Tag: 100-200

Doiuchi, Daiki;Uchida, Tatsuya published 《Catalytic Highly Regioselective C-H Oxygenation Using Water as the Oxygen Source: Preparation of ¹⁷O/¹⁸O-Isotope-Labeled Compounds》 in 2021. The article was appeared in 《Organic Letters》. They have made some progress in their research.Safety of 3,7-Dimethyloctan-3-ol The article mentions the following:

The oxygen atom of water was activated to iodosylbenzene derivatives via reversible hydrolysis of PhI(OOCR)₂ and was used to the oxygen source for ruthenium(bpga)-catalyzed site-selective C-H oxygenation was reported. Ru(bpga)/PhI(OOCR)₂/H₂O system, sterically less bulky methinic and methylenic C-H bonds in various compounds was converted to desired oxygen functional groups in a site-selective manner. Using this method, oxygen-isotope labeled compounds such as D-[3-¹⁷O/¹⁸O]-mannose can be prepared in a multigram scale. To complete the study, the researchers used 3,7-Dimethyloctan-3-ol (cas: 78-69-3) .

3,7-Dimethyloctan-3-ol(cas:78-69-3) is a fatty alcohol that is 3-octanol substituted by methyl groups at positions 3 and 7.Safety of 3,7-Dimethyloctan-3-ol Metabolite observed in cancer metabolism. It has a role as a human metabolite.

Reference:
Alcohol – Wikipedia,
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Lomas, John S. published 《¹H NMR spectra of alcohols and diols in chloroform: DFT/GIAO calculation of chemical shifts》 in 2014. The article was appeared in 《Magnetic Resonance in Chemistry》. They have made some progress in their research.Safety of 2,5-Dimethyl-2,5-hexanediol The article mentions the following:

Proton NMR shifts of aliphatic alcs. in chloroform have been computed on the basis of d. functional theory, the solvent being included by the integral-equation-formalism polarizable continuum model of Gaussian 09. Relative energies of all conformers are calculated at the Perdew, Burke and Ernzerhof (PBE)0/6-311+G(d,p) level, and NMR shifts by the gauge-including AO method with the PBE0/6-311+G(d,p) geometry and the cc-pVTZ basis set. The 208 computed CH proton NMR shifts for 34 alcs. correlate very well with the exptl. values, with a gradient of 1.00 ± 0.01 and intercept close to zero; the overall root mean square difference (RMSD) is 0.08 ppm. Shifts for CH protons of diols in chloroform are well correlated with the theor. values for (isotropic) benzene, with similar gradient and intercept (1.02 ± 0.01, -0.13 ppm), but the overall RMSD is slightly higher, 0.12 ppm. This approach generally gives slightly better results than the CHARGE model of Abraham et al. The shifts of unsaturated alcs. in benzene have been re-examined with Gaussian 09, but the overall fit for CH protons is not improved, and OH proton shifts are worse. Shifts of vinyl protons in alkenols are systematically overestimated, and the correlation of computed shifts against the exptl. data for unsaturated alcs. follows a quadratic equation. Splitting the 20 compounds studied into two sets, and applying empirical scaling based on the quadratic for the first set to the second set, gives an RMSD of 0.10 ppm. A multi-standard approach gives a similar result. Copyright © 2014 John Wiley & Sons, Ltd. The experimental procedure involved many compounds, such as 2,5-Dimethyl-2,5-hexanediol (cas: 110-03-2) .

