Day: November 21, 2022

Snyder, Rodney W. published the artcileMetabolism and Disposition of Bisphenol A in Female Rats, Application of (2S,3S,4S,5R,6S)-3,4,5-Trihydroxy-6-(4-(2-(4-hydroxyphenyl)propan-2-yl)phenoxy)tetrahydro-2H-pyran-2-carboxylic acid, the publication is Toxicology and Applied Pharmacology (2000), 168(3), 225-234, database is CAplus and MEDLINE.

Bisphenol A (BPA), which is used in the manufacture of polycarbonates, elicits weak estrogenic activity in in vitro and in vivo test systems. The objectives of this study were to compare the patterns of disposition of radioactivity in adult female F-344 and CD rats after oral administration of ¹⁴C BPA (100 mg/kg), to isolate the glucuronide of BPA and to assess its estrogenic activity in vitro, and to evaluate the transfer of radioactivity to pups from lactating dams administered ¹⁴C BPA. Over 6 days, F-344 rats excreted more radioactivity in urine than CD rats. The major metabolite in urine was identified as bisphenol A glucuronide (BPA gluc) by incubation with β-glucuronidase and ¹H and ¹³C NMR spectroscopy. In lactating CD rats administered ¹⁴C BPA (100 mg/kg) by gavage, only a small fraction of the label was found in milk, with 0.95±0.66, 0.63±0.13, and 0.26±0.10 μg equiv/mL (mean ± SD) from dams collected 1, 8, and 26 h after dosing, resp. Radioactivity in pup carcasses indicated exposure in the range of microgram equivalent per kg; those values ranged from 44.3±24.4 for pups separated from their lactating dams at 2 h to 78.4±10.9 at 24 h. BPA gluc was the prominent metabolite in milk and plasma. In test systems for activation of in vitro estrogen receptors α and β, BPA gluc did not show appreciable efficacy at concentrations up to 0.03 mM, indicating that metabolism via glucuronidation is a detoxication reaction. (c) 2000 Academic Press.

Toxicology and Applied Pharmacology published new progress about 267244-08-6. 267244-08-6 belongs to tetrahydropyran, auxiliary class Tetrahydropyran,Chiral,Carboxylic acid,Benzene,Phenol,Alcohol,Ether,, name is (2S,3S,4S,5R,6S)-3,4,5-Trihydroxy-6-(4-(2-(4-hydroxyphenyl)propan-2-yl)phenoxy)tetrahydro-2H-pyran-2-carboxylic acid, and the molecular formula is C7H5Cl2NO, Application of (2S,3S,4S,5R,6S)-3,4,5-Trihydroxy-6-(4-(2-(4-hydroxyphenyl)propan-2-yl)phenoxy)tetrahydro-2H-pyran-2-carboxylic acid.

Referemce:
https://en.wikipedia.org/wiki/Tetrahydropyran,
Tetrahydropyran – an overview | ScienceDirect Topics

Journet, Michel published the artcileRadical cyclization of (bromomethyl)dimethylsilyl propargyl ethers. Regio-, chemo- and stereoselectivity., Related Products of tetrahydropyran, the publication is Journal of Organic Chemistry (1992), 57(11), 3085-93, database is CAplus.

Radical cyclization of (bromomethyl)dimethylsilyl propargyl ether derivatives I [R¹ = R² = Me, R³ = (CH₂)_nCH:CH₂, n = 1,2,4, (CH₂)₃OTHP, Ph, SiMe₃; R¹ = H, R² = R³ = Bu; R¹ = R³ = H, R² = H, Me; R¹ = R² = H, R³ = pentyl; R¹ = H, R² = Me, R³ = Ph, pentyl] is a powerful reaction with a high degree of regio-, chemo-, and stereoselectivity. Trisubstituted olefins II (R⁴ = H, OH, SiMe₃), cyclopentene derivatives III, and diquinane system IV are obtained in good yields by a judicious choice of unsaturated substituents. Triquinane frameworks could be obtained stereoselectively from a suitable acyclic substrate of type I in a one-pot reaction. First attempts have not yet allowed us to aim at this goal due to interesting (1,5) hydrogen transfers. Moreover, intercepted, for the first time, is the α-cyclopropyl radical which is involved in the Stork-Beckwith mechanism of the 5- vs. 6-membered ring formation in the vinyl radical cyclization.

Journal of Organic Chemistry published new progress about 27943-46-0. 27943-46-0 belongs to tetrahydropyran, auxiliary class Tetrahydropyran,Alkynyl,Ether, name is 2-((2-Methylbut-3-yn-2-yl)oxy)tetrahydro-2H-pyran, and the molecular formula is C10H16O2, Related Products of tetrahydropyran.

