Category: esters-buliding-blocks

Unconventional Knoevenagel-type indoles: Synthesis and cell-based studies for the identification of pro-apoptotic agents was written by Spallarossa, Andrea;Caneva, Chiara;Caviglia, Matteo;Alfei, Silvana;Butini, Stefania;Campiani, Giuseppe;Gemma, Sandra;Brindisi, Margherita;Zisterer, Daniela M.;Bright, Sandra A.;Williams, Clive D.;Crespan, Emmanuele;Maga, Giovanni;Sanna, Giuseppina;Delogu, Ilenia;Collu, Gabriella;Loddo, Roberta. And the article was included in European Journal of Medicinal Chemistry in 2015.HPLC of Formula: 62020-09-1 This article mentions the following:

A new series of indole-based analogs were recently identified as potential anticancer agents. The Knoevenagel-type indoles herein presented were prepared via a one-pot condensation of iminium salts with active methylene reagents and were isolated as single geometric isomers. Biol. evaluation in different cell-based assays revealed an antiproliferative activity for some analogs already in the nanomolar range against leukemia, breast and renal cancer cell lines. To explain these effects, the most promising analogs of the series were engaged in further cell-based studies. Compounds I [R¹ = R³ = H, R² = Ph, X = CN, Y = thien-2-yl-(E), SO₂Ph-(E); R¹ = R³ = H, R² = Ph, X = C(:O)Me, Y = SO₂Ph-(E); R¹ = R³ = H, R² = C₆H₄OMe-4, X = CN, Y = CN, SO₂Ph-(E)] highlighted a pro-apoptotic potential being able to induce apoptosis in HL60, K562 and MCF-7 cell lines in a dose and time-dependent manner. The ability of these compounds to arrest cell cycle at the G2/M phase inspired the immunofluorescence studies which allowed us to identify tubulin as a potential target for compounds (E)-I [R¹ = R³ = H, R² = Ph, X = CN, Y = SO₂Ph; R¹ = R³ = H, R² = C₆H₄OMe-4, X = CN, Y = SO₂Ph]. In the experiment, the researchers used many compounds, for example, Methyl 2-(methylsulfonyl)acetate (cas: 62020-09-1HPLC of Formula: 62020-09-1).

Methyl 2-(methylsulfonyl)acetate (cas: 62020-09-1) 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. 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.HPLC of Formula: 62020-09-1

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

Analysis of the characteristics of foxtail millet during storage under different light environments was written by Liang, Kehong;Liu, Yuhang;Liang, Shan. And the article was included in Journal of Cereal Science in 2021.Synthetic Route of C10H18O2 This article mentions the following:

In this work, the impacts of white, red and blue light-emitting diodes on the quality of millet during long-term storage were investigated. It was found that millet stored under blue light for 90 days showed a significantly slower reduction in malondialdehyde (MDA) content and fatty acid value, and a higher iodine value, than that stored under white- or red-light conditions. Furthermore, blue light was also shown to lower lipoxygenase (LOX) and lipopolysaccharide (LPS) activity during storage. Scanning electron microscope observation revealed that narrow cracks became wider as storage time increased, while a rougher texture and more cracks were seen after 90 days in the millet irradiated with red light than in those either irradiated with blue light or stored in dark conditions. The components related to oxidation, such as 5-hexyldihydro-2(3h)-furanone, 3-octen-2-one, trans-β-ionone, and hexanal contents, were found to be lower under blue light than under either red or white light. Moreover, principal component anal. indicated that the volatile components present in the of millet during storage under different light conditions were mainly aldehydes, ketones, esters, alcs. and hydrocarbons. In order to limit the adverse effects of these volatile components during long-term storage, based on the results of this study, we recommend that blue light could be applied as a clean and cheap technol. to extend the shelf life of millet. In the experiment, the researchers used many compounds, for example, 5-Hexyldihydrofuran-2(3H)-one (cas: 706-14-9Synthetic Route of C10H18O2).

5-Hexyldihydrofuran-2(3H)-one (cas: 706-14-9) 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. 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.Synthetic Route of C10H18O2

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

A general synthesis of oligopeptides containing an oxirane ring in the place of a peptidic bond was written by Mann, Andre;Quaranta, Laura;Reginato, Gianna;Taddei, Maurizio. And the article was included in Tetrahedron Letters in 1996.Synthetic Route of C16H24N2O4 This article mentions the following:

Mols. structurally analogous to dipeptides, containing an oxirane ring in the place of the peptide bond, can be prepared by oxidative conversion of β-hydroxy selenides obtained by Mukaiyama aldol-type reaction of N-protected β-amino α-selenyl aldehydes derived from naturally occurring amino acids. In the experiment, the researchers used many compounds, for example, (S)-tert-Butyl (1-(methoxy(methyl)amino)-1-oxo-3-phenylpropan-2-yl)carbamate (cas: 87694-53-9Synthetic Route of C16H24N2O4).

(S)-tert-Butyl (1-(methoxy(methyl)amino)-1-oxo-3-phenylpropan-2-yl)carbamate (cas: 87694-53-9) 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. 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 C16H24N2O4

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

Regioselective Synthesis of N²-Aryl 1,2,3-Triazoles via Electro-oxidative Coupling of Enamines and Aryldiazonium Salts was written by Baidya, Mrinmay;Mallick, Samrat;De Sarkar, Suman. And the article was included in Organic Letters in 2022.Name: Ethyl 3-oxo-3-(thiophen-2-yl)propanoate This article mentions the following:

An efficient synthetic route for the construction of N²-aryl 1,2,3-triazoles I (R = Me, cyclopropyl, 4-chlorophenyl, thiophen-2-yl, etc.; R¹ = COOMe, COOEt, C(O)Me; Ar = Ph, 3-chlorophenyl, 2,4,6-trimethylphenyl, etc.) is reported via sequential C-N bond formation and electro-oxidative N-N coupling under metal-free conditions. Readily accessible 2-aminoacrylates NH₂RC=CHCOOR¹ and aryldiazonium salts ArN₂⁺BF₄^– were used as starting materials, and the developed protocol displays excellent functional group tolerance, allowing an extensive range of substrate scope up to 91% isolated yield. Various mechanistic studies, along with the isolation of an intermediate adduct, refer to successive ionic and radical reaction sequences. In the experiment, the researchers used many compounds, for example, Ethyl 3-oxo-3-(thiophen-2-yl)propanoate (cas: 13669-10-8Name: Ethyl 3-oxo-3-(thiophen-2-yl)propanoate).

Ethyl 3-oxo-3-(thiophen-2-yl)propanoate (cas: 13669-10-8) 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. 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: Ethyl 3-oxo-3-(thiophen-2-yl)propanoate

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

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

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

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

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

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