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Hesperetin

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Hesperetin
Hesperetin
Names
IUPAC name
(S)-2,3-Dihydro-5,7-dihydroxy-2-(3-hydroxy-4-methoxyphenyl)-4H-1-benzopyran-4-one
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
DrugBank
ECHA InfoCard 100.007.538 Edit this at Wikidata
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 checkY
    Key: AIONOLUJZLIMTK-AWEZNQCLSA-N checkY
  • 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).
checkY verify (what is checkY☒N ?)

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

  1. ^ https://pubchem.ncbi.nlm.nih.gov/compound/hesperetin
  2. ^ Lewinsohn, E; Britsch, L; Mazur, Y; Gressel, J (1989). "Flavanone Glycoside Biosynthesis in Citrus: Chalcone Synthase, UDP-Glucose:Flavanone-7-O-Glucosyl-Transferase and -Rhamnosyl-Transferase Activities in Cell-Free Extracts". Plant Physiology. 91 (4): 1323–1328. doi:10.1104/pp.91.4.1323. PMC 1062186. PMID 16667183.
  3. ^ Majumdar S.; Srirangam, R. (2009). "Solubility, stability, physicochemical characteristics and in vitro ocular tissue permeability of hesperidin: a natural bioflavonoid". Pharm Res. 26: 1217–1225. doi:10.1007/s11095-008-9729-6. PMC 2664388.
  4. ^ http://ccd.chemnetbase.com/AAA00.entry?parentCHNumber=CNB06-R:CNB07-S
  5. ^ http://www.newcropslisting.info/listing/species_pages_C/Cordia_obliqua.htm
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