Month: February 2023

Synthesis of α-Aryl Nitriles through Palladium-Catalyzed Decarboxylative Coupling of Cyanoacetate Salts with Aryl Halides and Triflates was written by Shang, Rui;Ji, Dong-Sheng;Chu, Ling;Fu, Yao;Liu, Lei. And the article was included in Angewandte Chemie, International Edition in 2011.SDS of cas: 587-88-2 This article mentions the following:

The synthesis of α-aryl nitriles through palladium-catalyzed decarboxylative coupling of cyanoacetate salts with aryl halides and triflates is reported. The reaction was extended to the preparation of α-aryl esters. 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 typically have a pleasant smell; those of low molecular weight are commonly used as fragrances and are found in essential oils and pheromones. 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

Simple Formation of an Abiotic Porphyrinogen in Aqueous Solution was written by Lindsey, Jonathan S.;Ptaszek, Marcin;Taniguchi, Masahiko. And the article was included in Origins of Life and Evolution of Biospheres in 2009.Name: Ethyl 4-methyl-1H-pyrrole-3-carboxylate This article mentions the following:

Porphyrins have long been proposed as key ingredients in the emergence of life yet plausible routes for forming their essential pyrrole precursor have heretofore not been identified. Here we show that the anaerobic reaction of δ-aminolevulinic acid (ALA, 1-5 mM) with the β-ketoester Me 4-methoxyacetoacetate (2-40 mM) in water (pH 5-7) at 70-100° for >6 h affords the porphyrinogen, which upon chem. oxidation gives the corresponding porphyrin in overall yield of up to 10%. The key intermediate is the α-methoxymethyl-substituted pyrrole, which undergoes tetramerization and macrocycle formation under kinetic control. The resulting type-I porphyrin bears four propionic acid and four carbomethoxy groups, is distinct from porphyrins (e.g., uroporphyrin or coproporphyrin) derivable from ALA alone via the extant universal biosynthetic path to tetrapyrroles, and is photoactive upon assembly into cationic micelles in aqueous solution The simple self-organization of eight acyclic mols. into a tetrapyrrole macrocycle, from which a porphyrin is derived that is photoactive in lipid assemblies, augurs well for the spontaneous origin of catalysts and pigments essential for prebiotic metabolism and proto-photosynthesis. In the experiment, the researchers used many compounds, for example, Ethyl 4-methyl-1H-pyrrole-3-carboxylate (cas: 2199-49-7Name: Ethyl 4-methyl-1H-pyrrole-3-carboxylate).

Ethyl 4-methyl-1H-pyrrole-3-carboxylate (cas: 2199-49-7) 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. 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.Name: Ethyl 4-methyl-1H-pyrrole-3-carboxylate

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

Decoding carob flavor aroma using HS-SPME-GC-MS and chemometrics was written by Krokou, Andriana;Kokkinofta, Rebecca;Stylianou, Marinos;Agapiou, Agapios. And the article was included in European Food Research and Technology in 2020.Recommanded Product: 868-57-5 This article mentions the following:

Abstract: Ceratonia siliqua L. is quite popular for the sweetness of its fruit (“natural chocolate”) and the strong, persistent, characteristic odor that associates not only carob fruit, but also its traditional food products. This is due to the emission of an array of volatile organic compounds (VOCs). The released odor is a complex mixture, and therefore, needs to be separated prior detected, especially when its origin varies and is engaged. Therefore, Headspace-Solid-Phase Microextraction-Gas Chromatog.-Mass Spectrometry (HS-SPME-GC-MS) anal. was performed in ground carob pods from three different European countries to decode their released aroma. The method was applied to Cypriot (Kountourka, Koumpota, Tilliria), Spanish (Negra, Rojal, Matalafera) and Italian (Saccarata, Racemosa, Gibiliana) cultivars, and the released volatile species were further processed with multivariate data anal. (MDA). The chromatog. separation highlighted 54 common VOCs in the grounded carob pods; the most abundant appeared to be propanoic acid 2-Me (isobutyric acid), acetic acid, butanoic acid, hexanoic acid, and propanoic acid 2-methyl-Me ester. The quant. results for acetic acid, propanoic acid 2-Me, butanoic acid, furfural and pentanoic acid revealed their emission in the low ppb_v levels. The engage of MDA on the obtained results showed a clear differentiation of the carobs based on their geog. and botanical origin. The combination of HS-SPME-GC-MS and chemometrics contributes to the quality characterization of carobs and highlights their authenticity markers. In the experiment, the researchers used many compounds, for example, Methyl2-methylbutyrate (cas: 868-57-5Recommanded Product: 868-57-5).

