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Record Information
Version1.0
Created at2007-01-22 09:25:30 UTC
Updated at2021-08-19 20:22:30 UTC
NP-MRD IDNP0000035
Secondary Accession NumbersNone
Natural Product Identification
Common NameHesperetin
DescriptionHesperetin, also known as prestwick_908 or YSO2, belongs to the class of organic compounds known as 4'-o-methylated flavonoids. These are flavonoids with methoxy groups attached to the C4' atom of the flavonoid backbone. Thus, hesperetin is considered to be a flavonoid lipid molecule. Hesperetin also seems to upregulate the LDL receptor. Hesperetin, in the form of its glycoside , is the predominant flavonoid in lemons and oranges. Hesperetin is a drug which is used for lowering cholesterol and, possibly, otherwise favorably affecting lipids. In vitro research also suggests the possibility that hesperetin might have some anticancer effects and that it might have some anti-aromatase activity. Hesperetin is a very hydrophobic molecule, practically insoluble in water, and relatively neutral. Hesperetin is a bitter tasting compound. Hesperetin is found, on average, in the highest concentration within a few different foods, such as limes, persian limes, and sweet oranges and in a lower concentration in pummelo, welsh onions, and lemons. Hesperetin has also been detected, but not quantified, in several different foods, such as yellow bell peppers, carrots, rapinis, hazelnuts, and beers. Hesperetin is a biomarker for the consumption of citrus fruits. 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.
Structure
Thumb
Synonyms
ValueSource
(-)-(S)-HesperetinChEBI
(-)-HesperetinChEBI
(2S)-HesperetinChEBI
(S)-2,3-Dihydro-5,7-dihydroxy-2-(3-hydroxy-4-methoxyphenyl)-4H-1-benzopyran-4-oneChEBI
3',5,7-Trihydroxy-4'-methoxyflavanoneChEBI
5,7, 3'-Trihydroxy-4'-methoxyflavanoneHMDB
5,7,3'-Trihydroxy-4'-methoxyflavanoneHMDB
Cyanidanon 4'-methyl ether 1626HMDB
HesperinHMDB
HesperitinHMDB
Prestwick_908HMDB
YSO2HMDB
Chemical FormulaC16H14O6
Average Mass302.2788 Da
Monoisotopic Mass302.07904 Da
IUPAC Name(2S)-5,7-dihydroxy-2-(3-hydroxy-4-methoxyphenyl)-3,4-dihydro-2H-1-benzopyran-4-one
Traditional Namehesperetin
CAS Registry Number520-33-2
SMILES
COC1=C(O)C=C(C=C1)[C@@H]1CC(=O)C2=C(O)C=C(O)C=C2O1
InChI Identifier
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
InChI KeyAIONOLUJZLIMTK-AWEZNQCLSA-N
Spectra
Spectrum TypeDescriptionDepositor IDDeposition DateView
1D NMR1H NMR Spectrum (1D, 400 MHz, DMSO-d6, experimental)Wishart Lab2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 50.23 MHz, DMSO-d6, experimental)Wishart Lab2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, Pyridine-d5, simulated)Wishart Lab2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 150 MHz, Pyridine-d5, simulated)Wishart Lab2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 50 MHz, Pyridine-d5, simulated)Wishart Lab2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 250 MHz, Pyridine-d5, simulated)Wishart Lab2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 175 MHz, Pyridine-d5, simulated)Wishart Lab2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 75 MHz, Pyridine-d5, simulated)Wishart Lab2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 100 MHz, Pyridine-d5, simulated)Wishart Lab2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 225 MHz, Pyridine-d5, simulated)Wishart Lab2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 200 MHz, Pyridine-d5, simulated)Wishart Lab2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 125 MHz, Pyridine-d5, simulated)Wishart Lab2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 25 MHz, Pyridine-d5, simulated)Wishart Lab2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, Pyridine-d5, simulated)Wishart Lab2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, Pyridine-d5, simulated)Wishart