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Hesperetin

Product Name
Hesperetin
CAS No.
520-33-2
Chemical Name
Hesperetin
Synonyms
(S)-2,3-dihydro-5,7-dihydroxy-2-(3-hydroxy-4-methoxyphenyl)-4-benzopyrone;2,3-DIHYDRO-5,7-DIHYDROXY-2S-(3-HYDROXY-4-METHOXPHENYL)-4H-1-BENZOPYRAN-4-ONE;4H-1-Benzopyran-4-one, 2,3-dihydro-5,7-dihydroxy-2-(3-hydroxy-4-methoxyphenyl)-, (2S)-;YSO2;NSC 57654;HESPERETIN;HESPERETINE;HESPERETIN(P);Hesperetin>Prestwick_908
CBNumber
CB4304735
Molecular Formula
C16H14O6
Formula Weight
302.28
MOL File
520-33-2.mol
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Hesperetin Property

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

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

Symbol(GHS)
Signal word
Warning
Hazard statements

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P304+P340IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

P405Store locked up.

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N-Bromosuccinimide Price

TCI Chemical
Product number
H0721
Product name
Hesperetin
Purity
>97.0%(HPLC)(T)
Packaging
5g
Price
$20
Updated
2025/07/31
TCI Chemical
Product number
H0721
Product name
Hesperetin
Purity
>97.0%(HPLC)(T)
Packaging
25g
Price
$52
Updated
2025/07/31
Cayman Chemical
Product number
10006084
Product name
Hesperetin
Packaging
25000mg
Price
$50
Updated
2024/03/01
Cayman Chemical
Product number
10006084
Product name
Hesperetin
Packaging
50000mg
Price
$94
Updated
2024/03/01
Cayman Chemical
Product number
10006084
Product name
Hesperetin
Packaging
100000mg
Price
$177
Updated
2024/03/01
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Hesperetin Chemical Properties,Usage,Production

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-).

Synthesis

520-26-3

520-33-2

Generic method: compound 2 was synthesized by the method reported in the literature. The raw material (S)-5-hydroxy-2-(3-hydroxy-4-methoxyphenyl)-7-(((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-((((2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyltetrahydro-2H-pyran-2-yl)oxy)methyl)tetrahydro-2H-pyran-2-yl)oxy )benzodihydropyran-4-one (3.5 g, 5.7 mmol) was mixed with 10 mL of concentrated sulfuric acid in 280 mL of anhydrous methanol and the reaction was stirred at 60 °C for 7.5 hours. Upon completion of the reaction, 1.2 L of ethyl acetate was added to the reaction mixture and extracted at 20 °C. Subsequently, the organic phase was washed with 420 mL of water and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure to give a light yellow powdery crude product. The crude product was dissolved in 70 mL of acetone and then slowly added dropwise (over 60 minutes) to a pre-stirred 700 mL solution consisting of water and acetic acid mixed at 150:1 by volume, maintaining the temperature at 95°C. After dropwise addition, the mixed slurry was cooled to 45°C, the product was collected by filtration and dried under vacuum.

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.]

References

[1] Journal of Medicinal Chemistry, 2011, vol. 54, # 1, p. 95 - 106
[2] Medicinal Chemistry Research, 2011, vol. 20, # 8, p. 1200 - 1205
[3] Bioorganic and Medicinal Chemistry Letters, 2012, vol. 22, # 23, p. 7194 - 7197
[4] Patent: CN105693682, 2016, A. Location in patent: Paragraph 0024; 0025
[5] Journal of Chemical Research, 2014, vol. 38, # 7, p. 396 - 398

Hesperetin Preparation Products And Raw materials

Raw materials

Preparation Products

BETA-PHENYLPROPIOPHENONE Neosperidin dihydrochalcone
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View Lastest Price from Hesperetin manufacturers

RongNa Biotechnology Co.,Ltd
Product
Hesperetin 520-33-2
Price
US $10.00/ASSAYS
Min. Order
1ASSAYS
Purity
99%
Supply Ability
1 ton
Release date
2025-08-21
Chongqing Zhihe Biopharmaceutical Co., Ltd.
Product
Hesperetin 520-33-2
Price
US $0.00-0.00/kg
Min. Order
0.10000000149011612kg
Purity
95% test by HPLC
Supply Ability
20tons
Release date
2025-05-23
WUHAN FORTUNA CHEMICAL CO., LTD
Product
Hesperetin 520-33-2
Price
US $0.00-0.00/kg
Min. Order
1kg
Purity
90%，95%，98%
Supply Ability
500kg
Release date
2025-04-10

