Tag: M.W=150-200

Dishman, Sarah N. published the artcileDivergent stereochemical outcomes in the insertion of donor/donor carbenes into the C-H bonds of stereogenic centers, Computed Properties of 86-48-6, the publication is Chemical Science (2022), 13(4), 1030-1036, database is CAplus and MEDLINE.

Herein, the insertion of donor/donor carbenes into stereogenic carbon centers allowing access to trisubstituted benzodihydrofurans in a single step was reported. This study illuminates, for the first time, the stereochem. impact on the carbene center and delineates the structural factors that enable control over both stereogenic centers. Sterically bulky, highly activated C-H insertion centers exhibit high substrate control yielding a single diastereomer and a single enantiomer of product regardless of the catalyst used. Less bulky, less activated C-H insertion centers exhibit catalyst control over the diastereomeric ratio (dr), where a single enantiomer of each diastereomer was observed with high selectivity. A combination of exptl. studies and DFT calculations was used to elucidate the origin of these results. First, hydride transfer from the stereogenic insertion site proceeds with high stereoselectivity to the carbene center, thus determining the absolute configuration of the product. Second, the short lived zwitterionic intermediate can diastereoselectively ring-close by a hitherto unreported SE2 mechanism that was either controlled by the substrate or the catalyst. These results demonstrate that donor/donor carbenes undergo uniquely stereoselective reactions that originate from a stepwise reaction mechanism, in contrast to the analogous concerted reactions of carbenes with one or more electron-withdrawing groups attached.

Chemical Science published new progress about 86-48-6. 86-48-6 belongs to alcohols-buliding-blocks, auxiliary class Organic Pigment,Natural product, name is 1-Hydroxy-2-naphthoic acid, and the molecular formula is C11H8O3, Computed Properties of 86-48-6.

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

Caffrey, Andrew J. published the artcileCharacterization of Humulus lupulus glycosides with porous graphitic carbon and sequential high performance liquid chromatography quadrupole time-of-flight mass spectrometry and high performance liquid chromatography fractionation, Quality Control of 106-25-2, the publication is Journal of Chromatography A (2022), 463130, database is CAplus and MEDLINE.

Monoterpenes contribute to the characteristic aroma of several hop varieties and may occur as nonvolatile glycosides. Upon hydrolysis, the volatile terpenes are released from the glycoside precursors. Little is known, however, about the glycoside composition of hops. Seven pentose-hexose monoterpene alc. glycosides from dried Humulus lupulus L. cv. Citra cones were isolated using high performance liquid chromatog. separation and fractionation on a reverse phase phenyl-hexyl column. Further evaluation of each isolated fraction through HPLC qTOF MS with porous graphitic carbon (PGC) showed that the seven isolated monoterpenyl glycoside fractions could be further resolved into 20 isomers. Isolation on phenyl-hexyl followed by separation on PGC was needed to distinguish each isomer present. Addnl., the hop cones were screened for potential aroma glycosides. Using the PGC column combined with a database of over 900 potential glycosides, the identification of 21 addnl. monoterpene-polyol, norisoprenoid, volatile phenol, and aliphatic alc. glycosides is reported.

Journal of Chromatography A published new progress about 106-25-2. 106-25-2 belongs to alcohols-buliding-blocks, auxiliary class Natural product, name is cis-3,7-Dimethyl-2,6-Octadien-1-Ol, and the molecular formula is C10H18O, Quality Control of 106-25-2.

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

Morgan, William Raymond published the artcileNitrogen inversion of tertiary amines in aqueous acid, Recommanded Product: 2-(Benzyl(methyl)amino)ethanol, the publication is Journal of the American Chemical Society (1970), 92(15), 4527-31, database is CAplus.

The kinetics of the N inversion of 3 tertiary amines was studied in aqueous acid by high-resolution NMR. Line-shape anal. of the AB NMR pattern of methylene protons on each compound provided a measure of the rate of interchange of the magnetic environments of these protons, which results upon the reprotonation of the free base following an odd number of inversions. The inversion rate followed a modification of the first-order protolysis reaction given by Grunwald. Inversion rate constants of 108-109 sec-1 are estimated These are compared to inversion rate constants for N atoms in ring systems. A second-order dependence of inversion on the concentration of amine was also found. The rate law for this inversion process follows very closely the second-order proton exchange reaction for the amine in question. Application of solvent isotope effects to the protolysis rate parameters predicted the observed results of N inversion in D2O.

Journal of the American Chemical Society published new progress about 101-98-4. 101-98-4 belongs to alcohols-buliding-blocks, auxiliary class Amine,Benzene,Alcohol, name is 2-(Benzyl(methyl)amino)ethanol, and the molecular formula is C10H15NO, Recommanded Product: 2-(Benzyl(methyl)amino)ethanol.

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

Pal, Vineet Kumar published the artcileDiurnal variability in urinary volatile organic compound metabolites and its association with oxidative stress biomarkers, Synthetic Route of 90-64-2, the publication is Science of the Total Environment (2022), 151704, database is CAplus and MEDLINE.

