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SML0295

Sigma-Aldrich

Dihydromyricetin

≥98% (HPLC)

Synonym(s):

(2R,3R)-3,5,7-Trihydroxy-2-(3,4,5-trihydroxyphenyl)-2,3-dihydrochromen-4-one, 3,3′,4′,5,5′,7-Hexahydroxyflavanone, Ampelopsin, Ampeloptin, DHM

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About This Item

Empirical Formula (Hill Notation):
C15H12O8
CAS Number:
27200-12-0
Molecular Weight:
320.25
MDL number:
MFCD00189451
UNSPSC Code:
12352200
PubChem Substance ID:
329825302
NACRES:
NA.77

Assay

≥98% (HPLC)

form

powder

storage condition

protect from light

color

white to beige

solubility

DMSO: ≥5 mg/mL (warmed)

storage temp.

−20°C

SMILES string

O=C1C2=C(O)C=C(O)C=C2O[C@H](C3=CC(O)=C(C(O)=C3)O)[C@H]1O

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

InChI key

KJXSIXMJHKAJOD-LSDHHAIUSA-N

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General description

Dihydromyricetin is a major flavonoid present in A. grossedentata.

Application

Dihydromyricetin has been used to study its effect on adipogenesis and glucose uptake in differentiated 3T3-L1 pre-adipocytes. It has also been used to study its antitumor activity against liver cancer cells.

Biochem/physiol Actions

Dihydromyricetin (Ampelopsin) is a flavanonol with antioxidant and anti-cancer activity, found to have anti-alcohol intoxication effects. Its anti-alcohol effects appear to be by its actions as a positive modulator of GABA-A receptors at the benzodiazepine site.
Dihydromyricetin possesses anti-inflammatory action.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Scott A Snyder et al.
Nature, 474(7352), 461-466 (2011-06-24)
Although much attention has been devoted to resveratrol, a unique polyphenol produced by plants and credited as potentially being responsible for the 'French paradox'--the observation that French people have a relatively low incidence of coronary heart disease, even though their
Jun Zhou et al.
Journal of separation science, 34(2), 160-168 (2011-01-20)
A simple, rapid and specific method based on cloud-point extraction (CPE) was developed to determine ampelopsin in rat plasma after oral administration by reversed-phase high-performance liquid chromatography. The non-ionic surfactant Genapol X-080 was chosen as the extract solvent. Some important
Li-Ping Ruan et al.
Journal of pharmaceutical and biomedical analysis, 38(3), 457-464 (2005-06-01)
The aim of this study was to increase the solubility of ampelopsin (AMP) in water by two systems: solid dispersions with polyethylene glycol 6000 (PEG 6000) or polyvinylpyrrolidone K-30 (PVP K30) and inclusion complexes with beta-cyclodextrin (BCD) and hydroxypropyl-beta-cyclodextrin (HPBCD).
Baolai Zhang et al.
Anti-cancer drugs, 23(6), 590-596 (2012-01-14)
The aim of this study was to establish xenograft models of tumor in mice bladder and evaluate the antitumor efficacy of ampelopsin sodium (Amp-Na). A total of 2×10 human bladder carcinoma EJ cells and murine sarcoma 180 cells were instilled
Jiantao Ye et al.
Planta medica, 74(3), 252-257 (2008-02-27)
Human immunodeficiency virus (HIV) infection can result in oxidative stress through production of reactive oxygen species (ROS). Simultaneously, oxidative stress is able to activate the replication of virus and lead to the apoptosis of T lymphocytes which is the defense
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