2,5-Dimethyl-2,5-hexanediol(cas:110-03-2) on heteropoly acid catalyzed dehydration yields cyclic ethers via stereospecific intramolecular SN2 mechanism. It reacts with nitriles in concentrated sulfuric acid to yield Δ1-pyrrolines.Safety of 2,5-Dimethyl-2,5-hexanediol

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Alcohol – Wikipedia,
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Liu, Guang-Xue;Xu, Feng;Shang, Ming-Ying;Wang, Xuan;Cai, Shao-Qing published 《The relative content and distribution of absorbed volatile organic compounds in rats administered asari radix et rhizoma are different between powder- and decoction-treated groups》. The research results were published in《Molecules》 in 2020.Recommanded Product: 80-46-6 The article conveys some information:

Asari Radix et Rhizoma (ARR) is an important traditional Chinese medicine. Volatile organic compounds (VOCs) are the main active constituents of ARR. Research on the metabolite profile of VOCs and the difference of absorbed constituents in vivo after an administration of ARR decoction and powder will be helpful to understand the pharmacol. activity and safety of ARR. In this study, headspace solid-phase microextraction gas chromatog. mass spectrometry (HS-SPME-GC-MS) was applied to profile the VOCs from ARR in rats in vivo. A total of 153 VOCs were tentatively identified; 101 were original constituents of ARR (98 in the powder-treated group and 43 in the decoction-treated group) and 15 were metabolites, and their metabolic reactions were mainly oxidation and reduction, with only two cases of methylation and esterification, and 37 unclassified compounds were identified only in the ARR-treated group. Of the 153 VOCs identified, 131 were reported in rats after oral administration of ARR for the first time, containing 79 original constituents, 15 metabolites, and 37 unclassified compounds In the powder-treated group, methyleugenol, safrole, 3,5-dimethoxytoluene (3,5-DMT), 2,3,5-trimethoxytoluene (2,3,5-TMT), and 3,4,5-trimethoxytoluene (3,4,5-TMT) were the main absorbed constituents, the relative contents of which were significantly higher compared to the decoction-treated group, especially methyleugenol, safrole, and 3,5-DMT. In the decoction-treated group, 3,4,5-TMT, 2,3,5-TMT, kakuol, and eugenol were the main constituents with a higher content and wider distribution. The results of this study provide a reference for evaluating the efficacy and safety of ARR. To complete the study, the researchers used 4-tert-Amylphenol (cas: 80-46-6) .

4-tert-acylphenol (cas:80-46-6) contains hydroxyl group.Some low molecular weight alcohols of industrial importance are produced by the addition of water to alkenes. Ethanol, isopropanol, 2-butanol, and tert-butanol are produced by this general method. Recommanded Product: 80-46-6

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Heyl, Dorothea;Harris, Stanton A.;Folkers, Karl published 《Chemistry of vitamin B₆. IX. Derivatives of 5-deoxypyridoxine》. The research results were published in《Journal of the American Chemical Society》 in 1953.Quality Control of 5-(hydroxymethyl)-2,4-dimethylpyridin-3-ol hydrochloride The article conveys some information:

