Esters-buliding-blocks

Design, synthesis, and cytotoxicity evaluation of threonine-based galactoceramide with aromatic groups and various fatty-acyl side chains was written by Vudhgiri, Srikanth;Routhu, Sunitha Rani;Kumar, C. Ganesh;Prasad, R. B. N.;Reddy Jala, Ram Chandra. And the article was included in Medicinal Chemistry Research in 2018.Quality Control of (2S,3R,4S,5S,6R)-6-(Acetoxymethyl)tetrahydro-2H-pyran-2,3,4,5-tetrayl tetraacetate This article mentions the following:

In galactoceramides, presence of fatty-acyl group on amide moiety or phytosphingosine group is some of the important features that influence the cytotoxicity. Continuous efforts are in progress to modify the fatty-acid moiety and phytosphingosine group present on the galactoceramides to enhance the cytotoxic potential of these compounds Hence, in the present study, threonine-based β-galactoceramide and its derivatives were prepared by modifying the fatty-acyl group on amide moiety with different fatty-acyl moieties and aromatic acids employing trichloroacetimidate methodol. The structurally related threonine-based ceramide part was synthesized in multi-step process using different reagents. The ceramide part was glycosylated with galactose using trichloroacetimidate as donor. Further, all the synthesized compounds were evaluated for in vitro cytotoxicity against three cancer cell lines and one normal cell line and all the compounds exhibited good to moderate cytotoxicity against all the tested cancer cell lines. In aromatic derivatives, the compound I exhibited promising activity against MCF7, A549 and HeLa cancer cell lines with IC₅₀ values of 14.08, 14.78, and 16.70 μM, resp. In fatty-acid derivatives, two compounds exhibited promising activity, i.e., compound II against HeLa with IC₅₀ value 16.34 μM and compound III against MCF7 with IC₅₀ value 18.05 μM. Based on structure-activity relationship, aromatic acid derivatives exhibited potential activity as compared to fatty-acid derivatives Further, the influence of some of the key factors such as spacer chain length between aromatic residue and amide functional group, methoxy substituents on aryl group, terminal unsaturation of fatty acid and branching chain effect on the cytotoxicity are discussed. 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: 4163-60-4Quality Control of (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, including apples, durians, pears, bananas, pineapples, and strawberries. 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.Quality Control of (2S,3R,4S,5S,6R)-6-(Acetoxymethyl)tetrahydro-2H-pyran-2,3,4,5-tetrayl tetraacetate

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

Molecular mechanism of high pressure shear grinding on Feng-flavour Chinese Baijiu ageing was written by Jia, Wei;Fan, Zibian;Du, An;Shi, Lin. And the article was included in Food Research International in 2022.SDS of cas: 106-79-6 This article mentions the following:

Ultrahigh-pressure homogenization is a powerful technique for accelerating Baijiu ageing. In this study, the mol. mechanism of artificial ageing was thoroughly investigated utilizing foodomics combined with a mass spectrum information optimization program. Various characterizations of compounds in the ageing process were performed through ultra high performance liquid chromatog. quadrupole-orbitrap high resolution mass spectrometry (UHPLC-Q-Orbitrap) based colloid theoretics. High-pressure shear grinding provides a high-pressure and high-temperature environment for Baijiu, accelerating the formation of flavor compounds and the decomposition of odor and harmful substances, thus improving the sensory characteristics of Feng-flavor Baijiu and shortening the ageing time. A total of 2069 substances were identified according to fragment spectra and Bayesian network model-based peak distribution. Mols. with VIP > 1, including 14 esters, 10 acids, 4 ketones, 3 aldehydes, 2 alcs. and 2 phenols, were quantified as potential markers of chemometric anal. A novel prediction model for Baijiu ageing degree was furnished, and ageing years of Feng-flavor Chinese Baijiu were accurately predicted by factor anal. with KMO 0.784 and a polynomial regression model with r 0.94. The results demonstrated that in 400 bar, fresh distilled Baijiu could reach a natural ageing effect of 6.43 years, which was consistent with the sensory evaluation. In the experiment, the researchers used many compounds, for example, Dimethyl decanedioate (cas: 106-79-6SDS of cas: 106-79-6).

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. 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: 106-79-6

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

High methane storage and working capacities in a NbO-type metal-organic framework was written by Song, Chengling;Liu, Huimin;Jiao, Jingjing;Bai, Dongjie;Zhou, Wei;Yildirim, Taner;He, Yabing. And the article was included in Dalton Transactions in 2016.Category: esters-buliding-blocks This article mentions the following:

To improve methane adsorption by pore structure optimization, we developed a new organic linker and used it to construct a NbO-type metal-organic framework ZJNU-53 that, after activation, exhibits exceptionally high methane storage and working capacities of 241 and 190 cm³ (STP) cm^-3 at 298 K and 65 bar, resp., if the packing loss is not considered, which are among the highest reported for MOF materials. In the experiment, the researchers used many compounds, for example, Dimethyl 5-ethynylisophthalate (cas: 313648-56-5Category: esters-buliding-blocks).

