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glycitein
7,4'-dihydroxy-6-methoxyisoflavone

Supplier Sponsors

CAS Number: 40957-83-3Picture of molecule3D/inchi
FDA UNII: 92M5F28TVF
Nikkaji Web:J17.583H
MDL:MFCD00016679
XlogP3-AA:2.40 (est)
Molecular Weight:284.26764000
Formula:C16 H12 O5
BioActivity Summary:listing
NMR Predictor:Predict (works with chrome, Edge or firefox)
Category:natural substances and extractives
 
US / EU / FDA / JECFA / FEMA / FLAVIS / Scholar / Patent Information:
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Physical Properties:
Assay: 95.00 to 100.00
Food Chemicals Codex Listed: No
Boiling Point: 547.40 °C. @ 760.00 mm Hg (est)
Flash Point: 410.00 °F. TCC ( 210.10 °C. ) (est)
logP (o/w): 2.570 (est)
Soluble in:
 water, 542.1 mg/L @ 25 °C (est)
 
Organoleptic Properties:
Odor and/or flavor descriptions from others (if found).
 
Cosmetic Information:
None found
 
Suppliers:
Alfa Biotechnology
For experimental / research use only.
Glycitein 98%
BOC Sciences
For experimental / research use only.
Glycitein >98%
Carbosynth
For experimental / research use only.
Glycitein
Coompo
For experimental / research use only.
Glycitein from Plants ≥98%
Odor: characteristic
Use: Gycitein has weak estrogenic activity, comparable to that of the other soy isoflavones but much lower than that of DES and 17beta-estradiol. the effects of genistein, daidzein and glycitein on the growth and DNA synthesis of aortic smooth muscle cells (SMC) from stroke-prone spontaneously hypertensive rats (SHRSP). SMC were cultured in dishes and proliferated on 10% dextran-coated charcoal/fetal bovine serum, and then treated with 0.1–30 µmol/L of genistein, daidzein or glycitein to investigate cell proliferation (cell number) and DNA synthesis (cell proliferation ELISA system), respectively. We also studied their effects on platelet-derived growth factor (PDGF)-BB (20 µg/L)–induced SMC proliferation. Soybean isoflavones inhibited proliferation and DNA synthesis of SMC from SHRSP in a concentration-dependent manner. Inhibition was significant at 3 µmol/L of genistein and 10 µmol/L of both daidzein and glycitein. For significant inhibition of PDGF-BB–induced SMC proliferation, concentrations as low as 0.1 µmol/L of each isoflavone were effective. These isoflavones, with their inhibitory effects on natural and PDGF-BB–induced SMC proliferation, may be useful in attenuatating such proliferation, a basic mechanism involved in atherosclerotic vascular change, thereby preventing atherosclerotic cardiovascular diseases.
ExtraSynthese
For experimental / research use only.
Glycitein (HPLC) ≥95%
Nacalai USA
For experimental / research use only.
Glycitein
Santa Cruz Biotechnology
For experimental / research use only.
Glycitein >99%
Sigma-Aldrich: Sigma
For experimental / research use only.
Glycitein ≥97% (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:
Not determined
Dermal Toxicity:
Not determined
Inhalation Toxicity:
Not determined
 
Safety in Use Information:
Category:
natural substances and extractives
Recommendation for glycitein usage levels up to:
 not for fragrance use.
 
Recommendation for glycitein flavor usage levels up to:
 not for flavor use.
 
Safety References:
European Food Safety Authority (EFSA) reference(s):

Preparatory work to support the risk assessment for peri- and postmenopausal women taking food supplements containing isolated isoflavones
View page or View pdf

Risk assessment for peri- and post-menopausal women taking food supplements containing isolated isoflavones
View page or View pdf

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 :5317750
National Institute of Allergy and Infectious Diseases:Data
WGK Germany:3
7-hydroxy-3-(4-hydroxyphenyl)-6-methoxychromen-4-one
Chemidplus:0040957833
 
References:
 7-hydroxy-3-(4-hydroxyphenyl)-6-methoxychromen-4-one
NIST Chemistry WebBook:Search Inchi
Pubchem (cid):5317750
Pubchem (sid):135049088
 
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
KEGG (GenomeNet):C14536
HMDB (The Human Metabolome Database):HMDB05781
FooDB:FDB000698
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
 soybean hypocotyl
Search Trop Picture
 soybean seed
Search Trop Picture
 soybean testa
Search Trop Picture
 