Referemce:
https://en.wikipedia.org/wiki/Tetrahydropyran,
Tetrahydropyran – an overview | ScienceDirect Topics

Elsby, Robert published the artcileComparison of the modulatory effects of human and rat liver microsomal metabolism on the estrogenicity of bisphenol A: implications for extrapolation to humans, Category: tetrahydropyran, the publication is Journal of Pharmacology and Experimental Therapeutics (2001), 297(1), 103-113, database is CAplus and MEDLINE.

Bisphenol A [BPA, 2,2-bis(4-hydroxyphenyl)propane], a xenoestrogen, is a monomer for the synthesis of polycarbonate plastics, epoxy resins, and composites. Metabolism of BPA to the monoglucuronide will determine the extent of its estrogenicity in vivo. Investigation of the metabolism of BPA (500 μM) by isolated female rat hepatocytes confirmed the formation of BPA glucuronide as the major metabolite. There was a significant difference (p < 0.05) between the V_max (mean ± S.E.M., n = 4) of glucuronidation by pooled male or female human (four livers in each case) and immature female rat liver microsomes (5.9±0.4, 5.2±0.3, and 31.6±8.1 nmol/min/mg of protein, resp.). Estrogenic activity of BPA, assessed in a coupled microsomal metabolism-yeast estrogenicity assay, was decreased 3- and 7-fold following glucuronidation by human female and immature female rat liver microsomes, resp. Incubations of BPA with pooled human or rat liver microsomes, in the presence of NADPH, resulted in the formation of 5-hydroxybisphenol A [2-(4,5-dihydroxyphenyl)-2-(4-hydroxyphenyl)propane], which was 10-fold less potent than BPA in the yeast estrogenicity assay. However, there was insufficient turnover to achieve a significant effect on the estrogenic activity of BPA. Because human liver microsomes did not glucuronidate BPA as extensively as the rat liver microsomes, estrogen target tissues in humans may be subject to greater exposure to BPA than the tissues of the immature female rats used for assessing estrogenicity of xenobiotics.

Journal of Pharmacology and Experimental Therapeutics published new progress about 267244-08-6. 267244-08-6 belongs to tetrahydropyran, auxiliary class Tetrahydropyran,Chiral,Carboxylic acid,Benzene,Phenol,Alcohol,Ether,, name is (2S,3S,4S,5R,6S)-3,4,5-Trihydroxy-6-(4-(2-(4-hydroxyphenyl)propan-2-yl)phenoxy)tetrahydro-2H-pyran-2-carboxylic acid, and the molecular formula is C21H24O8, Category: tetrahydropyran.

Referemce:
https://en.wikipedia.org/wiki/Tetrahydropyran,
Tetrahydropyran – an overview | ScienceDirect Topics

Naapuri, Janne M. published the artcileCascade Catalysis Through Bifunctional Lipase Metal Biohybrids for the Synthesis of Enantioenriched O-Heterocycles from Allenes, HPLC of Formula: 27943-46-0, the publication is ChemCatChem, database is CAplus.

Lipase/metal nanobiohybrids, generated by growth of silver or gold nanoparticles on protein matrixes are used as highly effective dual-activity heterogeneous catalysts for the production of enantiomerically enriched 2,5-dihydrofurans (R)-I [R¹ = Me, Et; R²₂ = (CH₂)₅; R³ = R⁴ = H] from allenic acetates II (X = MeCO) in a one-pot cascade process combining a lipase-mediated hydrolytic kinetic resolution with a metal-catalyzed allene cycloisomerization. Incorporating a novel strategy based on enzyme-polymer bioconjugates in the nanobiohybrid preparation enables excellent conversions in the process. Candida antarctica lipase B (CALB) in combination with a dextran-based polymer modifier (DexAsp) proved to be most efficient when merged with silver nanoparticles. A range of hybrid materials were produced, combining Ag or Au metals with Thermomyces lanuginosus lipase (TLL) or CALB and its DexAsp or polyethyleneimine polymer bioconjugates. The wider applicability of the biohybrids is demonstrated by their use in cyclization of allenic alcs. II [X = H; R¹ = Me, Et, Ph, etc., R³ = H; R¹ = Me, R³ = Ph; R¹R³ = (CH₂)₅; R² = Me, R²₂ = (CH₂)₅; R⁴ = H; R¹R⁴ = (CH₂)₄], where a variety of dihydrofurans I is obtained using a CALB/gold nanomaterial. These results underline the potential of the nanobiohybrid catalysis as promising approach to intricate one-pot synthetic strategies.

