Category: alcohols-buliding-blocks

Wang, Jingchen published the artcileOptimization of synthesis process for sodium ascorbate, Safety of (3S,4R,5S)-3,4,5,6-Tetrahydroxy-2-oxohexanoic acid, the publication is Advanced Materials Research (Durnten-Zurich, Switzerland) (2012), 550-553(Pt. 1), 10-15, database is CAplus.

With 2-keto-L-gulonic acid(2KLG) and methanol as raw materials, 98% concentrated sulfuric acid as catalyst, the Me esterification reaction is occurred. Then with sodium carbonate as a transforming agent, through a conversion reaction sodium carbonate is obtained. In this experiment, the effects of reaction time, reaction temperature and reactant ratio on conversion rate of sodium ascorbate were studied. The results showed that sodium carbonate as the reactant of lactonization reaction can effectively shorten the reaction time and improve reaction yield. By experiment under the optimum process conditions: the reaction temperature is 65 °C, reaction time is 150 min and the molar ratio of 2-keto-L-gu Me to sodium carbonate is 1:0.6, the conversion rate reaches 98 % and the effect is better than with sodium bicarbonate as transforming agent.

Advanced Materials Research (Durnten-Zurich, Switzerland) published new progress about 526-98-7. 526-98-7 belongs to alcohols-buliding-blocks, auxiliary class Sugar Units,Other Sugar Units, name is (3S,4R,5S)-3,4,5,6-Tetrahydroxy-2-oxohexanoic acid, and the molecular formula is C8H10N2O2, Safety of (3S,4R,5S)-3,4,5,6-Tetrahydroxy-2-oxohexanoic acid.

Referemce:
https://en.wikipedia.org/wiki/Alcohol,
Alcohols – Chemistry LibreTexts

Wang, Xianjin published the artcileCatalytic Boration of Alkyl Halides with Borane without Hydrodehalogenation Enabled by Titanium Catalyst, Application of 2-(2,3-Dihydro-1H-inden-2-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane, the publication is Angewandte Chemie, International Edition (2021), 60(22), 12298-12303, database is CAplus and MEDLINE.

An unprecedented and general Ti-catalyzed boration of alkyl (pseudo)halides (alkyl-X, X = I, Br, Cl, OMs) with borane (HBpin, HBcat) is reported. The use of Ti catalyst can successfully suppress the undesired hydrodehalogenation products that prevail using other transition-metal catalysts. Synthetically useful alkyl boronate esters are readily obtained from various (primary, secondary, and tertiary) alkyl electrophiles, including unactivated alkyl chlorides, with tolerance of other reducing functional groups such as ester, alkene, and carbamate. Preliminary studies on the mechanism revealed a possible radical reaction pathway. Further extension of the authors’ strategy to aryl bromides is also demonstrated.

Angewandte Chemie, International Edition published new progress about 608534-44-7. 608534-44-7 belongs to alcohols-buliding-blocks, auxiliary class Other Aromatic,Boronic acid and ester,Boronate Esters,Boronic Acids,Boronic acid and ester, name is 2-(2,3-Dihydro-1H-inden-2-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane, and the molecular formula is C22H12F6O6S2, Application of 2-(2,3-Dihydro-1H-inden-2-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane.

Referemce:
https://en.wikipedia.org/wiki/Alcohol,
Alcohols – Chemistry LibreTexts

Boscá, F published the artcilePhotochemistry of 2-hydroxy-4-trifluoromethylbenzoic acid, major metabolite of the photosensitizing platelet antiaggregant drug triflusal., COA of Formula: C8H5F3O3, the publication is Photochemistry and photobiology (2001), 73(5), 463-8, database is MEDLINE.

