dihydroquercetin

flavone, 2,3-dihydro-3,3',4',5,7-pentahydroxy-

CAS: 480-18-2 C15 H12 O7 MW: 304.25504000

Identification

Namedihydroquercetin
IUPAC(2R)-2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-2,3-dihydrochromen-4-one
CAS Number480-18-2
EINECS207-543-4
FDA UNII9SOB9E3987
Molecular FormulaC15 H12 O7
Molecular Weight304.25504000
MDL NumberMFCD00006845
Nikkaji NumberJ727.680J
Beilstein0093548

Regulatory

FDA/DG SANTE Petitions, Reviews, NoticesGRN 826
DG SANTE Food Additivesdihydroquercetin

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)

Cosmetic Information

CosIngcosmetic data
Cosmetic Usesantioxidants

No sensory data available

Safety Information

Oral/Parenteral Toxicityintraperitoneal-mouse LD50 985 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

Categoryantioxidants
Recommendation for dihydroquercetin usage levels up tonot for fragrance use.
Recommendation for dihydroquercetin flavor usage levels up tonot for flavor use.

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Potential Uses

None Found

Natural Occurrence

cherry sour cherry plant oregano leaf tea thyme

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 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.