Volatile organic compounds (VOCs) are ubiquitous environmental pollutants that are associated with birth defects, leukemia, neurocognitive deficits, reproductive impairment and cancer in humans exposed to these compounds Exposure to VOCs can be assessed by measuring their metabolites in urine. Little is known, however, about the temporal variability in urinary VOC metabolite (VOCM) concentrations within- and between-individuals. In this study, we determined the variability in the concentrations of 38 VOCMs in urine samples collected from 19 healthy individuals across a period of 44 days. We also measured seven biomarkers of oxidative stress (lipid, protein and DNA damage) in urine to assess the relationship of VOC exposure to oxidative stress. Seventeen VOCMs had detection frequencies (DFs) of >60% in urine, and we limited further data anal. to those compounds The creatinine-adjusted geometric mean concentrations of VOCMs ranged from 2.70 μg/g to 327 μg/g in spot and 2.60 μg/g to 551 μg/g in first morning void (FMV) urine samples. Calculation of the intra-class correlation coefficients (ICCs) for 17 VOCM concentrations to assess their predictability and repeatability in urinary measurements showed ranges of 0.080-0.425 in spot and 0.050-0.749 in FMV urine samples, revealing notable within-individual variability. Our results suggest that taking only single measurements of VOCM concentrations in urine in epidemiol. investigations may lead to exposure misclassification. In addition, VOCM concentrations were significantly and pos. correlated with oxidative stress biomarkers. This study thus provides important information for formulating sampling strategies in the biomonitoring of VOC exposure in human populations.

Science of the Total Environment published new progress about 90-64-2. 90-64-2 belongs to alcohols-buliding-blocks, auxiliary class Carboxylic acid,Benzene,Alcohol,Natural product, name is 2-Hydroxy-2-phenylacetic acid, and the molecular formula is C8H8O3, Synthetic Route of 90-64-2.

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

Luo, Ming published the artcileIntegrative analysis of multiple metabolomes and transcriptome revealed color expression mechanism in red skin root syndrome of Panax ginseng, HPLC of Formula: 621-37-4, the publication is Industrial Crops and Products (2022), 114491, database is CAplus.

Red skin root syndrome causes reduction of both production and quality of Panax ginseng (ginseng). However, its development process and key metabolites are still unknown. Multiple metabolomes including non-targeted metabolome, and anthocyanins-targeted and carotenoids-targeted metabolomes were performed on field grown red skin and healthy ginseng. The detected metabolites were analyzed in combination with previous transcriptome results. The total metabolite profiles revealed that primary metabolites especially citrate was decreased, but secondary metabolites mainly involved in phenylpropanoid pathway were increased in red skin ginseng compared to those in healthy ginseng. Targeted metabolome found that each gram of fresh red skin ginseng sample contained 8 μg β-carotene, 0.56 μg α-carotene, 0.017 μg rutin, 0.248 μg chalcone, and some anthocyanins including 0.023 μg cyanidin and 0.037 μg quercetin 3-O-glucoside, albeit in low concentrations but higher than those in healthy ginseng. Furthermore, integrative metabolome and transcriptome anal. revealed that changes of metabolites related to anthocyanins synthesis were correlated with the related gene expression patterns. Addnl., jasmonate (JA) and its precursor 12-oxophytodienoic acid increased their concentrations dramatically in red skin ginseng, suggesting the possible role of JA or JA signaling pathway in regulating red skin syndrome. Consistently, the expressions of 17 MYB transcription factors were differentially regulated in red skin ginseng. JA related cis-elements are widely distributed at their promoters. Taken together, our study revealed reduction of primary metabolism but increase of secondary metabolism in red skin ginseng. MYB transcription factors of JA signal pathway were supposed to mediate accumulation of anthocyanins and carotenoids that contributed to the development of red skin ginseng.

Industrial Crops and Products 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, HPLC of Formula: 621-37-4.

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

Wang, Jing published the artcileMetal-free visible-light-mediated aerobic oxidation of silanes to silanols, Related Products of alcohols-buliding-blocks, the publication is Science China: Chemistry (2018), 61(12), 1594-1599, database is CAplus.

Herein, the first metal-free visible-light-mediated aerobic oxidation of silanes to silanols using 2 mol% Rose Bengal as the catalyst, air (O₂) as the oxidant and water as the additive is reported. While this method produces various silanols in a simple, cost-effective, efficient (92%-99% yields) and scalable fashion, its reaction mechanism is very different than the reported ones associated with metal catalysis.

Science China: Chemistry published new progress about 17877-23-5. 17877-23-5 belongs to alcohols-buliding-blocks, auxiliary class Protection and Derivatization Reagent, name is Triisopropylsilanol, and the molecular formula is C10H15ClO3S, Related Products of alcohols-buliding-blocks.

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

Li, Lin published the artcileEnhancement of 2-keto-L-gulonic acid production using three-stage ventilation control strategy, Category: alcohols-buliding-blocks, the publication is Zhongguo Niangzao (2012), 31(4), 144-147, database is CAplus.

