(2R,3R)-3,5,7-trihydroxy-2-(3,4,5-trihydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-4-one

• ChemBase ID: 73019
• Molecular Formular: C15H12O8
• Molecular Mass: 320.25098
• Monoisotopic Mass: 320.05321734
• SMILES: c1(cc(c2c(c1)O[C@@H]([C@H](C2=O)O)c1cc(c(c(c1)O)O)O)O)O
• Canonical SMILES: Oc1cc2O[C@H](c3cc(O)c(c(c3)O)O)[C@H](C(=O)c2c(c1)O)O
• InChI: InChI=1S/C15H12O8/c16-6-3-7(17)11-10(4-6)23-15(14(22)13(11)21)5-1-8(18)12(20)9(19)2-5/h1-4,14-20,22H/t14-,15+/m0/s1
• InChIKey: KJXSIXMJHKAJOD-LSDHHAIUSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R,3R)-3,5,7-trihydroxy-2-(3,4,5-trihydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-4-one
• IUPAC Traditional name: (+)-dihydromyricetin; (2R,3R)-3,5,7-trihydroxy-2-(3,4,5-trihydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-4-one
• Synonyms: Ampeloptin; Ampelopsin; (+)-Ampelopsin; Dihydromyricetin(Ampeloptin); Dihydromyricetin; Dihydromyricetin; 3,3',4',5,5',7-Hexahydroxyflavanone; Ampelopsin

Database IDs

• CAS Number: 27200-12-0
• PubChem SID: 162037939
• PubChem CID: 161557

CALCULATED PROPERTIES

• Acid pKa: 7.722177
• H Acceptors: 8
• H Donor: 6
• LogD (pH = 5.5): 1.5102407
• LogD (pH = 7.4): 1.3389813
• Log P: 1.5128189
• Molar Refractivity: 76.5898 cm^3
• Polarizability: 29.281664 Å^3
• Polar Surface Area: 147.68 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Apperance: Powder

Safety Information

• Storage Condition: -20°C

Pharmacology Properties

• Mechanism of Action: Antioxidant

Product Information

• Purity: 98.0
• Biological Source: Isol. from Indisia bijuga, Soymida febrifuga, Rhododendron spp., flowers of Eugenia jambolana, Leptarrhena pyrofolia, Mahonia siamensis, Rhamnus pallasii, Cedrus deodara, Heuchera villosa, Adenanthera, Ampelopsis, Cercidiphyllum and Pinus spp.
• Application(s): Antioxidant

DETAILS

Selleck Chemicals - S2399

Research Area: Metabolic Disease
Biological Activity:
Dihydromyricetin (Ampelopsin (flavanol); Ampeloptin) is a natural antioxidant with good prospects. The physicochemical properties of dihydromyricetin (Ampelopsin (flavanol); Ampeloptin) were analyzed by ultraviolet–visible spectrometry, infrared spectrometry, scanning electron microscopy, differential scanning calorimetry, X-ray diffractometry. The result showed that dihydromyricetin (Ampelopsin (flavanol); Ampeloptin) and lecithin in the complex were combined by non-covalent bond, did not form a new compound and the solubility of dihydromyricetin in n-octanol was significantly enhanced. It was found that the dihydromyricetin–lecithin complex was an effective scavenger of DPPH radicals with an IC50 of 22.60 μg/mL. In the Rancimat antioxidant test using lard oil as substrate, the performance of the complex with protection factor of 6.67 was superior to that of butylated hydroxytoluene with protection factor of 5.54. [1]

REFERENCES

• Liu et al. European Food Research and Technology. 2009, 230(2):325-331
• Kho, K.F.F. et al., Pharm. Weekbl., 1979, 114, 325