(2S)-5,7-dihydroxy-2-(3-hydroxy-4-methoxyphenyl)-3,4-dihydro-2H-1-benzopyran-4-one

• ChemBase ID: 965
• Molecular Formular: C16H14O6
• Molecular Mass: 302.27876
• Monoisotopic Mass: 302.07903817
• SMILES: O1[C@@H](CC(=O)c2c1cc(O)cc2O)c1cc(O)c(OC)cc1
• Canonical SMILES: COc1ccc(cc1O)[C@@H]1CC(=O)c2c(O1)cc(cc2O)O
• InChI: 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
• InChIKey: AIONOLUJZLIMTK-AWEZNQCLSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-5,7-dihydroxy-2-(3-hydroxy-4-methoxyphenyl)-3,4-dihydro-2H-1-benzopyran-4-one
• IUPAC Traditional name: hesperetin
• Brand Name: Hesperin
• Synonyms: Hesperetin; 4'-Methoxy-3',5,7-trihydroxyflavanone; 3',5,7-Trihydroxy-4'-methoxyflavanone; Cyanidanon 4'-Methyl Ether 1626; Hesperitin; YSO2; Hesperetin; Hesperetin; 4'-甲氧基-3,5,7-三羟基黄烷酮

Database IDs

• CAS Number: 520-33-2
• EC Number: 208-290-2
• MDL Number: MFCD00075646
• Beilstein Number: 309850
• Merck Index: 144670
• PubChem SID: 46507998; 160964428
• PubChem CID: 72281
• CHEBI ID: 28230
• CHEMBL: 399121
• Chemspider ID: 65234
• DrugBank ID: DB01094
• KEGG ID: C01709
• Unique Ingredient Identifier: Q9Q3D557F1
• Wikipedia Title: Hesperetin

CALCULATED PROPERTIES

JChem

• Acid pKa: 7.8617015
• H Acceptors: 6
• H Donor: 3
• LogD (pH = 5.5): 2.675566
• LogD (pH = 7.4): 2.5483763
• Log P: 2.6774368
• Molar Refractivity: 77.753 cm^3
• Polarizability: 29.8365 Å^3
• Polar Surface Area: 96.22 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 2.52
• LOG S: -3.34
• Solubility (Water): 1.38e-01 g/l

PROPERTIES

Physical Property

• Solubility: 273 mg/L; Sol. EtOH, alkalis
• Apperance: Powder
• Melting Point: 226–228 °C; 227-232°C
• Hydrophobicity(logP): 1.1

Safety Information

• Storage Condition: -20°C
• European Hazard Symbols: Irritant (Xi)
• Risk Statements: 36/37/38
• Safety Statements: 26-37
• TSCA Listed: 否
• GHS Pictograms: GHS07
• GHS Hazard statements: H315-H319-H335
• GHS Precautionary statements: P261-P305+P351+P338-P302+P352-P321-P405-P501A

Product Information

• Purity: 97%
• Salt Data: Free Base

DETAILS

DrugBank - DB01094

• Drug Groups: approved
• Description: Hesperetin belongs to the flavanone class of flavonoids. Hesperetin, in the form of its glycoside hesperidin, is the predominant flavonoid in lemons and oranges.
• Indication: 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, as well as activity again.
• Pharmacology: 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.
• Affected Organisms: Humans and other mammals
• External Links: Wikipedia; PDRhealth

Selleck Chemicals - S2308

Research Area: Cardiovascular Disease
Biological Activity:
Hesperetin is a bioflavonoid and, to be more specific, a flavanone. Hesperidin (a flavonone glycoside) is water-soluble due to the presence of the sugar part in its structure, so on ingestion it releases its aglycone, i.e, hesperetin. [1] Hesperetin is a citrus flavonoid that has been reported to lower plasma cholesterol. It inhibits histamine release from IgE-challenged RBL-2H3 cells, with a potency comparable to the commercial anti-allergy drug azelastine. It also reduces the transcription of ACAT-2 mRNA in Hep-G2 cells and reduces ApoB protein synthesis in a dose-dependent manner. The EC50 for these responses is approximately 50 μM. [2][3]