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SML0295

Sigma-Aldrich

Dihydromyricetin

≥98% (HPLC)

Synonyme(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

Formule empirique (notation de Hill):
C15H12O8
Numéro CAS:
27200-12-0
Poids moléculaire :
320.25
Numéro MDL:
MFCD00189451
Code UNSPSC :
12352200
ID de substance PubChem :
329825302
Nomenclature NACRES :
NA.77

Pureté

≥98% (HPLC)

Forme

powder

Conditions de stockage

protect from light

Couleur

white to beige

Solubilité

DMSO: ≥5 mg/mL (warmed)

Température de stockage

−20°C

Chaîne SMILES 

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

Clé InChI

KJXSIXMJHKAJOD-LSDHHAIUSA-N

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Description générale

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.

Actions biochimiques/physiologiques

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.

Code de la classe de stockage

11 - Combustible Solids

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable

Certificats d'analyse (COA)

Recherchez un Certificats d'analyse (COA) en saisissant le numéro de lot du produit. Les numéros de lot figurent sur l'étiquette du produit après les mots "Lot" ou "Batch".

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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
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)
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
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
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