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

• ChemBase ID: 110311
• Molecular Formular: C16H14O6
• Molecular Mass: 302.27876
• Monoisotopic Mass: 302.07903817
• SMILES: COc1ccc(cc1O)C1CC(=O)c2c(O1)cc(O)cc2O
• Canonical SMILES: COc1ccc(cc1O)C1CC(=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
• InChIKey: AIONOLUJZLIMTK-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 5,7-dihydroxy-2-(3-hydroxy-4-methoxyphenyl)-3,4-dihydro-2H-1-benzopyran-4-one
• IUPAC Traditional name: hesperetine
• Synonyms: Hesperetin; 5,7-Dihydroxy-2-(3-hydroxy-4-methoxyphenyl)-4-chromanone; 3′,5,7-Trihydroxy-4′-methoxyflavanone; HESPERETIN; (2S)-2,3-Dihydro-5,7-dihydroxy-2-(3-hydroxy-4-methoxyphenyl)-4H-1-benzopyran-4-one; 3',5,7-Trihydroxy-4'-methoxy-flavanone; Eriodictyol 4'-Monomethyl Ether; 4’-Methoxy-3’,5,7-trihydroxyflavanone; NSC 57654; 3′,5,7-三羟基-4-甲氧基黄酮; 橙皮素; (2S)-5,7-二羟基-2-(3-羟基-4-甲氧基苯基)-4-苯并二氢吡喃-4-酮

Database IDs

• CAS Number: 31712-49-9; 69097-99-0; 520-33-2
• MDL Number: MFCD00016956
• PubChem SID: 24895619; 162096399
• PubChem CID: 3593
• FEMA ID: 4313

CALCULATED PROPERTIES

• Acid pKa: 7.916038
• H Acceptors: 6
• H Donor: 3
• LogD (pH = 5.5): 2.6757855
• LogD (pH = 7.4): 2.5623946
• 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

PROPERTIES

Physical Property

• Solubility: Ethanol; Methanol
• Apperance: Beige to Light Brown Solid; light yellow powder
• Melting Point: 226-228°C; 227-232 °C

Safety Information

• Storage Condition: -20°C Freezer
• German water hazard class: 3
• Storage Temperature: 2-8°C

Pharmacology Properties

• Gene Information: human ... CYP1A2(1544)

Product Information

• Purity: ≥95%; 98%
• Empirical Formula (Hill Notation): C16H14O6

DETAILS

MP Biomedicals - 05214516

MP Biomedicals Rare Chemical collection

Sigma Aldrich - W431300

Packaging
1 kg in poly bottle
50 g in poly bottle
5 g in glass bottle

Sigma Aldrich - H4125

Biochem/physiol Actions
具有化学预防作用的膳食黄烷酮。

Toronto Research Chemicals - H289500

The aglucon of Hesperidin (H281185), a flavanone found in citrus fruits.

REFERENCES

• Tsujimoto, M., et al.: Biol. Pharm. Bull., 32, 671 (2009)
• Wang, H., et al.: J. Pharm. Biomed. Anal., 49, 1157 (2009)
• Lee, S,. et al.: Bioorg. Med. Chem. Lett., 19, 2116 (2009)