Synonyms:
4H-1-benzopyran-4-one, 7-hydroxy-3-(4-hydroxyphenyl)-6-methoxy-
4',7-dihydroxy-6-methoxyisoflavone
7,4'-dihydroxy-6-methoxyisoflavone
7-hydroxy-3-(4-hydroxyphenyl)-6-methoxy-4H-1-benzopyran-4-one
7-hydroxy-3-(4-hydroxyphenyl)-6-methoxy-4H-chromen-4-one
7-hydroxy-3-(4-hydroxyphenyl)-6-methoxychromen-4-one
 

Articles:

PubMed:Isoflavones of the Soybean Components and the Effect of Germination Time in the Cotyledons and Embryonic Axis.
PubMed:Profile of the contents of different forms of soybean isoflavones and the effect of germination time on these compounds and the physical parameters in soybean sprouts.
PubMed:Primary and secondary metabolite profiling of doenjang, a fermented soybean paste during industrial processing.
PubMed:Assessment of dietary phytoestrogen intake via plant-derived foods in China.
PubMed:Large inter-individual variation in isoflavone plasma concentration limits use of isoflavone intake data for risk assessment.
PubMed:Identification and quantification of the main isoflavones and other phytochemicals in soy based nutraceutical products by liquid chromatography-orbitrap high resolution mass spectrometry.
PubMed:Soy and isoflavone intake associated with reduced risk of ovarian cancer in southern Chinese women.
PubMed:Malonyl isoflavone glucosides are chiefly hydrolyzed and absorbed in the colon.
PubMed:Quantitative trait loci for seed isoflavone contents in 'MD96-5722' by 'Spencer' recombinant inbred lines of soybean.
PubMed:Feeding soybean meal increases the blood level of isoflavones and reduces the steroidogenic capacity in bovine corpora lutea, without affecting peripheral progesterone concentrations.
PubMed:Habitual consumption of soy products and risk of nasopharyngeal carcinoma in Chinese adults: a case-control study.
PubMed:The isoflavone irilone contributes to the estrogenic potential of dietary supplements containing red clover.
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:Effect of soybean processing on content and bioaccessibility of folate, vitamin B12 and isoflavones in tofu and tempe.
PubMed:Population versus hospital controls in the assessment of dietary intake of isoflavone for case-control studies on cancers in China.
PubMed:Determination of the variations in levels of phenolic compounds in soybean (Glycine max Merr.) sprouts infected by anthracnose (Colletotrichum gloeosporioides).
PubMed:Development of a food compositional database for the estimation of dietary intake of phyto-oestrogens in a group of postmenopausal women previously treated for breast cancer and validation with urinary excretion.
PubMed:Bayesian statistical approaches to compositional analyses of transgenic crops 2. Application and validation of informative prior distributions.
PubMed:Effects of dietary genistein on hormone-dependent rat mammary carcinogenesis induced by ethyl methanesulphonate.
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:Polymorphisms in genes involved in the metabolism and transport of soy isoflavones affect the urinary metabolite profile in premenopausal women following consumption of a commercial soy supplement as a single bolus dose.
PubMed:Relationship between serum isoflavone levels and disability-free survival among community-dwelling elderly individuals: nested case-control study of the Tsurugaya project.
PubMed:Fast simultaneous determination of free and conjugated isoflavones in soy milk by UHPLC-UV.
PubMed:Bioavailability of glycitein relatively to other soy isoflavones in healthy young Caucasian men.
PubMed:Urinary isoflavonoids and risk of coronary heart disease.
PubMed:Correlations of urinary phytoestrogen excretion with lifestyle factors and dietary intakes among middle-aged and elderly Chinese women.
PubMed:Regulation of the immune response by soybean isoflavones.
PubMed:Flavonoids, a ubiquitous dietary phenolic subclass, exert extensive in vitro anti-invasive and in vivo anti-metastatic activities.
PubMed:Antiallergic activity of novel isoflavone methyl-glycosides from Cordyceps militaris grown on germinated soybeans in antigen-stimulated mast cells.
PubMed:Analysis of isoflavones in soybeans employing direct analysis in real-time ionization-high-resolution mass spectrometry.
PubMed:Legume, soy, tofu, and isoflavone intake and endometrial cancer risk in postmenopausal women in the multiethnic cohort study.
