Category: tetrahydropyran

Rosenkranz, Herbert S. published the artcileSAR: flavonoids and COX-2 inhibition, Product Details of C16H14O6, the publication is Oncology Research (2003), 13(12), 529-535, database is CAplus and MEDLINE.

An anal. based upon structure-activity relationships (SAR) of the COX-2-inhibiting properties of flavonoids, a group of potential cancer chemopreventive agents, reveals that there is a dual structural basis for these activities. Each of these structural determinants (pharmacophores) alone is sufficient for activity. One of the pharmacophores is a 2D 6.9 Å distance descriptor that spans the A and C rings and includes the 4-oxo and 7-hydroxyl moieties. The potency associated with that pharmacophore is determined by a series of structural modulators that can increase, decrease, or even abolish the COX-2-inhibiting potential associated with that pharmacophore. The second pharmacophore describes a para-substituted phenolic B ring that requires unsubstituted meta and ortho positions. Based upon this, it indicates that hydroxylation at the 4′-position and a free 5′-position are sufficient for COX-2-inhibiting activity. The potency associated with this pharmacophore is modulated by log P² and by the mol. weight

Oncology Research 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

Coughlin, Janis L. published the artcileInhibition of genistein glucuronidation by bisphenol A in human and rat liver microsomes, 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 Drug Metabolism & Disposition (2012), 40(3), 481-485, database is CAplus and MEDLINE.

Genistein is a natural phytoestrogen of the soybean, and bisphenol A (BPA) is a synthetic chem. used in the production of polycarbonate plastics. Both genistein and BPA disrupt the endocrine system in vivo and in vitro. Growing concerns of altered xenobiotic metabolism due to concomitant exposures from soy milk in BPA-laden baby bottles has warranted the investigation of the glucuronidation rate of genistein in the absence and presence (25 μM) of BPA by human liver microsomes (HLM) and rat liver microsomes (RLM). HLM yield V_max values of 0.93 ± 0.10 nmol/min^-1/mg^-1 and 0.62 ± 0.05 nmol/min^-1/mg^-1 in the absence and presence of BPA, resp. K_m values for genistein glucuronidation by HLM in the absence and presence of BPA are 15.1 ± 7.9 μM and 21.5 ± 7.7 μM, resp., resulting in a K_i value of 58.7 μM for BPA. Significantly reduced V_max and unchanged K_m in the presence of BPA in HLM are suggestive of noncompetitive inhibition. In RLM, the presence of BPA resulted in a K_i of 35.7 μM, an insignificant change in V_max (2.91 ± 0.26 nmol/min^-1/mg^-1 and 3.05 ± 0.41 nmol/min^-1/mg^-1 in the absence and presence of BPA, resp.), and an increase in apparent K_m (49.4 ± 14 μM with no BPA and 84.0 ± 28 μM with BPA), indicative of competitive inhibition. These findings are significant because they suggest that BPA is capable of inhibiting the glucuronidation of genistein in vitro, and that the type of inhibition is different between HLM and RLM.

Drug Metabolism & Disposition 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

Waechter, J. Jr. published the artcileFactors affecting the accuracy of bisphenol A and bisphenol A-monoglucuronide estimates in mammalian tissues and urine samples. [Erratum to document cited in CA146:373802], HPLC of Formula: 267244-08-6, the publication is Toxicology Mechanisms and Methods (2007), 17(2), 125, database is CAplus and MEDLINE.

On page 13, the author affiliations were incorrectly given. The correct affiliation list is given. On page 13, in the left column, the corresponding address was incorrectly given, and should read: “J. Waechter Jr., The Dow Chemical Company, Toxicology and Environmental Research and Consulting, Building 1803, Midland, MI, USA. E-mail: [email protected]”.

Toxicology Mechanisms and Methods 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 C9H11NO4, HPLC of Formula: 267244-08-6.

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

Domoradzki, J. Y. published the artcileAge and Dose Dependency of the Pharmacokinetics and Metabolism of Bisphenol A in Neonatal Sprague-Dawley Rats Following Oral Administration, Computed Properties of 267244-08-6, the publication is Toxicological Sciences (2004), 77(2), 230-242, database is CAplus and MEDLINE.

