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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=CC=C(C=C1O)[C@@H]2CC(=O)C3=C(O)C=C(O)C=C3O2

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

Molecular Formula C16H14O6
Molecular Weight 302.2788
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 1 / 1
E/Z Centers 0
Optical Activity UNSPECIFIED

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
Prediction of estrogen receptor agonists and characterization of associated molecular descriptors by statistical learning methods.
2006-11
Activity and mRNA levels of enzymes involved in hepatic fatty acid oxidation in mice fed citrus flavonoids.
2006-05
Inhibition of rat vas deferens contractions by flavonoids in-vitro.
2006-03
Different anticonvulsive effects of hesperidin and its aglycone hesperetin on electrical activity in the rat hippocampus in-vitro.
2006-03
Influence of cation adduction on the separation characteristics of flavonoid diglycoside isomers using dual gate-ion mobility-quadrupole ion trap mass spectrometry.
2006-03
Evaluation of the anti-allergic activity of Citrus unshiu using rat basophilic leukemia RBL-2H3 cells as well as basophils of patients with seasonal allergic rhinitis to pollen.
2006-03
The bioavailability of polyphenols is highly governed by the capacity of the intestine and of the liver to secrete conjugated metabolites.
2006-03
Capillary electrochromatography of biologically relevant flavonoids.
2006-02
The reaction of flavanols with nitrous acid protects against N-nitrosamine formation and leads to the formation of nitroso derivatives which inhibit cancer cell growth.
2006-01-15
Antiradical and anti-H2O2 properties of polyphenolic compounds from an aqueous peppermint extract.
2006-01-13
Characterization of flavonoids and pectins from bergamot (Citrus bergamia Risso) peel, a major byproduct of essential oil extraction.
2006-01-11
Polyphenol levels in human urine after intake of six different polyphenol-rich beverages.
2005-10
Anti-SARS coronavirus 3C-like protease effects of Isatis indigotica root and plant-derived phenolic compounds.
2005-10
Interactive effects of polyphenols, tocopherol and ascorbic acid on the Cu2+-mediated oxidative modification of human low density lipoproteins.
2005-10
The inclusion complexes of hesperetin and its 7-rhamnoglucoside with (2-hydroxypropyl)-beta-cyclodextrin.
2005-09-15
Determination of active components in rosemary by capillary electrophoresis with electrochemical detection.
2005-09-15
Modulatory effects of plant phenols on human multidrug-resistance proteins 1, 4 and 5 (ABCC1, 4 and 5).
2005-09
Kinetics of radical-scavenging activity of hesperetin and hesperidin and their inhibitory activity on COX-2 expression.
2005-08-17
Xanthine oxidase activity in vitro: effects of food extracts and components.
2005-08-10
Oral flavonoids delay recovery from experimental autoimmune encephalomyelitis in SJL mice.
2005-07-15
Interaction between hesperetin and human serum albumin revealed by spectroscopic methods.
2005-06-20
Impact of high pressure and pulsed electric fields on bioactive compounds and antioxidant activity of orange juice in comparison with traditional thermal processing.
2005-06-01
High-performance liquid chromatographic separation and chiroptical properties of the enantiomers of naringenin and other flavanones.
2005-05-27
Differential inhibition of oxidized LDL-induced apoptosis in human endothelial cells treated with different flavonoids.
2005-05
Protection by food-derived antioxidants from UV-A1-induced photodamage, measured using living skin equivalents.
2005-04-12
(-)Epigallocatechin gallate and quercetin enhance survival signaling in response to oxidant-induced human endothelial apoptosis.
2005-04
Stereospecific high-performance liquid chromatographic analysis of hesperetin in biological matrices.
2005-03-09
Anti-inflammatory effect of heme oxygenase 1: glycosylation and nitric oxide inhibition in macrophages.
2005-02
Passive cutaneous anaphylaxis-inhibitory activity of flavanones from Citrus unshiu and Poncirus trifoliata.
2005-01
Nobiletin, a citrus flavonoid isolated from tangerines, selectively inhibits class A scavenger receptor-mediated metabolism of acetylated LDL by mouse macrophages.
2005-01
Comparative study of the vasorelaxant activity, superoxide-scavenging ability and cyclic nucleotide phosphodiesterase-inhibitory effects of hesperetin and hesperidin.