PubMed:Antimicrobial compounds profile during Cheonggukjang fermentation against Xanthomonas oryzae pv. oryzae (Xoo).
PubMed:NTP-CERHR expert panel report on the developmental toxicity of soy infant formula.
PubMed:Polyphenol content and antioxidant properties of colored soybean seeds from central Europe.
PubMed:Lesser in vitro anaerobic cecal isoflavone disappearance was associated with greater apparent absorption of daidzein and genistein in Golden Syrian hamsters.
PubMed:Association between dietary phyto-oestrogens and bone density in men and postmenopausal women.
PubMed:Bacteroides uniformis is a putative bacterial species associated with the degradation of the isoflavone genistein in human feces.
PubMed:Soy-derived isoflavones inhibit HeLa cell growth by inducing apoptosis.
PubMed:Flavonoid conjugates interact with organic anion transporters (OATs) and attenuate cytotoxicity of adefovir mediated by organic anion transporter 1 (OAT1/SLC22A6).
PubMed:HPLC/DAD/MS and antioxidant activity of isoflavone-based food supplements.
PubMed:Estrogen receptor-β mediates the inhibition of DLD-1 human colon adenocarcinoma cells by soy isoflavones.
PubMed:Higher bioavailability of isoflavones after a single ingestion of aglycone-rich fermented soybeans compared with glucoside-rich non-fermented soybeans in Japanese postmenopausal women.
PubMed:Optimizing time and temperature of enzymatic conversion of isoflavone glucosides to aglycones in soy germ flour.
PubMed:Synthesis of isoflavone aglycones and equol in soy milks fermented by food-related lactic acid bacteria and their effect on human intestinal Caco-2 cells.
PubMed:Overnight urinary excretion of isoflavones as an indicator for dietary isoflavone intake in Korean girls of pubertal age.
PubMed:[Prevalence of equol producer phenotype and its relations to lifestyle factors and dietary intakes among lifestyle factors and dietary intakes among healthy Chinese adults in Beijing].
PubMed:Metabolomics revealed novel isoflavones and optimal cultivation time of Cordyceps militaris fermentation.
PubMed:Developmental and Reproductive Effects of SE5-OH: An Equol-Rich Soy-Based Ingredient.
PubMed:Breast, colorectal, and prostate cancer risk in the European Prospective Investigation into Cancer and Nutrition-Norfolk in relation to phytoestrogen intake derived from an improved database.
PubMed:Greater apparent absorption of flavonoids is associated with lesser human fecal flavonoid disappearance rates.
PubMed:Effect of genotype, environment, and their interaction on chemical composition and antioxidant properties of low-linolenic soybeans grown in Maryland.
PubMed:Changes of isoflavone profile in the hypocotyls and cotyledons of soybeans during dry heating and germination.
PubMed:Hypolipidemic effects of Monascus-fermented soybean extracts in rats fed a high-fat and -cholesterol diet.
PubMed:Changes in isoflavone profiles of soybean treated with gamma irradiation.
PubMed:Apparent bioavailability of isoflavones after intake of liquid and solid soya foods.
PubMed:Effect of glycosidation of isoflavones on their bioavailability and pharmacokinetics in aged male rats.
PubMed:Phytoestrogen content of cereals and cereal-based foods consumed in the UK.
PubMed:Stability of isoflavone isomers in steamed black soybeans and black soybean koji stored under different conditions.
PubMed:Soy, isoflavones, and prostate cancer.
PubMed:Phytoestrogen content of foods of animal origin: dairy products, eggs, meat, fish, and seafood.
PubMed:Gastrointestinal absorption and metabolism of soy isoflavonoids in ileal-canulated swine.
PubMed:Soy food and isoflavone intake in relation to semen quality parameters among men from an infertility clinic.
PubMed:Synthesis of haptens and conjugates for ELISA of glycitein: development and validation of an immunological test.
PubMed:Acute and subchronic toxicity and genotoxicity of SE5-OH, an equol-rich product produced by Lactococcus garvieae.
PubMed:Determination of phytoestrogens in dietary supplements by LC-MS/MS.
PubMed:beta-Conglycinins among sources of bioactives in hydrolysates of different soybean varieties that inhibit leukemia cells in vitro.
PubMed:Oral antibiotics decrease urinary isoflavonoid excretion in children after soy consumption.
