Tag: 100-200

Synthesis and in Vitro and in Vivo Evaluation of MMP-12 Selective Optical Probes was written by Bordenave, Thomas;Helle, Marion;Beau, Fabrice;Georgiadis, Dimitris;Tepshi, Livia;Bernes, Mylene;Ye, Yunpeng;Levenez, Laure;Poquet, Enora;Nozach, Herve;Razavian, Mahmoud;Toczek, Jakub;Stura, Enrico A.;Dive, Vincent;Sadeghi, Mehran M.;Devel, Laurent. And the article was included in Bioconjugate Chemistry in 2016.HPLC of Formula: 17920-23-9 This article mentions the following:

In designing new tracers consisting of a small peptide conjugated to a reporter of comparable size, particular attention needs to be paid to the selection of the reporter group, which can dictate both the in vitro and the in vivo performances of the whole conjugate. In the case of fluorescent tracers, this is particularly true given the large numbers of available dye moieties differing in their structures and properties. Here, the authors have studied the in vitro and in vivo properties of a novel series of MMP-12 selective probes composed of cyanine dyes varying in their structure, net charge, and hydrophilic character, tethered through a linker to a potent and specific MMP-12 phosphinic pseudopeptide inhibitor. The impact of linker length has been also explored. The crystallog. structure of one tracer in complex with MMP-12 has been obtained, providing the first crystal structure of a Cy5.5-derived probe and confirming that the binding of the targeting moiety is unaffected. MMP-12 remains the tracers’ privileged target, as attested by their affinity selectivity profile evaluated in solution toward a panel of 12 metalloproteases. In vivo assessment of four selected probes has highlighted not only the impact of the dye structure but also that of the linker length on the probes’ blood clearance rates and their biodistributions. These experiments also provided valuable data on the stability of the dye moieties in vivo. This has permitted the identification of one probe, which combines favorable binding to MMP-12 in solution and on cells with optimized in vivo performance including blood clearance rate suitable for short-time imaging. Through this series of tracers, the authors have identified various critical factors modulating the tracers’ in vivo behavior, which is both useful for the development and optimization of MMP-12 selective radiolabeled tracers and informative for the design of fluorescent probes in general. In the experiment, the researchers used many compounds, for example, Diethyl 2-(prop-2-yn-1-yl)malonate (cas: 17920-23-9HPLC of Formula: 17920-23-9).

Diethyl 2-(prop-2-yn-1-yl)malonate (cas: 17920-23-9) 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. 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.HPLC of Formula: 17920-23-9

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

Aromatic Profiles and Enantiomeric Distributions of Chiral Volatile Compounds in Pu-Erh Tea was written by Zhu, JianCai;Niu, YunWei;Xiao, ZuoBing. And the article was included in Journal of Agricultural and Food Chemistry in 2022.Electric Literature of C9H10O3 This article mentions the following:

Pu-Erh tea, as a typical post-fermented tea, can be divided into raw Pu-Erh tea (RAPT) and ripened Pu-Erh tea (RIPT) according to the processing technol. It is famous for its unique aroma after aging. Although previous research on the aroma characteristics of Pu-Erh tea mostly focused on the aroma compounds, little research on chiral compounds in RAPT and RIPT has been performed. Therefore, the current work aims to explore the aroma characteristics of Pu-Erh tea from the perspective of enantiomers of chiral compounds A total of 15 enantiomers were determined in this study, among which (R)-(-)-2,2,6-trimethylcyclohexanone, (R)-(-)-linalool, (S)-(+)-linalool, (R)-(+)-δ-octanolactone, (R)-(+)-γ-nonanolactone, (2R,5R)-(+)-theaspirone A, and (R)-(-)-dihydroactinidiolide were identified as enantiomeric compounds that play an important role in the aroma of RAPT and RIPT. Furthermore, (2S,5R)-trans-linalool oxide and (R)-(+)-α-terpineol were important contributors to the aroma profile of RAPT, while (S)-(+)-2-methylbutanal, (S)-(-)-limonene, S-(-)-α-terpineol, and (1R,2R)-(-)-Me jasmonate contributed to the characteristic aroma of RIPT. The addition of these enantiomeric compounds brings the aroma closer to that of the original tea sample. In addition, the anal. of chiral enantiomers of linalool, limonene, theaspirone A, and γ-nonanolactone can provide guidance for the quality and flavor control of Pu-Erh tea aroma. In the experiment, the researchers used many compounds, for example, Ethyl 2-hydroxybenzoate (cas: 118-61-6Electric Literature of C9H10O3).

