Robertson, Dale N.’s team published research in Journal of Organic Chemistry in 25 | CAS: 27943-46-0

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, Category: tetrahydropyran.

Robertson, Dale N. published the artcileAdducts of tert-alcohols containing an ethynyl group with dihydropyran. Potentially useful intermediates, Category: tetrahydropyran, the publication is Journal of Organic Chemistry (1960), 931-2, database is CAplus.

Acetylenic alcs. of the type RR’COHCCH (I) were found to add smoothly and in high yield to dihydropyran (II) to form tetrahydropyranyl (R2) compounds of the general structure RR’C(CCH)OR2 (III). The R2 grouping was stable to alkali but easily removed by aqueous acid or exchangeable with lower alcs. by acid catalysis. Organometallic intermediates were easily formed by reaction at the acetylenic H and compounds such as γ-hydroxy-α,β-acetylenic acids; esters and ketones thus were readily available. General procedure; the appropriate alc. (1 mole) and 1.2-2 moles II was swirled with a few crystals of p-MeC6H4SO3H (the exothermic reaction began almost at once and was usually complete within 0.5-1.0 hr.); with higher mol. weight alcs. the mixture was heated on the steam bath 0.5-1.0 hr. to ensure completion. Anhydrous K2CO3 (1-2 g.) was added to the cooled mixture and the whole stirred 0.5 hr. or left overnight, the salts removed, excess II distilled at atm. pressure, and the product distilled in vacuo. Even Me3COH added readily to II, although the product was not isolated. Since an equimolar mixture of the 2 reactants would contain the same C and H values as the products, the infrared spectrum of each product was determined The following III were obtained from I and II (R, R’, and b.p./mm. given): Me, Me, 64.5-5.5°/8; Et, Me, 62.5-4.5°/3.3; Me2CHCH2, Me, 47-50°/0.6-0.2; Me(CH2)5, Me, 76-7°/0.12; Ph, Me, 99-100.5°/0.02; (R,R’ = cyclohexyl), 101.5-2.5°/3.6-3.7.

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, Category: tetrahydropyran.

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

Martineau, Louis C.’s team published research in Biochimica et Biophysica Acta, General Subjects in 1820 | CAS: 69097-99-0

Biochimica et Biophysica Acta, General Subjects 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 C16H14O6, Formula: C16H14O6.

Martineau, Louis C. published the artcileLarge enhancement of skeletal muscle cell glucose uptake and suppression of hepatocyte glucose-6-phosphatase activity by weak uncouplers of oxidative phosphorylation, Formula: C16H14O6, the publication is Biochimica et Biophysica Acta, General Subjects (2012), 1820(2), 133-150, database is CAplus and MEDLINE.

Background: Perturbation of energy homeostasis in skeletal muscle and liver resulting from a transient inhibition of mitochondrial energy transduction can produce effects of relevance for the control of hyperglycemia through activation of the AMP-activated protein kinase, as exemplified by the antidiabetic drug metformin. The present study focuses on uncoupling of oxidative phosphorylation rather than its inhibition as a trigger for such effects. Methods: The reference weak uncoupler 2,4-dinitrophenol, fourteen naturally-occurring phenolic compounds identified as uncouplers in isolated rat liver mitochondria, and fourteen related compounds with little or no uncoupling activity were tested for enhancement of glucose uptake in differentiated C2C12 skeletal muscle cells following 18 h of treatment at 25-100 μM. A subset of compounds were tested for suppression of glucose-6-phosphatase (G6Pase) activity in H4IIE hepatocytes following 16 h at 12.5-25 μM. Metformin (400 μM) was used as a standard in both assays. Results: Dinitrophenol and nine of eleven compounds that induced 50% or more uncoupling at 100 μM in isolated mitochondria enhanced basal glucose uptake by 53 to 269%; the effect of the 4′-hydroxychalcone butein was more than 6-fold that of metformin; neg. control compounds increased uptake by no more than 25%. Dinitrophenol and four 4′-hydroxychalconoids also suppressed hepatocyte G6Pase as well as, or more effectively than metformin, whereas the unsubstituted parent compound chalcone, devoid of uncoupling activity, had no effect. Conclusions: Activities key to glycemic control can be induced by a wide range of weak uncouplers, including compounds free of difficult-to-metabolize groups typically associated with uncouplers. General significance: Uncoupling represents a valid and possibly more efficient alternative to inhibition for triggering cytoprotective effects of therapeutic relevance to insulin resistance in both muscle and liver. Identification of actives of natural origin and the insights into their structure-activity relationship reported herein may lead to alternatives to metformin.

