diadzein 7-O-glucoside

CAS: 552-66-9 C21 H20 O9 MW: 416.38320000

Identification

Namedaidzin
CAS Number552-66-9
FDA UNII4R2X91A5M5
Molecular FormulaC21 H20 O9
Molecular Weight416.38320000
MDL NumberMFCD00017466
Nikkaji NumberJ22.589D
Beilstein0059741

Regulatory

Physical Properties

Assay 95.00 to 100.00
Food Chemicals Codex Listed No
Boiling Point 727.56 °C. @ 760.00 mm Hg (est)
Flash Point 500.00 °F. TCC ( 259.80 °C. ) (est)
logP (o/w) 0.369 (est)
Soluble in water, 3198 mg/L @ 25 °C (est)

No sensory data available

Safety Information

Preferred SDSView
Oral/Parenteral Toxicityintraperitoneal-mouse LD50 > 2000 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

Categorynatural substances and extractives
Recommendation for daidzin usage levels up tonot for fragrance use.
Recommendation for daidzin flavor usage levels up tonot for flavor use.

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Potential Uses

None Found

Natural Occurrence

alfalfa bean mung bean kudzu root soybean cotyledon soybean embryo soybean hypocotyl soybean seed soybean seed coat soybean shoot soybean testa

Synonyms

daidzoside diadzein 7-O-glucoside 3-(4- hydroxyphenyl)-7-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxychromen-4-one PubMed: β-Glucosidase activity and bioconversion of isoflavones during fermentation of soymilk. PubMed: Malonylglucoside conjugates of isoflavones are much less bioavailable compared with unconjugated β-glucosidic forms in rats. PubMed: A diet formula of Puerariae radix, Lycium barbarum, Crataegus pinnatifida, and Polygonati rhizoma alleviates insulin resistance and hepatic steatosis in CD-1 mice and HepG2 cells. PubMed: Isoflavones profiling of soybean [Glycine max (L.) Merrill] germplasms and their correlations with metabolic pathways. PubMed: Isoflavone intake inhibits the development of 7,12-dimethylbenz(a)anthracene(DMBA)-induced mammary tumors in normal and ovariectomized rats. PubMed: 7,3',4'-Trihydroxyisoflavone Ameliorates the Development of Dermatophagoides farinae-Induced Atopic Dermatitis in NC/Nga Mice. PubMed: Chemical compounds related to nutraceutical and industrial qualities of non-transgenic soybean genotypes. PubMed: Inhibitory effects of a major soy isoflavone, genistein, on human DNA topoisomerase II activity and cancer cell proliferation. PubMed: Rapid magnetic solid-phase extraction for the selective determination of isoflavones in soymilk using baicalin-functionalized magnetic nanoparticles. PubMed: Enrichment of two isoflavone aglycones in black soymilk by using spent coffee grounds as an immobiliser for β-glucosidase. PubMed: TPGS emulsified zein nanoparticles enhanced oral bioavailability of daidzin: in vitro characteristics and in vivo performance. PubMed: Determination of the variations in levels of phenolic compounds in soybean (Glycine max Merr.) sprouts infected by anthracnose (Colletotrichum gloeosporioides). PubMed: A comparative analysis of the photo-protective effects of soy isoflavones in their aglycone and glucoside forms. PubMed: Enrichment of two isoflavone aglycones in black soymilk by immobilized β-glucosidase on solid carriers. PubMed: A modified QuEChERS method as sample treatment before the determination of isoflavones in foods by ultra-performance liquid chromatography-triple quadrupole mass spectrometry. PubMed: Antioxidant and Antityrosinase Activity of Flemingia macrophylla and Glycine tomentella Roots. PubMed: Fast simultaneous determination of free and conjugated isoflavones in soy milk by UHPLC-UV. PubMed: Apoptotic effects of cooked and in vitro digested soy on human prostate cancer cells. PubMed: Distribution of isoflavones and coumestrol in neglected tropical and subtropical legumes. PubMed: Bactericidal activity of soymilk fermentation broth by in vitro and animal models. PubMed: Hydrolysis of isoflavone glycosides by a thermostable β-glucosidase from Pyrococcus furiosus. PubMed: Effect of Lactobacillus sporogenes on oral isoflavones bioavailability: single dose pharmacokinetic study in menopausal women. PubMed: Modification of isoflavone profiles in a fermented soy food with almond powder. PubMed: Kudzu (Pueraria lobata) vine ethanol extracts improve ovariectomy-induced bone loss in female mice. PubMed: NTP-CERHR expert panel report on the developmental toxicity of soy infant formula. PubMed: Characterization of a GH3 family β-glucosidase from Dictyoglomus turgidum and its application to the hydrolysis of isoflavone glycosides in spent coffee grounds. PubMed: Lactobacillus rhamnosus JCM 2771: impact on metabolism of isoflavonoids in the fecal flora from a male equol producer. PubMed: Comparison of three thermostable β-glucosidases for application in the hydrolysis of soybean isoflavone glycosides. PubMed: Optimizing time and temperature of enzymatic conversion of isoflavone glucosides to aglycones in soy germ flour. PubMed: Effects of chitooligosaccharide lactate salt on activity of acetaldehyde dehydrogenase. PubMed: Yeast α-glucosidase inhibition by isoflavones from plants of Leguminosae as an in vitro alternative to acarbose. PubMed: Influence of natural coagulants on isoflavones and antioxidant activity of tofu. PubMed: Evaluation of quality of Radix Puerariae herbal medicine by isoflavonoids. PubMed: Formation of succinyl genistin and succinyl daidzin by Bacillus species. PubMed: Differential effects of whole soy extract and soy isoflavones on apoptosis in prostate cancer cells. PubMed: Characterization of fermented black soybean natto inoculated with Bacillus natto during fermentation. PubMed: Comprehensive profiling of isoflavones, phytosterols, tocopherols, minerals, crude protein, lipid, and sugar during soybean (Glycine max) germination. PubMed: Semipurified fractions from the submerged-culture broth of Agaricus blazei Murill reduce blood glucose levels in streptozotocin-induced diabetic rats. PubMed: 1H NMR fingerprinting of soybean extracts, with emphasis on identification and quantification of isoflavones. PubMed: Comparison of Puerariae Radix and its hydrolysate on stimulation of hyaluronic acid production in NHEK cells. PubMed: Effects of dietary ingredients on function and expression of P-glycoprotein in human intestinal epithelial cells. PubMed: Chromatographic quantification of isoflavone content from soy derivates using HPLC technique. PubMed: Glycosylation of dietary flavonoids decreases the affinities for plasma protein. PubMed: Hypolipidemic effects of Monascus-fermented soybean extracts in rats fed a high-fat and -cholesterol diet. PubMed: Identification of a naturally-occurring 8-[alpha-D-glucopyranosyl-(1-->6)-beta-D-glucopyranosyl]daidzein from cultivated kudzu root. PubMed: Effect of glycosidation of isoflavones on their bioavailability and pharmacokinetics in aged male rats. PubMed: Comparison of hormonal activity of isoflavone-containing supplements used to treat menopausal complaints. PubMed: Nanonized black soybean enhances immune response in senescence-accelerated mice. PubMed: Stability of isoflavone isomers in steamed black soybeans and black soybean koji stored under different conditions. PubMed: Effects of riboflavin photosensitization on the changes of isoflavones in soymilk. PubMed: Characterization of phenolic substances and antioxidant properties of food soybeans grown in the North Dakota-Minnesota region. PubMed: Isolation of radiolabeled isoflavones from kudzu (Pueraria lobata) root cultures. PubMed: Isoflavonoid composition of a callus culture of the relict tree Maackia amurensis Rupr. et Maxim. PubMed: Biomolecules and nutritional quality of soymilk fermented with probiotic yeast and bacteria. PubMed: Hydrolysis of isoflavone glucosides in soymilk fermented with single or mixed cultures of Lactobacillus paraplantarum KM, Weissella sp. 33, and Enterococcus faecium 35 isolated from humans. PubMed: Characterization of a thermostable extracellular beta-glucosidase with activities of exoglucanase and transglycosylation from Paecilomyces thermophila. PubMed: Cloning, expression, and characterization of two beta-glucosidases from isoflavone glycoside-hydrolyzing Bacillus subtilis natto. PubMed: Conversion of isoflavone glucosides to aglycones in soymilk by fermentation with lactic acid bacteria. PubMed: Comparison of isoflavone concentrations in soybean (Glycine max (L.) Merrill) sprouts grown under two different light conditions. PubMed: Solvent effects on extraction and HPLC analysis of soybean isoflavones and variations of isoflavone