Ethyl 2-hydroxybenzoate (cas: 118-61-6) 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. 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.Electric Literature of C9H10O3

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

Studies on Cyclic Ketones. I was written by Ruhemann, Siegfried. And the article was included in Journal of the Chemical Society, Transactions in 1912.Product Details of 39163-39-8 This article mentions the following:

(CO₂Et)₂, NaOEt, and cyclopentanone, in Et₂O, gave ethyl cyclopentanone-2,5-dioxalate (I), deep yellow plates, m. 114-5°, and ethyl cyclopentanone-2-oxalate, yellow, b₁₅ 152-3°; needles, m. 26-7°. Both esters give deep red colors with FeCl₃. (I) gives a salt containing 2 mols. PhNHNH₂; colorless crystals. Cyclopentanone 2,5-dioxalic acid, yellow needles, m. 210° (decompose). (CO₂Et)₂, NaOEt, and 1-methyl-cyclopentane-3-one form only ethyl 1-methylcyclopentane-3-one-4-oxalate, pale yellow oil, b₁₄ 150°. Ethyl 1,3-dimethyl-Δ³-cyclohexene-5-one-6-oxalate (II), yellow needles, m. 132-3°. Acid, yellow prisms, m. 178° (decompose). Ethyl 1-hydrindone-2-oxalate (III), colorless needles, m. 74-5°. Salt with 1 PhNHNH₂, colorless crystals; unstable. Acid, faintly yellow needles, m. 214° (decompose). 5,6-Methylenedioxy-1-hydrindone-β-oxalic acid, using C₆H₆ as solvent and hydrolyzing the ester, which could not be purified, yellow needles, m. 260° (decompose). (III), heated in EtOH with PhNHNH₂.HCl and a little HCl, gave ethyl 1-phenyl-4,5-indenopyrazole-3-carboxylate (IV), pale yellow needles, m. 117-8°. Acid, needles, m. 250-1° (decompose); also prepared direct from the acid of (III). Silver salt, curdy, not attacked by light. Ethyl 4,5-indenopyrazole-3-carboxylate, colorless prisms, m. 174°. Acid, very slightly soluble, m. 310° (decompose). α-Hydrindone, NaOEt, and PhC îŒ?CCO₂Et yielded 6-phenyl-2,3-indeno-4-pyrone (V), needles, with 1 H₂O, m. 169° (for this reaction cf. C. A., 2, 1830, 3062). Chloroplatinate, plates. p-ONC₆H₄NMe₂ acts on 1,3-dimethyl-Δ³-cyclohexene-5-one and succinylosuccinic ester as an oxidizing agent, instead of condensing with these. An additional double bond is introduced into the cyclic ketone and the base is reduced to Me₂NC₆H₄N₂OC₆H₄NMe₂. In the experiment, the researchers used many compounds, for example, Ethyl 2-oxo-2-(2-oxocyclopentyl)acetate (cas: 39163-39-8Product Details of 39163-39-8).

Ethyl 2-oxo-2-(2-oxocyclopentyl)acetate (cas: 39163-39-8) 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. 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.Product Details of 39163-39-8

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

Metal-free Catalytic Esterification of Aryl Alkyl Ketones with Alcohols via Free-radical Mediated C(sp³)-H Bond Oxygenation was written by Rammurthy, Banothu;Peraka, Swamy;Vasu, Amrutham;Krishna Sai, Gajula;Divya Rohini, Yennamaneni;Narender, Nama. And the article was included in Asian Journal of Organic Chemistry in 2021.Safety of Methyl 4-(2-hydroxyphenyl)butanoate This article mentions the following:

A novel metal-free catalytic one-pot approach has been developed for the esterification of aralkyl ketones RC(O)R¹ (R = Ph, naphth-2-yl, 2-bromophenyl, etc.; R¹ = Me, Et, benzyl) with alcs. R²OH (R² = Me, Et, i-Pr, n-Bu) under open-air atm. conditions. The inexpensive iodide/oxone reagent system allowed the cascade C(sp₃)-H bond oxygenation, selective C-C bond cleavage and esterification through the both radical and ionic pathways in a stepwise manner in one-pot. This mild, convenient and economically viable catalytic method tolerates the various functional groups to provide the corresponding alkyl benzoates RC(O)OR² in up to 98% yields with up to 99% selectivity. The efficiency and feasibility of scale-up of the present catalytic system were demonstrated with gram scale experiments (up to 10 g scale). In the experiment, the researchers used many compounds, for example, Methyl 4-(2-hydroxyphenyl)butanoate (cas: 93108-07-7Safety of Methyl 4-(2-hydroxyphenyl)butanoate).

