dihydroquercetin
flavone, 2,3-dihydro-3,3',4',5,7-pentahydroxy-
 
Notes:
a key intermediate between flavonols and flavanolignins.
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(2R)-2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-2,3-dihydrochromen-4-one (Click)
CAS Number: 480-18-2Picture of molecule
Other: 17654-26-1
ECHA EINECS - REACH Pre-Reg: 207-543-4
FDA UNII: 9SOB9E3987
Nikkaji Web: J727.680J
Beilstein Number: 0093548
MDL: MFCD00006845
XlogP3-AA: 1.50 (est)
Molecular Weight: 304.25504000
Formula: C15 H12 O7
BioActivity Summary: listing
NMR Predictor: Predict (works with chrome or firefox)
Category: antioxidants
 
US / EU / FDA / JECFA / FEMA / FLAVIS / Scholar / Patent Information:
Google Scholar: Search
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PubMed: Search
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DG SANTE Food Additives: dihydroquercetin
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Physical Properties:
Assay: 95.00 to 100.00 % 
Food Chemicals Codex Listed: No
Boiling Point: 687.60 °C. @ 760.00 mm Hg (est)
Flash Point: 508.00 °F. TCC ( 264.20 °C. ) (est)
logP (o/w): 0.950
Soluble in:
 water, 2.203e+004 mg/L @ 25 °C (est)
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Organoleptic Properties:
 
Odor and/or flavor descriptions from others (if found).
 
 
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Cosmetic Information:
CosIng: cosmetic data
Cosmetic Uses: antioxidants
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Suppliers:
BOC Sciences
For experimental / research use only.
Taxifolin >98%
Odor: characteristic
Use: Taxifolin is a flavonoid in many plants such as Taxus chinensis, Siberian larch, Cedrus deodara and so on. Taxifolin has shown to inhibit the ovarian cancer cell growth in a dose-dependent manner.
P.L. Thomas
Dihydroquercetin
Santa Cruz Biotechnology
For experimental / research use only.
(±)-Taxifolin ≥90%
Sigma-Aldrich
For experimental / research use only.
Dihydroquercetin
analytical standard
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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:
intraperitoneal-mouse LD50  985 mg/kg
Russian Pharmacology and Toxicology Vol. 38, Pg. 213, 1975.

intraperitoneal-rat LD50  1200 mg/kg
Japanese Journal of Pharmacology. Vol. 21, Pg. 377, 1971.

Dermal Toxicity:
Not determined
Inhalation Toxicity:
Not determined
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Safety in Use Information:
Category: antioxidants
Recommendation for dihydroquercetin usage levels up to:
 not for fragrance use.
 
Recommendation for dihydroquercetin flavor usage levels up to:
 not for flavor use.
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Safety References:
European Food Safety Authority (EFSA) reference(s):
Scientific Opinion on taxifolin-rich extract from Dahurian Larch (Larix gmelinii)
View page or View pdf
Statement on the safety of taxifolin-rich extract from Dahurian Larch (Larix gmelinii)
View page or View pdf
EPI System: View
Chemical Carcinogenesis Research Information System: Search
Cancer Citations: Search
Toxicology Citations: Search
Env. Mutagen Info. Center: Search
EPA Substance Registry Services (TSCA): 480-18-2
EPA ACToR: Toxicology Data
EPA Substance Registry Services (SRS): Registry
Laboratory Chemical Safety Summary : 10185
National Institute of Allergy and Infectious Diseases: Data
WGK Germany: 3
 (2R)-2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-2,3-dihydrochromen-4-one
Chemidplus: 0000480182
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References:
 (2R)-2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-2,3-dihydrochromen-4-one
NIST Chemistry WebBook: Search Inchi
Pubchem (cid): 10185
Pubchem (sid): 134974339
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Other Information:
(IUPAC): Atomic Weights of the Elements 2009
(IUPAC): Atomic Weights of the Elements 2009 (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
HMDB (The Human Metabolome Database): Search
FooDB: FDB002749
VCF-Online: VCF Volatile Compounds in Food
ChemSpider: View
Wikipedia: View
RSC Learn Chemistry: View
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Potential Blenders and core components note
 