cf. C.A. 47, 8745g. The 5-deoxy derivatives (I) of pyridoxine (II), pyridoxal (III), and pyridoxamine (IV) were prepared and characterized. The I can participate normally in biochemical reactions involving the substituent at the 4-position but cannot be phosphorylated like II, III, and IV. As expected the I had no vitamin B₆ activity but were effective antimetabolites. Codecarboxylase has been catalytically hydrogenated to 5-deoxypyridoxine (V); both II and III yielded under the same conditions a mixture of 4-deoxypyridoxine (VI) and V. The absorption spectra of 5-deoxypyridoxal (VII) (recorded) and pure pyridoxal-5-phosphate (codecarboxylase) (VIII) at pH 11.0 and 1.9, resp., are almost identical. The deep yellow color of both VII and VIII in alk. solution together with other absorption characteristics is ascribed to a quinoid structure. 2-Methyl-3-hydroxy-4-methoxymethyl-5-chloromethylpyridine (IX).HCl (2.38 g.) in 125 cc. MeOH was shaken with H in the presence of 2 g. 5% Pd-Darco, the mixture filtered, and the filtrate concentrated to 20 cc. to yield 1.5 g. (75%) 2,5-dimethyl-3-hydroxy-4-methoxymethylpyridine (X).HCl, m. 152-3° (from EtOH-Et₂O). IX.HCl (23.7 g.) reduced similarly in 2 equal portions, each one in 600 cc. MeOH with 5 g. Pd catalyst yielded 19.0 g. (94%) X.HCl. X.HCl (1.47 g.) in 50 cc. 4N HCl heated 3 hrs. at 180-90° in a sealed tube, the colorless solution filtered, the filtrate concentrated to dryness, and the H₂O removed azeotropically with EtOH and C₆H₆ yielded 0.96 g. (70%) V.HCl, m. 143-3.5° (from EtOH-Et₂O); treated with excess NaHCO₃ gave V, m. 181-2° (from EtOH). X.HCl was treated in H₂O with NaHCO₃, the mixture concentrated in vacuo and extracted with Et₂O, the extract evaporated, 3.1 g. of the residual free base heated 18 hrs. with 50 cc. MeOH and 50 cc. liquid NH₃ in a sealed tube, the mixture evaporated in vacuo to dryness, MeOH added and removed twice by distillation, and the residue extracted with Et₂O to leave 1.86 g. (60%) 5-deoxypyridoxamine (XI); m. 160-1° (from MeOH); 2,5-dimethyl-3-p-toluenesulfonoxy-4-p-toluenesulfonylaminopyridine-HCl, m. 194-5° (from EtOH). A small sample of XI was heated 20 min. with Ac₂O on a steam bath, the solution concentrated to dryness, the residue treated with EtOH, distilled to dryness, dissolved in HCl, treated with Darco, neutralized with NaHCO₃, chilled, and the crystalline deposit recrystallized from C₆H₆ containing a few drops EtOH to give 2,5-dimethyl-3-acetoxy-4-acetylaminomethylpyridine, m. 174-5°. V.HCl (5.7 g.) was stirred 2 hrs. at 60-70° with 2.8 g. MnO₂, 1.5 cc. H₂SO₄, and 75 cc. H₂O, the mixture filtered, the filtrate concentrated in vacuo, the sirup taken up in 15 cc. H₂O, excess solid AcONa added, and the thick, crystalline precipitate cooled, filtered off, and washed with ice water to give 1.30 g. (29%) VII, m. 108-9° (from petr. ether); the aqueous filtrate from VII gave with 2 g. NH₂OH.HCl 0.9 g. (18%) oxime of VII, m. 239-40° (decomposition) (from EtOH). To the aqueous filtrate of a similar run were added 12 g. NaOAc and 4.5 g. NH₂OH.HCl and the mixture was heated 10 min. on a steam bath to yield 2.43 g. (49%) oxime of VII. VII in CHCl₃ treated with excess alc. HCl, the solution evaporated in vacuo to dryness, a little H₂O added and removed in vacuo, and the residue treated with CHCl₃ yielded VII.HCl, m. 191-3° (decomposition). VII (90 mg.) in 1 cc. H₂O was cooled in ice, the pH adjusted to 11 with 6N NaOH, 4 drops 30% H₂O₂ added, the mixture adjusted to pH 3 with HCl and cooled, and the precipitate washed with H₂O, EtOH, and Et₂O to yield 70 mg. (85%) 2,5-dimethyl-3,4-dihydroxypyridine, decomposed 262-70°. Crude Ca codecarboxylase (0.5 g.) was suspended in H₂O and treated with 0.7 cc. 6N HCl, the mixture filtered, the filtrate diluted to 50 cc. shaken 2.25 hrs. at atm. pressure with H and 0.5 g. 10% Pd-C, filtered and concentrated to dryness in vacuo, the residue dissolved in about 3 cc. H₂O, the solution treated with excess solid NaHCO₃, filtered, the filter residue washed with H₂O, the combined filtrate and washings were concentrated in vacuo to 5 cc., the concentrate extracted 21 hrs. continuously with CHCl₃, the extract evaporated, and the residue treated with alc. HCl and precipitated with Et₂O to give 0.07 g. V.HCl, m. 140-1°. III.HCl (0.35 g.) was treated with 0.10 g. CaO and 0.17 g. H₃PO₄ and hydrogenated similarly to give 0.08 g. (24%) VI.HCl, m. 264-5°, and 0.11 g. (33%) V.HCl; the aqueous filtrate left from the CHCl₃-extraction was concentrated to dryness, the residue extracted with EtOH, and the extract acidified with alc. HCl to give 0.11 g. (30%) I.HCl. Similar hydrogenation of 0.40 g. I.HCl in 0.3 cc. 6N HCl and 50 cc. H₂O for 4-5 hrs. gave 0.16 g. (42%) VI.HCl and 0.09 g. (24%) V.HCl. Attempted similar hydrogenation of V gave only recovered starting material. To complete the study, the researchers used 5-(hydroxymethyl)-2,4-dimethylpyridin-3-ol hydrochloride (cas: 148-51-6) .