Dimethyl 5-ethynylisophthalate (cas: 313648-56-5) 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. 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.Category: esters-buliding-blocks

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

Synthesis of 2-aminothiazole derivatives was written by Choudhari, S. R.;Goswami, D. D.;Thakar, K. A.. And the article was included in Journal of the Indian Chemical Society in 1978.SDS of cas: 33166-79-9 This article mentions the following:

Fourteen I [R = 4,2-Cl(HO)C₆H₃ 3,4-Cl₂C₆H₃, 2,5-BrMeC₆H₃, etc.; R¹ = H] were prepared by cyclocondensation of acetophenones, 2-haloacetophenones, and benzoylacetate esters with thiourea. Six I (R¹ = p-H₂NC₆H₄SO₂) were prepared from the resp. I (R¹ = H). The hypo- and hyperglycemic activity of nine I were tabulated. In the experiment, the researchers used many compounds, for example, Ethyl 3-oxo-3-(m-tolyl)propanoate (cas: 33166-79-9SDS of cas: 33166-79-9).

Ethyl 3-oxo-3-(m-tolyl)propanoate (cas: 33166-79-9) 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. 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.SDS of cas: 33166-79-9

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

Rhodium(I)-Catalyzed Coupling-Cyclization of C=O Bonds with α-Diazoketones was written by Chen, Ziyang;Hu, Xinwei;Huang, Junmin;Zeng, Wei. And the article was included in Organic Letters in 2018.COA of Formula: C9H10O3S This article mentions the following:

An unprecedented intermol. nucleophilic attack of C=X bonds (X = O and S) on the rhodium(I)-carbenes has been developed. This transformation allows for the coupling-cyclization of aroylamides with α-diazoketones and provides concise access to 2,4,5-trisubstituted 1,3-oxazoles, e.g., I, and 1,3-thiazoles, e.g., II, with a broad tolerance of functional groups. In the experiment, the researchers used many compounds, for example, Ethyl 3-oxo-3-(thiophen-2-yl)propanoate (cas: 13669-10-8COA of Formula: C9H10O3S).

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.COA of Formula: C9H10O3S

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

The Synthesis of a Terminally Linked Homodimeric Bisdistamycin Analog was written by Al-Said, Naim H.. And the article was included in Monatshefte fuer Chemie in 2006.Synthetic Route of C7H8N2O4 This article mentions the following:

A practical synthetic route to a terminally linked homodimeric bisdistamycin analog is described. In this analog the two strands of tricarboxamides of the pyrrole-pyrrole-pyrrole array are tethered from the nitrogen atom of the terminal pyrrole by a bis(ethoxyethane)chain. In the experiment, the researchers used many compounds, for example, Ethyl 4-nitro-1H-pyrrole-2-carboxylate (cas: 5930-92-7Synthetic Route of C7H8N2O4).

Ethyl 4-nitro-1H-pyrrole-2-carboxylate (cas: 5930-92-7) 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. 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 C7H8N2O4

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

Improved Total Synthesis of Tubulysins and Design, Synthesis, and Biological Evaluation of New Tubulysins with Highly Potent Cytotoxicities against Cancer Cells as Potential Payloads for Antibody-Drug Conjugates was written by Nicolaou, K. C.;Erande, Rohan D.;Yin, Jun;Vourloumis, Dionisios;Aujay, Monette;Sandoval, Joseph;Munneke, Stefan;Gavrilyuk, Julia. And the article was included in Journal of the American Chemical Society in 2018.Formula: C16H24N2O4 This article mentions the following:

Improved, streamlined total syntheses of natural tubulysins such as V and U, I (R = β-OH, β-OAc, resp.), and pretubulysin D I (R = H), and their application to the synthesis of designed tubulysin analogs, are described. Cytotoxicity evaluation of the synthesized compounds against certain cancer cell lines revealed a number of novel analogs with exceptional potencies [e.g., II: IC₅₀ = 40 pM against MES SA (uterine sarcoma) cell line; IC₅₀ = 6 pM against HEK 293T (human embryonic kidney cancer) cell line; and IC₅₀ = 1.54 nM against MES SA DX (MES SA with marked multidrug resistance) cell line]. These studies led to a set of valuable structure-activity relationships that provide guidance to further mol. design, synthesis, and biol. evaluation studies. The extremely potent cytotoxic compounds discovered in these investigations are highly desirable as potential payloads for antibody-drug conjugates and other drug delivery systems for personalized targeted cancer chemotherapies. 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: 87694-53-9Formula: C16H24N2O4).