520-33-2, HesperetinRelated Search:

HESPERETIN-7-NEOHESPERIDOSIDE hplc,Neohesperidin，Hesperetin 7-neohesperidoside,HESPERETIN-7-NEOHESPERIDOSIDE,HESPERETIN-7-O-NEOHESPERIDOSIDE Paeoniflorin Quercetin dihydrate Naringin Resveratrol Ferulic Acid Luteolin Citric acid (+/-)-HESPERETIN,HESPERETIN HESPERETIN LAURATE 4'-METHOXYFLAVANONE Hesperidin 4'-METHOXYFLAVANONE hesperetin 5-O-glucoside HESPERETIN, [3H(G)] HESPERETIN CHALCONE HESPERETIN DIHYDROCHALCONE HESPERETIN DIHYDROCHALCONE(RG)

  • 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
  • HESPERETIN
  • (S)-2,3-dihydro-5,7-dihydroxy-2-(3-hydroxy-4-methoxyphenyl)-4-benzopyrone
  • HESPERETIN 97%
  • 5,7-DIHYDROXY-2-(3-HYDROXY-4-METHOXY-PHENYL)-CHROMAN-4-ONE
  • (2S)-5,7-dihydroxy-2-(3-hydroxy-4-methoxy-phenyl)chroman-4-one
  • HESPERETIN(P)
  • HESPERETIN hplc
  • HESPERETIN WITH HPLC
  • 4H-1-Benzopyran-4-one, 2,3-dihydro-5,7-dihydroxy-2-(3-hydroxy-4-methoxyphenyl)-, (2S)-
  • Nano Liposomal Hesperetin
  • Hesperetin 520-33-2
  • Diosmin ep imp G
  • (2S)-2-(3-Hydroxy-4-methoxyphenyl)-5,7-dihydroxy-2,3-dihydro-4H-1-benzopyran-4-one
  • (2S)-2-(3-Hydroxy-4-methoxyphenyl)-5,7-dihydroxy-2H-1-benzopyran-4(3H)-one
  • (S)-3',5,7-Trihydroxy-4'-methoxyflavanone
  • [S,(-)]-2,3-Dihydro-5,7-dihydroxy-2-(3-hydroxy-4-methoxyphenyl)-4H-1-benzopyran-4-one
  • Eriodictyol 4'-monomethyl ether
  • (2S)-2,3-Dihydro-5,7-dihydroxy-2-(3-hydroxy-4-Methoxyphenyl)-4H-1-benzopyran-4-one
  • NSC 57654
  • (S)-5,7-Dihydroxy-2-(3-hydroxy-4-methoxyphenyl)chroman-4-one
  • 2,3-Dihydro-5,7-dihydroxy-2-(3-hydroxy-4-methoxyphenyl)-4H-1-benzopyran-4-one
  • Diosmin Impurity G
  • Hesperetin&gt
  • (S)-Hesperetin
  • Hesperetin Discontinued. Please see H289480 or H289501
  • (2S)-5,7-dihydroxy-2-(3-hydroxy-4-methoxyphenyl)-2,3-dihydrochromen-4-one
  • hesperetin extract
  • (S)-2,3-Dihydro-5,7-dihydroxy-2-(3-hydroxy-4-methoxyphenyl)-4-benzopyron
  • Hesperitin（mixture of isomers）
  • 13C,2H3]-Hesperetin
  • Hesperetin (6CI)
  • (2S)-5,7-dihydroxy-2-(3-hydroxy-4-methoxyphenyl)-2,3-dihydro-4H-1-benzopyran-4-one (hesperetin).
  • Hesperetin (diosmine EP impurity G)
  • Prestwick_908
  • YSO2
  • Hesperetin, 10 mM in DMSO
  • Hesperetin (Diosmin EP Impurity G)
  • 520-33-2
  • C16H14O6
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