Methyl 4-(2-hydroxyphenyl)butanoate (cas: 93108-07-7) 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. 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.Safety of Methyl 4-(2-hydroxyphenyl)butanoate

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

Transmission of polar effects through aromatic systems. III. Hammett σ-constants was written by Norman, R. O. C.;Radda, G. K.;Brimacombe, D. A.;Ralph, P. D.;Smith, E. M.. And the article was included in Journal of the Chemical Society in 1961.Synthetic Route of C10H11FO2 This article mentions the following:

Hydrolysis of Et phenylacetate (I) and nine monosubstituted derivatives in aqueous Me₂CO at 25° were measured. The results supported the theory of van Bekkum, Verkade, and Wepster (CA 54, 16407g) that mesomeric p-interaction between substituent and functional center may affect the σ-value of a substituent. Variations in σ-values arising from the polar effect of the substituent on the resonance interaction of the functional center with the aromatic nucleus were noted. An improved method of obtaining σ-values was proposed in which use was made only of those reaction series where resonance interaction between the functional center and the aromatic ring was precluded. Substituted phenylacetic acids were prepared by known methods and converted into their Et esters. Liquid esters were purified by fractional distillation and the solid esters recrystallized from ligroine. The following phenylacetic acids and their Et esters were obtained (substituent, m.p. of acid, m.p. of Et ester, b.p./mm. of Et ester given): H, -, -, 227°/758; m-Me, 62°, -, 122-3°/18; m-NO₂, 118-20°, 11.5-12.5°, 127-35°/0.25; p-Me, 94°, -, 134-5°/25; p-OMe, 85-6°, -, 143-4°/11; p-F, 84.5°, 34°, 128-30°/31; p-Cl, -, 33-3.5°, -; p-Br, -, 31.0-1.5°, -; p-COMe, -, 62-3°, -; p-NO₂, -, 63°, -. The procedure for rate measurements was that described by Tommila and Hinshelwood (CA 33, 1199⁶). Atm. CO₂ was excluded by alkali solutions and these were restandardized frequently. Initial concentrations of alkali and ester were equal and the extent of hydrolysis was studied from 10-80% completion. Each reaction obeyed 2nd order kinetics. The following rate constants (l. mole^-1sec.^-1) for the alk. hydrolysis of Et phenylacetates at 25° were obtained (substituent, and 10²k given): II, 4.40; m-Me, 3.58; p-Me, 3.18; p-OMe, 3.93; p-F, 6.96; p-Cl, 9.71; p-Br, 10.10; p-COMe, 13.0; m-NO₂, 18.4; p-NO₂, 26.2. The following σⁿ and σ_G values were obtained (substituent, σⁿ, and σ_G given): p-Me, -0.129, -0.129; m-Me, -0.069, -0.105; p-OMe, -0.111, -0.097; p-F, 0.168, 0.143; p-Cl, 0.238, 0.256; p-Br, 0.265, 0.281; m-Cl, 0.373, 0.334; m-NO₂, 0.710, 0.576; p-NO₂, 0.778, 0.708. The σ_G and ρ values were obtained from the following reactions (reaction, solvent, temperature, ρ, s, r, n given): ArCH₂CO₂Et + OH^–, 60% Me₂CO, 25°, 1.069, 0.029, 0.996, 8; ArCH₂CO₂Et + OH^–, 85.4% alc., 24.8, 1.168, 0.021, 0.998, 5; ArCH₂CO₂H (pK_a), H₂O, 25°, 0.612, 0.027, 0.989, 8; ArCH₂OHc + OH^-1, 56% Me₂CO, 25°, 0.894, 0.019, 0.998, 8; ArCH₂NHAc + Cl₂, 40% AcOH, 18, -1.256, 0.049, 0.987, 5. 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. 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.Synthetic Route of C10H11FO2

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

Analysis of aromatic compounds in sauce-flavor Moutai lees by GC-MS was written by Zhang, Shixian;Jin, Qian;Zeng, Qihua;Gao, Zhixi. And the article was included in Zhongguo Niangzao in 2012.SDS of cas: 15399-05-0 This article mentions the following:

Aromatic compounds of Moutai lees were extracted by steam distillation and isolated by gas chromatog.-mass spectrometry. Thirty-two kinds of ingredients were identified, including furfural, Et linoleate, Et palmitate, Et oleate, 5-methyl-2-furfural, phenethyl alc., 2-formylpyrrole, benzaldehyde, hyacinthin, 2-acetylfuran, furfuralc., 2,3,5,6-tetra-Me pyrazine, Et 9-hexadecanoate, ethyl-2-hydroxy-3-phenylpropanoate, Et stearate, 3-acetylpyrrole and phytane, etc. They were main components of the sauce-flavor Moutai lees, counted for up to 93.9%. In the experiment, the researchers used many compounds, for example, Ethyl 2-hydroxy-3-phenylpropanoate (cas: 15399-05-0SDS of cas: 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. 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. SDS of cas: 15399-05-0

