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Hesperetin

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Hesperetin Basic information

Product Name:
Hesperetin
Synonyms:
  • 4'-METHOXY-3',5,7-TRIHYDROXYFLAVANONE
  • (+/-)-3',5,7-TRIHYDROXY-4'-METHOXYFLAVANONE
  • 3',5,7-TRIHYDROXY-4'-METHOXYFLAVANONE
  • 3',5,7-TRIHYDROXY-4-METHOXYFLAVANONE
  • 2,3-DIHYDRO-5,7-DIHYDROXY-2S-(3-HYDROXY-4-METHOXPHENYL)-4H-1-BENZOPYRAN-4-ONE
  • 5,7,3'-TRIHYDROXY-4'-METHOXYFLAVANONE
  • HESPERETINE
  • (+/-)-HESPERETIN
CAS:
520-33-2
MF:
C16H14O6
MW:
302.28
EINECS:
208-290-2
Product Categories:
  • natural product
  • chemical reagent
  • pharmaceutical intermediate
  • phytochemical
  • reference standards from Chinese medicinal herbs (TCM).
  • standardized herbal extract
  • Biochemistry
  • Flavonoids
  • Natural Plant Extract
  • Inhibitors
  • Chiral Reagents
  • Intermediates & Fine Chemicals
  • Pharmaceuticals
  • CITRIMORE
  • Flavanones
Mol File:
520-33-2.mol
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Hesperetin Chemical Properties

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
InChIKey
AIONOLUJZLIMTK-AWEZNQCLSA-N
LogP
2.90
CAS DataBase Reference
520-33-2(CAS DataBase Reference)
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Safety Information

Hazard Codes 
Xi
Risk Statements 
36/37/38
Safety Statements 
26-36/37/39-27-37
WGK Germany 
3
HS Code 
29329990

MSDS

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Hesperetin Usage And Synthesis

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

Uses

The aglucon of Hesperidin (H281185), a flavanone found in citrus fruits.

Uses

antiallergic

Uses

(±)-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.

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.]

Hesperetin Preparation Products And Raw materials

Preparation Products

HesperetinSupplier

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