Month: February 2023

Peripherally acting enkephalin analogs. 2. Polar tri- and tetrapeptides was written by Hardy, George W.;Lowe, Lawrence A.;Mills, Gail;Sang, Pang Yih;Simpkin, Dean S. A.;Follenfant, Rhonda L.;Shankley, Clare;Smith, Terence W.. And the article was included in Journal of Medicinal Chemistry in 1989.Safety of 2-(Trifluoromethyl)phenethyl alcohol This article mentions the following:

The design, synthesis, and biol. activity of a series of D-Arg²-enkephalin-derived tetrapeptide amides and tripeptide aralkylamides are reported. These polar analogs were designed to be excluded from the central nervous system, with their action thus limited to peripheral opioid receptors. The effects of the nature of the aromatic ring, aryl ring substitution and aralkylamide chain length on activity were investigated; in a number of cases the N-terminal amino group of Tyr¹ was converted to a guanidino group to further increase hydrophilicity. The peptides were all synthesized by classical solution methodol. The opioid activity of the peptides was assessed in vitro on the guinea pig ileum, and their antinociceptive activity was determined in vivo in chem. induced writhing models (peripheral activity) and in the hot-plate test (central activity) in rodents. The analgesic effects were predominantly mediated in the periphery, as demonstrated by antagonism of antinociception by the peripheral opioid antagonist N-methylnalorphine and by comparison of the activities in the writhing and hot-plate tests. As a class, the tetrapeptides were more potent than the tripeptides; N^α-amidination generally increased activity. A number of compounds exhibited very potent opioid activity and had the desired pharmacol. profile, indicating a high degree of peripheral selectivity. In the experiment, the researchers used many compounds, for example, 2-(Trifluoromethyl)phenethyl alcohol (cas: 94022-96-5Safety of 2-(Trifluoromethyl)phenethyl alcohol).

2-(Trifluoromethyl)phenethyl alcohol (cas: 94022-96-5) belongs to alcohols. Alkyl halides are often synthesized from alcohols, in effect substituting a halogen atom for the hydroxyl group. Alcohols may be oxidized to give ketones, aldehydes, and carboxylic acids. These functional groups are useful for further reactions. Oxidation of organic compounds generally increases the number of bonds from carbon to oxygen (or another electronegative element, such as a halogen), and it may decrease the number of bonds to hydrogen.Safety of 2-(Trifluoromethyl)phenethyl alcohol

Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

Enhanced ready biodegradability screening tests for the evaluation of potential PBT substances was written by Gartiser, Stefan;Brunswik-Titze, Andrea;Flach, Felicitas;Junker, Thomas;Saettler, Daniel;Joehncke, Ulrich. And the article was included in Science of the Total Environment in 2022.Application In Synthesis of 2,2′-Oxybis(ethan-1-ol) This article mentions the following:

In persistence assessment enhanced ready biodegradation tests (eRBT) are aimed to close the gap between screening tests and complex simulation tests. However, only few data from these tests are available and neither guidance on the design and interpretation of eRBTs, nor suitable validity criteria have been established so far. In a practical testing program 5 compounds with controversial degradation data have been tested in 4 test series including prolongation to 60 days and use of different inocula (activated sludge, final effluent from a STP), flask sizes, and endpoints (CO₂, O₂, DOC). The drug ibuprofen and the intermediate 4-fluorophenol were biodegraded by >60% within 28 days within a 10-day-window and therefore are considered as readily biodegradable and in conclusion fulfilling the criteria for “not persistent”. The mean mineralization of the pesticide synergist piperonylbutoxide and the antioxidant octadecyl 3-(3,5-di-tert-butyl-4-hydroxyphenyl)propionate achieved 20%-50% (=”potentially P”). The mineralization of the cosmetic ingredient cis-13-docosenonamide (Erucamide) was between 36%-64% after 60 days with activated sludge and 21% with the effluent from the STP. Diethylene glycol reached the pass level of 60% mineralization within 28 days in all test series without always meeting the 10-day window, and thus proved to be a suitable reference substance for eRBTs. Based on the results of the study several recommendations for the test design, the evaluation and the interpretation of eRBTs are made. However, a broader data set is required and further enhancements such as the quality and amount of the inoculum should also be considered in future research. In the experiment, the researchers used many compounds, for example, 2,2′-Oxybis(ethan-1-ol) (cas: 111-46-6Application In Synthesis of 2,2′-Oxybis(ethan-1-ol)).

