Hesperetin

Hesperetin

Names
IUPAC name (S)-2,3-Dihydro-5,7-dihydroxy-2-(3-hydroxy-4-methoxyphenyl)-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
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	302.28 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.
• Neohesperidin is the 7-O-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.

References