Methyl2-methylbutyrate (cas: 868-57-5) 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. 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.Recommanded Product: 868-57-5

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

On-bead peptoid dimerization induced by incorporation of glycosylated bridging units in submonomer solid-phase approach to glycopeptoids was written by Comegna, Daniela;Del Gatto, Annarita;Saviano, Michele;Zaccaro, Laura. And the article was included in Organic Letters in 2019.Recommanded Product: 4163-60-4 This article mentions the following:

A study on submonomer solid-phase synthesis of S-glycopeptoids has been carried out by screening different parameters. Dimeric species, featuring glycosylated bridging amino monomers, were found under suitable conditions. These dimers arise from an on-resin crosslinking reaction occurring with the incorporation of a glycoamino submonomer into the growing chain and subsequent nucleophilic attack of the resulting secondary amine to a still unreacted bromoacetylated unit. The arising byproduct can be regarded as a novel dimeric peptoid type. 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: 4163-60-4Recommanded Product: 4163-60-4).

(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. 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.Recommanded Product: 4163-60-4

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

Effect of Wort Boiling on Volatiles Formation and Sensory Properties of Mead was written by Starowicz, Malgorzata;Granvogl, Michael. And the article was included in Molecules in 2022.Name: 5-Hexyldihydrofuran-2(3H)-one This article mentions the following:

Mead is an alc. beverage based on bee honey, which can be prepared in different variations such as modified honey-water compositions, the addition of spices, and the use of different yeast strains. Moreover, the technol. process of mead production such as the step of wort preparation (with or without boiling of wort before fermentation) can be modified. All these factors might have a significant impact on the formation of aroma-active compounds, and therefore, sensory acceptance by consumers. High vacuum distillation, using the so-called solvent assisted flavor evaporation (SAFE) technique, or headspace-solid phase microextraction (HS-SPME) were applied for the isolation of the odorants. A sensory profile was used to monitor the changes in the aroma of the mead samples. Twenty-eight aroma-active compounds were detected during aroma extract dilution anal. (AEDA) based on gas chromatog.-olfactometry (GC-O) and were finally identified by gas chromatog.-mass spectrometry (GC-MS) using authentic reference compounds, including Me propanoate, Me 3-(methylthio)propanoate, and methional, all of them were identified for the first time in mead. Compounds with high flavor dilution (FD) factors were quantitated via stable isotope dilution anal. (SIDA) and revealed Et acetate (16.4 mg/L) to be the most abundant volatile compound, increasing to 57 mg/L after wort boiling, followed by Et hexanoate (both 1.2 mg/L). Furthermore, key aroma compounds were esters such as Et hexanoate, Et octanoate, and Et 3-methylbutanoate. The sensory panel evaluated ethanolic, honey-like, clove-like, sweet, and fruity notes as the main aroma descriptors of mead. The significant change in sensory evaluation was noted in the sweet odor of the heat-treated mead. In the experiment, the researchers used many compounds, for example, 5-Hexyldihydrofuran-2(3H)-one (cas: 706-14-9Name: 5-Hexyldihydrofuran-2(3H)-one).