Triflusal is a platelet antiaggregant drug with photoallergic side effects. However, it is considered a prodrug since it is metabolized to 2-hydroxy-4-trifluoromethylbenzoic acid (HTB)–the pharmacologically active form. HTB was found to be photolabile under various conditions. Its major photodegradation pathway appears to be the nucleophilic attack at the trifluoromethyl moiety. The involvement of the triplet state in the photodegradation has been unequivocally proved by direct detection of this transient in laser flash photolysis and by quenching experiments with oxygen, cyclohexadiene and naphthalene. Finally, the photobinding of HTB to proteins such as bovine serum albumin has been demonstrated using ultraviolet-visible (UV-Vis) and fluorescence spectroscopy. Nucleophilic groups present in the protein appear to be responsible for the formation of covalent drug photoadducts, which is the first step involved in the photoallergy shown by triflusal.

Photochemistry and photobiology published new progress about 328-90-5. 328-90-5 belongs to alcohols-buliding-blocks, auxiliary class Trifluoromethyl,Fluoride,Carboxylic acid,Benzene,Phenol, name is 2-Hydroxy-4-(trifluoromethyl)benzoic acid, and the molecular formula is C8H5F3O3, COA of Formula: C8H5F3O3.

Referemce:
https://en.wikipedia.org/wiki/Alcohol,
Alcohols – Chemistry LibreTexts

Lyons, Amanda Jane published the artcileScaling up a C-H Borylation: Addressing the Safety Concerns of an Iridium-Catalyzed Process for Multikilo Scale Manufacture, Category: alcohols-buliding-blocks, the publication is Organic Process Research & Development (2022), 26(5), 1378-1388, database is CAplus.

Ir-catalyzed C-H borylation reactions are a rapid and versatile entry into Suzuki coupling partners, but their inherent safety issues can limit their use in large-scale manufacture The stoichiometric byproduct from this reaction, HBpin, can liberate H gas on contact with moisture in air, as well as acting as an effective borylating agent in the reaction, resulting in an addnl. pathway for the generation of H. Using a targeted, multidisciplinary approach, a C-H borylation process to generate a key intermediate in the synthesis of an API was redesigned in preparation for large-scale manufacture Through careful evaluation of the existing process and the use of high-throughput experimentation, PAT techniques, NMR, process safety experimentation, and process engineering, the process was constructed so that inherent risks associated with this reaction were minimized and contained to a final controlled quench of the reactive byproducts of the reaction. The final process was transferred to a manufacturing facility, delivering >70 kg of the borylated product over two batches.

Organic Process Research & Development published new progress about 25240-59-9. 25240-59-9 belongs to alcohols-buliding-blocks, auxiliary class Boronic acid and ester,Boronic Acids,Boronate Esters, name is 4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-ol, and the molecular formula is C6H13BO3, Category: alcohols-buliding-blocks.

Referemce:
https://en.wikipedia.org/wiki/Alcohol,
Alcohols – Chemistry LibreTexts

Patel, Ekta published the artcileAlternative Surfactants for Improved Efficiency of In Situ Tryptic Proteolysis of Fingermarks, Computed Properties of 85618-21-9, the publication is Journal of the American Society for Mass Spectrometry (2015), 26(6), 862-872, database is CAplus and MEDLINE.

Despite recent improvements to in situ proteolysis strategies, a higher efficiency is still needed to increase both the number of peptides detected and the associated ion intensity, leading to a complete and reliable set of biomarkers for diagnostic or prognostic purposes. In the study presented here, an extract of a systematic study is illustrated studying a range of surfactants assisting trypsin proteolytic activity. Method development was trialled on fingermarks; this specimen results from a transfer of sweat from an individual’s fingertip to a surface upon contact. As sweat carries a plethora of biomols., including peptides and proteins, fingermarks are, potentially, a very valuable specimen for non-invasive prognostic or diagnostic screening. A recent study demonstrated the opportunity to quickly detect peptides and small proteins in fingermarks using Matrix Assisted Laser Desorption Ionization Mass Spectrometry Profiling (MALDI MSP). However, intact detection bears low sensitivity and does not allow species identification; therefore, a shotgun proteomic approach was employed involving in situ proteolysis. In fingermarks, further improvements to the existing method can be achieved using MEGA-8 as surfactant in higher percentages as well as combinations of different detergents. Also, for the first time, Rapigest SF, normally used in solution digestions, has been shown to successfully work also for in situ proteolysis. [Figure not available: see fulltext.].