PubMed:Estrogenic activities of isoflavones and flavones and their structure-activity relationships.
PubMed:Isoflavone glycitein diminished plasma cholesterol in female golden Syrian hamsters.
PubMed:Dietary phytoestrogens, including isoflavones, lignans, and coumestrol, in nonvitamin, nonmineral supplements commonly consumed by women in Canada.
PubMed:A comparison of changes in the transformation of isoflavones in soymilk using varying concentrations of exogenous and probiotic-derived endogenous beta-glucosidases.
PubMed:Anti-obesity activities of fermented soygerm isoflavones by Bifidobacterium breve.
PubMed:The association between isoflavone and lower urinary tract symptoms in elderly men.
PubMed:In vitro and in vivo metabolism of the soy isoflavone glycitein.
PubMed:Bioavailability of soy isoflavones in rats Part I: application of accurate methodology for studying the effects of gender and source of isoflavones.
PubMed:Analysis of isoflavonoids from leguminous plant extracts by RPHPLC/DAD and electrospray ionization mass spectrometry.
PubMed:Biotransformation of common bean (Phaseolus vulgaris L.) flavonoid glycosides by bifidobacterium species from human intestinal origin.
PubMed:Phytoestrogen exposure, polymorphisms in COMT, CYP19, ESR1, and SHBG genes, and their associations with prostate cancer risk.
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:Estimated intakes of isoflavones and coumestrol in Korean population.
PubMed:Consumption of Lactobacillus acidophilus and Bifidobacterium longum does not alter phytoestrogen metabolism and plasma hormones in men: a pilot study.
PubMed:Phytoestrogens regulate transcription and translation of vitamin D receptor in colon cancer cells.
PubMed:High urinary isoflavone excretion phenotype decreases plasma cholesterol in golden Syrian hamsters fed soy protein.
PubMed:Transformation of isoflavone phytoestrogens during the fermentation of soymilk with lactic acid bacteria and bifidobacteria.
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:Analysis of isoflavones in foods and dietary supplements.
PubMed:Phytoestrogen content of foods consumed in Canada, including isoflavones, lignans, and coumestan.
PubMed:An efficient HPLC method for the quantification of isoflavones in soy extracts and soy dietary supplements in routine quality control.
PubMed:Isoflavone profiles of red clovers and their distribution in different parts harvested at different growing stages.
PubMed:Oncogenicity evaluations of chemopreventive soy components in p53((+/-)) (p53 knockout) mice.
PubMed:Antioxidant activity of isoflavones and their major metabolites using different in vitro assays.
PubMed:Thermal degradation kinetics of isoflavone aglycones from soy and red clover.
PubMed:Distribution profiles of isoflavone isomers in black bean kojis prepared with various filamentous fungi.
PubMed:Determination of isoflavones in dietary supplements containing soy, Red Clover and kudzu: extraction followed by basic or acid hydrolysis.
PubMed:Polymorphisms in the CYP19 gene may affect the positive correlations between serum and urine phytoestrogen metabolites and plasma androgen concentrations in men.
PubMed:Metabolism of glycitein (7,4'-dihydroxy-6-methoxy-isoflavone) by human gut microflora.
PubMed:Isoflavone contents in germinated soybean seeds.
PubMed:In vitro effects of soy phytoestrogens on rat L6 skeletal muscle cells.
PubMed:Supercritical fluid extraction of isoflavones from biological samples with ultra-fast high-performance liquid chromatography/mass spectrometry.
PubMed:Isoflavones modulate the glucuronidation of estradiol in human liver microsomes.
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:Bioavailability of isoflavone phytoestrogens in postmenopausal women consuming soya milk fermented with probiotic bifidobacteria.
PubMed:Experimental determination of octanol-water partition coefficients of quercetin and related flavonoids.
PubMed:Analysis of isoflavone contents in vegetable soybeans.
PubMed:Quality, labeling accuracy, and cost comparison of purified soy isoflavonoid products.
PubMed:Soy and isoflavone intake are associated with reduced risk of ovarian cancer in southeast china.
PubMed:Isolation of 8-hydroxyglycitein and 6-hydroxydaidzein from soybean miso.
PubMed:Plant lignans in soy-based health supplements.
