Heterocyclic Building Blocks-Tetrahydropyran

Gounden, Verena published the artcileA pilot study: Bisphenol-A and Bisphenol-A glucuronide levels in mother and child pairs in a South African population, Synthetic Route of 267244-08-6, the publication is Reproductive Toxicology (2019), 93-99, database is CAplus and MEDLINE.

Exposure to Bisphenol A (BPA) during early development particularly in- utero has been linked to a wide range of pathol. The aim of this study was to determine serum levels of BPA and its naturally occurring metabolite BPA-glucuronide (BPA-g) in South African mother-child pairs. Third-trimester serum maternal samples and matching cord blood samples were analyzed for BPA and BPA-g using LC-MS/MS. Ninety maternal and child pairs were analyzed. BPA was detectable in more than 25% of maternal and cord blood samples. Spearman correlation demonstrated significant pos. correlation between maternal and child BPA and BPA-g levels with correlation coefficients of 0.892 and 0.744, resp. A significant pos. association between cord BPA levels and child birth-weight (p = 0.02) as well as with maternal BMI (p = 0.04) was noted. This is the first study to describe the presence of detectable BPA levels using LC-MS/MS methodol. in a South African population.

Reproductive Toxicology 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, Synthetic Route of 267244-08-6.

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

Wang, Yong published the artcile“Click” immobilized perphenylcarbamated and permethylated cyclodextrin stationary phases for chiral high-performance liquid chromatography application, Category: tetrahydropyran, the publication is Journal of Chromatography A (2010), 1217(31), 5103-5108, database is CAplus and MEDLINE.

Two cyclodextrin-based chiral stationary phases were prepared by immobilization of functionalized mono-6-azido-β-CD derivatives to alkynyl modified silica via click chem. and applied to the HPLC enantioseparation of various chiral compounds The perphenylcarbamated CD CSP (CCP-CSP) exhibited excellent chiral recognition of a wide range of analytes including racemic aryl alcs., flavonoids, bendroflumethiazide, atropine and some β-blockers. Methanol proved to be a better organic modifier than acetonitrile for most of the analytes with the exception of bendroflumethiazide. The click chem. immobilized permethylated CD CSP (CCM-CSP) afforded poor chiral recognition for most analytes, but could resolve nonaromatic ionone derivatives which were not separated on CCP-CSP. Probably resolution with cyclodextrin derived CSPs depend on a complex interplay of host’- guest’ inclusion, hydrogen bonding, π-π and hydrophobic interactions.

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 C33H22N4, Category: tetrahydropyran.

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

Eguchi, Tadashi published the artcileSynthesis and biological activities of 22-hydroxy and 22-methoxy derivatives of 1α,25-dihydroxyvitamin D₃: importance of side chain conformation for biological activities, Safety of 2-((2-Methylbut-3-yn-2-yl)oxy)tetrahydro-2H-pyran, the publication is Bioorganic Chemistry (1989), 17(3), 294-307, database is CAplus.

Title derivatives I (R = OH, OMe, R¹ = H; R = H, R¹ = OH, OMe) were prepared from 22-aldehyde II in order to clarify the precise structural requirement for exerting various biol. activities. While the synthetic vitamin D derivatives did not show any increase of serum calcium concentration in rats by oral administration, all derivatives induced into nitroblue tetrazolium (NBT)-pos. cells at a concentration more than 1 μg/mL in the NBT reduction test for induction of differentiation of HL-60 cells. The 22S-isomers I (R = H, R¹ = OH, OMe) were at least 30 times more effective than the corresponding 22R-isomers I (R = OH, OMe, R¹ = H). The binding affinity of I (R = H, R¹ = OMe) to the chick intestinal receptor for 1α,25-dihydroxyvitamin D₃ was about 3 times as potent as that of I (R = OMe, R¹ = H). A major structural difference was their side chain conformations, which were elucidated by mol. mechanics calculation (MM2 force field) and NMR studies. A zig-zag conformation turned out to be sterically most favorable for 22S-isomers, whereas such a zig-zag conformation is energetically unfavorable for 22R-isomers due to the interaction between the 22-substituent and the 16-methylene group. The side chain conformation seems to be responsible for the difference of their biol. activity and the zig-zag conformation plays an important role for the activities.

Bioorganic 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

Li, Xiaoxuan published the artcileEnantioseparation of single layer native cyclodextrin chiral stationary phases: Effect of cyclodextrin orientation and a modeling study, Safety of 5,7-Dihydroxy-2-(3-hydroxy-4-methoxyphenyl)chroman-4-one, the publication is Analytica Chimica Acta (2017), 174-184, database is CAplus and MEDLINE.

