Tag: M.W=300-350

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-6^A-azido-β-CD (CSP1) and per-5-chloro-2-methylphenylcarbamoylated mono-6^A-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

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

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

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

Yao, Xiaobin published the artcileEngineering Thiol-Ene Click Chemistry for the Fabrication of Novel Structurally Well-Defined Multifunctional Cyclodextrin Separation Materials for Enhanced Enantioseparation, Name: 5,7-Dihydroxy-2-(3-hydroxy-4-methoxyphenyl)chroman-4-one, the publication is Analytical Chemistry (Washington, DC, United States) (2016), 88(9), 4955-4964, database is CAplus and MEDLINE.

The preparation of two novel multifunctional cyclodextrin (CD) separation materials and their ultimate enantioseparation performances in HPLC are reported. A mild thiol-ene click reaction was used to anchor 1-allylimidazolium-per(p-methyl)phenylcarbamoylated-β-CD and 1-allylimidazolium-per(p-chloride)phenylcarbamoylated-β-CD onto thiol-modified porous silica giving structurally well-defined stable cationic multifunctional CD chiral stationary phases (CSP1 and CSP2, resp.). These covalently bonded CD phases have typical interaction modes such as H-bonding, π-π effect, electrostatic and dipole-dipole interactions as well as steric effects which result in superior chiral resolution for a variety of chiral compounds in different separation modes. In a reverse-phase mode, both CSPs exhibited excellent separation abilities for isoxazolines, flavonoids, β-blockers, and some other neutral and basic racemates. In a polar-organic mode, isoxazolines and flavonoids were well resolved. CSP1 with an electron-rich Ph substitution on the CD rims gave a better resolution for isoxazolines whereas CSP2 with an electron-deficient Ph substitution on the CD rims gave better resolution for flavonoids. Among isoxazolines, 4ClPh-OPr gained a high selectivity and resolution up to 18.6 and 38.7, resp., which is an amazing result for CD enantioseparation materials.

Analytical Chemistry (Washington, DC, United States) 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 C8H11NO, Name: 5,7-Dihydroxy-2-(3-hydroxy-4-methoxyphenyl)chroman-4-one.

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

Edwards, J. Michael published the artcileAntitumor plants. Part VII. Antineoplastic activity and cytotoxicity of flavones, isoflavones, and flavanones, Application of 5,7-Dihydroxy-2-(3-hydroxy-4-methoxyphenyl)chroman-4-one, the publication is Journal of Natural Products (1979), 42(1), 85-91, database is CAplus and MEDLINE.

Two hundred and seventeen natural and synthetic flavonoid derivatives I, II, and III, which were tested in the screening program of the National Cancer Institute, were examd for antineoplastic activity and cytotoxicity. No structure-activity relations were observed Apparently, in spite of occasional activity these compounds do not warrant further investigation as antitumor agents.

Journal of Natural Products 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, 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

Seka, R. published the artcileNew synthesis of chrysin and other hydroxyflavones, COA of Formula: C16H14O6, the publication is Monatshefte fuer Chemie (1936), 284-91, database is CAplus.

The complex prepared from 2.4 g. 1,3,5-C₆H₃(OH)₃ and 7.5 g. AlCl₃ in 40 cc. PhNO₂ and 3.12 g. PhCCCOCl, allowed to stand 14 days at room temperature, gives chrysin (5,7-dihydroflavone), purified by distillation of the Al compound with HCl, steam distillation of the PhNO₂, sublimation of the resinous residue and extraction with boiling C₆H₆. In the same manner m-C₆H₄(OH)₂ yields 7-hydroxyflavone and 1,2,3-C₆H₃(OH)₃ gives 7,8-dihydroxyflavone. Natural and synthetic hesperetin (4′-methoxy-3′,5,7-trihydroxyflavanone), m. 233°, are purified by sublimation at 0.003-0.004 mg. Hg at a temperature not exceeding 205°; homoeriodictyol. similarly purified, m. 324° (cf. Shinoda and Kawagoye, C. A. 23, 2957; S. and Sato, C. A. 23, 4210).

