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Details

Stereochemistry ABSOLUTE
Molecular Formula C16H14O6
Molecular Weight 302.2788
Optical Activity UNSPECIFIED
Defined Stereocenters 1 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of HESPERETIN

SMILES

COC1=C(O)C=C(C=C1)[C@@H]2CC(=O)C3=C(O2)C=C(O)C=C3O

InChI

InChIKey=AIONOLUJZLIMTK-AWEZNQCLSA-N
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

HIDE SMILES / InChI

Description
Curator's Comment: The description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/20696580 | https://www.ncbi.nlm.nih.gov/pubmed/26498393 |

Hesperetin is a cholesterol-lowering flavanoid found in a number of citrus juices. It appears to reduce cholesteryl ester mass and inhibit apoB secretion by up to 80%. Hesperetin may have antioxidant, anti-inflammatory, anti-allergic, hypolipidemic, vasoprotective and anticarcinogenic actions. In vitro research also suggests the possibility that hesperetin might have some anticancer effects and that it might have some anti-aromatase activity, as well as activity again. Hesperetin reduces or inhibits the activity of acyl-coenzyme A: cholesterol acyltransferase genes (ACAT1 and ACAT2) and it reduces microsomal triglyceride transfer protein (MTP) activity. Hesperetin also seems to upregulate the LDL receptor. This leads to the reduced assembly and secretion of apoB-containing lipoproteins and enhanced reuptake of those lipoproteins, thereby lowering cholesterol levels. Hesperetin's 7-O-glycoside, hesperidin, is a naturally occurring flavanon-glycoside, the main flavonoid in lemons and sweet oranges.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
34.6 µM [IC50]
2.7 µM [IC50]
3.3 nM [Ki]
102.1 nM [Ki]
454.1 nM [Ki]
511.0 nM [IC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
Effect of hesperetin, a citrus flavonoid, on the liver triacylglycerol content and phosphatidate phosphohydrolase activity in orotic acid-fed rats.
2001
Chemistry and pharmacology of the Citrus bioflavonoid hesperidin.
2001 Dec
In vitro biological activity of prenylflavanones.
2001 Jan-Feb
Specific flavonoids induced nod gene expression and pre-activated nod genes of Rhizobium leguminosarum increased pea (Pisum sativum L.) and lentil (Lens culinaris L.) nodulation in controlled growth chamber environments.
2001 Jul
Structure-activity relationships for a large diverse set of natural, synthetic, and environmental estrogens.
2001 Mar
Secretion of hepatocyte apoB is inhibited by the flavonoids, naringenin and hesperetin, via reduced activity and expression of ACAT2 and MTP.
2001 May
Antimicrobial activity of prenylflavanones.
2001 Nov-Dec
Effect of exogenous flavonoids on nodulation of pea (Pisum sativum L.).
2002 Aug
In vitro investigation of cytochrome P450-mediated metabolism of dietary flavonoids.
2002 May
Plasma concentrations of the flavonoids hesperetin, naringenin and quercetin in human subjects following their habitual diets, and diets high or low in fruit and vegetables.
2002 Sep
Interaction between flavonoids and the blood-brain barrier: in vitro studies.
2003 Apr
Separation of some chiral flavanones by micellar electrokinetic chromatography.
2003 Aug
Hypocholesterolemic activity of hesperetin derivatives.
2003 Aug 18
Screening of the inhibitory effect of vegetable constituents on the aryl hydrocarbon receptor-mediated activity induced by 2,3,7,8-tetrachlorodibenzo-p-dioxin.