Journal of the American Society for Mass Spectrometry published new progress about 85618-21-9. 85618-21-9 belongs to alcohols-buliding-blocks, auxiliary class Tetrahydropyran,Chiral,sulfides,Alcohol, name is (2R,3S,4S,5R,6S)-2-(Hydroxymethyl)-6-(octylthio)tetrahydro-2H-pyran-3,4,5-triol, and the molecular formula is C14H28O5S, Computed Properties of 85618-21-9.

Referemce:
https://en.wikipedia.org/wiki/Alcohol,
Alcohols – Chemistry LibreTexts

Kruger, Jacob S. published the artcileLignin Depolymerization with Nitrate-Intercalated Hydrotalcite Catalysts, Recommanded Product: 2-Phenoxy-1-phenylpropane-1,3-diol, the publication is ACS Catalysis (2016), 6(2), 1316-1328, database is CAplus.

Hydrotalcites (HTCs) exhibit multiple adjustable parameters to tune catalytic activity, including interlayer anion composition, metal hydroxide layer composition, and catalyst preparation methods. Here, we report the influence of several of these parameters on β-O-4 bond scission in a lignin model dimer, 2-phenoxy-1-phenethanol (PE), to yield phenol and acetophenone. We find that the presence of both basic and NO₃^– anions in the interlayer increases the catalyst activity by 2-3-fold. In contrast, other anions or transition metals do not enhance catalytic activity in comparison to blank HTC. The catalyst is not active for C-C bond cleavage on lignin model dimers and has no effect on dimers without an α-OH group. Most importantly, the catalyst is highly active in the depolymerization of two process-relevant lignin substrates, producing a significant amount of low-mol.-weight aromatic species. The catalyst can be recycled until the NO₃^– anions are depleted, after which the activity can be restored by replenishing the NO₃^– reservoir and regenerating the hydrated HTC structure. These results demonstrate a route to selective lignin depolymerization in a heterogeneous system with an inexpensive, earth-abundant, com. relevant, and easily regenerated catalyst.

ACS Catalysis published new progress about 70110-65-5. 70110-65-5 belongs to alcohols-buliding-blocks, auxiliary class Benzene,Alcohol,Ether,Benzene Compounds, name is 2-Phenoxy-1-phenylpropane-1,3-diol, and the molecular formula is C15H16O3, Recommanded Product: 2-Phenoxy-1-phenylpropane-1,3-diol.

Referemce:
https://en.wikipedia.org/wiki/Alcohol,
Alcohols – Chemistry LibreTexts

Punt, Philip M. published the artcileTailored Transition-Metal Coordination Environments in Imidazole-Modified DNA G-Quadruplexes, Computed Properties of 57044-25-4, the publication is Chemistry – A European Journal (2019), 25(61), 13987-13993, database is CAplus and MEDLINE.

Two types of imidazole ligands were introduced both at the end of tetramol. and into the loop region of unimol. DNA G-quadruplexes. The modified oligonucleotides were shown to complex a range of different transition-metal cations including Ni^II, Cu^II, Zn^II and Co^II, as indicated by UV/Vis absorption spectroscopy and ion mobility mass spectrometry. Mol. dynamics simulations were performed to obtain structural insight into the investigated systems. Variation of ligand number and position in the loop region of unimol. sequences derived from the human telomer region (htel) allows for a controlled design of distinct coordination environments with fine-tuned metal affinities. It is shown that Cu^II, which is typically square-planar coordinated, has a higher affinity for systems offering four ligands, whereas Ni^II prefers G-quadruplexes with six ligands. Likewise, the positioning of ligands in a square-planar vs. tetrahedral fashion affects binding affinities of Cu^II and Zn^II cations, resp. Gaining control over ligand arrangement patterns will spur the rational development of transition-metal-modified DNAzymes. Furthermore, this method is suited to combine different types of ligands, for example, those typically found in metalloenzymes, inside a single DNA architecture.

