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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, Ampelopsin, DHM, 3,3′,4′,5,5′,7-Hexahydroxyflavanone, Ampeloptin
Empirical Formula (Hill Notation):
C15H12O8
CAS Number:
Molecular Weight:
320.25
MDL number:
PubChem Substance ID:
NACRES:
NA.77

Quality Level

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[C@@H]1[C@H](Oc2cc(O)cc(O)c2C1=O)c3cc(O)c(O)c(O)c3

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.

Packaging

5, 25 mg in glass bottle

Biochem/physiol Actions

Dihydromyricetin possesses anti-inflammatory action.
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.

Certificate of Analysis

Certificate of Origin

Feng Ni et al.
PloS one, 7(6), e38802-e38802 (2012-06-14)
The objective of this study was to evaluate the chemopreventive effect of a novel flavonoid, ampelopsin (AMP) on the growth and metastasis of prostate cancer cells. AMP showed the more potent activity in inhibiting the proliferation of androgen-sensitive LNCaP and...
Dihydromyricetin promotes hepatocellular carcinoma regression via a p53 activation-dependent mechanism
Zhang Q, et al.
Scientific Reports, 4, 4628-4628 (2014)
Yanjun Shi et al.
Spectrochimica acta. Part A, Molecular and biomolecular spectroscopy, 87, 251-257 (2011-12-20)
The interaction between bovine serum albumin (BSA) and the anticancer drug molecule ampelopsin (AMP) was investigated using fluorescence spectroscopy, circular dichroism (CD) spectra, and time-resolved spectra under simulated physiological conditions. Fluorescence data showed that the intrinsic fluorescence of BSA was...
Tiange Cai et al.
Biological & pharmaceutical bulletin, 34(9), 1501-1507 (2011-09-02)
Stilbenes are a class of compounds that has been reported to inhibit a variety of pathological processes during inflammatory reactions. In this study, cis-ampelopsin E, a stilbene isolated from the seeds of Paeonia suffruticosa, was shown to dose-dependently reduce the...
Dihydromyricetin enhances glucose uptake by inhibition of MEK/ERK pathway and consequent down-regulation of phosphorylation of PPARgamma in 3T3-L1 cells
Liu L, et al.
Journal of Cellular and Molecular Medicine, 22(2), 1247-1256 (2018)

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