5-Hexyldihydrofuran-2(3H)-one (cas: 706-14-9) 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.Name: 5-Hexyldihydrofuran-2(3H)-one

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

Anomeric equilibria in derivatives of amino sugars. Nuclear magnetic resonance studies on acetylated amino sugars and specifically deuterated analogs was written by Horton, Derek;Hughes, Jack B.;Jewell, Jon S.;Philips, Kerstin D.;Turner, William Nelson. And the article was included in Journal of Organic Chemistry in 1967.Formula: C16H23NO10 This article mentions the following:

Acetylation of derivatives of 2-amino-2-deoxy-D-glucose and 2-amino-2-deoxy-D-mannose with Ac2O-d6 permitted definitive assignment of the signal for the N-Ac Me group in the N.M.R. spectra of the pyranose pentaacetates of the 2 amino sugars, and some related derivatives The anomeric compositions of the mixtures formed by acetylation of the amino sugars, and a number of simple sugars, with Ac2O in pyridine, were investigated. Aryl substituents in acetylated sugar derivatives are shown to cause shielding of certain Ac groups, with the result that, in CHCl3-d, the N.M.R. signals of these Ac groups are observed at unusually high field. In the experiment, the researchers used many compounds, for example, (2S,3S,4R,5S,6R)-3-Acetamido-6-(acetoxymethyl)tetrahydro-2H-pyran-2,4,5-triyl triacetate (cas: 6730-10-5Formula: C16H23NO10).

(2S,3S,4R,5S,6R)-3-Acetamido-6-(acetoxymethyl)tetrahydro-2H-pyran-2,4,5-triyl triacetate (cas: 6730-10-5) 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. 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.Formula: C16H23NO10

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

Competition between the β-hydroxylation of a primary and a tertiary carbon atom in rats was written by Moubarik, Soumaya Chraibi-Ben;Menager, Sabine;Lafont, Olivier. And the article was included in European Journal of Medicinal Chemistry in 2000.Name: Diethyl isobutylmalonate This article mentions the following:

In order to study the effect of steric hindrance on competition between two kinds of β-hydroxylation, a compound bearing on a pyrimidinetrione nucleus both a branched side chain with a tertiary carbon atom in position β (iso-Bu group) and a linear side chain (Et group), was selected and administered to rats. Urine and feces were collected and extracted Hydroxymetabolites and their derivatives were isolated and then identified. The β-hydroxylation of the linear chain was more important than the β-hydroxylation of the branched chain. Steric hindrance plays a decisive role in this regioselectivity. In the experiment, the researchers used many compounds, for example, Diethyl isobutylmalonate (cas: 10203-58-4Name: Diethyl isobutylmalonate).

Diethyl isobutylmalonate (cas: 10203-58-4) 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. Name: Diethyl isobutylmalonate

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

The alleviation of methyl jasmonate on loss of aroma lactones correlated with ethylene biosynthesis in peaches was written by Cai, Hongfang;Han, Shuai;Yu, Mingliang;Ma, Ruijuan;Yu, Zhifang. And the article was included in Journal of Food Science in 2020.Name: 5-Ethyldihydrofuran-2(3H)-one This article mentions the following:

