Month: February 2023

4-[4-(4-Fluorophenyl)-2-methyl-5-oxo-2,5-dihydroisoxazol-3-yl]pyridinium iodide-4-[3-(4-fluorophenyl)-2-methyl-5-oxo-2,5-dihydroisoxazol-4-yl]pyridinium iodide (0.6/0.4) was written by Margutti, Simona;Schollmeyer, Dieter;Laufer, Stefan. And the article was included in Acta Crystallographica, Section E: Structure Reports Online in 2008.Synthetic Route of C10H11FO2 This article mentions the following:

The crystal structure of 4-[4-(4-fluorophenyl)-2-methyl-5-oxo-2,5-dihydroisoxazol-3-yl]pyridinium iodide-4-[3-(4-fluorophenyl)-2-methyl-5-oxo-2,5-dihydroisoxazol-4-yl]pyridinium iodide (0.6/0.4), C₁₆H₁₆FN₂O₂⁺·I^–, was determined as part of a study of the biol. activity of isoxazolone derivatives as p38 mitogen-activated protein kinase (MAPK) inhibitors. The x-ray crystal structure of 4-[4-(4-fluorophenyl)-2-Me-5-oxo-2,5-dihydroisoxazol-3-yl]pyridinium iodide showed the regioisomer 4-[3-(4-fluorophenyl)-2-Me-5-oxo-2,5-dihydroisoxazol-4-yl]pyridinium iodide. The synthesis of the former compound was achieved by reacting 4-(4-fluorophenyl)-3-(4-pyridyl)isoxazol-5(2H)-one after treatment with Et₃N in DMF, with iodomethane. The unexpected formation of the regioisomer could be explained by a rearrangement occurring via aziridine of the isoxazolone compound The regioisomers have site occupancies of 0.632(4)/0.368(4). The 2 6 members rings make a dihedral angle of 66.8(2)°. Crystallog. data are given. In the experiment, the researchers used many compounds, for example, Ethyl 2-(4-fluorophenyl)acetate (cas: 587-88-2Synthetic Route of C10H11FO2).

Ethyl 2-(4-fluorophenyl)acetate (cas: 587-88-2) belongs to esters. Carboxylic acid esters of low molecular weight are colourless, volatile liquids with pleasant odours, slightly soluble in water. Many esters have the potential for conformational isomerism, but they tend to adopt an s-cis (or Z) conformation rather than the s-trans (or E) alternative, due to a combination of hyperconjugation and dipole minimization effects. The preference for the Z conformation is influenced by the nature of the substituents and solvent, if present. Lactones with small rings are restricted to the s-trans (i.e. E) conformation due to their cyclic structure.Synthetic Route of C10H11FO2

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

Characteristic components of botrytized wine. V. Some neutral volatile compounds of botrytized wine was written by Yunome, H.;Nishimura, K.;Masuda, M.;Zenibayashi, Y.;Ohkawa, E.. And the article was included in Hakko Kogaku Kaishi in 1981.Product Details of 15399-05-0 This article mentions the following:

The volatile neutral components of botrytized wines prepared from Riesling and Semillon grapes were isolated and enriched by liquid-liquid extraction (n-pentane) and then analyzed by gas chromatog. and GC-MS spectrometry. Among 143 flavor compounds identified, quant. differences between the botrytized wines and the normal wines were noted for 33 compounds The following compounds were present in larger amounts in the botrytized wines: 3-octanol [589-98-0], 1-octen-3-ol [3391-86-4], benzaldehyde [100-52-7], furfural [98-01-1], γ-nonalactone [104-61-0], phthalide [87-41-2], Et levulinate [539-88-8], Et phenylacetate [101-97-3], di-Et glutarate [818-38-2], di-Et azelate [624-17-9], and 3 unknown compounds Twenty compounds were present in larger amounts in the normal wines. Some of the botrytized wine flavor appeared in normal wine on addition of 13 volatile and 5 nonvolatile compounds characteristic of botrytized wine. In the experiment, the researchers used many compounds, for example, Ethyl 2-hydroxy-3-phenylpropanoate (cas: 15399-05-0Product Details of 15399-05-0).

