Details
| Stereochemistry | ACHIRAL |
| Molecular Formula | C16H12O5 |
| Molecular Weight | 284.2635 |
| Optical Activity | NONE |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
COC1=CC2=C(OC=C(C2=O)C3=CC=C(O)C=C3)C=C1O
InChI
InChIKey=DXYUAIFZCFRPTH-UHFFFAOYSA-N
InChI=1S/C16H12O5/c1-20-15-6-11-14(7-13(15)18)21-8-12(16(11)19)9-2-4-10(17)5-3-9/h2-8,17-18H,1H3
Approval Year
PubMed
| Title | Date | PubMed |
|---|---|---|
| Soy and isoflavone intake are associated with reduced risk of ovarian cancer in southeast china. | 2004 |
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| Reports: plasma and dietary phytoestrogens and risk of premalignant lesions of the cervix. | 2004 |
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| Soybean: feed quality and safety. Part 1: biologically active components. A review. | 2004 |
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| Dietary exposure estimates of isoflavones from the 1998 UK Total Diet Study. | 2004 Apr |
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| Quality, labeling accuracy, and cost comparison of purified soy isoflavonoid products. | 2004 Dec |
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| Isolation of 8-hydroxyglycitein and 6-hydroxydaidzein from soybean miso. | 2004 Jun |
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| Plant lignans in soy-based health supplements. | 2004 Jun 30 |
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| Decreased bone resorption with soy isoflavone supplementation in postmenopausal women. | 2004 Nov |
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| Potential beneficial metabolic interactions between tamoxifen and isoflavones via cytochrome P450-mediated pathways in female rat liver microsomes. | 2004 Nov |
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| Impact of the phytoestrogen content of laboratory animal feed on the gene expression profile of the reproductive system in the immature female rat. | 2004 Nov |
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| Cumulative dietary energy intake determines the onset of puberty in female rats. | 2004 Nov |
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| Soy isoflavones suppress invasiveness of breast cancer cells by the inhibition of NF-kappaB/AP-1-dependent and -independent pathways. | 2004 Nov |
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| Synthesis of phytoestrogenic isoflavonoid disulfates. | 2004 Sep |
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| Effects of a diet rich in phytoestrogens on prostate-specific antigen and sex hormones in men diagnosed with prostate cancer. | 2004 Sep |
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| Biotransformation of soy isoflavone-glycosides in laying hens: intestinal absorption and preferential accumulation into egg yolk of equol, a more estrogenic metabolite of daidzein. | 2004 Sep 24 |
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| Isoflavonoids in the Rutaceae family: 1. Fortunella obovata, Murraya paniculata and four Citrus species. | 2004 Sep-Oct |
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| Analysis of isoflavone contents in vegetable soybeans. | 2004 Spring |
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| Phytoestrogens: end of a tale? | 2005 |
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| Daidzein-rich isoflavone-aglycones for menopausal symptoms. | 2005 Apr |
|
| Supercritical fluid extraction of isoflavones from biological samples with ultra-fast high-performance liquid chromatography/mass spectrometry. | 2005 Aug |
|
| Determination of isoflavones in soy bits by fast column high-performance liquid chromatography coupled with UV-visible diode-array detection. | 2005 Aug 19 |
|
| Soy isoflavone glycitein protects against beta amyloid-induced toxicity and oxidative stress in transgenic Caenorhabditis elegans. | 2005 Aug 25 |
|
| [Preparation of soybean isoflavone aglycones by reversed-phase high performance liquid chromatography from Semen Sojae Praeparatum]. | 2005 Dec |
|
| Isoflavones modulate the glucuronidation of estradiol in human liver microsomes. | 2005 Dec |
|
| In vitro effects of soy phytoestrogens on rat L6 skeletal muscle cells. | 2005 Fall |
|
| Absorption and metabolism of genistein and its five isoflavone analogs in the human intestinal Caco-2 model. | 2005 Feb |
|
| Phytoestrogen exposure correlation with plasma estradiol in postmenopausal women in European Prospective Investigation of Cancer and Nutrition-Norfolk may involve diet-gene interactions. | 2005 Jan |
|
| A randomized, placebo-controlled trial on the effects of soy protein containing isoflavones on quality of life in postmenopausal women. | 2005 Jan-Feb |
|