Biochimica et Biophysica Acta, General Subjects 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 C16H14O6, Formula: C16H14O6.

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

Kaiser, Roman’s team published research in Helvetica Chimica Acta in 67 | CAS: 27943-46-0

Helvetica Chimica Acta 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, Formula: C10H16O2.

Kaiser, Roman published the artcileThe (5R*,9S*)- and (5R*,9R*)-2,2,9-trimethyl-1,6-dioxaspiro[4.4]non-3-ene and their dihydro derivatives as new constituents of geranium oil, Formula: C10H16O2, the publication is Helvetica Chimica Acta (1984), 67(5), 1198-203, database is CAplus.

(5R ,9S )- (I) [92356-08-6] and (5R ,9R )-2,2,9-trimethyl-1,6-dioxaspiro[4.4]non-3-ene (II) [92356-04-2] and their dihydro derivatives, III  [92356-09-7] and IV  [92356-10-0], were isolated from geranium oil and their structures determined by spectra and synthesis. Other trace monoterpenes such as nerol oxide  [1786-08-9] were also isolated.

Helvetica Chimica Acta 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, Formula: C10H16O2.

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

Jouve, Pierre’s team published research in Compt. Rend. in 256 | CAS: 27943-46-0

Compt. Rend. 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.

Jouve, Pierre published the artcileNuclear magnetic resonance of the acetylenic proton in 1-alkynes, Safety of 2-((2-Methylbut-3-yn-2-yl)oxy)tetrahydro-2H-pyran, the publication is Compt. Rend. (1963), 1497-9, database is CAplus.

The frequency of the N.M.R. signal of the acetylenic proton (CC-H) is determined for dilute CCl4 solutions of 1-alkynes at 60 Mc. (A Varian A-60 instrument was used). An external reference, 5% Me4Si in CCl4, χr = 0.684 × 10-6, is used Me4Si is taken as zero. The value of the chem. shift when dilution no longer influences its position, σ∞CCl4, is determined for 6 linear acetylenes, 1.73-1.87 (branching caused displacement toward weak fields, contrary to the inductive effect); for 4α- and ω-diynes, 1.78-1.84 (considerable interaction between bonds at ends of chain, but with longer chains similar to linear acetylenes); for 5 ene-ynes, 2.60-2.89 (strong displacement toward weak fields, resonance stabilization); for 3 acetylenes with conjugated benzene rings in the a position, 2.92-3.06 (same as ene-ynes, but more so); for 5 α-acetylenic alcs., 2.20-2.33 (characteristic for these compounds); for 3 acetals and propargyl ethers, 2.26-2.33 (like α-alcs., conjugation is not possible, only the electroneg. character of the O being affected the displacement); for 3 alcs. with benzene rings in the β position to the ethynyl group, 2.46-2.77 (homoallyl activation with orbital electrons of the triple bonds partially conjugated with those of the ring); and for 4 γ-oxygenated acetylenes, 1.89-1.93 (more like the corresponding hydrocarbons).

Compt. Rend. 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

Dick, William E. Jr.’s team published research in Journal of Agricultural and Food Chemistry in 29 | CAS: 69097-99-0

Journal of Agricultural and Food Chemistry 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 C16H14O6, Product Details of C16H14O6.

Dick, William E. Jr. published the artcileStructure-taste correlations for flavans and flavanones conformationally equivalent to phyllodulcin, Product Details of C16H14O6, the publication is Journal of Agricultural and Food Chemistry (1981), 29(2), 305-12, database is CAplus.