None Found
 
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Potential Uses:
None Found
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Occurrence (nature, food, other): note
 cherry sour cherry plant
Search Trop  Picture
 oregano leaf
Search Trop  Picture
 tea
Search Trop  Picture
 thyme
Search Trop  Picture
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Synonyms:
4H-1-benzopyran-4-one, 2-(3,4-dihydroxyphenyl)-2,3-dihydro-3,5,7-trihydroxy-
4H-1-benzopyran-4-one, 2-(3,4-dihydroxyphenyl)-2,3-dihydro-3,5,7-trihydroxy-, (2R,3R)-
4H-1-benzopyran-4-one, 2-(3,4-dihydroxyphenyl)-2,3-dihydro-3,5,7-trihydroxy-, (2R)-
(2R,3R)-dihydroquercetin
(2R-trans)-2-(3,4-dihydroxyphenyl)-2,3-dihydro-3,5,7-trihydroxy-4-benzopyrone
(2R)-2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-2,3-dihydro-4H-chromen-4-one
(2R)-2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-2,3-dihydrochromen-4-one
 flavanone, 3,3',4',5,7-pentahydroxy-
 flavone, 2,3-dihydro-3,3',4',5,7-pentahydroxy-
3,3',4',5,7-pentahydroxyflavanone
 quercetin, dihydro-
 taxifolin
 taxifoliol
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Articles:
PubMed: Phenolic Composition of Vinegars over an Accelerated Aging Process Using Different Wood Species (Acacia, Cherry, Chestnut, and Oak): Effect of Wood Toasting.
PubMed: Metmyoglobin reduction by polyphenols and mechanism of the conversion of metmyoglobin to oxymyoglobin by quercetin.
PubMed: New highly in vitro antioxidative 3,8″-linked Biflav(an)ones and Flavanone-C-glycosides from Garcinia buchananii stem bark.
PubMed: Taxifolin prevents diabetic cardiomyopathy in vivo and in vitro by inhibition of oxidative stress and cell apoptosis.
PubMed: In vitro study on the antioxidant activity of a polyphenol-rich extract from Pinus brutia bark and its fractions.
PubMed: Profiling polyphenols of two diploid strawberry (Fragaria vesca) inbred lines using UHPLC-HRMS(n.).
PubMed: Phenolic profile, antioxidant activity and palynological analysis of stingless bee honey from Amazonas, Northern Brazil.
PubMed: Enzyme-assisted extraction of cactus bioactive molecules under high hydrostatic pressure.
PubMed: Site-specific inhibitory mechanism for amyloid β42 aggregation by catechol-type flavonoids targeting the Lys residues.
PubMed: Structure-activity relationship for (+)-taxifolin isolated from silymarin as an inhibitor of amyloid β aggregation.
PubMed: Dihydroquercetin (DHQ) induced HO-1 and NQO1 expression against oxidative stress through the Nrf2-dependent antioxidant pathway.
PubMed: Structure selective complexation of cyclodextrins with five polyphenols investigated by capillary electrokinetic chromatography.
PubMed: Quantification of flavonoids in black rice by liquid chromatography-negative electrospray ionization tandem mass spectrometry.
PubMed: Production, composition and toxicology studies of Enzogenol® Pinus radiata bark extract.
PubMed: Picea mariana bark: a new source of trans-resveratrol and other bioactive polyphenols.
PubMed: The influence of flavonoids on the binding of pantoprazole to bovine serum albumin by spectroscopic methods: with the viewpoint of food/drug interference.
PubMed: Flavonoid deactivation of excited state flavins: reaction monitoring by mass spectrometry.
PubMed: Chemical composition of currant seed extracts and their protective effect on human lymphocytes DNA.
PubMed: Cloning, characterization, and activity analysis of a flavonol synthase gene FtFLS1 and its association with flavonoid content in tartary buckwheat.
PubMed: Chemical interaction between polyphenols and a cysteinyl thiol under radical oxidation conditions.
PubMed: A theoretical study on cellular antioxidant activity of selected flavonoids.
PubMed: Chemical constituents comparison between Rhizoma Smilacis Glabrae and Rhizoma Smilacis Chinae by HPLC-DAD-MS/MS.
PubMed: Development of HPLC fingerprint for species differentiation and quality assessment of Rhizoma Smilacis Glabrae.
PubMed: Structural and quantitative analysis of antioxidant and low-density lipoprotein-antioxidant flavonoids from the grains of sugary rice.
PubMed: New anthocyanidin and anthocyanin pigments from blue plumbago.
PubMed: Isolation and structure elucidation of highly antioxidative 3,8″-linked biflavanones and flavanone-C-glycosides from Garcinia buchananii bark.
PubMed: Investigation of flavonoids bearing different substituents on ring C and their cu2+ complex binding with bovine serum albumin: structure-affinity relationship aspects.
PubMed: Phenolic tyrosinase inhibitors from the stems of Cudrania cochinchinensis.
PubMed: Investigation on the interaction between ilaprazole and bovine serum albumin without or with different C-ring flavonoids from the viewpoint of food-drug interference.
PubMed: Structure and function of the oxidation products of polyphenols and identification of potent lipoxygenase inhibitors from Fe-catalyzed oxidation of resveratrol.
PubMed: Phenolic composition of Malbec grape skins and seeds from Valle de Uco (Mendoza, Argentina) during ripening. Effect of cluster thinning.
PubMed: Pharmacology in health foods: improvement of vascular endothelial function by French maritime pine bark extract (Flavangenol).
PubMed: Flavonoid Glycosides from the Seeds of Litchi chinensis.
PubMed: Stability of Pycnogenol® as an ingredient in fruit juices subjected to in vitro gastrointestinal digestion.
PubMed: Development of capillary electrophoresis fingerprint for quality control of rhizoma Smilacis Glabrae.