A novel native cyclodextrin (CD) chiral stationary phase (CSP) with single triazole-bridge at CD C2 position (CSP1) was prepared by anchoring mono(2^A-azido-2^A-deoxy)-β-CD onto alkynyl silica via click chem. The effect of CD orientation on single layer CD-CSP’s enantioseparation was comprehensively studied using CSP1 (reversed orientation) and the authors’ previously reported CSP2 (C6 single triazole-bridge, normal orientation) as well as a com. CD-CSP (Cyclobond I 2000, hybrid orientation) by separating several groups of analytes in chiral HPLC. The CD orientation on silica surface plays an important role in separating different racemates. CSP2 with normal CD orientation affords best separation for isoxazolines while CSP1 with reversed CD orientation better separates naringenin, hesperetin and Troger’s base. CSP2 and Cyclobond I 2000 show comparable separation ability for dansyl amino acids while poor separation was found on CSP1. Besides, mol. dynamics simulation was performed under real separation conditions using flavanone as model analyte to reveal the essential factors for CD’s chiral discrimination behaviors.

Analytica Chimica Acta 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

Shi, Jiachen published the artcileUptake, depuration and bioconcentration of bisphenol AF (BPAF) in whole-body and tissues of zebrafish (Danio rerio), 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 Ecotoxicology and Environmental Safety (2016), 339-344, database is CAplus and MEDLINE.

Bisphenol AF (BPAF) is an analog of Bisphenol A (BPA) and is widely used as a raw material in the plastics industry. However, an understanding of the potential risks posed by BPAF in the aquatic environment is lacking. The bioconcentration factor (BCF) is a measure used to assess the secondary poisoning potential as well as risks to human health. In this work we measured the accumulation and elimination of BPAF in the whole-body and in liver, muscle and gonad tissues of zebrafish. BPAF uptake was relatively rapid with equilibrium concentrations reached after 24-72 h of exposure. We observed gender differences both in whole-body and in tissue accumulation. Muscle was the primary BPAF storage tissue during the uptake phase in this study. In the elimination phase, BPAF concentrations declined rapidly during depuration, especially during the initial 2 h, and the rate of elimination in males was faster than females from the whole-body and from tissues. The appearance of BPAF glucuronide (BPAF-G) at the start of the uptake phase indicated the rapid biotransformation of BPAF to BPAF-G in vivo. The high lipid content of female gonad could act to delay the diffusion of the xenobiotic within the body in a contaminated environment, but it also acts to delay xenobiotic elimination from the body.

Ecotoxicology and Environmental Safety 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 C13H26N2, 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

He, Xiaoshu published the artcileSynthesis and characterization of homoeriodictyol and its analogs of B-ring, Product Details of C16H14O6, the publication is Yiyao Gongye (1987), 18(12), 534-7, database is CAplus.

Title compounds I (R = OH, R¹ = MeO) (6 compounds) were prepared in 5 steps starting from 1,3,5-(HO)₃C₆H₃. NMR and mass spectra of I are reported.

Yiyao Gongye 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

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

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

Martins, Francisco A. published the artcileConformational impact of structural modifications in 2-fluorocyclohexanone, Related Products of tetrahydropyran, the publication is Beilstein Journal of Organic Chemistry (2017), 1781-1787, database is CAplus and MEDLINE.

2-Haloketones are building blocks that combine phys., chem. and biol. features of materials and bioactive compounds, while organic fluorine plays a fundamental role in the design of performance organic mols. Since these features are dependent on the three-dimensional chem. structure of a mol., simple structural modifications can affect its conformational stability and, consequently, the corresponding physicochem./biol. property of interest. In this work, structural changes in 2-fluorocyclohexanone were theor. studied with the aim at finding intramol. interactions that induce the conformational equilibrium towards the axial or equatorial conformer. The interactions evaluated were hydrogen bonding, hyperconjugation, electrostatic and steric effects. While the gauche effect, originated from hyperconjugative interactions, does not appear to cause some preferences for the axial conformation of organofluorine heterocycles, more classical effects indeed rule the conformational equilibrium of the compounds Spectroscopic parameters (NMR chem. shifts and coupling constants), which can be useful to determine the stereochem. and the interactions operating in the series of 2-fluorocyclohexanone derivatives, were also calculated

Beilstein Journal of Organic Chemistry published new progress about 624734-19-6. 624734-19-6 belongs to tetrahydropyran, auxiliary class Tetrahydropyran,Fluoride,Ketone, name is 3-Fluorodihydro-2H-pyran-4(3H)-one, and the molecular formula is C5H7FO2, Related Products of tetrahydropyran.

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