2,2′-Oxybis(ethan-1-ol) (cas: 111-46-6) belongs to alcohols. A strong base can deprotonate an alcohol to yield an alkoxide ion (R―O−). For example, sodamide (NaNH2), a very strong base, abstracts the hydrogen atom of an alcohol. Tertiary alcohols cannot be oxidized at all without breaking carbon-carbon bonds, whereas primary alcohols can be oxidized to aldehydes or further oxidized to carboxylic acids.Application In Synthesis of 2,2′-Oxybis(ethan-1-ol)

Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

Synthesis of N-protected serine ethers as precursors of new photoactivatable amino acids cleavable by hydrogenolysis was written by Dugave, Christophe;Kessler, Pascal;Colas, Christophe;Hirth, Christian. And the article was included in Tetrahedron Letters in 1994.Name: 3-(Hydroxymethyl)-4-nitrophenol This article mentions the following:

Protected serine amino(hydroxy)benzyl ethers I (Boc = Me₃CO₂C, Fmoc = 9-fluorenylmethoxycarbonyl, MEM = 2-methoxyethoxymethyl) were synthesized. Spectral characteristics of the corresponding photoactivatable 4-diazocyclohexa-2,5-dienones II were determined In the experiment, the researchers used many compounds, for example, 3-(Hydroxymethyl)-4-nitrophenol (cas: 60463-12-9Name: 3-(Hydroxymethyl)-4-nitrophenol).

3-(Hydroxymethyl)-4-nitrophenol (cas: 60463-12-9) belongs to alcohols. Alcohols are weak acids. The most acidic simple alcohols (methanol and ethanol) are about as acidic as water, and most other alcohols are somewhat less acidic. Grignard and organolithium reagents are powerful tools for organic synthesis, and the most common products of their reactions are alcohols.Name: 3-(Hydroxymethyl)-4-nitrophenol

Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

Mechanically improved sol-gel derived methacrylate-siloxane hybrid materials with urethane linkage was written by Kim, Yun Hyeok;Choi, Gwang-Mun;Kim, Yong Ho;Bae, Byeong-Soo. And the article was included in Journal of Sol-Gel Science and Technology in 2019.Formula: C16H26O7 This article mentions the following:

UV-curable and highly condensed (>86%) methacrylate Ph oligo-siloxane (MPO) was synthesized by non-hydrolytic sol-gel condensation reaction between methacrylate and Ph silane precursor. The MPO resin was then cured by an UV-initiated free-radical polymerization to fabricate a transparent (>90% at 550 nm) methacrylate-siloxane hybrid material (methacrylate hybrimer). An urethane butanediol dimethacrylate (UBDM) monomer was synthesized as a cross-linker into the methacrylate hybrimer networks without micro-phase separation The UBDM increased methacrylate conversion and mech. properties due to the hydrogen bonding of the urethane linkage. The hardness, modulus, and strength were improved by UBDM insertion, the flexibility was even increased with 140% elongation, compared to neat MH. In addition, a storage modulus related to the thermo-mech. properties was also enhanced by a denser cross-linkage with the urethane linkage. In the experiment, the researchers used many compounds, for example, ((Oxybis(ethane-2,1-diyl))bis(oxy))bis(ethane-2,1-diyl) bis(2-methylacrylate) (cas: 109-17-1Formula: C16H26O7).

((Oxybis(ethane-2,1-diyl))bis(oxy))bis(ethane-2,1-diyl) bis(2-methylacrylate) (cas: 109-17-1) belongs to alcohols. Because alcohols are easily synthesized and easily transformed into other compounds, they serve as important intermediates in organic synthesis. Converting an alcohol to an alkene requires removal of the hydroxyl group and a hydrogen atom on the neighbouring carbon atom. Dehydrations are most commonly carried out by warming the alcohol in the presence of a strong dehydrating acid, such as concentrated sulfuric acid.Formula: C16H26O7

Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

Valorization of tomato pomace: extraction of value-added components by deep eutectic solvents and their application in the formulation of cosmetic emulsions was written by Vasyliev, Georgii;Lyudmyla, Khrokalo;Hladun, Kateryna;Skiba, Margarita;Vorobyova, Viktoria. And the article was included in Biomass Conversion and Biorefinery in 2022.Formula: C3H8O2 This article mentions the following:

Deep eutectic solvents (DESs) have been explored as an alternative to hazardous solvents to extract phenolic compounds The aim of this work was estimate the performance of choline chloride-based DESs regarding the extraction of phenolic compounds of tomato pomace and determination of their antioxidant activity. Green choline chloride-based DESs coupled with ultrasound-assisted extraction were performed to extract The solvents were choline chloride:1,2-propanediol (1:2 v/w):water (10% weight/weight) and choline chloride:lactic acid (1:2 v/w):water (10% weight/weight). The phytochem. constituents of tomato pomace extracts were verified with a combination of high-performance liquid chromatog. coupled to diode-array detection and tandem mass spectrometry (HPLC-DAD-MS). The total antioxidant activity of the extracts was assessed using phosphomolybdenum (PM) method. The redox behavior of tomato pomace extracts was evaluated by means of cyclic voltammetry. The DES-based tomato pomace extracts were used as the antioxidant agent to develop a natural cosmetic formulation (colloidal solutions). The -potential, colloidal stability, and the antioxidant, antimicrobial, and antifungal activity were studied. The antioxidant activity of the cosmetic emulsions has been studied by means of cyclic voltammetry. The tomato pomace extracts contain significant quantity of phenolic acids and flavanols (26-37% of the total compounds). Chlorogenic acid was detected as the main phenolic compound in tomato pomace extracts (ranging from 37.23 to 52.33μg/g). The total antioxidant power of the extracts varies in the range at 408 to 511.18μg/g extract Choline chloride-based DESs have low values of oxidation potentials. Zeta-potential of obtained colloidal solutions (cosmetic formulation) varies from – 0.0102 to – 0.0594 mV indicating the moderate stability of obtained cosmetic emulsions. The following ranking of antioxidants was obtained: cosmetic emulsions with extract obtained by choline chloride:lactic acid deep eutectic solvent > cosmetic emulsions with extract obtained by choline chloride:1,2-propanediol deep eutectic solvent. Antibacterial and antifungal activity of the cosmetic emulsions with DES extracts relative to Gram-pos. (Bacillus subtilis), Gram-neg. (Escherichia coli), and Candida albicans wound pathogens were studied. Thus the DESs could serve as solvents to produce a phenolic-rich tomato extract could be readily applicable to cosmetic formulations. In the experiment, the researchers used many compounds, for example, 1,2-Propanediol (cas: 57-55-6Formula: C3H8O2).

1,2-Propanediol (cas: 57-55-6) belongs to alcohols. Alkyl halides are often synthesized from alcohols, in effect substituting a halogen atom for the hydroxyl group. Grignard and organolithium reagents are powerful tools for organic synthesis, and the most common products of their reactions are alcohols.Formula: C3H8O2

Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

Base-Induced Mechanistic Variation in Palladium-Catalyzed Carbonylation of Aryl Iodides was written by Hu, Yanhe;Liu, Jing;Lu, Zhixin;Luo, Xiancai;Zhang, Heng;Lan, Yu;Lei, Aiwen. And the article was included in Journal of the American Chemical Society in 2010.Name: Sodium 2-methyl-2-propanethiolate This article mentions the following:

A mechanism, which is distinct from the traditional one when sodium alkoxide was used instead of tertiary amines, was proposed for the alkoxycarbonylation of aryl iodides. The catalytic cycle was composed of oxidative addition, subsequent ArPdOR formation, CO insertion to Pd-OR, and final reductive elimination of ArPdCOOR. The kinetic simultaneity of the formation of deiodinated side product from the aryl iodide and aldehyde from corresponding alc. provided strong evidence for the existence of ArPdOR species. The observation of thioether, as the other competitive product in palladium catalyzed thiocarbonylation of aryl iodides and sodium alkylthiolate, also indicate the possibility of metathesis between ArPdI and sodium alkylthiolate. Preliminary kinetic studies revealed that neither oxidative addition nor reductive elimination was rate limiting. DFT calculation displayed preference for CO insertion into Pd-OR bond. The advantage of this novel mechanism had been demonstrated in the facile alkoxycarbonylation and thiocarbonylation. The ethoxycarbonylation of aryl iodides under room temperature and balloon pressure of CO in the presence of EtONa were examined, and good to high yields were obtained; the t-butoxycarbonylation reactions in the presence of t-BuONa were achieved, and the alkylthiocarbonylation (including the t-butylthiocarbonylation) of aryl iodides in the presence of sodium alkylthiolate were also investigated. In the experiment, the researchers used many compounds, for example, Sodium 2-methyl-2-propanethiolate (cas: 29364-29-2Name: Sodium 2-methyl-2-propanethiolate).

