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Hesperetin

Chemical compound From Wikipedia, the free encyclopedia

Hesperetin

Hesperetin is the 4'-methoxy derivative of eriodictyol, a flavanone.[1] The 7-O-glycoside of hesperetin, hesperidin, is a naturally occurring flavanone-glycoside, the main flavonoid in grapefruits, lemons, and sweet oranges.[1][2]

Quick Facts Names, Identifiers ...
Hesperetin
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Hesperetin
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Hesperetin
Names
IUPAC name
(2S)-3′,5,7-Trihydroxy-4′-methoxyflavan-4-one
Systematic IUPAC name
(2S)-5,7-Dihydroxy-2-(3-hydroxy-4-methoxyphenyl)-2,3-dihydro-4H-1-benzopyran-4-one
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
DrugBank
ECHA InfoCard 100.007.538
EC Number
  • 208-290-2
KEGG
UNII
  • InChI=1S/C16H14O6/c1-21-13-3-2-8(4-10(13)18)14-7-12(20)16-11(19)5-9(17)6-15(16)22-14/h2-6,14,17-19H,7H2,1H3/t14-/m0/s1 Y
    Key: AIONOLUJZLIMTK-AWEZNQCLSA-N Y
  • InChI=1/C16H14O6/c1-21-13-3-2-8(4-10(13)18)14-7-12(20)16-11(19)5-9(17)6-15(16)22-14/h2-6,14,17-19H,7H2,1H3/t14-/m0/s1
    Key: AIONOLUJZLIMTK-AWEZNQCLBH
  • O=C2c3c(O[C@H](c1ccc(OC)c(O)c1)C2)cc(O)cc3O
Properties
C16H14O6
Molar mass 302.282 g·mol−1
Melting point 226–228 °C (439–442 °F; 499–501 K)
Solubility in other solvents Sol. EtOH, alkalis
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Glycosides

Various glycosides of hesperetin are known, including hesperidin (hesperetin-7-O-rutinoside), a water-insoluble flavonoid glycoside with low water solubility,[3] Hesperidin is found in citrus fruits and upon ingestion it releases its aglycone, hesperetin. Neohesperidin is the 7-O-neohesperidoside of hesperetin.

Metabolism

Hesperidin 6-O-α-L-rhamnosyl-β-D-glucosidase is an enzyme that uses hesperidin and H2O to produce hesperetin and rutinose.[1] Upon digestion in the gastrointestinal tract, hesperetin – as for all flavonoids – is rapidly metabolized in intestinal and liver cells, releasing smaller metabolites into the blood and urine for excretion.[1] The biological effects of such metabolites in vivo are unknown.

Laboratory research

In vitro, hesperetin may affect the slow inactivation phase of inward sodium current channels, and therefore could be used as a template to develop drugs against cardiac arrhythmias.[4] Hesperetin also inhibits TRPM3 channels in vitro.[5]

References

External links

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