ChemCatChem published new progress about 27943-46-0. 27943-46-0 belongs to tetrahydropyran, auxiliary class Tetrahydropyran,Alkynyl,Ether, name is 2-((2-Methylbut-3-yn-2-yl)oxy)tetrahydro-2H-pyran, and the molecular formula is C10H16O2, HPLC of Formula: 27943-46-0.

Referemce:
https://en.wikipedia.org/wiki/Tetrahydropyran,
Tetrahydropyran – an overview | ScienceDirect Topics

Huang, Qiansheng published the artcileNew insights into the metabolism and toxicity of bisphenol A on marine fish under long-term exposure, Quality Control of 267244-08-6, the publication is Environmental Pollution (Oxford, United Kingdom) (2018), 242(Part_A), 914-921, database is CAplus and MEDLINE.

Bisphenol A (BPA) exposure receives great ecotoxicol. concern. However, gaps in knowledge, such as metabolism of BPA and inconsistent reports on reproductive toxicity, still exist. In this study, a marine fish model (Oryzias melastigma) was exposed to serial concentrations of BPA throughout its whole life cycle. The level of BPA-glucuronide (BPAG) dramatically increased throughout the embryonic stage since 4 dpf. Accordingly, the mRNA level and enzymic activity of UDP-glucuronosyltransferases (UGTs) increased across the embryonic stage. The mRNA level of UGT2 subtype rather than UGT1 or UGT5 showed a concentration dependent response to BPA exposure. BPA exposure led to the morphol. disruption of the chorion and villi as shown by SEM; however, the hatchability was not significantly influenced after exposure. Newly hatching larvae were continuously exposed to BPA for 120 days. Lower mRNA levels of hormone metabolism-related genes, decreased ratio of E2/T, slower ovary development and decreased egg production confirmed the inhibitory effect of BPA on reproduction Overall, our results showed the conjugation of BPA into BPAG by UGT2 at the embryonic stage and convinced the reproductive toxicity from multiple levels after whole life exposure to BPA.

Environmental Pollution (Oxford, United Kingdom) published new progress about 267244-08-6. 267244-08-6 belongs to tetrahydropyran, auxiliary class Tetrahydropyran,Chiral,Carboxylic acid,Benzene,Phenol,Alcohol,Ether,, name is (2S,3S,4S,5R,6S)-3,4,5-Trihydroxy-6-(4-(2-(4-hydroxyphenyl)propan-2-yl)phenoxy)tetrahydro-2H-pyran-2-carboxylic acid, and the molecular formula is C21H24O8, Quality Control of 267244-08-6.

Referemce:
https://en.wikipedia.org/wiki/Tetrahydropyran,
Tetrahydropyran – an overview | ScienceDirect Topics

Zhang, Xia-Wei published the artcileDissection of Pharmacological Mechanism of Chinese Herbal Medicine Yihuo Huatan Formula on Chronic Obstructive Pulmonary Disease: A Systems Pharmacology-Based Study, SDS of cas: 69097-99-0, the publication is Scientific Reports (2019), 9(1), 1-11, database is CAplus and MEDLINE.

Chronic obstructive pulmonary disease (COPD) is one of the most common respiratory diseases. Yihuo Huatan Formula (YHF), as a proven Chinese Herbal Medicine (CHM), has been verified to be effective in the treatment of stable COPD through years’ of practice. Nevertheless, its working mechanism is still unclear. We sought to systematically decipher the mechanism of YHF for treating stable COPD using systems pharmacol.-based method that integrates pharmacokinetic screening, target prediction, network analyses, GO and KEGG enrichment analyses. Firstly, a total of 1267 chems. out of 15 herbal components were included in YHF chem. database. Among them, 180 potential active mols. were screened out through pharmacokinetic evaluation. Then 258 targets of the active mols. were predicted, of which 84 were chosen for further analyses. Finally, the network analyses and GO and KEGG enrichment methods suggested a therapeutic effect of YHF on the alleviation of airway inflammation, decrease of mucus secretion, maintenance of immune homeostasis and benefit of COPD comorbidities, by regulating multiple targets and pathways. The systems pharmacol.-based approach helps to understand the underlying working mechanism of YHF in stable COPD from a holistic perspective, and offers an exemplification for systematically uncovering the action mechanisms of CHM.

Scientific Reports published new progress about 69097-99-0. 69097-99-0 belongs to tetrahydropyran, auxiliary class Other Aliphatic Heterocyclic,Benzene,Phenol,Ether,Inhibitor, name is 5,7-Dihydroxy-2-(3-hydroxy-4-methoxyphenyl)chroman-4-one, and the molecular formula is C18H10F3NO3S2, SDS of cas: 69097-99-0.