Chemistry – A European Journal published new progress about 57044-25-4. 57044-25-4 belongs to alcohols-buliding-blocks, auxiliary class Epoxides,Chiral,Aliphatic hydrocarbon chain,Alcohol, name is (R)-Oxiran-2-ylmethanol, and the molecular formula is C3H6O2, Computed Properties of 57044-25-4.

Referemce:
https://en.wikipedia.org/wiki/Alcohol,
Alcohols – Chemistry LibreTexts

Pereira-Caro, Gema published the artcilePlasma pharmacokinetics of (poly)phenol metabolites and catabolites after ingestion of orange juice by endurance trained men, SDS of cas: 621-37-4, the publication is Free Radical Biology & Medicine (2020), 784-795, database is CAplus and MEDLINE.

The health benefits of orange juice (OJ) consumption are attributed in part to the circulating flavanone phase II metabolites and their microbial-derived ring fission phenolic catabolites. The present study investigated these compounds in the bloodstream after acute intake of 500 mL of OJ. Plasma samples obtained at 0, 1, 2, 3, 4, 5, 6, 7, 8 and 24 h after OJ intake were analyzed by HPLC-HR-MS. Eleven flavanone metabolites and 36 phenolic catabolites were identified and quantified in plasma. The main metabolites were hesperetin-3-sulfate with a peak plasma concentration (Cmax) of 80 nmol/L, followed by hesperetin-7-glucuronide (Cmax 24 nmol/L), hesperetin-3-glucuronide (Cmax 18 nmol/L) and naringenin-7-glucuronide (Cmax 21 nmol/L). Among the main phenolic catabolites to increase in plasma after OJ consumption were 3-methoxycinnamic acid-4-sulfate (Cmax 19 nmol/L), 3-hydroxy-3-(3-hydroxy-4-methoxyphenyl)propanoic acid (Cmax 20 nmol/L), 3-(3-hydroxy-4-methoxyphenyl)propanoic acid (Cmax 19 nmol/L), 3-(4-hydroxyphenyl)propanoic acid (Cmax 25 nmol/L), and 3-(phenyl)propanoic acid (Cmax 19 nmol/L), as well as substantial amounts of phenylacetic and hippuric acids. The comprehensive plasma pharmacokinetic profiles that were obtained are of value to the design of future ex vivo cell studies, aimed at elucidating the mechanisms underlying the potential health benefits of OJ consumption. This trial was registered at clinicaltrials.gov as NCT02627547.

Free Radical Biology & Medicine published new progress about 621-37-4. 621-37-4 belongs to alcohols-buliding-blocks, auxiliary class Carboxylic acid,Benzene,Phenol,Natural product, name is 3-Hydroxyphenylacetic acid, and the molecular formula is C8H8O3, SDS of cas: 621-37-4.

Referemce:
https://en.wikipedia.org/wiki/Alcohol,
Alcohols – Chemistry LibreTexts

Woller, Eric K. published the artcileMannose Functionalization of a Sixth Generation Dendrimer, Recommanded Product: (2R,3S,4S,5S,6R)-2-(Hydroxymethyl)-6-(4-isothiocyanatophenoxy)tetrahydro-2H-pyran-3,4,5-triol, the publication is Biomacromolecules (2001), 2(3), 1052-1054, database is CAplus and MEDLINE.

Saccharide functionalization of fourth through sixth generation PAMAM dendrimers was carried out using a thiourea linkage occurs in high yield (77-92 %) with 85% incorporation of sugar residues. Reaction of 4-isothiocyanatophenyl α-D-mannopyranoside with amine-terminated G(4)-, G(5)-, and G(6)-PAMAMs afforded mannosylated dendrimers. Only a slight excess of the isothiocyanate (≤1.1 equiv/amine) was used. Protection of the mannose hydroxy groups was not necessary as isothiocyanates react selectively with primary amines. Dialysis against a water/ DMSO mixture using a cellulose tube (MW cutoff of 1000 g/mol) afforded the functionalized dendrimers in purified form. A widely applicable MALDI-TOF MS procedure was used for the anal. of the degree of dendrimer surface functionalization achieved.