Previous studies demonstrated the rapid clearance of bisphenol A (BPA) from blood following oral administration to adult rats with the principal metabolite being BPA-monoglucuronide (BPA-glucuronide). Since the ontogeny of glucuronyl transferases (GT) differs with age, the pharmacokinetics of BPA were studied in neonatal animals. ¹⁴C-BPA was administered via gavage at 1 or 10 mg/kg body weight to rats at postnatal day (pnd) 4, pnd 7, pnd 21, or to 11 wk old adult rats (10 mg/kg dose only). Blood (neonates and adults) and selected tissues (neonates) were collected at 0.25, 0.75, 1.5, 3, 6, 12, 18, and 24 h postdosing. BPA and BPA-glucuronide in the plasma were quantified by high-performance liquid chromatog.; radioactivity in the plasma and tissues was quantified by liquid scintillation spectrometry. The data indicate that neonatal rats at all three ages metabolized BPA to BPA-glucuronide, although an age dependency in the number and concentration of plasma metabolites was observed, consistent with the ontogeny of GT. BPA-glucuronide and BPA concentrations in the plasma were greater in neonates than in adults, except at 24 h postdosing, suggesting an immaturity in the development of hepatic excretory function in neonatal rats. Nevertheless, the half-lives for the elimination of BPA-glucuronide in plasma were more rapid in neonatal animals than in adults, likely due to reduced microflora β-glucuronidase activity and an absence of enterohepatic recirculation. A dose dependency in the metabolism and pharmacokinetics of BPA administered to neonates was also observed with nearly complete metabolism of BPA to BPA-glucuronide (94-100% of the plasma radioactivity) at a dose of 1 mg/kg. This was in contrast to finding up to 13 different plasma metabolites observed at the 10 mg/kg dose. These data indicate that, from early in neonatal life through pnd 21, there is sufficient GT activity in rats to efficiently metabolize BPA to its nonestrogenic metabolite at low doses.

Toxicological Sciences 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, Computed Properties of 267244-08-6.

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

Modak, Brenda published the artcileAntioxidant capacity of flavonoids and a new arylphenol of the resinous exudate from Heliotropium sinuatum, Synthetic Route of 69097-99-0, the publication is Natural Product Research (2003), 17(6), 403-407, database is CAplus and MEDLINE.

From the resinous exudate of Heliotropium sinuatum (family Boraginaceae), a new compound: 4-(3′,5′-dihydroxynonadecyl)phenol, together with eight previously described flavonoids, were isolated and their antioxidant activities were assessed by quenching measurements with ABTS and DPPH cation radicals.

Natural Product Research 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

Wistuba, Dorothee published the artcileStereoisomeric separation of flavanones and flavanone-7-O-glycosides by capillary electrophoresis and determination of interconversion barriers, Application of 5,7-Dihydroxy-2-(3-hydroxy-4-methoxyphenyl)chroman-4-one, the publication is Analytical Chemistry (2006), 78(10), 3424-3433, database is CAplus and MEDLINE.

The stereoisomeric separation of several flavanones and flavanone-7-O-glycosides was achieved with capillary electrophoresis by adding native cyclodextrins or cyclodextrin derivatives to the background electrolyte. As an alternative method, micellar electrokinetic chromatog. with sodium cholate as a chiral surfactant was used for the epimeric separation of two flavanone-7-O-glycosides. The effect of buffer systems containing mixtures of cyclodextrin with either sodium dodecyl sulfate or sodium cholate upon the chiral recognition of flavanones and flavanone-7-O-glycosides as well as the variation of the background electrolyte (concentration of buffer and surfactant, pH value, organic modifier), and its influence on the resolution factor R_s was studied. Temperature- and pH-dependent enantiomerization or epimerization barriers of several flavanones (naringenin, homoeriodictyol) and flavanone-7-O-glycosides (naringin, neohesperidin, prunin, narirutin) in basic media (pH values of 9-11) were observed Interconversion profiles featuring characteristic plateau formation of the elution pattern were observed at high pH and evaluated with the simulation software ChromWin to determine rate constants k(T) and Eyring activation parameters, ΔG^#(T), ΔH^#, and ΔS^#.

Analytical 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 C12H19BrS, Application of 5,7-Dihydroxy-2-(3-hydroxy-4-methoxyphenyl)chroman-4-one.

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

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

Yi, Jingxuan published the artcilePreparation and Application of Partially Substituted Phenylcarbamate-(3-(2-O-β-cyclodextrin)-2-hydroxypropoxy)-propylsilyl-Appended Silica Particles as Chiral Stationary Phase for Multi-mode HPLC, Application In Synthesis of 69097-99-0, the publication is Chromatographia (2020), 83(8), 1021-1028, database is CAplus.

