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HomeProduct name listHesperetin

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
Hesperetin Structural

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)
ghs
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

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