2003 Dec
Anti-Sindbis activity of flavanones hesperetin and naringenin.
2003 Jan
Kinetic and stoichiometric assessment of the antioxidant activity of flavonoids by electron spin resonance spectroscopy.
2003 Mar 12
Degradation of flavonoid aglycones by rabbit, rat and human fecal flora.
2003 May
Hesperetin glucuronide, a photoprotective agent arising from flavonoid metabolism in human skin fibroblasts.
2003 Sep
Reports: plasma and dietary phytoestrogens and risk of premalignant lesions of the cervix.
2004
Flavonoids promote cell migration in nontumorigenic colon epithelial cells differing in Apc genotype: implications of matrix metalloproteinase activity.
2004
Effects of some natural flavonoids on retinal function recovery after ischemic insult in the rat.
2004 Apr
Improvement in solubility and dissolution rate of flavonoids by complexation with beta-cyclodextrin.
2004 Apr 16
Antiallergic activity of hesperidin is activated by intestinal microflora.
2004 Aug
The flavones luteolin and apigenin inhibit in vitro antigen-specific proliferation and interferon-gamma production by murine and human autoimmune T cells.
2004 Aug 15
Effect of the rootstock and interstock grafted in lemon tree (Citrus limon (L.) Burm.) on the flavonoid content of lemon juice.
2004 Jan 28
Combined effects of multiple flavonoids on breast cancer resistance protein (ABCG2)-mediated transport.
2004 Jul
Evaluation of hesperetin 7-O-lauryl ether as lipid-lowering agent in high-cholesterol-fed rats.
2004 Jul 1
Determination of hesperetin, cinnamic acid and nicotinic acid in propolis with micellar electrokinetic capillary chromatography.
2004 Jun
Validated high-performance liquid chromatographic method utilizing solid-phase extraction for the simultaneous determination of naringenin and hesperetin in human plasma.
2004 Mar 5
Identification and quantification of the conjugated metabolites derived from orally administered hesperidin in rat plasma.
2004 Oct 20
Anti-inflammatory effect of heme oxygenase 1: glycosylation and nitric oxide inhibition in macrophages.
2005 Feb
Oral flavonoids delay recovery from experimental autoimmune encephalomyelitis in SJL mice.
2005 Jul 15
Impact of high pressure and pulsed electric fields on bioactive compounds and antioxidant activity of orange juice in comparison with traditional thermal processing.
2005 Jun 1
High-performance liquid chromatographic separation and chiroptical properties of the enantiomers of naringenin and other flavanones.
2005 May 27
Polyphenol levels in human urine after intake of six different polyphenol-rich beverages.
2005 Oct
Interactive effects of polyphenols, tocopherol and ascorbic acid on the Cu2+-mediated oxidative modification of human low density lipoproteins.
2005 Oct
Capillary electrochromatography of biologically relevant flavonoids.
2006 Feb
Different anticonvulsive effects of hesperidin and its aglycone hesperetin on electrical activity in the rat hippocampus in-vitro.
2006 Mar
The bioavailability of polyphenols is highly governed by the capacity of the intestine and of the liver to secrete conjugated metabolites.
2006 Mar
Prediction of estrogen receptor agonists and characterization of associated molecular descriptors by statistical learning methods.
2006 Nov
Patents

