dihydromyricetin
ampelopsin
Identification
| Name | dihydromyricetin |
| IUPAC | (2R,3R)-3,5,7-trihydroxy-2-(3,4,5-trihydroxyphenyl)-2,3-dihydrochromen-4-one |
| CAS Number | 27200-12-0 |
| FDA UNII | KD8QND6427 |
| Molecular Formula | C15 H12 O8 |
| Molecular Weight | 320.25424000 |
| MDL Number | MFCD00189451 |
| Nikkaji Number | J17.065H |
| Beilstein | 5303758 |
Regulatory
Physical Properties
| Assay | 95.00 to 100.00 |
| Food Chemicals Codex Listed | No |
| Boiling Point | 780.70 °C. @ 760.00 mm Hg (est) |
| Flash Point | 566.00 °F. TCC ( 296.70 °C. ) (est) |
| logP (o/w) | 1.230 (est) |
| Soluble in | water, 4.004e+004 mg/L @ 25 °C (est) |
Cosmetic Information
| CosIng | cosmetic data |
| Cosmetic Uses | skin conditioning |
No sensory data available
Safety Information
| Preferred SDS | View |
| Oral/Parenteral Toxicity | oral-mouse LD > 5000 mg/kg |
| Dermal Toxicity | Not determined |
| Inhalation Toxicity | Not determined |
GHS Classification
['GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)', 'GHS Label elements, including precautionary statements']
Safety in Use
| Category | cosmetic agents |
| Recommendation for dihydromyricetin usage levels up to | not for fragrance use. |
| Recommendation for dihydromyricetin flavor usage levels up to | not for flavor use. |
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Potential Uses
Natural Occurrence
Synonyms
ampelopsin
ampeloptin
4H-1-
benzopyran-4-one, 2,3-dihydro-3,5,7-trihydroxy-2-(3,4,5-trihydroxyphenyl)-, (2R-trans)-
4H-1-
benzopyran-4-one, 2,3-dihydro-3,5,7-trihydroxy-2-(3,4,5-trihydroxyphenyl)-, (2R,3R)-
(2R-trans)-2,3-
dihydro-3,5,7-trihydroxy-2-(3,4,5-trihydroxyphenyl)-4H-1-benzopyran-4-one
(2R,3R)-2,3-
dihydro-3,5,7-trihydroxy-2-(3,4,5-trihydroxyphenyl)-4H-1-benzopyran-4-one
dihydromyricitin
flavanone, 3,3',4',5,5',7-hexahydroxy-
(2R,3R)-3,3',4',5,5',7-
hexahydroxy-2,3-dihydroflavanonol
3,3',4',5,5',7-
hexahydroxy-2,3-dihydroflavanonol
(2R,3R)-3,5,7,3',4',5'-
hexahydroxyflavanone
3,3',4',5,5',7-
hexahydroxyflavanone
(2R,3R)-3,5,7-
trihydroxy-2-(3,4,5-trihydroxyphenyl)-2,3-dihydro-4H-chromen-4-one
(2R,3R)-3,5,7-
trihydroxy-2-(3,4,5-trihydroxyphenyl)-2,3-dihydrochromen-4-one
PubMed:
A reduction in reactive oxygen species contributes to dihydromyricetin-induced apoptosis in human hepatocellular carcinoma cells.
PubMed:
Dihydromyricetin induces mouse hepatoma Hepalâ6 cell apoptosis via the transforming growth factorâβ pathway.
PubMed:
Isolation of dihydroflavonol 4-reductase cDNA clones from Angelonia x angustifolia and heterologous expression as GST fusion protein in Escherichia coli.
PubMed:
Dihydromyricetin prevents cardiotoxicity and enhances anticancer activity induced by adriamycin.
PubMed:
Dihydromyricetin induces apoptosis and inhibits proliferation in hepatocellular carcinoma cells.
PubMed:
A potent antibrowning agent from pine needles of Cedrus deodara: 2R,3R-dihydromyricetin.
PubMed:
Dihydromyricetin inhibits migration and invasion of hepatoma cells through regulation of MMP-9 expression.
PubMed:
Alcohol use disorders and current pharmacological therapies: the role of GABA(A) receptors.
PubMed:
Antioxidant activities and phytochemicals of leaf extracts from 10 native rhododendron species in taiwan.
PubMed:
Dihydromyricetin activates AMP-activated protein kinase and P38(MAPK) exerting antitumor potential in osteosarcoma.
PubMed:
Recrystallization of Dihydromyricetin from Ampelopsis grossedentata and Its Anti-Oxidant Activity Evaluation.
PubMed:
Dihydromyricetin induces cell cycle arrest and apoptosis in melanoma SK-MEL-28 cells.
PubMed:
Dihydromyricetin ameliorates behavioral deficits and reverses neuropathology of transgenic mouse models of Alzheimer's disease.
PubMed:
Dihydromyricetin promotes hepatocellular carcinoma regression via a p53 activation-dependent mechanism.
PubMed:
Inhibition of catechol-o-methyltransferase (COMT) by myricetin, dihydromyricetin, and myricitrin.
PubMed:
Dihydromyricetin prevents fetal alcohol exposure-induced behavioral and physiological deficits: the roles of GABAA receptors in adolescence.
PubMed:
Dihydromyricetin Improves Physical Performance under Simulated High Altitude.
PubMed:
Dihydromyricetin induces autophagy in HepG2 cells involved in inhibition of mTOR and regulating its upstream pathways.
PubMed:
Efficient conversion of myricetin from Ampelopsis grossedentata extracts and its purification by MIP-SPE.
PubMed:
Dihydromyricetin reduced Bcl-2 expression via p53 in human hepatoma HepG2 cells.
PubMed:
Dihydromyricetin suppresses the proliferation of hepatocellular carcinoma cells by inducing G2/M arrest through the Chk1/Chk2/Cdc25C pathway.
PubMed:
Interaction of dihydromyricetin and alpha-amylase.
PubMed:
Simultaneous determination of dihydromyricetin and resveratrol in Ampelopsis sinica (Miq.) W.T. Wang by high-performance liquid chromatography coupled with a diode array detection method.
PubMed:
Isolation and functional analysis of a homolog of flavonoid 3',5'-hydroxylase gene from Pericallis à hybrida.
PubMed:
[Effects of dihydromyricetin on tumor necrosis factor and NF-kappaB p65 of RAU rats].
PubMed:
Empirical, thermodynamic and quantum-chemical investigations of inclusion complexation between flavanones and (2-hydroxypropyl)-cyclodextrins.
PubMed:
Binding of dihydromyricetin to human hemoglobin: fluorescence and circular dichroism studies.
PubMed:
Probing the interaction of anti-cancer agent dihydromyricetin with human serum albumin: a typical method study.
PubMed:
Dihydromyricetin as a novel anti-alcohol intoxication medication.
PubMed:
Electrochemical detection of dihydromyricetin using a DNA immobilized ethylenediamine/polyglutamic modified electrode.
PubMed:
Molecular characterization and expression analysis of dihydroflavonol 4-reductase (DFR) gene in Saussurea medusa.
PubMed:
Identification of bioactive compounds from jambolão (Syzygium cumini) and antioxidant capacity evaluation in different pH conditions.
PubMed:
[Effect of serum containing tengcha total flavonoid and dihydromyricetin on proliferation and apoptosis of HepG2 cells].
PubMed:
Phytotoxic activity of flavonoids from Dicranostyles ampla.
PubMed:
New galloylated flavanonols from the Australian plant Glochidion sumatranum.
PubMed:
A new lignan dimer from Mallotus philippensis.
PubMed:
Phytochemical characterization of Rhododendron ferrugineum and in vitro assessment of an aqueous extract on cell toxicity.
PubMed:
Distribution and biosynthesis of flavan-3-ols in Camellia sinensis seedlings and expression of genes encoding biosynthetic enzymes.
PubMed:
Excision of an active CACTA-like transposable element from DFR2 causes variegated flowers in soybean [Glycine max (L.) Merr.].
PubMed:
[Studies on the chemical constituents of Xanthoceras sorbifolia].
PubMed:
Elderberry flavonoids bind to and prevent H1N1 infection in vitro.
PubMed:
Comparison of refluxing, ultrasonic- and microwave-assisted extraction of dihydromyricetin from Ampelopsis grossedentata.
PubMed:
Structure-activity relationship of flavonoids active against lard oil oxidation based on quantum chemical analysis.
PubMed:
Antioxidant phenolic compounds from the leaves of Erica Arborea (Ericaceae).
PubMed:
Cytotoxic constituents from the bark of Salix hulteni.
PubMed:
Simultaneous determination and pharmacokinetic studies of dihydromyricetin and myricetin in rat plasma by HPLC-DAD after oral administration of Ampelopsis grossedentata decoction.
PubMed:
Isolation and identification of metabolites from dihydromyricetin.
PubMed:
Simultaneous determination of homoeriodictyol-7-O-beta-D-Glccopyranoside and its metabolite homoeriodictyol in rat tissues and urine by liquid chromatography-mass spectrometry.
PubMed:
[Studies on the effect of dihydromyricetin on antilipid-peroxidation].
PubMed:
Analysis of polyphenolic antioxidants from the fruits of three pouteria species by selected ion monitoring liquid chromatography-mass spectrometry.
PubMed:
Antioxidation properties and mechanism of action of dihydromyricetin from Ampelopsis grossedentata.
PubMed:
Bioactive novel polyphenols from the fruit of Manilkara zapota (Sapodilla).
PubMed:
[Determination of total flavonoids and dihydromyricetin in Ampelopsis grossedentala (Hand-Mazz) W. T. Wang].
PubMed:
A flavonol O-methyltransferase from Catharanthus roseus performing two sequential methylations.
PubMed:
Polyphenols from the heartwood of Cercidiphyllum japonicum and their effects on proliferation of mouse hair epithelial cells.
PubMed:
Purification of (+)-dihydromyricetin from leaves extract of Ampelopsis grossedentata using high-speed countercurrent chromatograph with scale-up triple columns.
PubMed:
High-flavonol tomatoes resulting from the heterologous expression of the maize transcription factor genes LC and C1.
PubMed:
[Study on flavonoids in seeds of Hovenia dulcis].
PubMed:
Enzymatic conversion of dihydroflavonols to flavan-3,4-diols using flower extracts of Dianthus caryophyllus L. (carnation).
PubMed:
Purification and characterization of (+)dihydroflavonol (3-hydroxyflavanone) 4-reductase from flowers of Dahlia variabilis.
PubMed:
Enzymatic reduction of (+)-dihydroflavonols to flavan-3,4-cis-diols with flower extracts from Matthiola incana and its role in anthocyanin biosynthesis.
PubMed:
Flavan-3-ol Biosynthesis : The Conversion of (+)-Dihydromyricetin to Its Flavan-3,4-Diol (Leucodelphinidin) and to (+)-Gallocatechin by Reductases Extracted from Tissue Cultures of Ginkgo biloba and Pseudotsuga menziesii.
PubMed:
Genetic control of the conversion of dihydroflavonols into flavonols and anthocyanins in flowers of Petunia hybrida.
PubMed:
Modification of the B-ring during flavonoid synthesis in Petunia hybrida: Effect of the hydroxylation gene Hf1 on dihydroflavonol intermediates.