(S)-tert-Butyl (1-(methoxy(methyl)amino)-1-oxo-3-phenylpropan-2-yl)carbamate (cas: 87694-53-9) belongs to esters. Carboxylic acid esters of low molecular weight are colourless, volatile liquids with pleasant odours, slightly soluble in water. 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: C16H24N2O4

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

Gas chromatographic enantiomer separation of mandelates and its analogs on permethylated cyclodextrin chiral stationary phases was written by Nie, Mengyan;Zhou, Liangmo;Wang, Qinghai;Zhu, Taoqian. And the article was included in Fenxi Huaxue in 2000.Name: Ethyl 2-hydroxy-3-phenylpropanoate This article mentions the following:

Gas chromatog. enantiomer separation of mandelates and its analogs was studied on permethylated β-cyclodextrin (PMBCD) and permethylated γ-cyclodextrin (PMGCD) chiral stationary phases (CSPs). The compounds studied included Me and Et mandelates, Me and Et α-methoxymandelates, Me and Et 3-phenylacetates, Et 2-hydroxy-4-Ph butyrate. All the compounds studied can be chirally separated to baseline on PMBCD CSPs, but no enantiomer separation was observed on PMGCD CSPs for all the tested compounds Some thermodn. data were evaluated for the mechanism of chiral recognition between permethylated cyclodextrins and mandelates and their analogs. In the experiment, the researchers used many compounds, for example, Ethyl 2-hydroxy-3-phenylpropanoate (cas: 15399-05-0Name: Ethyl 2-hydroxy-3-phenylpropanoate).

Ethyl 2-hydroxy-3-phenylpropanoate (cas: 15399-05-0) 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. 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.Name: Ethyl 2-hydroxy-3-phenylpropanoate

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

Characterization of the key aroma-active compounds in Yongchuan douchi (fermented soybean) by application of the sensomics approach was written by Wang, Shuqi;Chang, Yuan;Liu, Bing;Chen, Haitao;Sun, Baoguo;Zhang, Ning. And the article was included in Molecules in 2021.Application In Synthesis of 5-Ethyldihydrofuran-2(3H)-one This article mentions the following:

Yongchuan douchi is a traditional fermented soya bean product which is popular in Chinese dishes due to its unique flavor. In this study, the key aroma-active compounds of Yongchuan douchi were characterized by the combined gas chromatog.-olfactometry (GC-O) and gas chromatog.-mass spectrometry (GC-MS) with sensory evaluation. In total, 49 aroma compounds were sniffed and identified, and 20 of them with high flavor dilution factors (FD) and odor activity values (OAVs) greater than one were screened by applied aroma extract dilution anal. (AEDA) and quantitated anal. Finally, aroma recombination and omission experiments were performed and 10 aroma-active compounds were thought to have contributed significantly including 2,3-butanedione (butter, cheese), di-Me trisulfide (garlic-like), acetic acid (pungent sour), acetylpyrazine (popcorn-like), 3-methylvaleric acid (sweaty), 4-methylvaleric acid (sweaty), 2-mehoxyphenol (smoky), maltol (caramel), γ-nonanolactone (coconut-like), eugenol (woody) and phenylacetic acid (flora). In addition, sensory evaluation showed that the flavor profile of Yongchuan douchi mainly consisted of sauce-like, sour, nutty, smoky, caramel and fruity notes. In the experiment, the researchers used many compounds, for example, 5-Ethyldihydrofuran-2(3H)-one (cas: 695-06-7Application In Synthesis of 5-Ethyldihydrofuran-2(3H)-one).

5-Ethyldihydrofuran-2(3H)-one (cas: 695-06-7) 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. 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. Application In Synthesis of 5-Ethyldihydrofuran-2(3H)-one

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

Larvicidal Activity of Essential Oils of Five Apiaceae Taxa and Some of Their Main Constituents Against Culex quinquefasciatus was written by Pavela, Roman;Maggi, Filippo;Cianfaglione, Kevin;Bruno, Maurizio;Benelli, Giovanni. And the article was included in Chemistry & Biodiversity in 2018.Application of 659-70-1 This article mentions the following:

Apiaceae are aromatic herbs producing essential oils which are used on an industrial scale for various purposes. Notably, Apiaceae essential oils may replace synthetic insecticides keeping most of their efficacy and avoiding environmental pollution and human poisoning. In the present work, we explored the insecticidal potential of the essential oils from five Apiaceae taxa, namely Sison amomum, Echinophora spinosa, Heracleum sphondylium subsp. sphondylium, Heracleum sphondylium subsp. ternatum, and Trachyspermum ammi, as well as their major constituents (sabinene, p-cymene, terpinolene, myristicin, and thymol), against the filariasis vector Culex quinquefasciatus. For the purpose, the essential oils were obtained by hydrodistillation and their composition was achieved by gas chromatog./mass spectrometry (GC/MS). Their acute toxicity on third instar larvae of C. quinquefasciatus was determined The two most active essential oils were those from T. ammi fruits and E. spinosa roots, showing LC₅₀ below 20 μl/l and LD₉₀ below 50 μl/l. These oils were dominated by the monoterpene phenol thymol and the phenylpropanoid myristicin, resp., which showed the strongest larvicidal activity (LC₅₀ of 15.1 and 16.3 μl/l, resp.) among the pure compounds tested. These results showed that Apiaceae may be useful as source of larvicidal compounds to be used for the development of cheap, effective and eco-friendly insecticidal formulations. In the experiment, the researchers used many compounds, for example, Isopentyl 3-methylbutanoate (cas: 659-70-1Application of 659-70-1).

Isopentyl 3-methylbutanoate (cas: 659-70-1) 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. 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.Application of 659-70-1

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