieu, Veronique;de Tullio, Pascal;Kim, Kyu-Won;Dicato, Mario;Berger, Walter;Han, Byung Woo;Kiss, Robert;Pirotte, Bernard;Diederich, Marc. And the article was included in Journal of Medicinal Chemistry in 2017.Product Details of 16413-26-6 This article mentions the following:

A new series of (N-aryl-N’-3,4-dihydro-2,2-dimethyl-2H-1-benzopyran-4-yl)ureas bearing an alkoxycarbonylamino group at the 6-position were synthesized and examined as putative anticancer agents targeting sirtuins in glioma cells. On the basis of computational docking combined to in vitro sirtuin 1/2 inhibition assays, we selected compound I [R/S-N-3-cyanophenyl-N’-(6-tert-butoxycarbonylamino-3,4-dihydro-2,2-dimethyl-2H-1-benzopyran-4-yl)urea] which displays a potent antiproliferative activity on various glioma cell types, assessed by quant. video microscopy, eventually triggering senescence. The impact on normal glial cells was lower with a selectivity index of >10. Furthermore, human U373 and Hs683 glioblastoma cell lines served to demonstrate the inhibitory activity of I against histone deacetylase (HDAC) class III sirtuins 1 and 2 (SIRT1/2) by quantifying acetylation levels of histone and non-histone proteins. The translational potential of I was validated by an NCI-60 cell line screen and validation of growth inhibition of drug resistant cancer cell models. Eventually, the anticancer potential of I was validated in 3D glioblastoma spheroids and in vivo by zebrafish xenografts. In summary, compound I is the first representative of a new class of SIRT inhibitors opening new perspectives in the medicinal chem. of HDAC inhibitors. In the experiment, the researchers used many compounds, for example, 3-Cyanophenylisocyanate (cas: 16413-26-6Product Details of 16413-26-6).

3-Cyanophenylisocyanate (cas: 16413-26-6) belongs to esters. Esters are widespread in nature and are widely used in industry. In nature, fats are in general triesters derived from glycerol and fatty acids. Esters are responsible for the aroma of many fruits, including apples, durians, pears, bananas, pineapples, and strawberries. Esters are more polar than ethers but less polar than alcohols. They participate in hydrogen bonds as hydrogen-bond acceptors, but cannot act as hydrogen-bond donors, unlike their parent alcohols. This ability to participate in hydrogen bonding confers some water-solubility.Product Details of 16413-26-6

Referemce:
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Isoindolinone ureas: a novel class of KDR kinase inhibitors was written by Curtin, Michael L.;Frey, Robin R.;Heyman, H. Robin;Sarris, Kathy A.;Steinman, Douglas H.;Holmes, James H.;Bousquet, Peter F.;Cunha, George A.;Moskey, Maria D.;Ahmed, Asma A.;Pease, Lori J.;Glaser, Keith B.;Stewart, Kent D.;Davidsen, Steven K.;Michaelides, Michael R.. And the article was included in Bioorganic & Medicinal Chemistry Letters in 2004.Formula: C8H4N2O This article mentions the following:

A series of substituted isoindolinone ureas was prepared and evaluated for enzymic and cellular inhibition of KDR kinase activity. Several of these analogs, such as I, are potent inhibitors of KDR both enzymically (<50 nM) and cellularly (�00 nM). A 3D KDR/CDK2/MAP kinase overlay model with several structurally related tyrosine kinase inhibitors was used to predict the binding interactions of the isoindolinone ureas with the KDR active site. In the experiment, the researchers used many compounds, for example, 3-Cyanophenylisocyanate (cas: 16413-26-6Formula: C8H4N2O).

3-Cyanophenylisocyanate (cas: 16413-26-6) belongs to esters. Esters perform as high-grade solvents for a broad array of plastics, plasticizers, resins, and lacquers, and are one of the largest classes of synthetic lubricants on the commercial market. Polyesters are important plastics, with monomers linked by ester moieties. Because of their lack of hydrogen-bond-donating ability, esters do not self-associate. Consequently, esters are more volatile than carboxylic acids of similar molecular weight.Formula: C8H4N2O

Referemce:
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Assembly of Divalent Ligands and Their Effect on Divalent Binding to Pseudomonas aeruginosa Lectin LecA was written by Yu, Guangyun;Vicini, Anna Chiara;Pieters, Roland J.. And the article was included in Journal of Organic Chemistry in 2019.Name: (2S,3R,4S,5S,6R)-6-(Acetoxymethyl)tetrahydro-2H-pyran-2,3,4,5-tetrayl tetraacetate This article mentions the following:

Divalent ligands were prepared as inhibitors for the adhesion protein of the problematic Pseudomonas aeruginosa pathogen. Bridging two binding sites enables simultaneous binding of two galactose moieties which strongly enhances binding. An alternating motif of glucose and triazole and aryl groups was shown to have the right mix of rigidity, solubility and ease of synthesis. Spacers were varied with respect to the core unit as well as the aglycon portions, to optimize dynamics and enhance interactions with the protein. Affinities of the divalent ligands were measured by ITC and Kd’s as low as 12 nM were determined, notably for a com-pounds with either a rigid (phenyl) or flexible (butyl) unit at the core. Introducing a Ph aglycon moiety next to the galactoside ligands on both termini did indeed lead to a higher enthalpy of binding which was more than compensated by entropic costs. The results were discussed in terms of thermodn. and theor. calculations of the expected and observed multivalency effects. In the experiment, the researchers used many compounds, for example, (2S,3R,4S,5S,6R)-6-(Acetoxymethyl)tetrahydro-2H-pyran-2,3,4,5-tetrayl tetraacetate (cas: 4163-60-4Name: (2S,3R,4S,5S,6R)-6-(Acetoxymethyl)tetrahydro-2H-pyran-2,3,4,5-tetrayl tetraacetate).