The aim of this study was to improve 2-keto-L-gulonic acid (2-KLG) production by Ketogulonicigenium vulgare and Bacillus megaterium. A three-stage ventilation control strategy was developed: the flask content was kept at 95 mL/750 mL during the first 10 h, and maintained at 95 mL/750 mL for the following 15 h, and then decreased to 70 mL/750 mL till the end of fermentation With this strategy, K. vulgare growth rate, B. megaterium growth rate and 2-KLG production were increased by 14.7%, 10.5% and 10.9%, resp., compared with those of the control.

Zhongguo Niangzao 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 C6H10O7, Category: alcohols-buliding-blocks.

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

Wu, Yusen published the artcileRegulatory effect of root restriction on aroma quality of Red Alexandria grape, Synthetic Route of 106-25-2, the publication is Food Chemistry (2022), 131118, database is CAplus and MEDLINE.

To systematically study the impact of root restriction (RR) on the aroma quality of grape berry, in this study, free and bound compounds were investigated in ‘Red Alexandria’ grape skin and pulp produced with and without RR during development and ripening. Compared with the control, RR advanced the initiation of free-terpene synthesis and increased their concentrations at 14-18 wk post-flowering (wpf) by promoting the conversion of bound terpenes to free terpenes. In addition, RR significantly regulated the aromatic series at 14-18 wpf and advanced the date of aroma maturation. Network analyses indicated that the correlations among bound compounds were more conserved than those among free compounds, and the skin network displayed tight coordination compared with the pulp network. Terpenes were highly intercorrelated and played a core role in these networks. Finally, 10 bound compounds in pulp were screened out as indicators of the developmental timing of grape.

Food Chemistry published new progress about 106-25-2. 106-25-2 belongs to alcohols-buliding-blocks, auxiliary class Natural product, name is cis-3,7-Dimethyl-2,6-Octadien-1-Ol, and the molecular formula is C16H18Br2ClN3O3, Synthetic Route of 106-25-2.

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

Choi, Younghun published the artcileIdentification, quantification, and prioritization of new emerging pollutants in domestic and industrial effluents, Korea: Application of LC-HRMS based suspect and non-target screening, Application of Triisopropanolamine, the publication is Journal of Hazardous Materials (2021), 123706, database is CAplus and MEDLINE.

The present study was designed to identify recently (or rarely) recognized or unreported substances (RRS or URS) contained in the effluents from water treatment plants in two industrialized urban areas, Gumi and Daegu, in Korea. In addition to 30 initial targets, 72 substances were identified through suspect and non-target screening (SNTS). Among them were 4 RRSs and 22 URSs, resp. The quant. analyses were applied to 35 pharmaceuticals, 15 pesticides, 13 poly-/perfluorinated alkyl substances (PFASs), 2 organophosphate flame retardants (OPFRs), 2 corrosion inhibitors, and 3 metabolites. The highest average concentration was observed for benzotriazole, followed by those for niflumic acid, and metformin. Effluents from Gumi mainly contained benzotriazole and metformin whereas niflumic acid and tramadol were the major components in effluents from Daegu. According to a scoring system based on risk relevant parameters, higher priorities were given to telmisartan, PFOA, and cimetidine. Yet, priorities for some substances were area specific (e.g., benzotriazole from Gumi, PFASs from Daegu), reflecting differences in industry profiles and populations. Many of the RRSs and URSs were recognized as potential hazards. The new identifications and evaluations should be taken into consideration for constant monitoring and management, as do the previously recognized contaminants.

Journal of Hazardous Materials published new progress about 122-20-3. 122-20-3 belongs to alcohols-buliding-blocks, auxiliary class Organic Pigment, name is Triisopropanolamine, and the molecular formula is C9H21NO3, Application of Triisopropanolamine.

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

Duraiswamy, Athisayamani Jeyaraj published the artcileDiscovery and Optimization of a Porcupine Inhibitor, Application In Synthesis of 23351-09-9, the publication is Journal of Medicinal Chemistry (2015), 58(15), 5889-5899, database is CAplus and MEDLINE.

Wnt proteins regulate various cellular functions and serve distinct roles in normal development throughout life. Wnt signaling is dysregulated in various diseases including cancers. Porcupine (PORCN) is a membrane-bound O-acyltransferase that palmitoleates the Wnts and hence is essential for their secretion and function. The inhibition of PORCN could serve as a therapeutic approach for the treatment of a number of Wnt-dependent cancers. Herein, the authors describe the identification of a Wnt secretion inhibitor from cellular high throughput screening. Classical SAR based cellular optimization provided us with a PORCN inhibitor I with nanomolar activity and excellent bioavailability that demonstrated efficacy in a Wnt-driven murine tumor model. Finally, the authors also discovered that enantiomeric PORCN inhibitors show very different activity in the reporter assay, suggesting that such compounds may be useful for mode of action studies on the PORCN O-acyltransferase.

Journal of Medicinal Chemistry published new progress about 23351-09-9. 23351-09-9 belongs to alcohols-buliding-blocks, auxiliary class Pyrrole,Benzene,Alcohol, name is 4-(1H-Pyrrol-1-yl)phenol, and the molecular formula is C10H9NO, Application In Synthesis of 23351-09-9.

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