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.Product Details of 15399-05-0

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

Aminopyrazine Inhibitors Binding to an Unusual Inactive Conformation of the Mitotic Kinase Nek2: SAR and Structural Characterization was written by Whelligan, Daniel K.;Solanki, Savade;Taylor, Dawn;Thomson, Douglas W.;Cheung, Kwai-Ming J.;Boxall, Kathy;Mas-Droux, Corine;Barillari, Caterina;Burns, Samantha;Grummitt, Charles G.;Collins, Ian;van Montfort, Rob L. M.;Aherne, G. Wynne;Bayliss, Richard;Hoelder, Swen. And the article was included in Journal of Medicinal Chemistry in 2010.Quality Control of Methyl 2-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate This article mentions the following:

We report herein the first systematic exploration of inhibitors of the mitotic kinase Nek2. Starting from HTS hit aminopyrazine I, compounds with improved activity were identified using structure-based design. Our structural biol. investigations reveal two notable observations. First, I and related compounds bind to an unusual, inactive conformation of the kinase which to the best of our knowledge has not been reported for other types of kinase inhibitors. Second, a phenylalanine residue at the center of the ATP pocket strongly affects the ability of the inhibitor to bind to the protein. The implications of these observations are discussed, and the work described here defines key features for potent and selective Nek2 inhibition, which will aid the identification of more advanced inhibitors of Nek2. In the experiment, the researchers used many compounds, for example, Methyl 2-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate (cas: 525362-07-6Quality Control of Methyl 2-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate).

Methyl 2-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate (cas: 525362-07-6) 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. 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.Quality Control of Methyl 2-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate

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

Comparison of the acyl chain specificities of human myristoyl-CoA synthetase and human myristoyl-CoA:protein N-myristoyltransferase was written by Kishore, Nandini S.;Wood, David C.;Mehta, Pramod P.;Wade, Arlene C.;Lu, Tianbao;Gokel, George W.;Gordon, Jeffrey I.. And the article was included in Journal of Biological Chemistry in 1993.Reference of 3903-40-0 This article mentions the following:

Myristoyl-CoA synthetase (I) and protein N-myristoyltransferase (II) were partially purified from a human erythroleukemia cell line. Their substrate specificities were examined using 2 in vitro assays of enzyme activity together with a panel of C₇-C₁₇ saturated fatty acids plus 72 myristic acid analogs containing O, S, ketocarbonyl, ester, amide, cis and trans double bonds, triple bonds, and para-substituted Ph groups. There was an inverse relation between the polarity and the activity of C₁₄ fatty acid substrates of I. Surveys of tetradecenoic and tetradecynoic acids suggested that myristate is bound to I in a bent conformation with a principal bend occurring in the vicinity of C5-C6. I was able to tolerate a somewhat wider range of physicochem. properties in acyl chains than was the monomeric human II. However, like I, there was an inverse relation between acyl chain polarity and the activities of the acyl-CoA substrates of II. Moreover, the acyl chain of myristoyl-CoA appeared to be bound to II in a bent conformation with bends located in the vicinity of C5 and C8. The acyl chain specificities of both enzymes make them well suited to utilize efficiently any cellular pools of 5Z-tetradecenoic and 5Z,8Z-tetradecadienoic acids and their CoA derivatives This feature may account for the recent observation that in some mammalian cell lineages, certain N-myristoyl-proteins are heterogeneously acylated with these C₁₄ fatty acids. Finally, the acyl-CoA binding sites of human and Saccharomyces cerevisiae II appeared to have been highly conserved. Given their overlapping yet distinct peptide substrate specificities, the development of species-specific inhibitors of II should probably focus on structural features recognized in the enzyme peptide substrates rather than in the acyl chain of their acyl-CoA substrates. In the experiment, the researchers used many compounds, for example, 12-Methoxy-12-oxododecanoic acid (cas: 3903-40-0Reference of 3903-40-0).