(2S,3R,4S,5S,6R)-6-(Acetoxymethyl)tetrahydro-2H-pyran-2,3,4,5-tetrayl tetraacetate (cas: 4163-60-4) belongs to esters. Esters are widespread in nature and are widely used in industry. In nature, fats are in general triesters derived from glycerol and fatty acids. Esters are responsible for the aroma of many fruits. Acyl chlorides and acid anhydrides alcoholysis is another way to produce esters. Acyl chlorides and acid anhydrides react with alcohols to produce esters. Anydrous conditions are recommended since both acyl chlorides and acid anhydrides react with water.Name: (2S,3R,4S,5S,6R)-6-(Acetoxymethyl)tetrahydro-2H-pyran-2,3,4,5-tetrayl tetraacetate

Referemce:
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Genomic and hormonal biomarkers of phthalate induced male rat reproductive developmental toxicity part II: a targeted RT-qPCR array approach that defines a unique adverse outcome pathway was written by Gray, Leon Earl Jr.;Lambright, Christy S.;Conley, Justin M.;Evans, Nicola;Furr, Johnathan R.;Hannas, Bethany R.;Wilson, Vickie S.;Sampson, Hunter;Foster, Paul M. D.. And the article was included in Toxicological Sciences in 2021.COA of Formula: C20H26O4 This article mentions the following:

Previously, we demonstrated that exposure to some diortho-phthalate esters during sexual differentiation disrupts male reproductive development by reducing fetal rat testis testosterone production (T Prod) and gene expression in a dose-related manner. The objectives of the current project were to expand the number of test compounds that might reduce fetal T Prod, including phthalates, phthalate alternatives, pesticides, and drugs, and to compare reductions in T Prod with altered testis mRNA expression. We found that PEs that disrupt T Prod also reduced expression of a unique “cluster” of mRNAs for about 35 genes related to sterol transport, testosterone and insulin-like hormone 3 hormone syntheses, and lipoprotein signaling and cholesterol synthesis. However, phthalates had little or no effect on mRNA expression of genes in peroxisome proliferator-activated receptor (PPAR) pathways in the fetal liver, whereas the 3 PPAR agonists induced the expression of mRNA for multiple fetal liver PPAR pathway genes without reducing testis T Prod. In summary, phthalates that disrupt T Prod act via a novel adverse outcome pathway including down regulation of mRNA for genes involved in fetal endocrine function and cholesterol synthesis and metabolism This profile was not displayed by PEs that did not reduce T Prod, PPAR agonists or the other chems. Reductions in fetal testis gene expression and T Prod in utero can be used to establish relative potency factors that can be used quant. to predict the doses of individual PEs and mixtures of phthalates that produce adverse reproductive tract effects in male offspring. In the experiment, the researchers used many compounds, for example, Dicyclohexyl phthalate (cas: 84-61-7COA of Formula: C20H26O4).

Dicyclohexyl phthalate (cas: 84-61-7) belongs to esters. Esters perform as high-grade solvents for a broad array of plastics, plasticizers, resins, and lacquers, and are one of the largest classes of synthetic lubricants on the commercial market. Polyesters are important plastics, with monomers linked by ester moieties. Esterification is the general name for a chemical reaction in which two reactants (typically an alcohol and an acid) form an ester as the reaction product. Esters are common in organic chemistry and biological materials.COA of Formula: C20H26O4

Referemce:
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Iodide ion promotion of benzyl chloride-borate ester carbonylation reactions was written by Alper, Howard;Hamel, Nathalie;Smith, David J. H.;Woell, James B.. And the article was included in Tetrahedron Letters in 1985.SDS of cas: 587-88-2 This article mentions the following:

Esters RC₆H₄CH₂CO₂R¹ (R = H, p-Me, o-OMe, m-Me, p-F; R¹ = Et, CHMe₂, Bu, CMe₃) and R²CH₂CO₂R¹ (R² = 1-, 2-naphthyl) were isolated (54-100% yield) from the Rh(I)-catalyzed reaction of RC₆H₄CH₂Cl and R²CH₂Cl with B(OR¹)₃ and CO, in the presence of KI. In the experiment, the researchers used many compounds, for example, Ethyl 2-(4-fluorophenyl)acetate (cas: 587-88-2SDS of cas: 587-88-2).