| 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. | 2005 Jul 27 |
|
| Quantitative determination and structural characterization of isoflavones in nutrition supplements by liquid chromatography-mass spectrometry. | 2005 Jul 29 |
|
| Bioavailability of isoflavone phytoestrogens in postmenopausal women consuming soya milk fermented with probiotic bifidobacteria. | 2005 Jun |
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| Experimental determination of octanol-water partition coefficients of quercetin and related flavonoids. | 2005 Jun 1 |
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| Optimization of conditions for the enzymatic hydrolysis of phytoestrogen conjugates in urine and plasma. | 2005 Jun 15 |
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| Expression profiling of the estrogen responsive genes in response to phytoestrogens using a customized DNA microarray. | 2005 Mar 14 |
|
| Pharmacokinetics of isoflavones, daidzein and genistein, after ingestion of soy beverage compared with soy extract capsules in postmenopausal Thai women. | 2005 Mar 3 |
|
| Metabolism of glycitein (7,4'-dihydroxy-6-methoxy-isoflavone) by human gut microflora. | 2005 Nov 2 |
|
| Identifying 6,7,4'-trihydroxyisoflavone as a potent tyrosinase inhibitor. | 2005 Oct |
|
| Isoflavone contents in germinated soybean seeds. | 2005 Sep |
|
| Thermal degradation kinetics of isoflavone aglycones from soy and red clover. | 2006 Apr |
|
| Prostatic fluid concentrations of isoflavonoids in soy consumers are sufficient to inhibit growth of benign and malignant prostatic epithelial cells in vitro. | 2006 Apr 1 |
|
| Antioxidant activity of isoflavones and their major metabolites using different in vitro assays. | 2006 Apr 19 |
|
| Distribution profiles of isoflavone isomers in black bean kojis prepared with various filamentous fungi. | 2006 Feb 22 |
|
| Determination of isoflavones in dietary supplements containing soy, Red Clover and kudzu: extraction followed by basic or acid hydrolysis. | 2006 Feb 24 |
|
| Soybean isoflavones alter parvalbumin in hippocampus of mid-aged normal female, ovariectomized female, and normal male rats. | 2006 Jan |
|
| Genistein and other soya isoflavones are potent ligands for transthyretin in serum and cerebrospinal fluid. | 2006 Jun |
|
| The science of soy: what do we really know? | 2006 Jun |
|
| Isoflavones inhibit nicotine C-oxidation catalyzed by human CYP2A6. | 2006 Mar |
|
| Development and validation of a RP-HPLC method for quantification of isoflavone aglycones in hydrolyzed soy dry extracts. | 2006 May 19 |
|
| Oncogenicity evaluations of chemopreventive soy components in p53((+/-)) (p53 knockout) mice. | 2006 May-Jun |
|
| Prediction of estrogen receptor agonists and characterization of associated molecular descriptors by statistical learning methods. | 2006 Nov |
Sample Use Guides
dietary supplement containing high-dose purified soy isoflavones (genistein, 558 mg/day; daidzein, 296 mg/day; and glycitein, 44 mg/day) to 30 postmenopausal women for 84 days and collected peripheral lymphocytes at timed intervals
Route of Administration:
Oral
Bone marrow-derived osteoclasts were cultured with various concentrations (0.01-100 nM) of glycitein. Osteoclast generation was inhibited by glycitein in a biphasic-dose-dependent manner and showed the greatest inhibitory effects at 10 nM (-70%, p < 0.01). Glycitein increased caspase 3/7 activity by 15% at a concentration of 10 nM (p < 0.001). Further, 10 nM glycitein significantly decreased the expression of IL-6 (-53%, p < 0.05) and RANKL (-64%, p < 0.05) in osteoblasts but did not change mRNA levels of OPG.
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| Classification Tree | Code System | Code | ||
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DSLD |
1428 (Number of products:4)
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DSLD |
3258 (Number of products:29)
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NCI_THESAURUS |
C599
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| Code System | Code | Type | Description | ||
|---|---|---|---|---|---|
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C086566
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1295844
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34778
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GLYCITEIN
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92M5F28TVF
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40957-83-3
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5317750
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C63949
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DTXSID40193960
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SUBSTANCE RECORD