Monatshefte fuer Chemie 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 C5H6N2O2, COA of Formula: C16H14O6.

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

Khan, Muhammad Kamran published the artcileChemical Synthesis of Citrus Flavanone Glucuronides, Application In Synthesis of 69097-99-0, the publication is Journal of Agricultural and Food Chemistry (2010), 58(14), 8437-8443, database is CAplus and MEDLINE.

Flavanone glucuronides are the major phenolic metabolites detected in human plasma after consumption of citrus fruits. As such, they might display significant cardioprotective effects. In this work, glucuronides of naringenin (4′- and 7-O-β-D-glucuronides) and hesperetin (3′- and 7-O-β-D-glucuronides), the major flavanone aglycons in grapefruit and orange, resp., have been chem. synthesized. On the one hand, the most reactive hydroxyl group, C7-OH, was protected by selective benzoylation to allow subsequent glucuronidation of C4′-OH (naringenin) or C3′-OH (hesperetin) (B-ring). On the other hand, the selective debenzoylation at C₇-OH of the per-benzoylated flavanone aglycons allowed glucuronidation at the same position (A-ring). After careful deprotection, the target compounds were purified and characterized by NMR and mass spectrometry.

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, Application In Synthesis of 69097-99-0.

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

Kumari, G. N. Krishna published the artcileCarbon-13 NMR data of flavonol methyl ethers of Solanum pubescens, HPLC of Formula: 69097-99-0, the publication is Proceedings – Indian Academy of Sciences, Chemical Sciences (1986), 97(2), 171-6, database is CAplus.

The ¹³C NMR data of flavonol 3-Me ethers indicated that the methylation of one of the OH groups in the o-dihydroxy system causes an upfield shift in the unsubstituted o-carbon as usual, but with the other hydroxylated o-carbon the shift is always downfield. The spectra of the acetates indicated that 5-acetoxy resonated downfield compared to that of other acetoxy groups. The ¹³C NMR data of these compounds is reported for the 1st time.

Proceedings – Indian Academy of Sciences, Chemical Sciences 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, HPLC of Formula: 69097-99-0.

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

Yanez, Jaime A. published the artcilePharmacokinetics of selected chiral flavonoids: hesperetin, naringenin and eriodictyol in rats and their content in fruit juices, Application of 5,7-Dihydroxy-2-(3-hydroxy-4-methoxyphenyl)chroman-4-one, the publication is Biopharmaceutics & Drug Disposition (2008), 29(2), 63-82, database is CAplus and MEDLINE.

The majority of pharmacokinetic studies of individual flavonoids or after ingestion of foodstuffs have overlooked the chirality of some of these xenobiotics. In order to characterize for the first time the stereoselective pharmacokinetics of three flavonoids, hesperetin, naringenin and eriodictyol were i.v. administered (20 mg/kg) to male Sprague-Dawley rats, and their stereospecific content was assessed in various fruit juices. Concentrations in serum, urine and fruit juices were characterized via HPLC and verified by LC/MS. Short half-lives (3-7 h) in serum were observed, while a better estimation of half-life (12-48 h) and the other pharmacokinetic parameters was observed using urinary data. The three flavonoids are predominantly excreted via non-renal routes (f_e values of 3-7%), and undergo rapid and extensive phase II metabolism The (2S)-epimers of the flavonoid glycosides and the S(-)-enantiomers of the aglycons were predominant and in some instances the organic fruit juices had higher concentrations than the conventional fruit juices. This study reports for the first time the stereospecific pharmacokinetics of three chiral flavonoids and their stereospecific content in fruit juices. It also reports for the first time the stereospecific pharmacokinetics of flavonoids employing urine as a more reliable biol. matrix.

Biopharmaceutics & Drug Disposition 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 C12H15NO, 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