| Identification | More | [Name]
HESPERETIN | [CAS]
520-33-2 | [Synonyms]
2,3-DIHYDRO-5,7-DIHYDROXY-2S-(3-HYDROXY-4-METHOXPHENYL)-4H-1-BENZOPYRAN-4-ONE
(+/-)-3',5,7-TRIHYDROXY-4'-METHOXYFLAVANONE
3',5,7-TRIHYDROXY-4'-METHOXYFLAVANONE
3',5,7-TRIHYDROXY-4-METHOXYFLAVANONE
4'-METHOXY-3',5,7-TRIHYDROXYFLAVANONE
5,7,3'-TRIHYDROXY-4'-METHOXYFLAVANONE
(+/-)-HESPERETIN
HESPERETIN
HESPERETINE
(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
4H-1-Benzopyran-4-one, 2,3-dihydro-5,7-dihydroxy-2-(3-hydroxy-4-methoxyphenyl)-, (2S)-
(2S)-5,7-dihydroxy-2-(3-hydroxy-4-methoxy-phenyl)chroman-4-one
HESPERETIN(P)
HESPERETIN hplc
HESPERETIN WITH HPLC
(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 | [EINECS(EC#)]
208-290-2 | [Molecular Formula]
C16H14O6 | [MDL Number]
MFCD00075646 | [Molecular Weight]
302.28 | [MOL File]
520-33-2.mol |
| Chemical Properties | Back Directory | [Appearance]
Beige to Light Brown Crystalline Solid | [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. ]
2-8°C
| [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). | [Usage]
The aglucon of hesperidin | [Merck ]
14,4670 | [BRN ]
309850 | [Cosmetics Ingredients Functions]
ANTIOXIDANT
SKIN CONDITIONING | [InChIKey]
AIONOLUJZLIMTK-AWEZNQCLSA-N | [LogP]
2.90 | [CAS DataBase Reference]
520-33-2(CAS DataBase Reference) |
| Hazard Information | Back Directory | [Description]
Hesperetin is a flavonoid that has been found in citrus fruits and has diverse biological activities.1,2,3,4,5 It reduces ApoB protein levels, ACAT2 expression, and LDL degradation in HepG2 cells when used at a concentrations ranging from 10 to 200 μM.1 Hesperetin inhibits IgG-induced β-hexosaminidase release from RBL-2H3 cells (IC50 = 0.099 mg/ml).2 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.3 Hesperetin (5 mg/kg) inhibits passive cutaneous anaphylaxis in mice.2 It reduces body weight loss, colon shortening, and ulcer severity in a mouse model of TNBS-induced ulcerative colitis.4 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.5 | [Chemical Properties]
Beige to Light Brown Crystalline Solid | [Uses]
antiallergic | [Uses]
The aglucon of Hesperidin (H281185), a flavanone found in citrus fruits. | [Definition]
ChEBI: A trihydroxyflavanone having the three hydroxy gropus located at the 3'-, 5- and 7-positions and an additional methoxy substituent at the 4'-position. | [Synthesis]
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 |
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Energy Chemical
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