Referemce:
https://en.wikipedia.org/wiki/Tetrahydropyran,
Tetrahydropyran – an overview | ScienceDirect Topics

Peng, Bo published the artcileCompetitive Biotransformation Among Phenolic Xenobiotic Mixtures: Underestimated Risks for Toxicity Assessment, Safety of (2S,3S,4S,5R,6S)-3,4,5-Trihydroxy-6-(4-(2-(4-hydroxyphenyl)propan-2-yl)phenoxy)tetrahydro-2H-pyran-2-carboxylic acid, the publication is Environmental Science & Technology (2019), 53(20), 12081-12090, database is CAplus and MEDLINE.

Humans are inevitably exposed to a complex mixture of organic contaminants (i.e., xenobiotics) through diet, environment, and behavior. Biotransformation makes key contributions to the elimination of xenobiotics and greatly mediates the toxicity. However, most biotransformation studies were conducted using individual chem., and whether coexposure of multiple environmental chems. will affect each other’s fate in the human body is still in its infancy. In this study, bisphenol A (BPA) was selected as a model compound Its biotransformation was investigated under single exposure/coexposure to other phenolic xenobiotics (triclosan, tetrabromobisphenol A, and bisphenol S) in liver microsome and cell models. The result shows that binary exposures exhibit significant inhibitory effects on the BPA metabolism, especially the sulfate conjugation. In combination of anal. on inhibition models and enzyme activity, the inhibition effect was suggested to be primarily driven by competition for metabolizing enzymes. A mixture with 22 phenolic chems. was further examined to disrupt BPA at various human-relevant levels. Again, the result demonstrates significant inhibition on the BPA metabolism, indicating the possible natural existence of our finding. Overall, our results show that biotransformation of phenolic xenobiotics can be significantly altered by coexposure, which provides referential evidence on underestimated risks of simultaneous exposure to environmental toxicants.

Environmental Science & Technology published new progress about 267244-08-6. 267244-08-6 belongs to tetrahydropyran, auxiliary class Tetrahydropyran,Chiral,Carboxylic acid,Benzene,Phenol,Alcohol,Ether,, name is (2S,3S,4S,5R,6S)-3,4,5-Trihydroxy-6-(4-(2-(4-hydroxyphenyl)propan-2-yl)phenoxy)tetrahydro-2H-pyran-2-carboxylic acid, and the molecular formula is C21H24O8, Safety of (2S,3S,4S,5R,6S)-3,4,5-Trihydroxy-6-(4-(2-(4-hydroxyphenyl)propan-2-yl)phenoxy)tetrahydro-2H-pyran-2-carboxylic acid.

Referemce:
https://en.wikipedia.org/wiki/Tetrahydropyran,
Tetrahydropyran – an overview | ScienceDirect Topics

Wang, Di published the artcileEvaluation of the active ingredients and potential targets of Radix Sophorae Flavescentis-Radix Sanguisorbae in the treatment of ulcerative colitis with a network pharmacology approach, Related Products of tetrahydropyran, the publication is Shijie Zhongyiyao (2021), 16(16), 2401-2407, database is CAplus.

Objective: To predict the mechanism of treatment of ulcerative colitis (UC) with Radix Sophorae Flavescentis-Radix Sanguisorbae Based on network pharmacol. Methods: Chem. composition and target genes of the Radix Sophorae Flavescentis-Radix Sanguisorbae drug pair were searched through the TCMSP database of traditional Chinese medicines (TCM), and the potential active ingredients of the drug pair were screened under the condition of bioavailability (OB)>30% and drug-like properties (DL)>0.18. The TCMSP database was used to predict potential targets for the drug pair. Uniprot database was used to find the name of the human gene corresponding to the potential target. The disease target of UC were retrieved through Genecards and OMIM database, and was then mapped to the potential target of the drug pair into a Wayne diagram. The target gene of the component is introduced into Cytoscape 3.7.2 to construct the drug-component-disease-target network diagram. The STRING database was used to construct a PPI protein interaction network diagram to select the core target. Finally, the Radix Sophorae Flavescentis-Radix Sanguisorbae drug pair was used for GO anal. and KEGG anal. of effective targets for the treatment of ulcerative colitis. Results: A total of 27 active ingredients and 74 effective targets were obtained from the Radix Sophorae Flavescentis-Radix Sanguisorbae drug pair. GO enrichment anal. results showed a total of 90 biol. processes, mainly related to DNA binding and protein or cofactor binding; KEGG pathway enrichment results showed totally 115 pathways, including PI3K-AKT signaling pathway and cancer pathway. Conclusion: Radix Sophorae Flavescentis-Radix Sanguisorbae drug pair can act on multiple targets, multiple channels, and multiple pathways to treat UC in a variety of active ingredients. This study provides a theor. reference for further research on the mechanism of action of Radix Sophorae Flavescentis-Radix Sanguisorbae drug pair on UC clin. treatment.