Sodium 2-methyl-2-propanethiolate (cas: 29364-29-2) belongs to alcohols. Similar to water, an alcohol can be pictured as having an sp3 hybridized tetrahedral oxygen atom with nonbonding pairs of electrons occupying two of the four sp3 hybrid orbitals. Under carefully controlled conditions, simple alcohols can undergo intermolecular dehydration to give ethers. This reaction is effective only with methanol, ethanol, and other simple primary alcohols.Name: Sodium 2-methyl-2-propanethiolate

Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

Total synthesis of (±)-monomorine was written by Le, Tri Q.;Oliver, Robert M. III;Arcari, Joel T.;Mitton-Fry, Mark J.. And the article was included in Tetrahedron Letters in 2012.HPLC of Formula: 1122-71-0 This article mentions the following:

An efficient, two-operation synthesis of the trail ant pheromone (±)-monomorine (I) is reported. The synthesis features an aqueous Claisen-Schmidt condensation followed by the stereocontrolled installation of the three resident stereocenters in a single operation. In the experiment, the researchers used many compounds, for example, 6-Methyl-2-pyridinemethanol (cas: 1122-71-0HPLC of Formula: 1122-71-0).

6-Methyl-2-pyridinemethanol (cas: 1122-71-0) belongs to alcohols. Similar to water, an alcohol can be pictured as having an sp3 hybridized tetrahedral oxygen atom with nonbonding pairs of electrons occupying two of the four sp3 hybrid orbitals. A multistep synthesis may use Grignard-like reactions to form an alcohol with the desired carbon structure, followed by reactions to convert the hydroxyl group of the alcohol to the desired functionality.HPLC of Formula: 1122-71-0

Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

Synthesis of chiral α-benzyl-β²-hydroxy carboxylic acids through iridium-catalyzed asymmetric hydrogenation of α-oxymethylcinnamic acids was written by Li, Ze-Yu;Song, Song;Zhu, Shou-Fei;Guo, Na;Wang, Li-Xin;Zhou, Qi-Lin. And the article was included in Chinese Journal of Chemistry in 2014.Category: alcohols-buliding-blocks This article mentions the following:

An asym. hydrogenation of α-oxymethylcinnamic acids was developed by using chiral spiro phosphine-oxazoline/iridium complexes as catalysts to prepare β²-hydroxycarboxylic acids I [R = C₆H₅, 3,5-(OCH₃)₂C₆H₃, C₆H₄CH₂, etc.; Ar = C₆H₅, 3,4-(OCH₂O)C₆H₃, 3-H₃CO-4-C₆H₅CH₂O-C₆H₃, etc.] with high reactivity (TON up to 2000) and excellent enantioselectivity (up to 99.5% ee) under mild conditions. By using this highly efficient asym. hydrogenation as a key step, a concise enantioselective total synthesis of natural product homoisoflavone II was accomplished in 7 steps with 59% overall yield. In the experiment, the researchers used many compounds, for example, Benzo[d][1,3]dioxol-4-ol (cas: 69393-72-2Category: alcohols-buliding-blocks).