Lab2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, Pyridine-d5, simulated)Wishart Lab2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, Pyridine-d5, simulated)Wishart Lab2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, Pyridine-d5, simulated)Wishart Lab2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, Pyridine-d5, simulated)Wishart Lab2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, Pyridine-d5, simulated)Wishart Lab2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, Pyridine-d5, simulated)Wishart Lab2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, Pyridine-d5, simulated)Wishart Lab2021-06-20View Spectrum
Species
Species of Origin
Species NameSourceReference
Anthurium spp.KNApSAcK Database
Brickellia vernicosaKNApSAcK Database
Citrus aurantium L. var. amaraKNApSAcK Database
Citrus spp.KNApSAcK Database
Dalbergia parvifloraKNApSAcK Database
Isatis indigoticaKNApSAcK Database
Medicago sativaKNApSAcK Database
Mentha aquatica L.KNApSAcK Database
Mentha spp.KNApSAcK Database
Prunus persicaKNApSAcK Database
Rhaponticum carthamoidesKNApSAcK Database
Rosmarinus officinalisKNApSAcK Database
Salvia officinalisKNApSAcK Database
Taxus fuanaKNApSAcK Database
Taxus yunnanensisKNApSAcK Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as 4'-o-methylated flavonoids. These are flavonoids with methoxy groups attached to the C4' atom of the flavonoid backbone.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassFlavonoids
Sub ClassO-methylated flavonoids
Direct Parent4'-O-methylated flavonoids
Alternative ParentsNot Available
SubstituentsNot Available
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point227.5 °CNot Available
Boiling Point586.00 to 587.00 °C. @ 760.00 mm HgThe Good Scents Company Information System
Water Solubility272.5 mg/L @ 25 °C (est)The Good Scents Company Information System
LogP2.60PERRISSOUD,D & TESTA,B (1986)
Predicted Properties
PropertyValueSource
Water Solubility0.14 g/LALOGPS
logP2.52ALOGPS
logP2.68ChemAxon
logS-3.3ALOGPS
pKa (Strongest Acidic)7.86ChemAxon
pKa (Strongest Basic)-4.6ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area96.22 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity77.75 m³·mol⁻¹ChemAxon
Polarizability29.3 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
External Links
HMDB IDHMDB0005782
DrugBank IDDB01094
Phenol Explorer Compound ID203
FoodDB IDFDB002677
KNApSAcK IDC00000968
Chemspider ID65234
KEGG Compound IDC01709
BioCyc IDCPD-7072
BiGG IDNot Available
Wikipedia LinkHesperetin
METLIN IDNot Available
PubChem Compound72281
PDB IDNot Available
ChEBI ID28230
Good Scents IDrw1594741
References
General References
  1. Cho J: Antioxidant and neuroprotective effects of hesperidin and its aglycone hesperetin. Arch Pharm Res. 2006 Aug;29(8):699-706. doi: 10.1007/BF02968255. [PubMed:16964766 ]
  2. Nalini N, Aranganathan S, Kabalimurthy J: Chemopreventive efficacy of hesperetin (citrus flavonone) against 1,2-dimethylhydrazine-induced rat colon carcinogenesis. Toxicol Mech Methods. 2012 Jun;22(5):397-408. doi: 10.3109/15376516.2012.673092. Epub 2012 Apr 19. [PubMed:22409373 ]
  3. Srirangam R, Hippalgaonkar K, Avula B, Khan IA, Majumdar S: Evaluation of the intravenous and topical routes for ocular delivery of hesperidin and hesperetin. J Ocul Pharmacol Ther. 2012 Dec;28(6):618-27. doi: 10.1089/jop.2012.0040. Epub 2012 Jul 13. [PubMed:22794525 ]
  4. Aranganathan S, Nalini N: Antiproliferative efficacy of hesperetin (citrus flavanoid) in 1,2-dimethylhydrazine-induced colon cancer. Phytother Res. 2013 Jul;27(7):999-1005. doi: 10.1002/ptr.4826. Epub 2012 Aug 17. [PubMed:22899565 ]
  5. Murata K, Takano S, Masuda M, Iinuma M, Matsuda H: Anti-degranulating activity in rat basophil leukemia RBL-2H3 cells of flavanone glycosides and their aglycones in citrus fruits. J Nat Med. 2013 Jul;67(3):643-6. doi: 10.1007/s11418-012-0699-y. Epub 2012 Aug 18. [PubMed:22903244 ]