compositions as affected by crop season. PubMed: Anti-obesity activities of fermented soygerm isoflavones by Bifidobacterium breve. PubMed: Bioavailability of soy isoflavones in rats Part I: application of accurate methodology for studying the effects of gender and source of isoflavones. PubMed: Review of the factors affecting bioavailability of soy isoflavones in humans. PubMed: Phytoestrogens levels determination in the cord blood from Malaysia rural and urban populations. PubMed: Biotransformation of common bean (Phaseolus vulgaris L.) flavonoid glycosides by bifidobacterium species from human intestinal origin. PubMed: Kinetic modeling of malonylgenistin and malonyldaidzin conversions under alkaline conditions and elevated temperatures. PubMed: Isoflavone phytoestrogen degradation in fermented soymilk with selected beta-glucosidase producing L. acidophilus strains during storage at different temperatures. PubMed: Enhanced estrogenic responses and sensitivity to azoxymethane following dietary soy isoflavone supplementation in older female rats. PubMed: Isolation of an isoflavone-metabolizing, Clostridium-like bacterium, strain TM-40, from human faeces. PubMed: Heat and pH effects on the conjugated forms of genistin and daidzin isoflavones. PubMed: An accurate and reproducible method for the quantitative analysis of isoflavones and their metabolites in rat plasma using liquid chromatography/mass spectrometry combined with photodiode array detection. PubMed: Influence of the application of three different elicitors on soybean plants on the concentrations of several isoflavones in soybean seeds. PubMed: Isoflavonoids are present in Arabidopsis thaliana despite the absence of any homologue to known isoflavonoid synthases. PubMed: Prevalence of daidzein-metabolizing phenotypes differs between Caucasian and Korean American women and girls. PubMed: Distribution profiles of isoflavone isomers in black bean kojis prepared with various filamentous fungi. PubMed: Isoflavone levels in five soybean (Glycine max) genotypes are altered by phytochrome-mediated light treatments. PubMed: Suppression of arachidonic acid metabolism and nitric oxide formation by kudzu isoflavones in murine macrophages. PubMed: Contrasting effects of puerarin and daidzin on glucose homeostasis in mice. PubMed: Supercritical fluid extraction of isoflavones from biological samples with ultra-fast high-performance liquid chromatography/mass spectrometry. PubMed: Evaluation of isoflavone aglycon and glycoside distribution in soy plants and soybeans by fast column high-performance liquid chromatography coupled with a diode-array detector. PubMed: Human gut microbial degradation of flavonoids: structure-function relationships. PubMed: Pharmacokinetics of a slow-release formulation of soybean isoflavones in healthy postmenopausal women. PubMed: Effects of purified puerarin on voluntary alcohol intake and alcohol withdrawal symptoms in P rats receiving free access to water and alcohol. PubMed: Kudzu root extract suppresses voluntary alcohol intake and alcohol withdrawal symptoms in P rats receiving free access to water and alcohol. PubMed: Rapid yeast estrogen bioassays stably expressing human estrogen receptors alpha and beta, and green fluorescent protein: a comparison of different compounds with both receptor types. PubMed: Enhancement of tofu isoflavone recovery by pretreatment of soy milk with koji enzyme extract. PubMed: Biotechnological production of highly soluble daidzein glycosides using Thermotoga maritima maltosyltransferase. PubMed: Effect of water-to-bean ratio on the contents and compositions of isoflavones in tofu. PubMed: Purification and characterization of an isoflavone-conjugates-hydrolyzing beta-glucosidase from endophytic bacterium. PubMed: Simultaneous determination of isoflavones and bisphenol A in rat serum by high-performance liquid chromatography coupled with coulometric array detection. PubMed: Fermented grain products, production, properties and benefits to health. PubMed: Anti-dipsotropic isoflavones: the potential therapeutic agents for alcohol dependence. PubMed: Plant derivatives in the treatment of alcohol dependency. PubMed: Profiling and quantification of isoflavonoids in kudzu dietary supplements