dihydromyricetin

ampelopsin

CAS: 27200-12-0 C15 H12 O8 MW: 320.25424000

Identification

Namedihydromyricetin
IUPAC(2R,3R)-3,5,7-trihydroxy-2-(3,4,5-trihydroxyphenyl)-2,3-dihydrochromen-4-one
CAS Number27200-12-0
FDA UNIIKD8QND6427
Molecular FormulaC15 H12 O8
Molecular Weight320.25424000
MDL NumberMFCD00189451
Nikkaji NumberJ17.065H
Beilstein5303758

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

CosIngcosmetic data
Cosmetic Usesskin conditioning

No sensory data available

Safety Information

Preferred SDSView
Oral/Parenteral Toxicityoral-mouse LD > 5000 mg/kg
Dermal ToxicityNot determined
Inhalation ToxicityNot determined

GHS Classification

['GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)', 'GHS Label elements, including precautionary statements']

Safety in Use

Categorycosmetic agents
Recommendation for dihydromyricetin usage levels up tonot for fragrance use.
Recommendation for dihydromyricetin flavor usage levels up tonot for flavor use.

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Potential Uses

None Found

Natural Occurrence

ampelosis grossedentata jambul flower

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 Hepal‑6 cell apoptosis via the transforming growth factor‑β 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 × 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.