5-(hydroxymethyl)-2,4-dimethylpyridin-3-ol hydrochloride(cas:148-51-6 Quality Control of 5-(hydroxymethyl)-2,4-dimethylpyridin-3-ol hydrochloride) is a vitamin B6 antimetabolite with diverse biological activities. It inhibits transport of pyridoxine , pyridoxal, and pyridoxamine in and reduces growth of S. carlsbergensis cells. DOP inhibits sphingosine-1-phosphate (S1P) lyase and reduces cyclic stretch-induced apoptosis in alveolar epithelial MLE-12 cells.

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Formula: C11H16O《Predicting the toxicity of substituted aromatic compounds to fathead minnows using artificial neural network》 was published in 2017. The authors were Li, Qinling;Yang, Yuliang, and the article was included in《Jisuanji Yu Yingyong Huaxue》. The author mentioned the following in the article:

Ninety-two substituted aromatic compounds (containing alkyl-benzenes, nitrobenzene, phenols and anilines) were calculated and 13 quantum chem. parameters were obtained using ab initio. The prediction model was established quant. relationship between the acute toxicity to fathead minnows of a set of substituted aromatic compounds on using BP-ANN and RBF-ANN method. The correlation coefficients of the prediction model were 0.958 and 0.967. Exptl. results showed: BP-ANN and RFB-ANN were better than the multiple regression methods. The results showed that there was nonlinear relationship between toxicity and the quantum chem. parameters. And 4-tert-Amylphenol (cas: 80-46-6) was used in the research process.

4-tert-acylphenol (cas:80-46-6) contains hydroxyl group. Alcohols are among the most common organic compounds. They are used as sweeteners and in making perfumes, are valuable intermediates in the synthesis of other compounds, and are among the most abundantly produced organic chemicals in industry. Formula: C11H16O

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Product Details of 110-03-2In 2019, Ye, Yang;Chen, Haifeng;Sessler, Jonathan L.;Gong, Hegui published 《Zn-Mediated Fragmentation of Tertiary Alkyl Oxalates Enabling Formation of Alkylated and Arylated Quaternary Carbon Centers》. 《Journal of the American Chemical Society》published the findings. The article contains the following contents:

Zn-mediated reduction of readily accessible dialkyl oxalates derived from tertiary alcs. provides an efficient approach to C-O bond fragmentation and alkyl radical formation. With MgCl₂ as the indispensable additive and Ni as the promoter, trapping the radical with activated alkenes and aryl-Ni intermediates allows for the generation of alkylated and arylated all-carbon quaternary centers. To complete the study, the researchers used 2,5-Dimethyl-2,5-hexanediol (cas: 110-03-2) .