by high-performance liquid chromatography and electrospray ionization tandem mass spectrometry. PubMed: The effect of oestrogen and dietary phyto-oestrogens on transepithelial calcium transport in human intestinal-like Caco-2 cells. PubMed: Evaluation of the estrogenic effects of legume extracts containing phytoestrogens. PubMed: Hydrolysis by lactase phlorizin hydrolase is the first step in the uptake of daidzein glucosides by rat small intestine in vitro. PubMed: [Comparison of soyasaponin and isoflavone contents between genetically modified (GM) and non-GM soybeans]. PubMed: Determination of isoflavones in ready-to-feed soy-based infant formula. PubMed: Determination of daidzein and genistein in soybean foods by automated on-line in-tube solid-phase microextraction coupled to high-performance liquid chromatography. PubMed: Isoflavone, glyphosate, and aminomethylphosphonic acid levels in seeds of glyphosate-treated, glyphosate-resistant soybean. PubMed: Composition, red blood cell uptake, and serum protein binding of phytoestrogens extracted from commercial kudzu-root and soy preparations. PubMed: Stabilities of daidzin, glycitin, genistin, and generation of derivatives during heating. PubMed: Inhibitory effects of isoflavones on nitric oxide- or peroxynitrite-mediated DNA damage in RAW 264.7 cells and phiX174 DNA. PubMed: Daidzein and genistein content of cereals. PubMed: Phytoestrogen-low diet for endocrine disruptor studies. PubMed: Isoflavone aglycon and glucoconjugate content of high- and low-soy U.K. foods used in nutritional studies. PubMed: Inhibitory effect of isoflavones on peroxynitrite-mediated low-density lipoprotein oxidation. PubMed: Determination of isoflavones in soy and selected foods containing soy by extraction, saponification, and liquid chromatography: collaborative study. PubMed: Indigenous mucuna tempe as functional food. PubMed: Isoflavone transformation during soybean koji preparation and subsequent miso fermentation supplemented with ethanol and NaCl. PubMed: Preparative separation of isoflavone components in soybeans using high-speed counter-current chromatography. PubMed: Changes in the profile of genistein, daidzein, and their conjugates during thermal processing of tofu. PubMed: MALDI-TOF MS analysis of isoflavones in soy products. PubMed: Daidzein and genistein contents of vegetables. PubMed: Retention and changes of soy isoflavones and carotenoids in immature soybean seeds (Edamame) during processing. PubMed: Daidzein and genistein content of fruits and nuts. PubMed: Determination of the levels of isoflavonoids in soybeans and soy-derived foods and estimation of isoflavonoids in the Japanese daily intake. PubMed: Soybean meal fermented by Aspergillus awamori increases the cytochrome P-450 content of the liver microsomes of mice. PubMed: Antioxidant action and potential antidiabetic properties of an isoflavonoid-containing soyabean phytochemical extract (SPE). PubMed: Phenolics: blocking agents for heterocyclic amine-induced carcinogenesis. PubMed: Antimutagenic activity of chemical fractions isolated from a commercial soybean processing by-product. PubMed: Daidzein and genistein but not their glucosides are absorbed from the rat stomach. PubMed: Isoflavone-mediated inhibition of tyrosine kinase: a novel antiinflammatory approach. PubMed: Effects of isoflavones on alcohol pharmacokinetics and alcohol-drinking behavior in rats. PubMed: Soy isoflavone analysis: quality control and a new internal standard. PubMed: Extraction and quantification of daidzein and genistein in food. PubMed: Analysis of phytoestrogens and polyphenols in plasma, tissue, and urine using HPLC with coulometric array detection. PubMed: Daidzin decreases ethanol consumption in rats. PubMed: Isoflavonoid compounds extracted from Pueraria lobata suppress alcohol preference in a pharmacogenetic rat model of alcoholism. PubMed: Therapeutic lessons from traditional Oriental medicine to contemporary Occidental pharmacology. PubMed: Daidzin and daidzein suppress free-choice ethanol intake by Syrian golden hamsters. PubMed: Oestrogenic potency of genistin and daidzin in mice. PubMed: Oestrogenic response of the CD-1 mouse to the soya-bean isoflavones genistein, genistin and daidzin.