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daidzin
diadzein 7-O-glucoside

Supplier Sponsors

CAS Number: 552-66-9Picture of molecule3D/inchi
Other(deleted CASRN):1329-08-4
FDA UNII: 4R2X91A5M5
Nikkaji Web:J22.589D
Beilstein Number:0059741
MDL:MFCD00017466
XlogP3-AA:0.70 (est)
Molecular Weight:416.38320000
Formula:C21 H20 O9
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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NCBI:Search
 
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)
 
Organoleptic Properties:
Odor and/or flavor descriptions from others (if found).
 
Cosmetic Information:
None found
 
Suppliers:
Alfa Biotechnology
For experimental / research use only.
Daidzin 98%
BOC Sciences
For experimental / research use only.
Daidzin
Carbosynth
For experimental / research use only.
Daidzin
Coompo
For experimental / research use only.
Daidzin from Plants ≥98%
Odor: characteristic
Use: Daidzin: A potent, selective inhibitor of human mitochondrial aldehyde dehydrogenase. Daidzin selectively suppresses ethanol intake in all rodent models tested. It also inhibits mitochondrial aldehyde dehydrogenase (ALDH-2).
ExtraSynthese
For experimental / research use only.
Daidzin (HPLC) ≥90%
Nacalai USA
For experimental / research use only.
Daidzin
Santa Cruz Biotechnology
For experimental / research use only.
Daidzin
Sigma-Aldrich: Sigma
For experimental / research use only.
Daidzin ≥95.0% (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:
intraperitoneal-mouse LD50 > 2000 mg/kg
Pharmaceutical Chemistry Journal Vol. 13, Pg. 51, 1979.

Dermal Toxicity:
Not determined
Inhalation Toxicity:
Not determined
 
Safety in Use Information:
Category:
natural substances and extractives
Recommendation for daidzin usage levels up to:
 not for fragrance use.
 
Recommendation for daidzin flavor usage levels up to:
 not for flavor use.
 
Safety References:
European Food Safety Authority (EFSA) reference(s):

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 :107971
National Institute of Allergy and Infectious Diseases:Data
WGK Germany:3
3-(4-hydroxyphenyl)-7-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxychromen-4-one
Chemidplus:0000552669
RTECS:DJ3094000 for cas# 552-66-9
 
References:
 3-(4-hydroxyphenyl)-7-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxychromen-4-one
NIST Chemistry WebBook:Search Inchi
Pubchem (cid):107971
Pubchem (sid):135066166
 
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):C10216
HMDB (The Human Metabolome Database):HMDB33991
FooDB:FDB012225
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
 alfalfa
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 bean mung bean
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 kudzu root
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 soybean cotyledon
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 soybean embryo
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 soybean hypocotyl
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 soybean seed
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 soybean seed coat
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 soybean shoot
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 soybean testa
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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
 

Articles:

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.
 
Notes:
a potent, selective, and reversible inhibitor of human mitochondrial aldehyde dehydrogenase. Isol. from soya bean (Glycine max) and soya bean meal, kudzu root (Pueraria lobata), alfalfa (Medicago sativa) and other Leguminosae Daidzin is a cancer preventive and an alcohol dependency treatment (antidipsotropic) in animal models.; Daidzin is a natural organic compound in the class of phytochemicals known as isoflavones. Daidzin can be found in Japanese plant Kudzu (Pueraria lobata, Fabaceae) and from soybean leaves.
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