Preparation of a conformationally defined series of compounds related to phyllodulcin (I) [21499-23-0] allows more accurate correlations of structural features with taste. Four flavans (3,4-dihydro-2H-1-benzopyrans) and their parent flavones (2,3-dihydro-4H-1-benzopyran-4-ones) were prepared from chalcones derived from 2-hydroxyacetophenone [582-24-1], 2,4-dihydroxyacetophenone [89-84-9], 2,6-dihydroxyacetophenone [699-83-2], or 2,4,6-trihydroxyacetophenone [480-66-0], and isovanillin (3-hydroxy-4-methoxybenzaldehyde) [621-59-0]. These compounds can exist both as semiplanar and bent conformers, equivalent to those of phyllodulcin, permitting a close comparison of structural features with taste. Semiplanar conformations were established for phyllodulcin and the analogous compounds by 1H NMR. Evidence for bent conformations was lacking. Flavans derived from 2-hydroxy and 2,4-dihydroxyacetophenone were sweet, the latter intensely so, whereas the 2,3 analog was intensely bitter. Comparisons with phyllodulcin and derivatives demonstrated the effects of nonaromatic ring heteroatom location A-ring hydroxylation, and a carbonyl group.

Journal of Agricultural and Food Chemistry 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 C16H14O6, Product Details of C16H14O6.

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

Claesson, Alf’s team published research in Acta Chemica Scandinavica, Series B: Organic Chemistry and Biochemistry in 29 | CAS: 27943-46-0

Acta Chemica Scandinavica, Series B: Organic Chemistry and Biochemistry 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.

Claesson, Alf published the artcileAllenes and acetylenes. X. Convenient method for conversion of acetylenic derivatives into conjugated dienes via α-allenic alcohols, Safety of 2-((2-Methylbut-3-yn-2-yl)oxy)tetrahydro-2H-pyran, the publication is Acta Chemica Scandinavica, Series B: Organic Chemistry and Biochemistry (1975), 29(5), 609-16, database is CAplus.

4-Alkoxy- and 4-(tetrahydro-2-pyranyloxy)-2-butyn-1-ols are in most cases quantitatively converted into conjugated dienes when treated with LiAlH4 in refluxing THF or similar solvents. The reactions proceed via α- allenic alcohols. The dienes are free from positional isomers and the formation of alkenynes, which occurs in some cases, can be completely suppressed by a combination of LiAlH4 and AlCl3. Most of the conjugated dienes seem to be formed with low stereoselectivity. The E,E form is the predominant isomer of 2,4-hexadiene while of 4,6-decadiene the E,Z isomer predominates. These latter results may indicate that the attack by hydride on the central carbon atom of the propadienyl group is sterically hindered when the double bond remaining in the same position is formed with E configuration.

Acta Chemica Scandinavica, Series B: Organic Chemistry and Biochemistry 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

Borujeni, Kaveh Parvanak’s team published research in Synthetic Communications in 36 | CAS: 27943-46-0

Synthetic Communications 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.

Borujeni, Kaveh Parvanak published the artcileSilica-gel-supported aluminum chloride. A stable, efficient, selective, and reusable catalyst for tetrahydropyranylation of alcohols and phenols, Safety of 2-((2-Methylbut-3-yn-2-yl)oxy)tetrahydro-2H-pyran, the publication is Synthetic Communications (2006), 36(18), 2705-2710, database is CAplus.

A simple, effective, and highly chemoselective method to form 2-tetrahydropyranyl ethers of alcs. and phenols in the presence of silica-gel-supported aluminum chloride as a heterogeneous Lewis acid catalyst is described. The catalyst can be easily recovered and reused without appreciable change in its efficiency.

Synthetic Communications 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

Pang, Limin’s team published research in Journal of Chromatography A in 1363 | CAS: 69097-99-0

Journal of Chromatography A 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 C16H14O6, Synthetic Route of 69097-99-0.

Pang, Limin published the artcileEvaluation of perphenylcarbamated cyclodextrin clicked chiral stationary phase for enantioseparations in reversed phase high performance liquid chromatography, Synthetic Route of 69097-99-0, the publication is Journal of Chromatography A (2014), 119-127, database is CAplus and MEDLINE.

Perphenylcarbamated cyclodextrin clicked chiral stationary phase (CSP) was developed with high column efficiency. The characteristics of the column were evaluated in terms of linearity, limit of detection and limit of quantification. The enantioselectivity of the as-prepared clicked CSP was explored with 26 recemates including aryl alcs., flavanoids and adrenergic drugs in reversed phase HPLC. The effect of separation parameters including flow rate, column temperature, organic modifier and buffer on the enantioselectivity of the clicked CSP was studied. The correlation study of the analytes structure and their chiral resolution revealed the great influence of analytes’ structure on the enantioseparations with cyclodextrin CSP. Methanol with 1% of triethylammonium acetate buffer (pH 4) is the best choice for the chiral separation of basic enantiomers.

Journal of Chromatography A 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 C16H14O6, Synthetic Route of 69097-99-0.

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

Lin, Yuzhou’s team published research in Journal of Chromatography A in 1406 | CAS: 69097-99-0

Journal of Chromatography A 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 C16H14O6, COA of Formula: C16H14O6.

Lin, Yuzhou published the artcileCyclodextrin clicked chiral stationary phases with functionalities-tuned enantioseparations in high performance liquid chromatography, COA of Formula: C16H14O6, the publication is Journal of Chromatography A (2015), 342-346, database is CAplus and MEDLINE.

Two cyclodextrin (CD) chiral stationary phases (CSPs) were developed by clicking per-4-chloro-3-methylphenylcarbamoylated mono-6A-azido-β-CD (CSP1) and per-5-chloro-2-methylphenylcarbamoylated mono-6A-azido-β-CD (CSP2) onto alkynylated silica support. The enantioslectivies of the as-obtained new CSPs were evaluated using 29 model racemates including aromatic alcs., flavonoids, β-blocker and FMOC-amino acids in both reversed-phase (RP) and normal-phase (NP) HPLC. The CD functionalities tuned enantioselectivities were elucidated in different HPLC elution modes. Higher chiral resolutions were achieved in RP-elution mode with the aid of the inclusion complexation in comparison to NP-elution mode. The π-π stacking interaction and dipole-dipole interaction provided by phenylcarbamate moieties can also contribute to the enantioseparation

Journal of Chromatography A 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 C16H14O6, COA of Formula: C16H14O6.

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

Chen, You-Lan’s team published research in World Journal of Gastroenterology in 25 | CAS: 69097-99-0

World Journal of Gastroenterology 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 C16H14O6, Safety of 5,7-Dihydroxy-2-(3-hydroxy-4-methoxyphenyl)chroman-4-one.

Chen, You-Lan published the artcileSystems pharmacology approach reveals protective mechanisms of Jian-Pi Qing-Chang decoction on ulcerative colitis, Safety of 5,7-Dihydroxy-2-(3-hydroxy-4-methoxyphenyl)chroman-4-one, the publication is World Journal of Gastroenterology (2019), 25(21), 2603-2622, database is CAplus and MEDLINE.

To investigate the protective mechanisms of Jian-Pi Qing-Chang (JPQC) decoction on ulcerative colitis (UC) based on systems pharmacol. approach. We performed systems pharmacol. to predict the active ingredients, the matched targets, and the potential pharmacol. mechanism of JPQC on UC. In vivo, we explored the effects of JPQC in a colitis model induced by dextran sulfate sodium. In vitro, we adopted the bone marrow-derived macrophages as well as BMDMs co-cultured with Caco2 cells to verify the underlying mechanisms and effects of JPQC on UC under TNF-α stimulation. Protein-protein interaction networks were established to identify the underlying therapeutic targets of JPQC on UC. Based on enrichment analyses, we proposed our hypothesis that JPQC might have a protective effect on UC via the NF-κB/HIF-1a signaling pathway. Subsequent exptl. validation revealed that treatment with TNFa activated the NF- κB/HIF-1a signaling pathway in BMDMs, thereby damaging the epithelial barrier permeability in co-cultured Caco2 cells, while JPQC rescued this situation. The findings were also confirmed in a dextran sulfate sodium-induced colitis model. JPQC could improve the mucosal inflammatory response and intestinal epithelial barrier function via the NF-κB/HIF-1α signaling pathway, which provides new perspectives on the pharmaceutical development and clin. practice of TCM.

World Journal of Gastroenterology 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 C16H14O6, Safety of 5,7-Dihydroxy-2-(3-hydroxy-4-methoxyphenyl)chroman-4-one.

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