The occurrence of CI results in irreversible aroma loss, especially ‘peach-like’ lactones loss during cold storage and subsequent shelf life. Me jasmonate (MeJA) treatment is effective in alleviating CI symptoms in peach fruit; however, its effect on peach aroma volatiles is still unknown. To explore the effect and mechanism of MeJA treatment on aroma loss of peaches, fruit was treated with 10μmol/L MeJA, then stored at 4°C for 3 wk, and subsequently transferred to 20°C to simulate shelf life for 3 days. Here, the ability of MeJA to regulate aroma lactones of ‘Xiahui 6’ peaches was investigated, and the expression of genes responsible for ethylene and lactones biosynthesis was considered. MeJA treatment significantly reduced internal browning index, increased ethylene production, and promoted the emission of aroma-related lactones in peaches during shelf life at room temperature In addition, MeJA also elevated the expression of PpSAMS, PpACS3, PpACS4, PpACO, and PpACX3 during or after cold storage. These results suggested that MeJA treatment could enhance chilling tolerance in peaches and induce the recovery of ethylene and aroma lactones, which is closely related to ethylene biosynthesis as revealed by upregulated genes expression of PpSAMS, PpACS3/4, and PpACO. Practical Application : This research provides theor. basis for the application of Me jasmonate in fruit preservation and the basis for mol. breeding to cultivate aroma-abundant peach fruits. In the experiment, the researchers used many compounds, for example, 5-Ethyldihydrofuran-2(3H)-one (cas: 695-06-7Name: 5-Ethyldihydrofuran-2(3H)-one).

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

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

Sulfonate Version of OHPAS Linker Has Two Distinct Pathways of Breakdown: Elimination Route Allows Para-Hydroxy-Protected Benzylsulfonate (PHP-BS) to Serve as an Alternative Self-Immolative Group was written by Park, Suho;Kim, Sun Young;Cho, Jongun;Jung, Doohwan;Ha, Jihyeon;Seo, Donghoon;Lee, Jaeho;Lee, Sangkwang;Yun, Sanghyeon;Lee, Hyangsook;Park, Okku;Seo, Beomseok;Kim, Sena;Seol, Minah;Song, Jina;Park, Tae Kyo. And the article was included in Bioconjugate Chemistry in 2020.Formula: C16H22O11 This article mentions the following:

Recently we have reported that the ortho-hydroxy-protected aryl sulfate (OHPAS) system can be exploited as a new self-immolative group (SIG) for phenolic payloads. We extended the system to nonphenolic payloads by simply introducing a para-hydroxy benzyl (PHB) spacer. As an addnl. variation of the system, we explored a benzylsulfonate version of the OHPAS system and found that it has two distinct breakdown pathways, cyclization and 1,4-elimination, the latter of which implies that para-hydroxy-protected (PHP) benzylsulfonate (BS) can also be used as an alternative SIG. The PHP-BS system was found to be stable chem. and in mouse and human plasma, having payload release rates comparable to those of the original OHPAS conjugates. 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: 4163-60-4Formula: C16H22O11).

(2S,3R,4S,5S,6R)-6-(Acetoxymethyl)tetrahydro-2H-pyran-2,3,4,5-tetrayl tetraacetate (cas: 4163-60-4) 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.Formula: C16H22O11

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

Stratigraphic Examination of a Korean Lacquered Wooden Coffin Sample by Pyrolysis/GC/MS was written by Park, Jongseo;Schilling, Michael R.;Khanjian, Herant;Lee, Jiyoung. And the article was included in Chromatographia in 2018.Formula: C12H22O4 This article mentions the following:

A lacquered wooden coffin decorated with gilded Sanskrit letters excavated in the Nongso ancient tomb site was constructed around the fourteenth century in Korea. Pyrolysis/gas chromatog./mass spectrometry was employed to identify the materials of the lacquered surface by analyzing the individual layers. The components of lacquer were detected in all four layers of wood substrate, black, brown, and gilded layers, indicating the coating material was Asian lacquer. The wood seems to be a kind of pine tree from the observation that pine resin-related components were detected in much of the wood substrate and decreasing in the upward direction. Markers of drying oil like azelaic acid and palmitic acid existed in large quantities in the black, brown, and gilded layers, indicating that drying oil was intentionally added to give a luster. In addition, compared with dried Asian lacquer from Korea, the lacquer used in the coffin was determined to be of the same type. In the experiment, the researchers used many compounds, for example, Dimethyl decanedioate (cas: 106-79-6Formula: C12H22O4).

Dimethyl decanedioate (cas: 106-79-6) 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. 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: C12H22O4

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