Hesperetin

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
CAS Number	520-33-2 Y
3D model ( JSmol )	Interactive image
ChEBI	CHEBI:28230 Y
ChEMBL	ChEMBL399121 Y
ChemSpider	65234 Y
DrugBank	DB01094 Y
ECHA InfoCard	100.007.538
EC Number	208-290-2
KEGG	C01709 Y
PubChem CID	72281
UNII	Q9Q3D557F1 Y
CompTox Dashboard (EPA)	DTXSID4022319
InChI 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
SMILES O=C2c3c(O[C@H](c1ccc(OC)c(O)c1)C2)cc(O)cc3O
Properties
Chemical formula	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). Y verify (what is YN ?) Infobox references

Hesperetin is the 4'-methoxy derivative of eriodictyol, a flavanone. Hesperetin's 7-O-glycoside, hesperidin, is a naturally occurring flavanon-glycoside, the main flavonoid in lemons and sweet oranges.^[1] Hesperetin (and naringenin, the parent flavanone of naringin) are not found to a significant extent in Citrus spp.^[2]

Glycosides

A variety of glycosides of hesperetin are known, including:

• Hesperidin (hesperetin-7-O-rutinoside) is a water-insoluble flavonoid glycoside whose solubility is below 5 μg/ml in water.^[3] Hesperidin is found in citrus fruits and upon ingestion it releases its aglycone, hesperetin.
• neohesperidoside
  of hesperetin.
• Hesperetin-7-O-α-L-Rhamnopyranoside (CAS 66513-83-5) is found in the roots of clammy cherry^[4] (Cordia obliqua a.k.a. Cordia obliqua var. wallichii^[5]).

Metabolism

Hesperidin 6-O-α-L-rhamnosyl-β-D-glucosidase is an enzyme that uses hesperidin and H₂O to produce hesperetin and rutinose. It is found in the hyphomycetes species Stilbella fimetaria.

Effects

Hesperetin was found to be affecting the slow inactivation phase of inward sodium current channels (INa) and therefore could be used as a template to develop drugs against lethal cardiac arrhythmias in LQT3.^[6] Hesperetin also inhibits TRPM3 channels.^[7]

References