12-Methoxy-12-oxododecanoic acid (cas: 3903-40-0) 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 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. Reference of 3903-40-0

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

Bicyclic Picomolar OGA Inhibitors Enable Chemoproteomic Mapping of Its Endogenous Post-translational Modifications was written by Gonzalez-Cuesta, Manuel;Sidhu, Peter;Ashmus, Roger A.;Males, Alexandra;Proceviat, Cameron;Madden, Zarina;Rogalski, Jason C.;Busmann, Jil A.;Foster, Leonard J.;Garcia Fernandez, Jose M.;Davies, Gideon J.;Ortiz Mellet, Carmen;Vocadlo, David J.. And the article was included in Journal of the American Chemical Society in 2022.Electric Literature of C8H6FNS This article mentions the following:

Owing to its roles in human health and disease, the modification of nuclear, cytoplasmic, and mitochondrial proteins with O-linked N-acetylglucosamine residues (O-GlcNAc) has emerged as a topic of great interest. Despite the presence of O-GlcNAc on hundreds of proteins within cells, only two enzymes regulate this modification. One of these enzymes is O-GlcNAcase (OGA), a dimeric glycoside hydrolase that has a deep active site cleft in which diverse substrates are accommodated. Chem. tools to control OGA are emerging as essential resources for helping to decode the biochem. and cellular functions of the O-GlcNAc pathway. Here we describe rationally designed bicyclic thiazolidine inhibitors that exhibit superb selectivity and picomolar inhibition of human OGA. Structures of these inhibitors in complex with human OGA reveal the basis for their exceptional potency and show that they extend out of the enzyme active site cleft. Leveraging this structure, we create a high affinity chemoproteomic probe that enables simple one-step purification of endogenous OGA from brain and targeted proteomic mapping of its post-translational modifications. These data uncover a range of new modifications, including some that are less-known, such as O-ubiquitination and N-formylation. We expect that these inhibitors and chemoproteomics probes will prove useful as fundamental tools to decipher the mechanisms by which OGA is regulated and directed to its diverse cellular substrates. Moreover, the inhibitors and structures described here lay out a blueprint that will enable the creation of chem. probes and tools to interrogate OGA and other carbohydrate active enzymes. In the experiment, the researchers used many compounds, for example, 4-Fluorobenzylisothiocyanate (cas: 2740-88-7Electric Literature of C8H6FNS).

4-Fluorobenzylisothiocyanate (cas: 2740-88-7) 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 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. Electric Literature of C8H6FNS

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

Effects of Diet on the Volatile Flavor and Nutritional Ingredients of Common Octopus (Octopus vulgaris) was written by Luo, Qihao;Wang, Weijun;Li, Zan;Zhu, Xinghua;Wang, Xue;Zhang, Tonghua;Xu, He;Yang, Jianmin. And the article was included in Journal of Ocean University of China in 2021.Application of 868-57-5 This article mentions the following:

Cephalopods are important economic shellfish that have been developed extensively in the coastal water of various countries. This study explored the effect of different diets on the volatile flavor and nutritional ingredients of O. vulgaris. Four diets were tested in four groups: Group A (fish (Scomberomorus niphonius)), Group B (crab (Helice tridens tientsinensis Rathbun)), Group C (clam (Mactra veneriformis)), and Group D (squid (Loligo japonica)). Octopus muscles were sampled after 36 days of feeding, and volatile flavor substances (VFSs), fatty acids (FAs), and amino acids (AAs) were detected. Results showed that the VFSs, FAs, and AAs of octopus in the four groups were obviously different. The sum of volatile ketones and aldehydes was higher in Group B than in the other groups, which could present much more flavors. All groups were abundant in unsaturated FAs, including eicosapentaenoic acid (EPA) and docosahexaenoic acid (DHA). In terms of content and variety, the FAs in Group B were more beneficial to human health than those in the other groups. The content of each AA in Group B was basically higher than those in the other groups and was significantly higher than that in Group D (P < 0.05). Comparing the VFSs, FAs, and AAs in samples fed with four kinds of diets, the results indicate that using crab to feed O. vulgaris can achieve better effects on volatile flavor and nutritional ingredients. In the experiment, the researchers used many compounds, for example, Methyl2-methylbutyrate (cas: 868-57-5Application of 868-57-5).