Ethyl 2-(4-fluorophenyl)acetate (cas: 587-88-2) belongs to esters. Esters perform as high-grade solvents for a broad array of plastics, plasticizers, resins, and lacquers, and are one of the largest classes of synthetic lubricants on the commercial market. Liquid esters of low volatility serve as softening agents for resins and plastics. Esters also include many industrially important polymers. Polymethyl methacrylate is a glass substitute sold under the names Lucite and Plexiglas; polyethylene terephthalate is used as a film (Mylar) and as textile fibres sold as Terylene, Fortrel, and Dacron.SDS of cas: 587-88-2

Referemce:
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Rh(III)-Catalyzed C-H Functionalization of N-Nitrosoanilines with α-Sulfonylcarbenes was written by Peng, Rui-jun;Chen, Lei;Zhang, Xue-jing;Yan, Ming. And the article was included in Advanced Synthesis & Catalysis in 2022.Reference of 62020-09-1 This article mentions the following:

A Rh(III)-catalyzed ortho C-H functionalization of N-nitrosoanilines with α-sulfonylcarbenes had been developed. The reaction was carried out under mild conditions and fuctionalized N-nitrosoanilines I [R¹ = H, 4-Me, 5-Cl, etc.; R² = Me, Et, i-Pr, Bn; R³ = Me, Ph, 4-MeC₆H₄; R⁴ = C(O)Me, CO₂Me, C(O)Ph, SO₂Ph, naphthalene-2-carbonyl] were obtained with good to excellent yields. The diverse transformations of the products to ortho-functionalized anilines and nitrogen heterocycles were achieved. Furthermore, a cascade reaction of N-nitrosoanilines and α-sulfonyl-α-diazo-ketones provided 3-sulfonyl-indoles II [R⁵ = H, 5-F, 6-Cl, etc.; R⁶ = Me, Bn; R⁷ = Me, Ph, 2-naphthyl; R⁸ = Me, Ph, 4-MeC₆H₄] efficiently. In the experiment, the researchers used many compounds, for example, Methyl 2-(methylsulfonyl)acetate (cas: 62020-09-1Reference of 62020-09-1).

Methyl 2-(methylsulfonyl)acetate (cas: 62020-09-1) belongs to esters. Esters typically have a pleasant smell; those of low molecular weight are commonly used as fragrances and are found in essential oils and pheromones. Acyl chlorides and acid anhydrides alcoholysis is another way to produce esters. Acyl chlorides and acid anhydrides react with alcohols to produce esters. Anydrous conditions are recommended since both acyl chlorides and acid anhydrides react with water.Reference of 62020-09-1

Referemce:
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Analysis of volatile flavor compounds of γ-aminobutyric acid soybean paste was written by Li, Fu-xiao;Li, Dong-long;Wang, Hui-yi;Li, Qiu-feng;Liu, Ji-dong. And the article was included in Xiandai Shipin Keji in 2021.Synthetic Route of C10H20O2 This article mentions the following:

To evaluate the flavor difference between com. soybean paste and γ-aminobutyric acid (GABA) bean paste, headspace solid-phase microextraction (HS-SPME) and gas chromatog.-mass spectrometry (GC-MS) were used to measure and analyze the volatile components and the common indexes in nine com. soybean paste samples (S1-S9) and the GABA soybean paste sample (S10) . The key volatile components were determined by principal component anal. (PCA) and odor activity value (OAV) . The results showed that 144 compounds in eight categories were detected in 10 soybean paste samples and the content of γ-aminobutyric acid in S10 reached 1.87 mg/g, the pH value was 4.69, and the color was bright without impurities. Among them, esters, alcs. and acids accounted for more than 60% of the total volatile components. Addnl., the results of PCA of 41 common volatile substances were identified in 10 soybean paste samples, demonstrating that 2-methyl-butyraldehyde, 3-methyl-butyraldehyde, dimethyl-trisulfide and guaiacol significantly contributed to the flavor formation of bean paste. Besides, the GABA soybean paste has a rich variety of flavors, in which the contents of 2-pentylfuran, 2-ethyl-6-methylpyrazine, guaiacol and di-Me trisulfide (which exhibited aromas of mung bean, nut and clove) were significantly higher than other samples. This could be the reason for some differences in flavor substances between GABA soybean paste and other samples. The results of this study could provide theor. reference for the development of functional soybean paste and the flavor improvement in soybean paste products. In the experiment, the researchers used many compounds, for example, Isopentyl 3-methylbutanoate (cas: 659-70-1Synthetic Route of C10H20O2).

Isopentyl 3-methylbutanoate (cas: 659-70-1) belongs to esters. Esters perform as high-grade solvents for a broad array of plastics, plasticizers, resins, and lacquers, and are one of the largest classes of synthetic lubricants on the commercial market. Polyesters are important plastics, with monomers linked by ester moieties. Esters contain a carbonyl center, which gives rise to 120° C–C–O and O–C–O angles. Unlike amides, esters are structurally flexible functional groups because rotation about the C–O–C bonds has a low barrier. Their flexibility and low polarity is manifested in their physical properties; they tend to be less rigid (lower melting point) and more volatile (lower boiling point) than the corresponding amides. Synthetic Route of C10H20O2

Referemce:
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics