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Merck
CN

SML0295

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
NACRES:
NA.77
PubChem Substance ID:
329825302
UNSPSC Code:
12352200
MDL number:
MFCD00189451

Key Documents

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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

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 key

KJXSIXMJHKAJOD-LSDHHAIUSA-N

assay

≥98% (HPLC)

form

powder

storage condition

protect from light

color

white to beige

solubility

DMSO: ≥5 mg/mL (warmed)

storage temp.

−20°C

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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 (Ampelopsin) is a flavanonol with antioxidant and anti-cancer activity.
Dihydromyricetin possesses anti-inflammatory action.

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

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Certificates of Analysis (COA)

Lot/Batch Number
0000044747
0000044839
0000029333
0000029402
0000026040

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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)
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
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
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
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
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