Sample Use Guides

150 mg of hesperetin as a single dose.
Route of Administration: Oral
Effectiveness of a plasma hesperetin metabolite on the release of nitric oxide (NO) and the activity of nicotinamide adenine dinucleotide phosphate-oxidase (NADPH oxidase) in endothelial cells was examined. Hesperetin or Hp7GA were dissolved in methanol and diluted with the medium. The final methanol concentration of the cell culture had no effect on the cell viability. Cells were placed in a dish (diameter, 15.5 mm) in an atmosphere of 5% CO2 /95% air at 37 C. Then the medium was replaced with fresh medium containing the test compounds. After treatment with test compounds (1, 5, 10, 25, and 50 mM) for 24 h, NO released from HUVECs was measured using 4-amino-5-methylamino-2,7-difluorofluorescein (DAF-FM) as a fluorescence probe.
Name Type Language
HESPERETIN
FHFI   INCI   MI  
INCI  
Official Name English
2,3-DIHYDRO-5,7-DIHYDROXY-2-(3-HYDROXY-4-METHOXYPHENYL)-4H-1-BENZOPYRAN-4-ONE
Systematic Name English
HESPERITIN
Common Name English
(-)-HESPERETIN
Common Name English
HESPERETIN [MI]
Common Name English
4H-1-BENZOPYRAN-4-ONE, 2,3-DIHYDRO-5,7-DIHYDROXY-2-(3-HYDROXY-4-METHOXYPHENYL)-, (S)-
Systematic Name English
NSC-57654
Code English
HESPERETIN [FHFI]
Common Name English
HESPERETIN [INCI]
Common Name English
ERIODICTYOL 4'-MONOMETHYL ETHER
Common Name English
4H-1-BENZOPYRAN-4-ONE, 2,3-DIHYDRO-5,7-DIHYDROXY-2-(3-HYDROXY-4-METHOXYPHENYL)-, (2S)-
Systematic Name English
FLAVANONE, 3',5,7-TRIHYDROXY-4'-METHOXY-
Systematic Name English
3',5,7-TRIHYDROXY-4'-METHOXYFLAVANONE
Systematic Name English
FEMA NO. 4313
Code English
5,7,3'-TRIHYDROXY-4'-METHOXYFLAVANONE
Systematic Name English
Code System Code Type Description
DRUG BANK
DB01094
Created by admin on Sat Dec 16 20:17:54 GMT 2023 , Edited by admin on Sat Dec 16 20:17:54 GMT 2023
PRIMARY
EPA CompTox
DTXSID4022319
Created by admin on Sat Dec 16 20:17:54 GMT 2023 , Edited by admin on Sat Dec 16 20:17:54 GMT 2023
PRIMARY
DAILYMED
Q9Q3D557F1
Created by admin on Sat Dec 16 20:17:54 GMT 2023 , Edited by admin on Sat Dec 16 20:17:54 GMT 2023
PRIMARY
JECFA MONOGRAPH
2002
Created by admin on Sat Dec 16 20:17:54 GMT 2023 , Edited by admin on Sat Dec 16 20:17:54 GMT 2023
PRIMARY
NSC
57654
Created by admin on Sat Dec 16 20:17:54 GMT 2023 , Edited by admin on Sat Dec 16 20:17:54 GMT 2023
PRIMARY
DRUG CENTRAL
1362
Created by admin on Sat Dec 16 20:17:54 GMT 2023 , Edited by admin on Sat Dec 16 20:17:54 GMT 2023
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FDA UNII
Q9Q3D557F1
Created by admin on Sat Dec 16 20:17:54 GMT 2023 , Edited by admin on Sat Dec 16 20:17:54 GMT 2023
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WIKIPEDIA
HESPERETIN
Created by admin on Sat Dec 16 20:17:54 GMT 2023 , Edited by admin on Sat Dec 16 20:17:54 GMT 2023
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ECHA (EC/EINECS)
208-290-2
Created by admin on Sat Dec 16 20:17:54 GMT 2023 , Edited by admin on Sat Dec 16 20:17:54 GMT 2023
PRIMARY
RXCUI
1314255
Created by admin on Sat Dec 16 20:17:54 GMT 2023 , Edited by admin on Sat Dec 16 20:17:54 GMT 2023
PRIMARY RxNorm
CHEBI
28230
Created by admin on Sat Dec 16 20:17:54 GMT 2023 , Edited by admin on Sat Dec 16 20:17:54 GMT 2023
PRIMARY
NCI_THESAURUS
C68461
Created by admin on Sat Dec 16 20:17:54 GMT 2023 , Edited by admin on Sat Dec 16 20:17:54 GMT 2023
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CAS
520-33-2
Created by admin on Sat Dec 16 20:17:54 GMT 2023 , Edited by admin on Sat Dec 16 20:17:54 GMT 2023
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PUBCHEM
72281
Created by admin on Sat Dec 16 20:17:54 GMT 2023 , Edited by admin on Sat Dec 16 20:17:54 GMT 2023
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MERCK INDEX
m5975
Created by admin on Sat Dec 16 20:17:54 GMT 2023 , Edited by admin on Sat Dec 16 20:17:54 GMT 2023
PRIMARY Merck Index