PubMed:Dietary exposure estimates of isoflavones from the 1998 UK Total Diet Study.
PubMed:Isoflavones found in Korean soybean paste as 3-hydroxy-3-methylglutaryl Coenzyme A reductase inhibitors.
PubMed:Evaluation of the preventive effect of isoflavone extract on bone loss in ovariectomized rats.
PubMed:LC/UV/ESI-MS analysis of isoflavones in Edamame and Tofu soybeans.
PubMed:Differential effects of isoflavones and lignans on invasiveness of MDA-MB-231 breast cancer cells in vitro.
PubMed:Influence of soya-based infant formula consumption on isoflavone and gut microflora metabolite concentrations in urine and on faecal microflora composition and metabolic activity in infants and children.
PubMed:Isoflavones inhibit 3-hydroxy-3-methylglutaryl coenzyme A reductase in vitro.
PubMed:Simultaneous determination of isoflavones and bisphenol A in rat serum by high-performance liquid chromatography coupled with coulometric array detection.
PubMed:Stability and bioaccessibility of isoflavones from soy bread during in vitro digestion.
PubMed:Soy protein with or without isoflavones, soy germ and soy germ extract, and daidzein lessen plasma cholesterol levels in golden Syrian hamsters.
PubMed:The influence of dietary isoflavone on the uterotrophic response in juvenile rats.
PubMed:Serum isoflavones and soya food intake in Japanese, Thai and American end-stage renal disease patients on chronic haemodialysis.
PubMed:Quantification of isoflavones and lignans in urine using gas chromatography/mass spectrometry.
PubMed:Determination of isoflavones in ready-to-feed soy-based infant formula.
PubMed:Isoflavone, glyphosate, and aminomethylphosphonic acid levels in seeds of glyphosate-treated, glyphosate-resistant soybean.
PubMed:Stabilities of daidzin, glycitin, genistin, and generation of derivatives during heating.
PubMed:Oxidative metabolism and genotoxic potential of major isoflavone phytoestrogens.
PubMed:Hydrolysis of isoflavone glycosides to aglycones by beta-glycosidase does not alter plasma and urine isoflavone pharmacokinetics in postmenopausal women.
PubMed:Potent antimutagenic and their anti-lipid peroxidative effect of kaikasaponin III and tectorigenin from the flower of Pueraria thunbergiana.
PubMed:Potassium fertilization effects on isoflavone concentrations in soybean [Glycine max (L.) Merr.].
PubMed:Characterization of isoflavones and their conjugates in female rat urine using LC/MS/MS.
PubMed:Isoflavone aglycon and glucoconjugate content of high- and low-soy U.K. foods used in nutritional studies.
PubMed:Characterisation of soy isoflavones and screening for novel malonyl glycosides using high-performance liquid chromatography-electrospray ionisation-mass spectrometry.
PubMed:Determination of isoflavones in soy and selected foods containing soy by extraction, saponification, and liquid chromatography: collaborative study.
PubMed:Soy for breast cancer survivors: a critical review of the literature.
PubMed:Quantitative analysis of the principle soy isoflavones genistein, daidzein and glycitein, and their primary conjugated metabolites in human plasma and urine using reversed-phase high-performance liquid chromatography with ultraviolet detection.
PubMed:Estimated dietary isoflavone intake of Korean population based on National Nutrition Survey.
PubMed:Suppression effect of soy isoflavones on nitric oxide production in RAW 264.7 macrophages.
PubMed:Determination of the levels of isoflavonoids in soybeans and soy-derived foods and estimation of isoflavonoids in the Japanese daily intake.
PubMed:Estrogenic activity of glycitein, a soy isoflavone.
PubMed:Usual dietary consumption of soy foods and its correlation with the excretion rate of isoflavonoids in overnight urine samples among Chinese women in Shanghai.
PubMed:Urinary excretion of isoflavonoids and the risk of breast cancer.
PubMed:Soy isoflavone analysis: quality control and a new internal standard.
PubMed:Isoflavones in human breast milk and other biological fluids.
PubMed:Isoflavonoid levels in spot urine are associated with frequency of dietary soy intake in a population-based sample of middle-aged and older Chinese in Singapore.
 
Notes:
Isoflavone present in soya foods (inc. tofu, miso); potential nutriceutical [DFC]
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