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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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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
Wei-Ming Zhou et al.
Molecules (Basel, Switzerland), 15(4), 2114-2123 (2010-04-30)
This study reports two novel 5-fluorouracil-substituted ampelopsin derivatives. The structures of two new derivatives were characterized by elemental analysis, 1H-NMR, 13C-NMR, IR and MS. Their anticancer activities in vitro against two cancer cell lines, K562 and K562/ADR, were investigated using
Shimei Qi et al.
International immunopharmacology, 12(1), 278-287 (2011-12-24)
Ampelopsin (AMP), a plant flavonoid, has potent anti-inflammatory properties in vitro and in vivo. The molecular mechanisms of ampelopsin on pharmacological and biochemical actions of RAW264.7 macrophages in inflammation have not been clearly elucidated yet. In the present study, non-cytotoxic
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