Methyl2-methylbutyrate (cas: 868-57-5) belongs to esters. Volatile esters with characteristic odours are used in synthetic flavours, perfumes, and cosmetics. Certain volatile esters are used as solvents for lacquers, paints, and varnishes. 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.Application of 868-57-5

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

Influence of fruit ripening on color, organic acid contents, capsaicinoids, aroma compounds, and antioxidant capacity of Shimatogarashi (Capsicum frutescens) was written by Manikharda;Takahashi, Makoto;Arakaki, Mika;Yonamine, Kaoru;Hashimoto, Fumio;Takara, Kensaku;Wada, Koji. And the article was included in Journal of Oleo Science in 2018.Product Details of 659-70-1 This article mentions the following:

Shimatogarashi (Capsicum frutescens) is a typical chili pepper domesticated in southern Japan. Important traits of Shimatogarashi peppers, such as color; proportion of organic acids, capsaicinoids, and aromatic compounds; and antioxidant activity in three stages of maturity (green (immature), orange (turning), and red (mature) stages) were characterized. The results indicated that the concentration of organic acids, including ascorbic, citric, and malic acid, increased during ripening. In addition, the amount of capsaicinoids, which are responsible for the pungent taste of chili peppers, increased as the fruit matured to the orange and red stages. The volatile compound profile of Shimatogarashi was dominated by the presence of esters, which mainly contributed to fruity notes. The total amount of volatile compounds analyzed by gas chromatog.-headspace solid-phase microextraction (GC-HS-SPME), especially esters, decreased as the fruit changed in color from green to red. This was in contrast to the amount of terpenoids, especially limonene, which increased at the red stage, denoting a change in flavor from fruity to a more citrus-like aroma. Based on the total phenolic content (TPC), the oxygen radical absorbance capacity (ORAC) and the diphenylpicrylhydrazyl (DPPH) free radical method, the antioxidant capacity of Shimatogarashi showed an increase at the mature red stage. However, while the red stage showed higher pungency and antioxidant capacity as well as an attractive color, the results of aromatic compound anal. revealed that the immature green stage had the advantages of having pleasant fruity smell, making it suitable for use in condiments. In the experiment, the researchers used many compounds, for example, Isopentyl 3-methylbutanoate (cas: 659-70-1Product Details of 659-70-1).

Isopentyl 3-methylbutanoate (cas: 659-70-1) belongs to esters. Carboxylic acid esters of low molecular weight are colourless, volatile liquids with pleasant odours, slightly soluble in water. 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.Product Details of 659-70-1

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

Aroma characterization and their changes during the processing of black teas from the cultivar, Camellia sinensis (L.) O. Kuntze cv. Jinmudan was written by Li, Junyao;Hao, Changhong;Jia, Huiyan;Zhang, Jing;Wu, Huiting;Ning, Jingming;Wang, Rangjian;Deng, Wei-Wei. And the article was included in Journal of Food Composition and Analysis in 2022.Reference of 695-06-7 This article mentions the following:

Jinmudan (JMD) black tea is processed from the JMD cultivar (Camellia sinensis (L.) O. Kuntze cv. Jinmudan). Dried JMD black tea (JMD-D) received a score of 7.43 in the quant. descriptive anal., indicating that it had the strongest fruity flavor. Many volatile compounds (129) were identified by solvent assisted flavor evaporation and gas chromatograph mass spectrometry. In total, 26 aroma active compounds, including (Z)-Me epi-jasmonate (flavor dilution factor (FD): 128-1024), benzeneacetaldehyde (FD: 512-1024), linalool (FD: 256-1024), geraniol (FD: 256-512), jasmine lactone (FD: 64-1024), were identified in JMD-D and controls through an aroma extract dilution anal. and gas chromatog.-mass spectrometry olfactometry. On the basis of the FD values, odor activity values, and relative quantification results, the volatiles of fruit flavor derived from lipids, such as jasmine lactone, were prominent in JMD-D compared to the controls. During the processing of the four types of black tea, the volatile fraction concentration increased mainly from the fresh leaf to the fermentation stage and decreased in the drying stage. In the experiment, the researchers used many compounds, for example, 5-Ethyldihydrofuran-2(3H)-one (cas: 695-06-7Reference of 695-06-7).

