CAS 27200-12-0|Dihydromyricetin(Ampeloptin)|Ampelopsin|(+)-dihydromyricetin|Ampeloptin|(2R,3R)-3,5,7-trihydroxy-2-(3,4,5-trihydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-4-one|(+)-Ampelopsin|Dihydromyr...

General Information

Structure

Molecular Formula

C₁₅H₁₂O₈

Molecular Mass

320.25098

Exact Mass

320.05321734

Charge

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

Canonic Smiles

Oc1cc2O[C@H](c3cc(O)c(c(c3)O)O)[C@H](C(=O)c2c(c1)O)O

Isomeric Smiles

c1(cc(c2c(c1)O[C@@H]([C@H](C2=O)O)c1cc(c(c(c1)O)O)O)O)O

Calculated Properties

JChem

LogD (pH = 7.4)

1.34

LogD (pH = 5.5)

1.51

Log P

1.51

Rotatable Bonds

H Donor

H Acceptors

Lipinski's Rule of Five

false

Acid pKa

7.72

Polar Surface Area

147.68

Polarizability

29.21

Molar Refractivity

76.59

LOG S

-1.85

Data Source

Commercial Catalog

Academic Data

Data Source

Names and Identifiers

Synonyms

Dihydromyricetin(Ampeloptin)AmpelopsinAmpeloptin(+)-AmpelopsinDihydromyricetinDihydromyricetinAmpelopsin3,3',4',5,5',7-Hexahydroxyflavanone(+)-Ampelopsin(2R,3R)-2,3-dihydro-3,5,7-trihydroxy-2-(3,4,5-trihydroxyphenyl)-4H-1-benzopyran-4-one(2R,3R)-3,5,7,3',4',5'-hexahydroxyflavanoneAmpeloptin(2R,3R)-3,3',4',5,5',7-hexahydroxy-2,3-dihydroflavanonolDihydromyricetinAmpelopsin(+)-dihydromyricetin(+)-Dihydromyricetin(2R,3R)-dihydromyricetin(2S,3S)-3,5,7,3',4',5'-hexahydroxyflavanone(-)-dihydromyricetin

IUPAC Traditional name

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

IUPAC name

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

Names and Identifiers

Registration numbers

CAS Number

27200-12-0

PubChem CID

16155712306070

PubChem SID

1620379392669738146530698

UniProt Database

Q9XHG2Q96418Q96330P48419Q96581O04395P48418Q8GSN1P37120O04773O04790Q41452Q9ZWQ9Q07512Q9M547

PubMed Citation Links

128891192269364917059013

Rhea Database

RHEA:61108RHEA:61116RHEA:61140

Beilstein Number

530375843312566612734

IntAct Database

EBI-25766913

BindingDB Database

212434

BKMS React Database

56437740097499

Golm Database

aa464780-f734-45bf-82b2-d6be8eeb93ef3c3ab1a4-1f13-4fb8-8ca7-1cc26972f4f6

BRENDA Database

3.4.21.51.1.1.2192.1.1.61.17.1.31.14.14.812.1.1.2671.14.20.63.5.1.882.7.11.313.5.2.2

KEGG ID

C02906

SureChEMBL Database

SCHEMBL723736SCHEMBL134531

KNApSAcK Database

C00000938

MetaCyc Database

CPD-7087

BRENDA Ligand Database

74009749956437

CHEBI ID

CHEBI:21CHEBI:28429CHEBI:18447CHEBI:48027

Reaxys Registry

Wikipedia Title

CHEMBL

SABIO-RK Database

CompTox Database

ACToR Database

Registration numbers

Properties

Safety Information

Storage Condition

-20°C

Pharmacology Properties

Mechanism of Action

Antioxidant

Product Information

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

Purity

98.0

Physical Property

Apperance

Powder

Properties

Related Proteins

No Data Available

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Molecular Spectra

No Data Available

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Molecule 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]

ChEBI

CHEBI:28429

An optically active form of dihydromyricetin having (2R,3R)-configuration.

CHEBI:48027

The (2S,3S)-stereoisomer of dihydromyricetin.

Molecule Details

References

PubChem Literature

From Data Sources

• Liu et al. European Food Research and Technology. 2009, 230(2):325-331

• Kho, K.F.F. et al., Pharm. Weekbl., 1979, 114, 325

References