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????? ??? ???
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520-33-2
???:
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???(??):
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Hesperetin
???(??):
(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
???:
C16H14O6
??? ??:
302.28
MOL ??:
520-33-2.mol

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???
230-232°C
?? ?
363.32°C (rough estimate)
??
1.2514 (rough estimate)
???
-4 ° (C=1.8, EtOH)
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Inert atmosphere,Room Temperature
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DMSO(?? ???), ???(?? ???)
?? ?? (pKa)
7.49±0.40(Predicted)
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??
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?(??), ?? ??? ? ???(50mg/ml)? ?????.
Merck
14,4670
BRN
309850
InChIKey
AIONOLUJZLIMTK-AWEZNQCLSA-N
LogP
2.90
CAS ??????
520-33-2(CAS DataBase Reference)
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  • ?? ? ?? ??
  • ?? ? ???? ?? (GHS)
??? ?? Xi
?? ???? ?? 36/37/38
????? 26-36/37/39-27-37
WGK ?? 3
HS ?? 29329990
????(GHS): GHS hazard pictograms
?? ?: Warning
??·?? ??:
?? ??·?? ?? ?? ?? ?? ?? ? ?? ?? P- ??
H315 ??? ??? ??? ????? ?? ????? ?? 2 ?? GHS hazard pictograms P264, P280, P302+P352, P321,P332+P313, P362
H319 ?? ?? ??? ??? ?? ? ?? ?? ??? ?? ?? 2A ?? GHS hazard pictograms P264, P280, P305+P351+P338,P337+P313P
H335 ?? ???? ??? ? ?? ?? ???? ?? - 1? ??;???? ?? ?? 3 ?? GHS hazard pictograms
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P261 ??·?·??·???·??·...·????? ??? ????.
P264 ?? ??? ?? ??? ????.
P264 ?? ??? ?? ??? ????.
P280 ????/???/???/?????? ?????.
P304+P340 ???? ??? ??? ?? ??? ??? ???? ?? ??? ??? ????.
P305+P351+P338 ?? ??? ? ?? ?? ???? ????. ???? ?????? ?????. ?? ????.
P405 ???? ?????.
NFPA 704
1
2 0

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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.

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Beige to Light Brown Crystalline Solid

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(±)-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.

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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.]

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