2,5-Dimethyl-2,5-hexanediol(cas:110-03-2) on heteropoly acid catalyzed dehydration yields cyclic ethers via stereospecific intramolecular SN2 mechanism. It reacts with nitriles in concentrated sulfuric acid to yield Δ1-pyrrolines.Product Details of 110-03-2

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Smoum, Reem;Haj, Christeene;Hirsch, Shira;Nemirovski, Alina;Yekhtin, Zhannah;Bogoslavsky, Benny;Bakshi, Gaganjyot Kaur;Chourasia, Mukesh;Gallily, Ruth;Tam, Joseph;Mechoulam, Raphael published 《Fenchone Derivatives as a Novel Class of CB2 Selective Ligands: Design, Synthesis, X-ray Structure and Therapeutic Potential》 in 2022. The article was appeared in 《Molecules》. They have made some progress in their research.Product Details of 80-46-6 The article mentions the following:

A series of novel cannabinoid-type derivatives was synthesized by the coupling of (1S,4R)-(+) and (1R,4S)-(-)-fenchones I (R = H, Me, n-pentyl, 2-methylbutan-2-yl, etc.; R¹ = H, hexyl; R² = H, OMe) with various resorcinols RC₆H₃(OH)₂/phenols RC₆H₄OH. The fenchone-resorcinol derivatives I were fluorinated using Selectfluor and demethylated using sodium ethanethiolate in DMF (DMF). The absolute configurations of four compounds were determined by X-ray single crystal diffraction. The fenchone-resorcinol analogs I possessed high affinity and selectivity for the CB2 cannabinoid receptor. One of the analogs synthesized, I (R = 2-methyloctan-2-yl, R¹ = H, R² = OMe (II)), had a high affinity (K_i = 3.51 nM) and selectivity for the human CB2 receptor (hCB2). In the [³⁵S]GTPγS binding assay, the lead compound was found to be a highly potent and efficacious hCB2 receptor agonist (EC₅₀ = 2.59 nM, E_(max) = 89.6%). Two of the fenchone derivatives I were found to possess anti-inflammatory and analgesic properties. Mol.-modeling studies elucidated the binding interactions of (II) within the CB2 binding site.4-tert-Amylphenol (cas: 80-46-6) were involved in the experimental procedure.

4-tert-acylphenol (cas:80-46-6) contains hydroxyl group.Some low molecular weight alcohols of industrial importance are produced by the addition of water to alkenes. Ethanol, isopropanol, 2-butanol, and tert-butanol are produced by this general method. Product Details of 80-46-6

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Alcohol – Wikipedia,
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Kamata, Ryo;Nakajima, Daisuke;Shiraishi, Fujio published 《Agonistic effects of diverse xenobiotics on the constitutive androstane receptor as detected in a recombinant yeast-cell assay》. The research results were published in《Toxicology In Vitro》 in 2018.Product Details of 80-46-6 The article conveys some information:

The constitutive androstane receptor (CAR) is a nuclear receptor and transcription factor regulating proteins involved in xenobiotic metabolism Agonist activation of the CAR can trigger metabolic activation and toxification as well as detoxification and clearance; accordingly, xenobiotic substances acting as CAR ligands may pose a threat to human and animal health. The authors used yeast cells transduced with the human CAR and the response pathway to measure the CAR-agonistic activities of 549 synthetic or natural compounds: 216 of the tested compounds exhibited CAR-agonistic effects. Eighty-four percent of CAR-activating compounds were aromatic compounds, and >65% of these active compounds were aromatic hydrocarbons, bisphenols, monoalkyl phenols, phthalates, styrene dimers, di-Ph ethers, organochlorines, and organophosphates. The ten most potent compounds were 4-tert-octylphenol (4tOP; reference substance), 4-nonylphenol, diethylstilbestrol, benzyl Bu phthalate, 2-(4-hydroxyphenyl)-2,4,4-trimethylchroman, o,p’-DDT, methoxychlor, di-Pr phthalate, hexestrol, and octachlorostyrene. The activities of these nine non-reference compounds exceeded 10% of the 4tOP activity. Anal. of para-monoalkyl phenols suggests that branching of the alkyl group and chlorination at the ortho position raises potency. This study provides critical information for identifying the potential of CAR-mediated toxic hazards and for understanding the relevant mechanism. The experimental procedure involved many compounds, such as 4-tert-Amylphenol (cas: 80-46-6) .