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

Highly efficient asymmetric michael addition reaction of malonates to α,β-unsaturated ketones promoted by a chiral thiourea/PPY dual-catalyst system was written by Moritaka, Maya;Miyamae, Naomu;Nakano, Keiji;Ichikawa, Yoshiyasu;Kotsuki, Hiyoshizo. And the article was included in Synlett in 2012.Formula: C10H14O4 This article mentions the following:

The enantioselective Michael addition reaction of malonates to α,β-unsaturated ketones is efficiently promoted by a combined dual-catalyst system composed of chiral thiourea and 4-pyrrolidinopyridine (PPY) in toluene. The expected Michael adducts with cyclic and acyclic enones are obtained in excellent yields and with excellent enantioselectivities. In the experiment, the researchers used many compounds, for example, Diethyl 2-(prop-2-yn-1-yl)malonate (cas: 17920-23-9Formula: C10H14O4).

Diethyl 2-(prop-2-yn-1-yl)malonate (cas: 17920-23-9) 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. 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.Formula: C10H14O4

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

Rhodium(III)-catalyzed sulfonamide directed ortho C-H carbenoid functionalization via metal carbene migratory insertion was written by Dong, Yi;Chen, Jiajing;Xu, Heng. And the article was included in Chemical Communications (Cambridge, United Kingdom) in 2019.Application In Synthesis of Methyl 2-(methylsulfonyl)acetate This article mentions the following:

A rhodium(III)-catalyzed sulfonamide directed ortho C-H carbenoid functionalization was developed with good yields. This method was attractive due to its broad substrate scope and enabled derivation of diverse biol. active sulfonamide structures and late-stage modification of sulfa drugs. In the experiment, the researchers used many compounds, for example, Methyl 2-(methylsulfonyl)acetate (cas: 62020-09-1Application In Synthesis of Methyl 2-(methylsulfonyl)acetate).

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. 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.Application In Synthesis of Methyl 2-(methylsulfonyl)acetate

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

Regioregularity and Electron Deficiency Control of Unsymmetric Diketopyrrolopyrrole Copolymers for Organic Photovoltaics was written by Aoshima, Kenta;Nomura, Mayuka;Saeki, Akinori. And the article was included in ACS Omega in 2019.Safety of Ethyl 3-oxo-3-(thiophen-2-yl)propanoate This article mentions the following:

Manipulating the electron deficiency and controlling the regioregularity of π-conjugated polymers are important for the fine-tuning of their electronic and electrochem. properties to make them suitable for an organic solar cell. Here, we report such a mol. design of unsym. diketopyrrolopyrrole (DPP) based copolymers with different aromatic side units of either thiophene (Th), pyridine (Py), or fluorobenzene (FBz). The unsym. electron acceptors of Th-DPP-Py and Th-DPP-FBz were polymerized with the electron donor of two-dimensional benzobisthiophene (BDT-Th), affording two regiorandom DPP copolymers. They exhibited contrasting MO levels and bulk heterojunction morphol. in methanofullerene-blended films, leading to power conversion efficiencies of 3.75 and 0.18%, resp. We further synthesized a regioregular DPP copolymer via sandwiching the centrosym. BDT-Th unit by two Th-DPP-Py units in an axisym. manner. The extensive characterization through morphol. observation, X-ray diffraction, and space-charge-limited current mobilities highlight the case-dependent pos./neg. effects of regioregularity and electron deficiency control. In the experiment, the researchers used many compounds, for example, Ethyl 3-oxo-3-(thiophen-2-yl)propanoate (cas: 13669-10-8Safety of 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. 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 Ethyl 3-oxo-3-(thiophen-2-yl)propanoate

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

Phenylhydrazide as an enzyme-labile protecting group in peptide synthesis was written by Voelkert, Martin;Koul, Surrinder;Mueller, Gernot H.;Lehnig, Manfred;Waldmann, Herbert. And the article was included in Journal of Organic Chemistry in 2002.Quality Control of Ethyl 2-hydroxy-3-phenylpropanoate This article mentions the following:

The enzymic cleavage of amino acid phenylhydrazides with the enzyme tyrosinase (EC 1.14.18.1) offers a new, mild, and selective method for C-terminal deprotection of peptides. The advantages of the described methodol. are the very mild oxidative removal of the protecting group at room temperature and pH 7, a high chemo- and regioselectivity, and the availability of the biocatalyst. Even in oxygen-saturated solution, the oxidation of sensitive methionine residues was not observed These features make the methodol. suitable for the synthesis of sensitive peptide conjugates. Mechanistic data suggest that the hydrolysis of the oxidized adducts proceeds by a free-radical mechanism. In the experiment, the researchers used many compounds, for example, Ethyl 2-hydroxy-3-phenylpropanoate (cas: 15399-05-0Quality Control of 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. 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 Ethyl 2-hydroxy-3-phenylpropanoate

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