Shijie Zhongyiyao published new progress about 69097-99-0. 69097-99-0 belongs to tetrahydropyran, auxiliary class Other Aliphatic Heterocyclic,Benzene,Phenol,Ether,Inhibitor, name is 5,7-Dihydroxy-2-(3-hydroxy-4-methoxyphenyl)chroman-4-one, and the molecular formula is C33H29N3O3, Related Products of tetrahydropyran.

Referemce:
https://en.wikipedia.org/wiki/Tetrahydropyran,
Tetrahydropyran – an overview | ScienceDirect Topics

Larock, Richard C. published the artcileMercury in organic chemistry. 24. Mercuration and subsequent carbonylation of 4-hydroxy-2-alkyn-1-ones: a novel route to furans, Safety of 2-((2-Methylbut-3-yn-2-yl)oxy)tetrahydro-2H-pyran, the publication is Journal of Organic Chemistry (1983), 48(13), 2151-8, database is CAplus.

HgCl₂ readily adds to the CC bond of certain 4-hydroxy-2-alkyn-1-ones (e.g., HOCHMeCCAc) to give vinylmercurials [e.g., HOCHMeCCl:C(HgCl)COMe] which appear to be the 1st syn-addition compounds of HgCl₂. These vinylmcercurials readily dehydrate to 3-furylmercurials (e.g., I). Pd-promoted carbonylation of these compounds affords 3-furylcarbonyl compounds

Journal of Organic Chemistry published new progress about 27943-46-0. 27943-46-0 belongs to tetrahydropyran, auxiliary class Tetrahydropyran,Alkynyl,Ether, name is 2-((2-Methylbut-3-yn-2-yl)oxy)tetrahydro-2H-pyran, and the molecular formula is C10H16O2, Safety of 2-((2-Methylbut-3-yn-2-yl)oxy)tetrahydro-2H-pyran.

Referemce:
https://en.wikipedia.org/wiki/Tetrahydropyran,
Tetrahydropyran – an overview | ScienceDirect Topics

Hopf, Henning published the artcileSterically hindered double bond systems. 2. On the preparation of highly substituted 1,3-dienes, Recommanded Product: 2-((2-Methylbut-3-yn-2-yl)oxy)tetrahydro-2H-pyran, the publication is Chemische Berichte (1991), 124(9), 2075-84, database is CAplus.

Highly alkylated 1,3-dienes were prepared in good yield by treatment of 2-butyne-1,4-diol derivatives with organocuprates. Thus, the 2,3-dialkylated butadienes (Me₂C:CR)₂ (R = Me₃C, Me₂CH, Et, Me) are obtained by treating diacetate AcOCMe₂CCCMe₂OAc with two equivalent of the cuprates prepared from the Grignard reagents RMgX with CuBr/LiBr. The procedure may be extended to the synthesis of unsym. substituted 1,3-dienes by either treating the appropriate diacetates with two equivalent of the same cuprate as exemplified by the conversion of AcOCMe₂CCCH₂OAc into Me₂C:CRCR:CH₂ (R = Me₃C, Me₂CH) or by employing a stepwise approach in which only one reactive acetate leaving group is available for the cuprate reagent at any given time, thus allowing the change of the organometallic reagent in the course of the synthesis [preparation of the dienes Me₂C:CR²CR¹:CH₂ (R¹, R² = Me₃C, Me₂CH; Me₂CH, Me₃C) from the monoacetates AcOCMe₂CCCH₂OTHP (THP = tetrahydropyranyl)]. Mechanisms of these reactions are discussed.

Chemische Berichte published new progress about 27943-46-0. 27943-46-0 belongs to tetrahydropyran, auxiliary class Tetrahydropyran,Alkynyl,Ether, name is 2-((2-Methylbut-3-yn-2-yl)oxy)tetrahydro-2H-pyran, and the molecular formula is C10H16O2, Recommanded Product: 2-((2-Methylbut-3-yn-2-yl)oxy)tetrahydro-2H-pyran.

Referemce:
https://en.wikipedia.org/wiki/Tetrahydropyran,
Tetrahydropyran – an overview | ScienceDirect Topics