Biomacromolecules published new progress about 96345-79-8. 96345-79-8 belongs to alcohols-buliding-blocks, auxiliary class Sugar Units,Gal and Man, name is (2R,3S,4S,5S,6R)-2-(Hydroxymethyl)-6-(4-isothiocyanatophenoxy)tetrahydro-2H-pyran-3,4,5-triol, and the molecular formula is C8H5F3O2S, Recommanded Product: (2R,3S,4S,5S,6R)-2-(Hydroxymethyl)-6-(4-isothiocyanatophenoxy)tetrahydro-2H-pyran-3,4,5-triol.

Referemce:
https://en.wikipedia.org/wiki/Alcohol,
Alcohols – Chemistry LibreTexts

Rietjens, Ivonne M. C. M. published the artcileDifferent metabolic pathways of 2,5-difluoronitrobenzene and 2,5-difluoroaminobenzene compared to molecular orbital substrate characteristics, SDS of cas: 120103-18-6, the publication is Chemico-Biological Interactions (1995), 94(1), 49-72, database is CAplus and MEDLINE.

The in vivo metabolite patterns of 2,5-difluoroaminobenzene and of its nitrobenzene analog, 2,5-difluoronitrobenzene, were determined using ¹⁹F NMR anal. of urine samples. Results obtained demonstrate significant differences between the biotransformation patterns of these two analogs. For the aminobenzene, cytochrome P 450 catalyzed aromatic hydroxylation presents the main metabolic pathway. 2,5-Difluoronitrobenzene was predominantly metabolized through glutathione conjugation leading to excretion of 5-fluoro-2-(N-acetylcysteinyl)-nitrobenzene and fluoride anions, and, to a minor extent, through cytochrome P 450 catalyzed hydroxylation and nitro reduction Pretreatment of the rats with various inducers of cytochrome P 450 enzymes, known also to influence glutathione S-transferase enzyme patterns, followed by exposure to the 2,5-difluoroamino- or 2,5-difluoronitrobenzene, generally resulted in metabolite patterns that varied only to a small (≤12%) extent. Based on these results it was concluded that the biotransformation enzyme pattern is not the predominant factor in determining the metabolic route of these two model compounds Addnl. in vitro microsomal and cytosolic incubations with 2,5-difluoroaminobenzene and 2,5-difluoronitrobenzene qual. confirmed the in vivo results. NADPH/oxygen supported microsomal cytochrome P 450 catalyzed hydroxylation was observed only for 2,5-difluoroaminobenzene whereas cytosolic GSH conjugation occurred only in incubations with 2,5-difluoronitrobenzene as the substrate. Outcomes from MO calculations provided a working hypothesis that can explain the difference in metabolic pathways of the nitro- and aminobenzene derivative on the basis of their chem. characteristics. This hypothesis states that the chances for a nitro- or aminobenzene derivative to enter either a cytochrome P 450 or a glutathione conjugation pathway are determined by the relative energy levels of the frontier orbitals of the compounds The aminobenzene derivative has relatively high energy MOs leading to an efficient reaction of its HOMO (HOMO) with the singly occupied MO of the cytochrome P 450 (FeO)³⁺ intermediate, but a low reactivity of its LUMO with the HOMO of glutathione. The nitrobenzene, on the other hand, has MOs of relatively low energy, explaining the efficient interaction, and, thus, reaction between its LUMO and the HOMO electrons of glutathione, but resulting in low reactivity with the SOMO electron of the cytochrome P 450 (FeO)³⁺ reaction intermediate.

Chemico-Biological Interactions published new progress about 120103-18-6. 120103-18-6 belongs to alcohols-buliding-blocks, auxiliary class Fluoride,Nitro Compound,Benzene,Phenol, name is 2,5-Difluoro-4-nitrophenol, and the molecular formula is C6H3F2NO3, SDS of cas: 120103-18-6.

Referemce:
https://en.wikipedia.org/wiki/Alcohol,
Alcohols – Chemistry LibreTexts