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Chemical Structure| 480-19-3 Chemical Structure| 480-19-3

Structure of Isorhamnetin
CAS No.: 480-19-3

Chemical Structure| 480-19-3

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CAS No.: 480-19-3

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Isorhamnetin, a natural flavonol aglycone, can inhibit xanthine oxidase with IC50 of 400nM and stabilize β-catenin as well as up-regulate the Wnt signaling pathway. Isorhamnetin could also be act as an apoptosia inducer with antitumor activities.

Synonyms: 3'-Methylquercetin; 3'-O-methyl Quercetin; Quercetin

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Product Details of Isorhamnetin

CAS No. :480-19-3
Formula : C16H12O7
M.W : 316.26
SMILES Code : O=C1C(O)=C(C2=CC=C(O)C(OC)=C2)OC3=CC(O)=CC(O)=C13
Synonyms :
3'-Methylquercetin; 3'-O-methyl Quercetin; Quercetin
MDL No. :MFCD00017310
InChI Key :IZQSVPBOUDKVDZ-UHFFFAOYSA-N
Pubchem ID :5281654

Safety of Isorhamnetin

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302
Precautionary Statements:P280-P305+P351+P338

Related Pathways of Isorhamnetin

MAPK

Isoform Comparison

Biological Activity

In Vitro:

Cell Line
Concentration Treated Time Description References
Human amniotic epithelial stem cells 20 μM 10 days Investigate the gene expression profile of ISO in hAESCs, showing significant suppression of TGF-β, collagen-related functions, and inflammatory processes PMC7552739
Human amnion epithelial cells (hAECs) 20 mM 10 days Induced hepatic-lineage specific differentiation in hAECs, activating essential biological processes, molecular functions, and signaling pathways for hepatic differentiation. PMC7674172
Porcine ovarian granulosa cells 20 μM 24 hours To investigate the therapeutic effect of isorhamnetin on ZEA-induced damage in porcine ovarian granulosa cells and elucidate its molecular mechanism. Results showed that isorhamnetin suppressed ZEA-induced apoptosis, endoplasmic reticulum stress, and oxidative stress via the PI3K/Akt signaling pathway, promoting cell proliferation and hormone secretion. PMC9618982
Canine mammary tumor U27 cells 10, 20, 40 μM 48 hours Inhibited cell migration and invasion, induced apoptosis PMC10779303
Bovine endometrial epithelial cells (bEECs) 2.5 μM 24 hours To evaluate the protective effect of isorhamnetin on NEFA-induced cell damage. Results showed that isorhamnetin significantly improved cell viability, reduced apoptosis, and decreased the expression of BAX and cleaved caspase-3. PMC11852151
BV2 microglial cells 0, 50, 100, 200 μM 24 hours To evaluate the effect of isorhamnetin on LPS-induced inflammatory responses, results showed that isorhamnetin significantly suppressed LPS-induced secretion of NO and PGE2 without significant cytotoxicity. PMC6317673
NOZ cells 0, 40, 60, 80, 100 μM 24, 48, 72 hours Isorhamnetin significantly inhibited the proliferation of NOZ cells in a time- and dose-dependent manner PMC7927673
GBC-SD cells 0, 40, 60, 80, 100 μM 24, 48, 72 hours Isorhamnetin significantly inhibited the proliferation of GBC-SD cells in a time- and dose-dependent manner PMC7927673
Porcine oocytes 5, 10, 20, 30 μM 44 hours To investigate the protective effect of isorhamnetin on ZEA-induced damage in porcine oocytes. Results showed that isorhamnetin significantly increased the polar body extrusion rate of ZEA-exposed oocytes and inhibited ZEA-induced early apoptosis. PMC9896747
Corneal epithelial cells (CorE) and conjunctival epithelial cells (ConjE) 30 μM 48 hours The cytotoxic effect of isorhamnetin was evaluated, showing that isorhamnetin at 30 μM did not affect cell viability. PMC8070004
CD274-knockout U27 cells (U27?/?) 10, 20, 40 μM 48 hours Reduced sensitivity to ISO, weaker inhibition of migration and invasion PMC10779303
Human bladder cancer T24 cells 127.86 μM (IC50) 48 hours Isorhamnetin inhibited T24 cell proliferation via G2/M phase arrest and apoptosis, accompanied by decreased expression of Wee1 and cyclin B1, increased expression of p21WAF1/CIP1, and enhanced binding of p21 to Cdk1. PMC6826535
Primary pancreatic acinar cells 10 μM 50 minutes To evaluate the protective effect of isorhamnetin on STC-induced acinar cell necrosis, results showed that isorhamnetin significantly alleviated STC-induced acinar cell necrosis PMC11011973
FRT cells 30 μM The effect of isorhamnetin on CFTR chloride channel activity was measured, showing that isorhamnetin fully activated CFTR at 30 μM. PMC8070004

In Vivo:

Species
Animal Model
Administration Dosage Frequency Description References
CD-1 mice Scopolamine-induced dry eye model Topical ocular administration 30 μM Three times a day for 10 days The therapeutic effect of isorhamnetin on dry eye disease was evaluated, showing that isorhamnetin significantly reduced corneal damage and increased tear volume. PMC8070004
Caenorhabditis elegans Wild-type and mutant C. elegans Liquid media 50-200 μM 2 days Isorhamnetin reduced fat accumulation dependent on nhr-49, a functional homolog of PPARα, by upregulating an NHR-49 downstream target (ech-1.1) involved in fatty acid β-oxidation in C. elegans. PMC7473354
C57BL/6 mice Aspergillus fumigatus keratitis model Topical administration 80 μg/mL Four times per day for 1 to 5 days To evaluate the antifungal and anti-inflammatory effects of isorhamnetin in a Mice model of A. fumigatus keratitis. Results showed that isorhamnetin treatment alleviated the severity of FK by reducing corneal fungal load and inhibiting neutrophil recruitment and inflammatory factor expression. PMC8010362
C57 mice Bleomycin-induced pulmonary fibrosis model Intragastrically 10 and 30 mg/kg Once a day for 28 days To investigate the effect of Isor on bleomycin-induced pulmonary fibrosis. Results showed that Isor attenuated fibrotic changes, reduced collagen deposition and α-SMA expression, and alleviated EMT and ERS. PMC6257865
BALB/SCID nude mice U27 cell xenograft model Intraperitoneal injection 50 mg/kg Every 3 days for 9 days Inhibited tumor growth, reduced tumor volume and mass PMC10779303
C57BL/6 mice STC or L-arginine-induced SAP model Intraperitoneal injection 10 mg/kg or 30 mg/kg 24 hours or 72 hours after a single injection To evaluate the protective effect of isorhamnetin on SAP, results showed that isorhamnetin significantly alleviated pancreatic damage and reduced serum lipase and amylase levels PMC11011973
Nude mice Ishikawa cell xenograft model Intraperitoneal injection 20 mg/kg Once daily for 15 days Isorhamnetin significantly inhibited the growth of Ishikawa xenografts with an inhibition rate up to 50.42%, and suppressed tumor growth by regulating key proteins of mitochondrial and endoplasmic reticulum-related pathways. PMC9654916
C57BL/6 mice Angiotensin II-induced cardiac hypertrophy and fibrosis model Intraperitoneal injection 5 mg/kg Once daily for 3 weeks Investigate the protective effect of ISO on Angiotensin II-induced cardiac hypertrophy and fibrosis, showing significant suppression of myocardial hypertrophy and fibrosis PMC7552739
BALB/c nude mice NOZ cell xenograft model Intraperitoneal injection 1 or 5 mg/kg Once daily for 14 days Isorhamnetin significantly inhibited tumor growth in a dose-dependent manner PMC7927673

Clinical Trial:

NCT Number Conditions Phases Recruitment Completion Date Locations
NCT02627547 Healthy Not Applicable Completed - United Kingdom ... More >> University of Glasgow School of Medicine Glasgow, United Kingdom Less <<
NCT02425436 Intrauterine Growth Restrictio... More >>n (IUGR) Less << Phase 2 Completed - -
NCT04851821 a Randomized Double-blind Stud... More >>y|Severe Acute Respiratory Syndrome Coronavirus 2 (SARS-CoV-2)|PHYTOTHERAPIE Less << PHASE1 COMPLETED 2021-06-30 Riadh Boukef, Sahloul, Sousse,... More >> Tunisia Less <<
NCT03989271 Chronic Obstructive Pulmonary ... More >>Disease Less << PHASE1|PHASE2 RECRUITING 2025-07-01 Nathaniel Marchetti, Philadelp... More >>hia, Pennsylvania, 19140, United States Less <<
NCT02226484 Gastroesophageal Reflux Diseas... More >>e|GERD|Acid Reflux|Reflux Less << PHASE1 COMPLETED 2025-06-16 UNC Chapel Hill, Chapel Hill, ... More >>North Carolina, 27599, United States Less <<
NCT03943459 Coronary Artery Disease Progre... More >>ssion Less << PHASE3 UNKNOWN 2022-06-30 INCOR - Heart Institute, S?o P... More >>aulo, 05403-900, Brazil Less <<

Protocol

Bio Calculators
Preparing Stock Solutions 1mg 5mg 10mg

1 mM

5 mM

10 mM

3.16mL

0.63mL

0.32mL

15.81mL

3.16mL

1.58mL

31.62mL

6.32mL

3.16mL
Dissolving Methods
Please choose the appropriate dissolution scheme according to your animal administration guide.For the following dissolution schemes, clear stock solution should be prepared according to in vitro experiments, and then cosolvent should be added in turn:

in order to ensure the reliability of the experimental results, the clarified stock solution can be properly preserved according to the storage conditions; The working fluid for in vivo experiment is recommended to be prepared now and used on the same day;

The percentage shown in front of the following solvent refers to the volume ratio of the solvent in the final solution; If precipitation or precipitation occurs in the preparation process, it can be assisted by heating and/or ultrasound.
Protocol 1

References

 

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