PubMed: Characterization of a Vitis vinifera cv. Cabernet Sauvignon 3',5'-O-methyltransferase showing strong preference for anthocyanins and glycosylated flavonols.
PubMed: Depsides and other polar constituents from Origanum dictamnus L. and their in vitro antimicrobial activity in clinical strains.
PubMed: Phenolic compounds in cherry ( Prunus avium ) heartwood with a view to their use in cooperage.
PubMed: Effects of phenolic compounds on the browning of cooked barley.
PubMed: Chromatographic fingerprint analysis of Pycnogenol dietary supplements.
PubMed: Permeation of astilbin and taxifolin in Caco-2 cell and their effects on the P-gp.
PubMed: HPLC-DAD-ESI-MS/MS analysis and antioxidant activities of nonanthocyanin phenolics in mulberry (Morus alba L.).
PubMed: Differential effects of dietary flavonoids on reactive oxygen and nitrogen species generation and changes in antioxidant enzyme expression induced by proinflammatory cytokines in Chang Liver cells.
PubMed: Onions: a source of unique dietary flavonoids.
PubMed: Identification and quantification of flavonoids of Mexican oregano (Lippia graveolens) by LC-DAD-ESI/MS analysis.
PubMed: Kinetic model for the antiradical activity of the isolated p-catechol group in flavanone type structures using the free stable radical 2,2-diphenyl-1-picrylhydrazyl as the antiradical probe.
PubMed: Effects of various plant polyphenols on bladder carcinogen benzidine-induced mutagenicity.
PubMed: Small branches of olive tree: a source of biophenols complementary to olive leaves.
PubMed: Static-dynamic superheated liquid extraction of hydroxytyrosol and other biophenols from alperujo (a semisolid residue of the olive oil industry).
PubMed: HPLC-tandem mass spectrometric method to characterize resveratrol metabolism in humans.
PubMed: Novel transgenic rice overexpressing anthocyanidin synthase accumulates a mixture of flavonoids leading to an increased antioxidant potential.
PubMed: Phytochemical and nutrient composition of the freeze-dried amazonian palm berry, Euterpe oleraceae mart. (acai).
PubMed: An in vitro and in silico study on the flavonoid-mediated modulation of the transport of 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine (PhIP) through Caco-2 monolayers.
PubMed: Newly constructed stable reporter cell lines for mechanistic studies on electrophile-responsive element-mediated gene expression reveal a role for flavonoid planarity.
PubMed: Isolation and structure elucidation of phenolic antioxidants from Tamarind (Tamarindus indica L.) seeds and pericarp.
PubMed: Effects of structure on radical-scavenging abilities and antioxidative activities of tea polyphenols: NMR analytical approach using 1,1-diphenyl-2-picrylhydrazyl radicals.
PubMed: Antispasmodic saponins from bulbs of red onion, Allium cepa L. var. Tropea.
PubMed: Induction of cancer cell apoptosis by flavonoids is associated with their ability to inhibit fatty acid synthase activity.
PubMed: Effects of silymarin, a natural hepatoprotector, in periparturient dairy cows.
PubMed: Kinetic study of flavonoid reactions with stable radicals.
PubMed: Effect of flavonoids on feeding preference and development of the crucifer pest Mamestra configurata Walker.
PubMed: Structural requirements for the flavonoid-mediated modulation of glutathione S-transferase P1-1 and GS-X pump activity in MCF7 breast cancer cells.
PubMed: Antioxidant activity of knotwood extractives and phenolic compounds of selected tree species.
PubMed: Inhibitory effects of plant-derived flavonoids and phenolic acids on malonaldehyde formation from ethyl arachidonate.
PubMed: Inactivation of creatine kinase induced by quercetin with horseradish peroxidase and hydrogen peroxide. pro-oxidative and anti-oxidative actions of quercetin.
PubMed: Study of low molecular weight phenolic compounds during the aging of sparkling wines manufactured with red and white grape varieties.
PubMed: Pigmentation in the developing seed coat and seedling leaves of Brassica carinata is controlled at the dihydroflavonol reductase locus.
PubMed: Kinetic and stoichiometric assessment of the antioxidant activity of flavonoids by electron spin resonance spectroscopy.
PubMed: Structure-dependent phytotoxicity of catechins and other flavonoids: flavonoid conversions by cell-free protein extracts of Centaurea maculosa (spotted knapweed) roots.
PubMed: Isolation and characterization of novel benzoates, cinnamates, flavonoids, and lignans from Riesling wine and screening for antioxidant activity.
PubMed: Phenolic composition of grape stems.
PubMed: Regeneration of phenolic antioxidants from phenoxyl radicals: an ESR and electrochemical study of antioxidant hierarchy.
PubMed: Food constituents attenuate monoamine oxidase activity and peroxide levels in C6 astrocyte cells.
PubMed: In vitro attenuation of nitric oxide production in C6 astrocyte cell culture by various dietary compounds.
PubMed: In vitro biotransformation of flavonoids by rat liver microsomes.
PubMed: The flavonols quercetin, rutin and morin in DNA solution: UV-vis dichroic (and mid-infrared) analysis explain the possible association between the biopolymer and a nucleophilic vegetable-dye.
PubMed: [Dihydroquercetin--a new antioxidant and biologically active food additive].
PubMed: [Natural flavonoids as dietary antioxidants and biologically active additives].
PubMed: Suppression of active oxygen-induced cytotoxicity by flavonoids.
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