Benzo[d][1,3]dioxol-4-ol (cas: 69393-72-2) belongs to alcohols. Because alcohols are easily synthesized and easily transformed into other compounds, they serve as important intermediates in organic synthesis. Secondary alcohols are easily oxidized without breaking carbon-carbon bonds only as far as the ketone stage. No further oxidation is seen except under very stringent conditions.Category: alcohols-buliding-blocks

Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

Dynamic Kinetic Cross-Electrophile Arylation of Benzyl Alcohols by Nickel Catalysis was written by Guo, Peng;Wang, Ke;Jin, Wen-Jie;Xie, Hao;Qi, Liangliang;Liu, Xue-Yuan;Shu, Xing-Zhong. And the article was included in Journal of the American Chemical Society in 2021.Quality Control of 2-(4-Bromophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane This article mentions the following:

Herein, a dynamic kinetic cross-coupling approach for the direct functionalization of alcs were reported. The feasibility of this strategy was demonstrated by a nickel-catalyzed cross-electrophile arylation reaction of benzyl alcs. with (hetero)aryl electrophiles. The reaction proceeded with a broad substrate scope of both coupling partners. The electron-rich, electron-poor and ortho-/meta-/para-substituted (hetero)aryl electrophiles (e.g., Ar-OTf, Ar-I, Ar-Br, and inert Ar-Cl) all coupled well. Most of the functionalities, including aldehyde, ketone, amide, ester, nitrile, sulfone, furan, thiophene, benzothiophene, pyridine, quinolone, Ar-SiMe3, Ar-Bpin, and Ar-SnBu3, were tolerated. The dynamic nature of this method enabled the direct arylation of benzylic alc. in the presence of various nucleophilic groups, including non-activated primary/secondary/tertiary alcs., phenols, and free indoles. It thus offered a robust alternative to existing methods for the precise construction of diarylmethanes. The synthetic utility of the method was demonstrated by a concise synthesis of biol. active mols. and by its application to peptide modification and conjugation. Preliminary mechanistic studies revealed that the reaction of in situ formed benzyl oxalates with nickel, possibly via a radical process was an initial step in the reaction with aryl electrophiles. In the experiment, the researchers used many compounds, for example, 2-(4-Bromophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (cas: 68716-49-4Quality Control of 2-(4-Bromophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane).

2-(4-Bromophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (cas: 68716-49-4) belongs to alcohols. Alkyl halides are often synthesized from alcohols, in effect substituting a halogen atom for the hydroxyl group. Secondary alcohols are easily oxidized without breaking carbon-carbon bonds only as far as the ketone stage. No further oxidation is seen except under very stringent conditions.Quality Control of 2-(4-Bromophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

Efficient and simple method for the quantification of alkyl polyglycosides by hydrolysis and photometric determination of reducing sugars was written by Buttler, Judith R.;Bechtold, Thomas;Pham, Tung. And the article was included in Arabian Journal of Chemistry in 2022.Quality Control of 1,2-Propanediol This article mentions the following:

Alkyl polyglycosides (APG) are important biodegradable surfactants for many applications. The lack of a chromophoric group and the mixture of stereoisomers and oligomers make the quantification by merely chromatic separation difficult. A simple and efficient quantification assay was developed based on the acid hydrolysis of alkyl polyglycoside and subsequent quantification of the hydrolytically cleaved glucose using the neocuproine assay. Complete hydrolysis of alkyl polyglycoside is achieved with 16 wt% sulfuric acid at 100 °C after 30 min and the separation of fatty alc. and clouding of the reaction mixture is prevented by adding 1,2-propylene-glycol. Hydrolytically cleaved sugars reduce the Cu(II)-neocuproine complex, leading to a color shift which permits the spectrophotometric quantification at 452 nm. A linear correlation between the absorbance of reduced Cu(II)-neocuproine complex and glucose or alkyl polyglycoside concentration is observed up to an analyte concentration of 25 mg/L. Statistical anal. according to one-tailled T-test (S′ 95%), has shown that the lower detection limit for alkyl polyglycosides is 2.97 mg/L and the limit of quantification 8.24 mg/L, resp. Apart from the simple execution, the assay is reliable and can be utilized both as scientific technique to quantify APG as well as for process and quality control in the industry. In the experiment, the researchers used many compounds, for example, 1,2-Propanediol (cas: 57-55-6Quality Control of 1,2-Propanediol).

1,2-Propanediol (cas: 57-55-6) belongs to alcohols. Alcohols are weak acids. The most acidic simple alcohols (methanol and ethanol) are about as acidic as water, and most other alcohols are somewhat less acidic. Under carefully controlled conditions, simple alcohols can undergo intermolecular dehydration to give ethers. This reaction is effective only with methanol, ethanol, and other simple primary alcohols.Quality Control of 1,2-Propanediol

Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts