Category: tetrahydropyran

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

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

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

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

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, χ_r = 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

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

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

Jaeg, Jean Philippe published the artcileCharacterization of New Bisphenol A Metabolites Produced by CD1 Mice Liver Microsomes and S9 Fractions, 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 Journal of Agricultural and Food Chemistry (2004), 52(15), 4935-4942, database is CAplus and MEDLINE.

Bisphenol A [2,2-bis(4-hydroxyphenyl)propane] (BPA) is a widely used industrial chem. resulting in occupational and consumer exposure. BPA possesses weak estrogenomimetic activity and can be cytotoxic, though the underlying mechanisms of its toxicity toward cells are not completely understood. The metabolism of BPA by CD1 mice liver microsomal and S9 fractions was investigated. Nine metabolites were isolated and characterized using HPLC and mass spectrometry. Many of these metabolites were characterized for the first time in mammals, namely isopropyl-hydroxyphenol (produced by the cleavage of BPA), a bisphenol A glutathione conjugate, glutathionyl-phenol, glutathionyl 4-isopropylphenol, and BPA dimers. Most of these metabolites apparently share a common metabolic pathway, for which considerable evidence supports the hypothesis of the production of a reactive intermediate, and also helps explain BPA cytotoxicity.

Journal of Agricultural and Food Chemistry 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

Gauderat, Glenn published the artcilePrediction of human prenatal exposure to bisphenol A and bisphenol A glucuronide from an ovine semi-physiological toxicokinetic model, SDS of cas: 267244-08-6, the publication is Scientific Reports (2017), 7(1), 1-13, database is CAplus and MEDLINE.

Bisphenol A (BPA) risk assessment is hampered by the difficulty of determiningthe extent of internal exposure in the human fetus and uncertainties regarding BPA toxicokinetics (TK) in the maternal-fetal unit. A feto-maternal TK model describing BPA and BPA glucuronide (BPAG) disposition in sheep was humanized, using human TK data obtained after d6-BPA administration on a cookie, to predict BPA and BPAG kinetics in the human mother-fetus unit. Validation of the model predictions included the assessed dose proportionality of BPA and BPAG disposition and the similarity between the simulated and measured time courses of BPA and BPAG in fetal rhesus monkeys after BPA maternal dosing. The model predicted fluctuations in fetal BPA concentrationsassociatedwith typical maternal exposure to BPA through the diet, with similar trough (0.011 ng/L vs 0.014 ng/L) and lower peak BPA concentrations(0.023 ng/L vs 0.14 ng/L) in fetal than in maternal plasma. BPAG concentrationsin fetal plasma were predicted to increase over time to reach a steady value (29 ng/L) reflecting the cumulative BPA dose received by the fetus. Model-predicted BPAG concentrationsin fetal plasma are consistent with reported levels in human cord blood that may be considered as relevant markers of the BPA dose entering blood throughout fetal life.

Scientific Reports 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, SDS of cas: 267244-08-6.

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

Pruvost-Couvreur, Manon published the artcileLifetime dietary exposure to bisphenol A in the general population and during pregnancy: Foetal exposure and health risk assessment, Recommanded Product: (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 International Journal of Hygiene and Environmental Health (2021), 113733, database is CAplus and MEDLINE.

Bisphenol A is a well-known chem. substance triggering reprotoxic and endocrine disruptor effects. Pregnancy is considered as a critical period of exposure to BPA because of the fetal sensitivity to endocrine disruption. Because of its wide use in food packaging, BPA is found in common foods and in infant formulas. We used a lifetime approach to simulate dietary exposure trajectories of a French population and to assess the associated health risk. Moreover, a semi-physiol. based toxicokinetic model was used to simulate the maternal-fetal exchanges of BPA during pregnancy. Metabolism was taken into account by considering the glucuronidation of BPA by the fetal-placental unit, as well as the reactivation of BPA-glucuronide into BPA in the fetal compartment. From maternal critical daily exposures defined by ANSES based on effects for different endpoints of BPA in the unborn child (i.e. 0.083, 0.17, 0.29 and 0.33μg/kg bw/d, resp. based on effects on mammary gland, brain and behavior, metabolism and obesity and female reproductive system), resulting concentrations of BPA in the fetal compartment were estimated and health risk was assessed for the sub-population of unborn children. This work leads to the conclusion that while a health risk due to dietary exposures of the general population can be excluded, this is not the case for the sub-population of pregnant women, in view of the levels of fetal exposure to BPA.

International Journal of Hygiene and Environmental Health 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, Recommanded Product: (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