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dihydromyricetin
ampelopsin

Supplier Sponsors

Name:(2R,3R)-3,5,7-trihydroxy-2-(3,4,5-trihydroxyphenyl)-2,3-dihydrochromen-4-one
CAS Number: 27200-12-0Picture of molecule3D/inchi
FDA UNII: KD8QND6427
Nikkaji Web:J17.065H
Beilstein Number:5303758
MDL:MFCD00189451
XlogP3-AA:1.10 (est)
Molecular Weight:320.25424000
Formula:C15 H12 O8
NMR Predictor:Predict (works with chrome, Edge or firefox)
Category:cosmetic agents
 
US / EU / FDA / JECFA / FEMA / FLAVIS / Scholar / Patent Information:
Google Scholar:Search
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Google Patents:Search
US Patents:Search
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PubMed:Search
NCBI:Search
 
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)
 
Organoleptic Properties:
Odor and/or flavor descriptions from others (if found).
 
Cosmetic Information:
CosIng:cosmetic data
Cosmetic Uses: skin conditioning
 
Suppliers:
Alfa Biotechnology
For experimental / research use only.
Dihydromyricetin 98%
BOC Sciences
For experimental / research use only.
Ampelopsin >98%
Odor: characteristic
Use: Dihydromyricetin (Ampelopsin, Ampeloptin) is a natural antioxidant flavonoid from Ampelopsis grossedentata.
ExtraSynthese
For experimental / research use only.
Dihydromyricetin (HPLC) ≥95%
Shaanxi Y-Herb Biotechnology
Herbal Extract Vine Tea Extract Powder Dihydromyricetin Powder 50% 98% Ampelopsin Myricetin
Sigma-Aldrich: Sigma
For experimental / research use only.
Dihydromyricetin ≥98% (HPLC)
sds
 
Safety Information:
Preferred SDS: View
 
Hazards identification
 
Classification of the substance or mixture
GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)
None found.
GHS Label elements, including precautionary statements
 
Pictogram
 
Hazard statement(s)
None found.
Precautionary statement(s)
None found.
Oral/Parenteral Toxicity:
oral-mouse LD > 5000 mg/kg
Zhongguo Yaoxue Zazhi. Chinese Pharmacuetical Journal. Vol. 31, Pg. 458, 1996.

intraperitoneal-mouse LD50 1410 mg/kg
Zhongguo Yaoxue Zazhi. Chinese Pharmacuetical Journal. Vol. 31, Pg. 458, 1996.

Dermal Toxicity:
Not determined
Inhalation Toxicity:
Not determined
 
Safety in Use Information:
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.
 
Safety References:
EPI System: View
AIDS Citations:Search
Cancer Citations:Search
Toxicology Citations:Search
EPA ACToR:Toxicology Data
EPA Substance Registry Services (SRS):Registry
Laboratory Chemical Safety Summary :161557
National Institute of Allergy and Infectious Diseases:Data
WGK Germany:3
(2R,3R)-3,5,7-trihydroxy-2-(3,4,5-trihydroxyphenyl)-2,3-dihydrochromen-4-one
Chemidplus:0027200120
 
References:
 (2R,3R)-3,5,7-trihydroxy-2-(3,4,5-trihydroxyphenyl)-2,3-dihydrochromen-4-one
NIST Chemistry WebBook:Search Inchi
Pubchem (cid):161557
Pubchem (sid):135117278
 
Other Information:
(IUPAC):Atomic Weights of the Elements 2011 (pdf)
Videos:The Periodic Table of Videos
tgsc:Atomic Weights use for this web site
(IUPAC):Periodic Table of the Elements
CHEBI:View
CHEMBL:View
Golm Metabolome Database:Search
KEGG (GenomeNet):C02906
HMDB (The Human Metabolome Database):Search
FooDB:FDB002791
VCF-Online:VCF Volatile Compounds in Food
ChemSpider:View
Wikipedia:View
 
Potential Blenders and core components note
None Found
 
Potential Uses:
None Found
 
Occurrence (nature, food, other):note
 ampelosis grossedentata
Search Trop Picture
 jambul flower
Search Trop Picture
 
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
 

Articles:

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.
 
Notes:
hepatoprotective agent; isolated from hovenia dulcis. Isol. from flowers of Eugenia jambolana (jambolan)
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