Hesperetin

Alias:
Cat No.:V1375 Purity: ≥98%
Hesperetin (YSO-2; YSO 2;Hesperitin; Hesperin; Prestwick_908) is a naturally occuring flavonoid with a vareity of biological properties such as antioxidant,neuroprotective and anti-inflammatory activity.
Hesperetin Chemical Structure CAS No.: 520-33-2
Product category: MT Receptor
This product is for research use only, not for human use. We do not sell to patients.
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250mg
500mg
1g
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5g
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Purity & Quality Control Documentation

Purity: ≥98%

Product Description

Hesperetin (YSO-2; YSO 2; Hesperitin; Hesperin; Prestwick_908) is a naturally occuring flavonoid with a vareity of biological properties such as antioxidant, neuroprotective and anti-inflammatory activity. Hesperetin acts by inhibiting NF-κB activation.

Biological Activity I Assay Protocols (From Reference)
ln Vitro
Hesperetin has antioxidant properties in drug delivery systems that self-nanoemulsify [1]. Human μgT is broadly inhibited by hesperetin and NGR. Furthermore, Hesperetin exhibits moderate inhibition of μgT1A4, ugT1A7, and ugT1A8 (IC 50 values 29.68-63.87 μM) and strong suppression of μgT1A1, 1A3, and 1A9 (IC50 and Ki values are lower than 10 μM) [2]. Hesperetin exhibits a range of binding energies in its interactions with various protein types, including hydrogen bonding, pi-pi effects, pi-cation bonding, and pi-sigma interactions. Hesperetin may be used to treat CHIKV infection because of its drug-like characteristics [3]. Hesperetin dose-dependently decreases the caspase-3 activity generated by GCDCA in primary rat hepatocyte cultures. Additionally, hesperetin dose-dependently decreased the hepatocytes' CM-induced Nos2 (iNOS) expression. Remarkably, when compared to the cytokine cocktail alone, hesperetin caused the expression of the antioxidant gene heme oxygenase 1 (HO-1) to increase by about four times [5].
ln Vivo
Oral Hesperetin at a dose of 40 mg/kg can prevent oxidative stress and mitochondrial dysfunction caused by Cd, increase antioxidant and membrane-bound enzyme activity, and lessen rat brain cell death [4]. In mouse hepatocytes, hesperetin (200 mg/kg) reduces hepatic Nos2 (iNOS) production and apoptosis triggered by con A. The co-administration of hesperetin also decreased the incidence of bleeding, edematous degeneration, nuclear fragmentation, autolysis, and apoptotic bodies. Hesperetin dramatically decreased the amount of leukocytes invading the liver tissue of mice with fulminant hepatitis caused by D-GalN/LPS in a mouse model [5].
Animal Protocol
After 7 days of adjusting, the animals are randomly divided into 10 experimental groups. Control group (n=8): These animals are treated with the equivalent volume of PBS as used for the administration of Con A and D-GalN/LPS. Control hesperetin group (n=8): The mice are treated with hesperetin 400 mg/kg p.o. in 0.5% sodium carboxymethylcellulose (CMC-Na) solution for 10 days. Con A group (n=15): The animals are treated with the same volume of CMC-Na as used for administration of hesperetin for 10 days and are challenged with Con A (i.v.15 mg/kg). Con A + hesperetin groups: The animals receive various doses of hesperetin (100, 200, 400 mg/kg) p.o. for 10 days before Con A injection (each group n=15). D-GalN/LPS group (n=15): The animals are given CMC-Na for 10 days and injected i.p. with D-GalN (700 mg/kg)/LPS (5 μg/kg). D-GalN/LPS + hesperetin groups: Three doses of hesperetin (100, 200, 400 mg/kg) are given to mice once daily for 10 days. D-GalN (700 mg/kg)/LPS (5 μg/kg) are injected i.p. (each group n=15).
Rats, Murine
References
[1]. Arya A, et al. Bioflavonoid hesperetin overcome bicalutamide induced toxicity by co-delivery in novel SNEDDS formulations: Optimization, in vivo evaluation and uptake mechanism. Mater Sci Eng C Mater Biol Appl. 2017 Feb 1;71:954-964
[2]. Liu D, et al. Inhibitory Effect of Hesperetin and Naringenin on Human UDP-Glucuronosyltransferase Enzymes: Implications for Herb-Drug Interactions. Biol Pharm Bull. 2016;39(12):2052-2059.
[3]. Oo A, et al. In silico study on anti-Chikungunya virus activity of hesperetin. PeerJ. 2016 Oct 26;4:e2602. eCollection 2016.
[4]. Shagirtha K, et al. Neuroprotective efficacy of hesperetin against cadmium induced oxidative stress in the brain of rats. Toxicol Ind Health. 2016 Nov 1. pii: 0748233716665301
[5]. Bai X, et al. The protective effect of the natural compound hesperetin against fulminant hepatitis in vivo and in vitro. Br J Pharmacol. 2017 Jan;174(1):41-56
[6]. Li Q, et al. Hesperetin Induces Apoptosis in Human Glioblastoma Cells via p38 MAPK Activation. Nutr Cancer. 2019 Jul 11:1-8
These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C16H14O6
Molecular Weight
302.27
CAS #
520-33-2
Related CAS #
520-33-2
SMILES
O1C2=C([H])C(=C([H])C(=C2C(C([H])([H])[C@@]1([H])C1C([H])=C([H])C(=C(C=1[H])O[H])OC([H])([H])[H])=O)O[H])O[H]
InChi Key
AIONOLUJZLIMTK-AWEZNQCLSA-N
InChi Code
InChI=1S/C16H14O6/c1-21-13-3-2-8(4-10(13)18)14-7-12(20)16-11(19)5-9(17)6-15(16)22-14/h2-6,14,17-19H,7H2,1H3/t14-/m0/s1
Chemical Name
(2S)-5,7-dihydroxy-2-(3-hydroxy-4-methoxyphenyl)-2,3-dihydrochromen-4-one
Synonyms

YSO2; Hesperetin; YSO-2; YSO 2;Hesperitin; Hesperin; Prestwick_908

Storage

Powder      -20°C    3 years

                     4°C     2 years

In solvent   -80°C    6 months

                  -20°C    1 month

Shipping Condition
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
Solubility Data
Solubility (In Vitro)
DMSO: 60 mg/mL (198.5 mM)
Water:<1 mg/mL
Ethanol:<1 mg/mL
Solubility (In Vivo)
Solubility in Formulation 1: ≥ 2.5 mg/mL (8.27 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL.
Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution.

Solubility in Formulation 2: ≥ 2.5 mg/mL (8.27 mM) (saturation unknown) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly.
Preparation of 20% SBE-β-CD in Saline (4°C,1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution.

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Solubility in Formulation 3: ≥ 2.5 mg/mL (8.27 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 900 μL of corn oil and mix evenly.


Solubility in Formulation 4: 20 mg/mL (66.16 mM) in 0.5% CMC/saline water (add these co-solvents sequentially from left to right, and one by one), suspension solution; with ultrasonication.
Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution.

 (Please use freshly prepared in vivo formulations for optimal results.)
Preparing Stock Solutions 1 mg 5 mg 10 mg
1 mM 3.3083 mL 16.5415 mL 33.0830 mL
5 mM 0.6617 mL 3.3083 mL 6.6166 mL
10 mM 0.3308 mL 1.6542 mL 3.3083 mL

*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.

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Note: Chemical formula is case sensitive: C12H18N3O4  c12h18n3o4
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In vivo Formulation Calculator (Clear solution)
Step 1: Enter information below (Recommended: An additional animal to make allowance for loss during the experiment)
Step 2: Enter in vivo formulation (This is only a calculator, not the exact formulation for a specific product. Please contact us first if there is no in vivo formulation in the solubility section.)
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Calculation results

Working concentration mg/mL;

Method for preparing DMSO stock solution mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.

Method for preparing in vivo formulation:Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O,mix and clarify.

(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
             (2) Be sure to add the solvent(s) in order.

Biological Data
  • Hesperetin

    Effects of hesperetin on TGF-β downstream signaling. Eur J Med Chem. 2012 Dec;58:390-5.
  • Hesperetin

    Evaluation of Hesperetin on TGF-β1-stimulated scattering migration (a-b) and invasion in HeLa cells (Boyden chamber assay) (c). Eur J Med Chem. 2012 Dec;58:390-5.
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