Hesperetin
Synonym(s):3′,5,7-Trihydroxy-4′-methoxyflavanone;5,7-Dihydroxy-2-(3-hydroxy-4-methoxyphenyl)-4-chromanone
- CAS NO.:520-33-2
- Empirical Formula: C16H14O6
- Molecular Weight: 302.28
- MDL number: MFCD00075646
- EINECS: 208-290-2
- SAFETY DATA SHEET (SDS)
- Update Date: 2024-08-21 22:41:43
What is Hesperetin?
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.
Chemical properties
Beige to Light Brown Crystalline Solid
The Uses of Hesperetin
(±)-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.
The Uses of Hesperetin
The aglucon of Hesperidin (H281185), a flavanone found in citrus fruits.
The Uses of Hesperetin
antiallergic
What are the applications of Application
(±)-Hesperetin is an antioxidant flavonoid
Definition
ChEBI: Hesperetin is a trihydroxyflavanone having the three hydroxy gropus located at the 3'-, 5- and 7-positions and an additional methoxy substituent at the 4'-position. It has a role as an antioxidant, an antineoplastic agent and a plant metabolite. It is a monomethoxyflavanone, a trihydroxyflavanone, a member of 3'-hydroxyflavanones and a member of 4'-methoxyflavanones. It is a conjugate acid of a hesperetin(1-).
Purification Methods
Crystallise it from EtOAc or ethanol. The natural S(-) form crystallises from EtOH and has m 216-218o and [] D -37.6o (c 2, EtOH). Note that C2 is chiral. [Beilstein 18 II 204, 18 III/IV 3215, 18/5 V 214.]
Properties of Hesperetin
Melting point: | 230-232°C |
Boiling point: | 363.32°C (rough estimate) |
Density | 1.2514 (rough estimate) |
refractive index | -4 ° (C=1.8, EtOH) |
storage temp. | Inert atmosphere,Room Temperature |
solubility | DMSO (Slightly), Methanol (Slightly) |
form | Solid |
pka | 7.49±0.40(Predicted) |
color | White to Pale Yellow |
Water Solubility | Soluble in water (partly), dilute alkalis, and ethanol (50 mg/ml). |
Merck | 14,4670 |
BRN | 309850 |
CAS DataBase Reference | 520-33-2(CAS DataBase Reference) |
Safety information for Hesperetin
Signal word | Warning |
Pictogram(s) |
Exclamation Mark Irritant GHS07 |
GHS Hazard Statements |
H315:Skin corrosion/irritation H319:Serious eye damage/eye irritation H335:Specific target organ toxicity, single exposure;Respiratory tract irritation |
Precautionary Statement Codes |
P261:Avoid breathing dust/fume/gas/mist/vapours/spray. P264:Wash hands thoroughly after handling. P264:Wash skin thouroughly after handling. P280:Wear protective gloves/protective clothing/eye protection/face protection. P304+P340:IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing. P305+P351+P338:IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing. P405:Store locked up. |
Computed Descriptors for Hesperetin
InChIKey | AIONOLUJZLIMTK-AWEZNQCLSA-N |
Abamectin manufacturer
Sri Neelima Laboratories
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