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[ CAS No. 93-35-6 ] {[proInfo.proName]}

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Cat. No.: {[proInfo.prAm]}
Chemical Structure| 93-35-6
Chemical Structure| 93-35-6
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Product Citations

Product Citations

Aleksandra Grzelakowska ; Balaraman Kalyanaraman ; Jacek Zielonka DOI:

Abstract: Peroxynitrite (ONOO?/ONOOH) is a short-lived but highly reactive species that is formed in the diffusion-controlled reaction between nitric oxide and the superoxide radical anion. It can oxidize certain biomolecules and has been considered as a key cellular oxidant formed under various pathophysiological conditions. It is crucial to selectively detect and quantify ONOO– to determine its role in biological processes. In this review, we discuss various approaches used to detect ONOO? in cell-free and cellular systems with the major emphasis on small-molecule chemical probes. We review the chemical principles and mechanisms responsible for the formation of the detectable products, and plausible limitations of the probes. We recommend the use of boronate-based chemical probes for ONOO?, as they react directly and rapidly with ONOO–, they produce minor but ONOO??specific products, and the reaction kinetics and mechanism have been rigorously characterized. Specific experimental approaches and protocols for the detection of ONOO– in cell-free, cellular, and in vivo systems using boronate-based molecular probes are provided (as shown in BOX 1, BOX 2, BOX 3, BOX 4, BOX 5, BOX 6).

Keywords: peroxynitrite ; molecular ; ; bioluminescence ; chromatography ; biomarkers

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Product Details of [ 93-35-6 ]

CAS No. :93-35-6 MDL No. :MFCD00006878
Formula : C9H6O3 Boiling Point : -
Linear Structure Formula :- InChI Key :ORHBXUUXSCNDEV-UHFFFAOYSA-N
M.W : 162.14 Pubchem ID :5281426
Synonyms :
7-Hydroxycoumarin;Hydrangin;7-Hydroxycoumarin, 7 Hydroxycoumarin, 7Hydroxycoumarin, Hydrangin, Skimmetin, Umbelliferone;beta-umbelliferone;skimmetine;hydrangine;NSC 19790
Chemical Name :7-Hydroxy-2H-chromen-2-one

Calculated chemistry of [ 93-35-6 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 12
Num. arom. heavy atoms : 10
Fraction Csp3 : 0.0
Num. rotatable bonds : 0
Num. H-bond acceptors : 3.0
Num. H-bond donors : 1.0
Molar Refractivity : 44.51
TPSA : 50.44 ?2

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.17 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.44
Log Po/w (XLOGP3) : 1.58
Log Po/w (WLOGP) : 1.5
Log Po/w (MLOGP) : 1.04
Log Po/w (SILICOS-IT) : 1.97
Consensus Log Po/w : 1.51

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 1.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -2.46
Solubility : 0.566 mg/ml ; 0.00349 mol/l
Class : Soluble
Log S (Ali) : -2.25
Solubility : 0.912 mg/ml ; 0.00562 mol/l
Class : Soluble
Log S (SILICOS-IT) : -3.03
Solubility : 0.153 mg/ml ; 0.000942 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.56

Safety of [ 93-35-6 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 93-35-6 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Downstream synthetic route of [ 93-35-6 ]

[ 93-35-6 ] Synthesis Path-Downstream   1~8

  • 1
  • [ 93-35-6 ]
  • [ 6642-30-4 ]
  • Methyl-carbamic acid 2-oxo-2H-chromen-7-yl ester [ No CAS ]
  • 2
  • [ 93-35-6 ]
  • [ 54737-34-7 ]
  • [ 32942-70-4 ]
  • [ 619-60-3 ]
  • 3
  • [ 32942-70-4 ]
  • [ 619-60-3 ]
  • [ 93-35-6 ]
  • [ 54737-34-7 ]
  • 4
  • [ 93-35-6 ]
  • [ 19063-56-0 ]
  • 5
  • [ 93-35-6 ]
  • [ 109431-87-0 ]
  • (S)-tert-butyl 3-(2-oxo-2H-chromen-7-yloxy)pyrrolidine-1-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
52% With di-isopropyl azodicarboxylate; triethylamine; triphenylphosphine; In tetrahydrofuran; at 0 - 20℃; Step A: Diisopropyl azodicarboxylate (5.5 mL, 28 mmol) was added dropwise to a mixture of 7-hydroxycoumarin (4.6 g, 28 mmol), (R)-tert-butyl 3-hydroxypyrrolidine-l- carboxylate (6.0 g, 31 mmol), triphenylphosphine (7.4 g, 28 mmol) and triethylamine (3.9 mL, 28 mmol) in THF (28 mL) at 0 C. The mixture was stirred at room temperature overnight. The solids were removed by filtration and washed with cold THF. The solid was dissolved in EtOAc. The solution was washed with aqueous HC1 (0.5 N), dried over NaS04, then filtered and concentrated to give (S)-tert-butyl 3-(2-oxo-2H-chromen-7-yloxy)pyrrolidine-l-carboxylate (4.85 g, 52%) as a pale yellow solid. MS m/z 232.2 [M-Boc+H]+.
  • 6
  • [ 93-35-6 ]
  • [ 60481-51-8 ]
  • 3-(3,4-dimethylphenyl)-7-hydroxy-2H-chromen-2-one [ No CAS ]
  • 7
  • [ 93-35-6 ]
  • [ 109431-87-0 ]
  • (R)-tert-butyl 3-(2-oxo-2H-chromen-7-yloxy)pyrrolidine-1-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
52% With di-isopropyl azodicarboxylate; triethylamine; triphenylphosphine; In tetrahydrofuran; at 0 - 20℃; for 16h; Step A: Diisopropyl azodicarboxylate (5.5 mL, 28 mmol) was added dropwise to a mixture of 7-hydroxycoumarin (4.6 g, 28 mmol), <strong>[109431-87-0](R)-tert-butyl 3-hydroxypyrrolidine-1-carboxylate</strong> (6.0 g, 31 mmol), triphenylphosphine (7.4 g, 28 mmol) and triethylamine (3.9 mL, 28 mmol) in THF (28 mL) at 0 C. The mixture was stirred at room temperature overnight. The solids were removed by filtration and washed with cold THF. The solid was dissolved in EtOAc. The solution was washed with aqueous HCl (0.5 N), dried over NaSO4, then filtered and concentrated to give (S)-tert-butyl 3-(2-oxo-2H-chromen-7-yloxy)pyrrolidine-1-carboxylate (4.85 g, 52%) as a pale yellow solid. MS m/z 232.2 [M-Boc+H]+.
  • 8
  • [ 93-35-6 ]
  • [ 302348-51-2 ]
  • 7-((4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzyl)oxy)-2H-chromen-2-one [ No CAS ]
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