Abstract: A new type of partially substituted cyclodextrin-bonded silica particles, phenylcarbamate-(3-(2-O-β-cyclodextrin)-2-hydroxypropoxy)-propylsilyl-appended silica (P-CD-HPS), has been successfully prepared and used as chiral stationary phase (CSP) in high-performance liquid chromatog. (HPLC) under normal-phase, reversed-phase, and polar organic mobile-phase conditions. The P-CD-HPS was characterized by elemental anal. and Fourier transform IR spectroscopic (FTIR) anal. The chromatog. performance of the new-phase P-CD-HPS has been evaluated in HPLC under multi-mode conditions via separating positional isomers of some disubstituted benzenes and enantiomers of some chiral drug compounds The separation results show that P-CD-HPS exhibited excellent selectivity for separating the positional isomers of nitrophenol and nitraniline and the enantiomers of some chiral drug compounds The hydroxyl residues of partially substituted β-cyclodextrin and chiral spacer linking to secondary hydroxyl site of the β-cyclodextrin in the P-CD-HPS not only have important contributions to chiral recognitions and separations, but also allow the P-CD-HPS to be used under multi-mode mobile-phase conditions in HPLC.

Chromatographia 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 C4H6O3, Application In Synthesis of 69097-99-0.

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

Fujii, Satoshi published the artcileNovel molecular conformation of (R,S)-hesperetin in anhydrous crystal, Product Details of C16H14O6, the publication is Chemical & Pharmaceutical Bulletin (1994), 42(5), 1143-5, database is CAplus.

Novel mol. conformation of racemic hesperetin, (±)-2,3-dihydro-5,7-dihydroxy-2-(3-hydroxy-4-methoxyphenyl)-4H-1-benzopyran-4-one, was determined by x-ray anal. A new form was crystallized from ethanol solution and its mol. conformation is quite different from that of monohydrate crystal. The aromatic ring part of benzopyrone and the Ph ring from the twist orientation (dihedral angle of two rings, Φ is 53.1(3)°), in contrast to the parallel arrangement in the monohydrate from (Φ = 0.6°). The pyrone ring forms a slightly flattened sofa conformation, where C(2) is displaced by 0.40(2) Å from the pyrone plane, in contrast to the large displacement in the monohydrate form (0.54 Å). There is a strong intramol. hydrogen bond between keto O(4) atom and hydroxy H(O5)-O(5) group which forms a six-membered ring conjugated with benzopyrone rings. The degree of conjugation is also slightly different for the two forms and may relate to the difference of hydrogen bonding network and stacking mode of aromatic rings.

Chemical & Pharmaceutical Bulletin 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

Zhou, Jie published the artcileCationic cyclodextrin clicked chiral stationary phase for versatile enantioseparations in high-performance liquid chromatography, Application of 5,7-Dihydroxy-2-(3-hydroxy-4-methoxyphenyl)chroman-4-one, the publication is Journal of Chromatography A (2016), 169-177, database is CAplus and MEDLINE.

A novel cationic cyclodextrin (CD) chiral stationary phase (CSPs) was developed by clicking 6^A-azido-6^C-[(3-methoxylpropyl)-1- ammonium]-heptakis[2,3-di-O-(3-chloro-4-methylphenylcarbamate)-6^B,6^D,6^E,6^F,6^G-pentakis-O-per(3-chloro-4-methylphenylcarbamate)]-β-CD chloride onto alkynyl silica support. The enantioselectivies of the as-obtained novel CSP were evaluated using 21 model racemates including flavonoids, aromatic alcs., acidic drugs, β-blocker and amino acids. Good enantioseparations were achieved in polar-organic phase HPLC, with the highest resolution of 8.07 observed for 7-methoxyflavanone. The enantioseparations in normal-phase HPLC were fine-tuned with the polarity of the mobile phase with different alcs. as organic modifiers. Improved chiral resolutions of analytes but longer retention were observed in mobile phases with decreased polarity. On comparison with previously reported clicked CD CSP, the cationic CD clicked CSP exhibited better enenatiosepns. for selected racemates even in normal-phase HPLC. 3-Methoxypropylammonium and phenylcarbamoylated moieties of the cationic CSP may provide intermol. interactions such as hydrogen bonding, π-π conjugation and dipole-dipole besides inclusion complexation to drive 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 C18H22O4, Application of 5,7-Dihydroxy-2-(3-hydroxy-4-methoxyphenyl)chroman-4-one.

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