2004-12
Inhibitory effects of flavonoids on phosphodiesterase isozymes from guinea pig and their structure-activity relationships.
2004-11-15
Identification and quantification of the conjugated metabolites derived from orally administered hesperidin in rat plasma.
2004-10-20
Vasorelaxing effects of flavonoids: investigation on the possible involvement of potassium channels.
2004-10
A validated solid-phase extraction HPLC method for the simultaneous determination of the citrus flavanone aglycones hesperetin and naringenin in urine.
2004-09-21
Reactions of the flavonoid hesperetin with chlorine: a spectroscopic study of the reaction pathways.
2004-09-01
[Interaction between AM fungi and Rhizobium and effects of flavonoids on it].
2004-09
The pig caecum model: a suitable tool to study the intestinal metabolism of flavonoids.
2004-09
High-performance liquid chromatography methods for the analysis of adrenergic amines and flavanones in Citrus aurantium L. var. amara.
2004-08-18
The flavones luteolin and apigenin inhibit in vitro antigen-specific proliferation and interferon-gamma production by murine and human autoimmune T cells.
2004-08-15
Antiallergic activity of hesperidin is activated by intestinal microflora.
2004-08
Evaluation of hesperetin 7-O-lauryl ether as lipid-lowering agent in high-cholesterol-fed rats.
2004-07-01
Hesperetin: a potent antioxidant against peroxynitrite.
2004-07
Combined effects of multiple flavonoids on breast cancer resistance protein (ABCG2)-mediated transport.
2004-07
Determination of hesperetin, cinnamic acid and nicotinic acid in propolis with micellar electrokinetic capillary chromatography.
2004-06
Apple phytochemicals and their health benefits.
2004-05-12
Urinary excretion of flavonoids reflects even small changes in the dietary intake of fruits and vegetables.
2004-05
Effects of some natural flavonoids on retinal function recovery after ischemic insult in the rat.
2004-04
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
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.
Substance Class Chemical
Created
by admin
on Wed Apr 02 18:49:58 GMT 2025
Edited
by admin
on Wed Apr 02 18:49:58 GMT 2025
Record UNII
Q9Q3D557F1
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
HESPERETIN
FHFI   INCI   MI  
INCI  
Official Name English
FEMA NO. 4313
Preferred 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
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
5,7,3'-TRIHYDROXY-4'-METHOXYFLAVANONE
Systematic Name English
Code System Code Type Description
DRUG BANK
DB01094
Created by admin on Wed Apr 02 18:49:58 GMT 2025 , Edited by admin on Wed Apr 02 18:49:58 GMT 2025
PRIMARY
EPA CompTox
DTXSID4022319
Created by admin on Wed Apr 02 18:49:58 GMT 2025 , Edited by admin on Wed Apr 02 18:49:58 GMT 2025
PRIMARY
DAILYMED
Q9Q3D557F1
Created by admin on Wed Apr 02 18:49:58 GMT 2025 , Edited by admin on Wed Apr 02 18:49:58 GMT 2025
PRIMARY
JECFA MONOGRAPH
2002
Created by admin on Wed Apr 02 18:49:58 GMT 2025 , Edited by admin on Wed Apr 02 18:49:58 GMT 2025
PRIMARY
NSC
57654
Created by admin on Wed Apr 02 18:49:58 GMT 2025 , Edited by admin on Wed Apr 02 18:49:58 GMT 2025
PRIMARY
DRUG CENTRAL
1362
Created by admin on Wed Apr 02 18:49:58 GMT 2025 , Edited by admin on Wed Apr 02 18:49:58 GMT 2025
PRIMARY
FDA UNII
Q9Q3D557F1
Created by admin on Wed Apr 02 18:49:58 GMT 2025 , Edited by admin on Wed Apr 02 18:49:58 GMT 2025
PRIMARY
WIKIPEDIA
HESPERETIN
Created by admin on Wed Apr 02 18:49:58 GMT 2025 , Edited by admin on Wed Apr 02 18:49:58 GMT 2025
PRIMARY
ECHA (EC/EINECS)
208-290-2
Created by admin on Wed Apr 02 18:49:58 GMT 2025 , Edited by admin on Wed Apr 02 18:49:58 GMT 2025
PRIMARY
RXCUI
1314255
Created by admin on Wed Apr 02 18:49:58 GMT 2025 , Edited by admin on Wed Apr 02 18:49:58 GMT 2025
PRIMARY RxNorm
CHEBI
28230
Created by admin on Wed Apr 02 18:49:58 GMT 2025 , Edited by admin on Wed Apr 02 18:49:58 GMT 2025
PRIMARY
NCI_THESAURUS
C68461
Created by admin on Wed Apr 02 18:49:58 GMT 2025 , Edited by admin on Wed Apr 02 18:49:58 GMT 2025
PRIMARY
CAS
520-33-2
Created by admin on Wed Apr 02 18:49:58 GMT 2025 , Edited by admin on Wed Apr 02 18:49:58 GMT 2025
PRIMARY
PUBCHEM
72281
Created by admin on Wed Apr 02 18:49:58 GMT 2025 , Edited by admin on Wed Apr 02 18:49:58 GMT 2025
PRIMARY
MERCK INDEX
m5975
Created by admin on Wed Apr 02 18:49:58 GMT 2025 , Edited by admin on Wed Apr 02 18:49:58 GMT 2025
PRIMARY Merck Index