4-tert-acylphenol (cas:80-46-6) contains hydroxyl group. Owing to the presence of the polar OH alcohols are more water-soluble than simple hydrocarbons. Methanol, ethanol, and propanol are miscible in water. Butanol, with a four-carbon chain, is moderately soluble.Product Details of 80-46-6

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Product Details of 224434-01-9In 2020, Shao, Wen;Besnard, Celine;Guenee, Laure;Mazet, Clement published 《Ni-Catalyzed Regiodivergent and Stereoselective Hydroalkylation of Acyclic Branched Dienes with Unstabilized C(sp³) Nucleophiles》. 《Journal of the American Chemical Society》published the findings. The article contains the following contents:

Two complementary regiodivergent [(P,N)Ni]-catalyzed hydroalkylations of branched dienes are reported. When amides are employed as unstabilized C(sp³) nucleophiles, a highly regioselective 1,4-addition process is favored. The addition products are obtained in high yield and with excellent stereocontrol of the internal olefin. With use of a chiral ligand and imides as carbon nucleophiles, a 3,4-addition protocol was developed, enabling construction of two contiguous tertiary stereocenters in a single step with moderate to high levels of diastereocontrol and excellent enantiocontrol. Both methods operate under mild reaction conditions, display a broad scope, and show excellent functional group tolerance. The synthetic potential of the 3,4-hydroalkylation reaction was established via a series of postcatalytic modifications. To complete the study, the researchers used (S)-2-Amino-2-(4-fluorophenyl)ethanol (cas: 224434-01-9) .

(S) – 2-amino-2 – (4-fluorophenyl) ethanol (cas: 224434-01-9) has the characteristics of alcohol. In general, the hydroxyl group makes alcohols polar. Those groups can form hydrogen bonds to one another and to most other compounds. Product Details of 224434-01-9

Reference:
Alcohol – Wikipedia,
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Incili, Gokhan Kursad;Karatepe, Pinar;Akgol, Muzeyyen;Tekin, Ali;Kanmaz, Hilal;Kaya, Busra;Calicioglu, Mehmet;Hayaloglu, Ali Adnan published 《Impact of chitosan embedded with postbiotics from Pediococcus acidilactici against emerging foodborne pathogens in vacuum-packaged frankfurters during refrigerated storage》. The research results were published in《Meat Science》 in 2022.Computed Properties of C10H22O The article conveys some information:

The objective of the study was to carry out characterization of postbiotics from Pediococcus acidilactici and to assess their efficacy (50% and 100%) in combination with chitosan (0.5 and 1%) against Escherichia coli O157:H7, Salmonella Typhimurium, Listeria monocytogenes on frankfurters during refrigerated storage for 35 days. High amounts of total phenolic content (1708.15 ± 93.28 mg GAE/L) and carboxylic acids, which comprised 74.89% of the total volatiles, were found in the postbiotics. On day 0, the postbiotic-chitosan combinations decreased the E. coli O157:H7, L. monocytogenes and S. Typhimurium counts ranging from 1.58 to 3.21 log10 compared to the control in frankfurters (P < 0.05). Total viable count and number of lactic acid bacteria were effectively reduced in all treatment groups (P < 0.05), and postbiotic and chitosan treatments did not cause any changes in pH and color of the frankfurters. In conclusion, postbiotic-chitosan combinations can be used to reduce the risks that might be associated with E. coli O157:H7, L. monocytogenes, and S. Typhimurium in frankfurters. The experimental procedure involved many compounds, such as 3,7-Dimethyloctan-3-ol (cas: 78-69-3) .

3,7-Dimethyloctan-3-ol(cas:78-69-3) is a fatty alcohol that is 3-octanol substituted by methyl groups at positions 3 and 7.Computed Properties of C10H22O Metabolite observed in cancer metabolism. It has a role as a human metabolite.

Reference:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts