Hesperetin

Base Information

• Chemical Name: Hesperetin
• CAS No.: 520-33-2
• Molecular Formula: C16H14O6
• Molecular Weight: 302.284
• Hs Code.: 29329990
• European Community (EC) Number: 208-290-2
• UNII: Q9Q3D557F1
• DSSTox Substance ID: DTXSID4022319
• Nikkaji Number: J9.235E
• Wikipedia: Hesperetin
• Wikidata: Q411310
• NCI Thesaurus Code: C68461
• RXCUI: 1314255
• Pharos Ligand ID: 1V6DLQDBRF1B
• Metabolomics Workbench ID: 27168
• ChEMBL ID: CHEMBL399121
• Mol file: 520-33-2.mol

Synonyms:(-)-hesperetin;3',5,7-trihydroxy-4'-methoxyflavanone;hesperetin;hesperitin

Chemical Property of Hesperetin

Chemical Property:

• Appearance/Colour: Beige to Light Brown Crystalline Solid
• Vapor Pressure: 2.45E-14mmHg at 25°C
• Melting Point: 230-232 °C
• Refractive Index: -4 ° (C=1.8, EtOH)
• Boiling Point: 586.2 °C at 760 mmHg
• PKA: 7.49±0.40(Predicted)
• Flash Point: 223 °C
• PSA: 96.22000
• Density: 1.458 g/cm³
• LogP: 2.51850
• Storage Temp.: 2-8°C
• Solubility.: DMSO (Slightly), Methanol (Slightly)
• Water Solubility.: Soluble in water (partly), dilute alkalis, and ethanol (50 mg/ml).
• XLogP3: 2.4
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 2
• Exact Mass: 302.07903816
• Heavy Atom Count: 22
• Complexity: 413

Purity/Quality:

≥98% ^*data from raw suppliers

(S)-Hesperetin ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36/37/39-27-37

MSDS Files:

Useful:

• Canonical SMILES: COC1=C(C=C(C=C1)C2CC(=O)C3=C(C=C(C=C3O2)O)O)O
• Isomeric SMILES: COC1=C(C=C(C=C1)[C@@H]2CC(=O)C3=C(C=C(C=C3O2)O)O)O
• Recent ClinicalTrials: Impact of Hesperetin in Combination With Sucrose on Energy Metabolism
• Recent NIPH Clinical Trials: The application of water-dispersible hesperetin to the retina as a drug which improves retinal circulation
• Description: Hesperetin is a flavonoid that has been found in citrus fruits and has diverse biological activities. It reduces ApoB protein levels, ACAT2 expression, and LDL degradation in HepG2 cells when used at a concentrations ranging from 10 to 200 μM. Hesperetin inhibits IgG-induced β-hexosaminidase release from RBL-2H3 cells (IC50 = 0.099 mg/ml). It inhibits LPS-induced nitric oxide (NO) production and reduces levels of inducible nitric oxide synthase (iNOS), IL-6, and IL-1β in BV-2 microglial cells. Hesperetin (5 mg/kg) inhibits passive cutaneous anaphylaxis in mice. It reduces body weight loss, colon shortening, and ulcer severity in a mouse model of TNBS-induced ulcerative colitis. Hesperetin reduces cortical and hippocampal neuronal apoptosis and increases time spent in the target quadrant in the Morris water maze in a mouse model of LPS-induced neuronal inflammation.
• Uses: The aglucon of Hesperidin (H281185), a flavanone found in citrus fruits. antiallergic (±)-Hesperetin is an antioxidant flavonoid. Induces G1-phase cell cycle arrest. Anti-inflammatory. (±)-Hesperetin suppresses NF-κB activation. Reduces cholesterol biosynthesis. Inhibits lipid peroxidation. Neuroprotective against neuronal oxidative damage.

Technology Process of Hesperetin

There total 36 articles about Hesperetin which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 28.0%

7-hydroxy-4-methyl-chromen-2-one (90-33-5,79566-13-5) + hesperidin (520-26-3) → 4-methylumbelliferyl-rutinoside (1356391-89-3) + hesperetin (520-33-2,41001-90-5,69097-99-0)

Guidance literature:

With water; In dimethyl sulfoxide; at 30 ℃; for 1h; pH=5; aq. buffer; Enzymatic reaction;

DOI:10.1016/j.carres.2011.11.008

Reference yield: 3.5%

hesperidin (520-26-3) → hesperetin (520-33-2,41001-90-5,69097-99-0) + 3′,5,7,8-tetrahydroxy-4′-methoxyflavanone

Guidance literature:

With Aspergillus saitoi; In water; dimethyl sulfoxide; at 30 ℃; pH=5.0;

DOI:10.1271/bbb.67.1443

Reference yield:

hesperetin 7‐O‐β‐D‐glucopyranoside → β-D-glucose (492-61-5) + hesperetin (520-33-2,41001-90-5,69097-99-0)

Guidance literature:

With water; Enzymatic reaction;

DOI:10.1016/j.carres.2011.11.008

upstream raw materials:

hesperidin

4^G-α-D-glucopyranosyl hesperidin

(S)-2,3-dihydro-5,7-dihydroxy-2-(3-hydroxy-4-methoxyphenyl)-4-benzopyrone

methanol

Downstream raw materials:

5-hydroxy-3′4′7-trimethoxy flavanone

(S)-2,3-dihydro-5,7-dihydroxy-2-(3-hydroxy-4-methoxyphenyl)-4-benzopyrone

(S)-5,7-diacetoxy-2-(3-acetoxy-4-methoxy-phenyl)-chroman-4-one

(-)-hesperetin oxime

Refernces

In vitro binding affinities of a series of flavonoids for m-opioid receptors. Antinociceptive effect of the synthetic flavonoid 3,3-dibromoflavanone in mice

10.1016/j.neuropharm.2013.04.020

The research primarily investigates the binding affinity of various flavonoids to the μ-opioid receptor and evaluates the antinociceptive effects of a synthetic flavonoid, 3,3-dibromo?avanone, in mice. The study employs in vitro binding assays using [3H]DAMGO to assess the interaction of different flavonoids with μ-opioid receptors in rat forebrain membranes. The most potent compound, 3,3-dibromo?avanone, is further synthesized and tested in vivo using several pain models, including the acetic acid-induced writhing test, hot plate test, and formalin test, to evaluate its antinociceptive properties. Additional experiments assess potential side effects such as sedation, motor coordination, and gastrointestinal transit inhibition. The synthetic procedure for 3,3-dibromo?avanone is described, and its chemical structure is analyzed using techniques like NMR and EIMS. A series of natural and synthetic flavonoids were tested for their binding affinity to μ-opioid receptors. These included hesperidin, neohesperidin, naringin, rutin, hesperetin, naringenin, flavone, diosmetin, quercetin, apigenin, chrysin, among others. These compounds were obtained from Sigma-Aldrich, Extrasynthese, or were synthesized in the laboratory. The study concludes that 3,3-dibromo?avanone exhibits μ-opioid receptor activation-related antinociceptive effects without significant motor or gastrointestinal side effects, suggesting its potential as an alternative pain treatment.

DNA binding affinity and antioxidative activity of copper(II) and zinc(II) complexes with a novel hesperetin Schiff base ligand

10.1016/j.ica.2009.07.008

The research investigates the interaction of a novel hesperetin Schiff base ligand (H4L) and its copper(II) and zinc(II) complexes with DNA, as well as their antioxidative properties. The study aims to explore the binding mechanisms of these compounds to DNA and their potential as antitumor drugs and antioxidants. Key chemicals used include hesperetin, benzoyl hydrazine, copper(II) acetate, zinc(II) acetate, and calf thymus DNA. The researchers synthesized the ligand and its complexes and characterized them using various spectroscopic techniques. They found that all compounds bind to DNA through an intercalative mode, with the metal complexes showing stronger binding affinity than the free ligand. Additionally, the complexes exhibited higher antioxidative activity in scavenging superoxide radicals and hydroxyl radicals compared to the ligand. The findings suggest that these metal complexes could be valuable candidates for developing new antitumor drugs and antioxidants.