5-Ethyldihydrofuran-2(3H)-one (cas: 695-06-7) 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. 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 695-06-7

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

Heats of Combustion of Fatty Acids and Fatty Acid Esters was written by Levine, Felicia;Kayea, Ronald V. III;Wexler, Robert;Sadvary, D. J.;Melick, Cory;La Scala, John. And the article was included in Journal of the American Oil Chemists’ Society in 2014.Synthetic Route of C12H22O4 This article mentions the following:

The military uses JP-8, a kerosene type hydrocarbon, to fuel most of its vehicles and is seeking a renewable alternative fuel that meets strict JP-8 specifications. Biodiesel is typically a mixture of different alkyl esters produced from the transesterification of triglycerides readily available in plant oils and used cooking oil. To date, no traditional biodiesel meets the requirements for heat of combustion, f.p., viscosity and oxidative stability to be a stand-alone replacement for JP-8. This work is a fundamental survey of the heat of combustion of single fatty acid esters and a predictive model for estimating the heat of combustion given a known mol. structure. The gross heat of combustion of various C6-C18 fatty acids and the Me, Pr and iso-Pr esters of these fatty acids was measured. This study sought to relate the effect of chain length, degree of unsaturation and branching to the critical fuel property of the gross heat of combustion (H_c). It was found that H_c (kJ/g) increased with chain length. A nearly linear relationship was found between wt% carbon and hydrogen, and H_c. Group contribution models previously published for hydrocarbons and polymers were modified to more accurately predict the heat of combustion of the fatty acids and esters. Modification of the molar heat values of carboxylic acid, Me, and methylene groups improved correlation of the model with the exptl. results. In the experiment, the researchers used many compounds, for example, Dimethyl decanedioate (cas: 106-79-6Synthetic Route of C12H22O4).

Dimethyl decanedioate (cas: 106-79-6) belongs to esters. Carboxylic acid esters of low molecular weight are colourless, volatile liquids with pleasant odours, slightly soluble in water. 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.Synthetic Route of C12H22O4

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

A Three-Dimensional Dynamic Supramolecular “Sticky Fingers” Organic Framework was written by Fernandez-Bartolome, Estefania;Santos, Jose;Gamonal, Arturo;Khodabakhshi, Saeed;McCormick, Laura J.;Teat, Simon J.;Sanudo, E. Carolina;Costa, Jose Sanchez;Martin, Nazario. And the article was included in Angewandte Chemie, International Edition in 2019.Reference of 1190-39-2 This article mentions the following:

Engineering high-recognition host-guest materials is a burgeoning area in basic and applied research. The challenge of exploring novel porous materials with advanced functionalities prompted us to develop dynamic crystalline structures promoted by soft interactions. The first example of a pure mol. dynamic crystalline framework is demonstrated, which is held together by means of weak “sticky fingers” van der Waals interactions. The presented organic-fullerene-based material exhibits a non-porous dynamic crystalline structure capable of undergoing single-crystal-to-single-crystal reactions. Exposure to hydrazine vapors induces structural and chem. changes that manifest as toposelective hydrogenation of alternating rings on the surface of the [60]fullerene. Control experiments confirm that the same reaction does not occur when performed in solution Easy-to-detect changes in the macroscopic properties of the sample suggest utility as mol. sensors or energy-storage materials. In the experiment, the researchers used many compounds, for example, malonic acid dibutyl ester (cas: 1190-39-2Reference of 1190-39-2).

malonic acid dibutyl ester (cas: 1190-39-2) 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. Polyesters are important plastics, with monomers linked by ester moieties. Cyclic esters are called lactones, regardless of whether they are derived from an organic or inorganic acid. One example of an organic lactone is γ-valerolactone.Reference of 1190-39-2

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