Hesperetin

Structural formula
General
Surname	Hesperetin
other names	( S ) -2,3-dihydro-5,7-dihydroxy-2- (3-hydroxy-4-methoxyphenyl) -4 H -1-benzopyran-4-one; ( S ) -2,3-dihydro-5,7-dihydroxy-2- (3-hydroxy-4-methoxyphenyl) -4-benzopyrone; Hesperetol; ( S ) -3 ', 5,7-trihydroxy-4'-methoxyflavanone; HESPERETIN ( INCI ) ;
Molecular formula	C 16 H 14 O 6
Brief description	Leaflets
External identifiers / databases
EC number	208-290-2
ECHA InfoCard	100.007.538
PubChem	72281
ChemSpider	65234
DrugBank	DB01094
Wikidata	Q411310
properties
Molar mass	302.28 g · mol -1
Physical state	firmly
Melting point	216-218 ° C
solubility	Slightly soluble in water, benzene , chloroform ; soluble in ethanol ; soluble in dilute alkalis ;
safety instructions
GHS labeling of hazardous substances Caution
H and P phrases	H: 315-319-335
	P: 261-280-305 + 351 + 338-304 + 340-362-312-321-405-403 + 233-501
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Hesperetin is the aglycon of hesperidin and belongs to the group of flavonoids .

history

Hesperetin was first obtained in 1928 by hydrolysis of hesperidin.

Occurrence

Whole and sliced lemon

Along with hesperidin, hesperetin occurs in the peels of oranges and other citrus fruits .

properties

The natural hesperetin is chiral . The specific rotation of the natural ( S ) - (-) - hesperetin is -37.6 ° (c = 1.8 M in ethanol at 27 ° C).

Pharmacological effect

Hesperetin inhibit a potent antioxidant that lipid peroxidation and can protect brain cells from certain harmful influences protect ( neuroprotection ).

Furthermore, hesperetin and its metabolites lower the lipid content of the blood, whereby there is also evidence of an inhibition of cholesterol biosynthesis .

Individual evidence

↑ Entry on HESPERETIN in the CosIng database of the EU Commission, accessed on April 6, 2020.
^ Entry on hesperetin. In: Römpp Online . Georg Thieme Verlag, accessed on December 29, 2014.
↑ ^a ^b ^c ^d The Merck Index , 12th edition. Edition, Merck & Co. , Whitehouse Station, New Jersey, USA, 1996. .
↑ ^a ^b ^c data sheet 3 ′, 5,7-trihydroxy-4′-methoxyflavanone, 97% from AlfaAesar, accessed on November 1, 2016 ( PDF )(JavaScript required) .
↑ Hesperetin data sheet from Sigma-Aldrich , accessed on April 3, 2011 ( PDF ).

↑ Shinoda, J. & Kawagoye, M. (1928): Polyhydroxychalcones, polyhydroxyhydrochalcones and polyhydroxyflavanones. III. Synthesis of hesperetin. In: Yakugaku Zasshi. Vol. 48, pp. 938-941.

↑ J. Cho (2006): Antioxidant and neuroprotective effects of hesperidin and its aglycone hesperetin. In: Arch Pharm Res . Vol. 29, p. 699, PMID 16964766 .

↑ HK Kim, et al. (2003): Lipid-lowering efficacy of hesperetin metabolites in high-cholesterol fed rats. In: Clin. Chim. Acta. Vol. 327, p. 129, doi : 10.1016 / S0009-8981 (02) 00344-3 .

[CosIng-1] Entry on HESPERETIN in the CosIng database of the EU Commission, accessed on April 6, 2020.

[Römpp-2] Entry on hesperetin. In: Römpp Online . Georg Thieme Verlag, accessed on December 29, 2014.

[merck_index-3] The Merck Index , 12th edition. Edition, Merck & Co. , Whitehouse Station, New Jersey, USA, 1996. .

[Alfa-4] ta sheet 3 ′, 5,7-trihydroxy-4′-methoxyflavanone, 97% from AlfaAesar, accessed on November 1, 2016 ( PDF )(JavaScript required) .

[Sigma-5] Hesperetin data sheet from Sigma-Aldrich , accessed on April 3, 2011 ( PDF ).

[6] Shinoda, J. & Kawagoye, M. (1928): Polyhydroxychalcones, polyhydroxyhydrochalcones and polyhydroxyflavanones. III. Synthesis of hesperetin. In: Yakugaku Zasshi. Vol. 48, pp. 938-941.

[7] J. Cho (2006): Antioxidant and neuroprotective effects of hesperidin and its aglycone hesperetin. In: Arch Pharm Res . Vol. 29, p. 699, PMID 16964766 .

[8] HK Kim, et al. (2003): Lipid-lowering efficacy of hesperetin metabolites in high-cholesterol fed rats. In: Clin. Chim. Acta. Vol. 327, p. 129, doi : 10.1016 / S0009-8981 (02) 00344-3 .