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68682-02-0,MFCD00272175
Catalog No.:AA00FDUQ

68682-02-0 | 5,7-Dihydroxy-2-(4-hydroxyphenyl)-8-(3-methylbut-3-en-1-yl)chroman-4-one

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1mg
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5mg
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10mg
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25mg
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  • Technical Information
  • Properties
  • Literature
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  • Technical Information
  • Properties
  • Literature
Technical Information
Catalog Number:
AA00FDUQ
Chemical Name:
5,7-Dihydroxy-2-(4-hydroxyphenyl)-8-(3-methylbut-3-en-1-yl)chroman-4-one
CAS Number:
68682-02-0
Molecular Formula:
C20H20O5
Molecular Weight:
340.3698
MDL Number:
MFCD00272175
SMILES:
CC(=CCc1c(O)cc(c2c1OC(CC2=O)c1ccc(cc1)O)O)C
Properties
Computed Properties
 
Complexity:
504  
Covalently-Bonded Unit Count:
1  
Heavy Atom Count:
25  
Hydrogen Bond Acceptor Count:
5  
Hydrogen Bond Donor Count:
3  
Rotatable Bond Count:
3  
Undefined Atom Stereocenter Count:
1  
XLogP3:
4.3  

Literature

Title: The influence of 8-prenylnaringenin on the activity of voltage-gated Kv1.3 potassium channels in human Jurkat T cells.

Journal: Cellular & molecular biology letters 20121201

Title: Comparison between 8-prenylnarigenin and narigenin concerning their activities on promotion of rat bone marrow stromal cells' osteogenic differentiation in vitro.

Journal: Cell proliferation 20121201

Title: The phytoestrogen 8-prenylnaringenin inhibits agonist-dependent activation of human platelets.

Journal: Biochimica et biophysica acta 20121101

Title: Transformation of 8-prenylnaringenin by Absidia coerulea and Beauveria bassiana.

Journal: Bioorganic & medicinal chemistry letters 20121015

Title: Effect of 17β-estradiol and flavonoids on the regulation of expression of newly identified oestrogen responsive genes in a rat raphe nuclei-derived cell line.

Journal: Journal of cellular physiology 20121001

Title: Xanthohumol, a prenylated chalcone derived from hops, suppresses cancer cell invasion through inhibiting the expression of CXCR4 chemokine receptor.

Journal: Current molecular medicine 20120201

Title: Combinatorial analysis of lupulin gland transcription factors from R2R3Myb, bHLH and WDR families indicates a complex regulation of chs_H1 genes essential for prenylflavonoid biosynthesis in hop (Humulus Lupulus L.).

Journal: BMC plant biology 20120101

Title: Prevention of disuse muscle atrophy by dietary ingestion of 8-prenylnaringenin in denervated mice.

Journal: PloS one 20120101

Title: Toxicological aspects of the use of phenolic compounds in disease prevention.

Journal: Interdisciplinary toxicology 20111201

Title: A study in balance: how microbiomes are changing the shape of environmental health.

Journal: Environmental health perspectives 20110801

Title: Production of monoclonal antibodies against hop-derived (Humulus lupulus L.) prenylflavonoids and the development of immunoassays.

Journal: Talanta 20110715

Title: Production of 8-prenylnaringenin from isoxanthohumol through biotransformation by fungi cells.

Journal: Journal of agricultural and food chemistry 20110713

Title: Agonistic and antagonistic estrogens in licorice root (Glycyrrhiza glabra).

Journal: Analytical and bioanalytical chemistry 20110701

Title: Inhibitors of hyaluronan export from hops prevent osteoarthritic reactions.

Journal: Molecular nutrition & food research 20110301

Title: Phytoestrogen biological actions on Mammalian reproductive system and cancer growth.

Journal: Scientia pharmaceutica 20110101

Title: Prebiotic effects of wheat arabinoxylan related to the increase in bifidobacteria, Roseburia and Bacteroides/Prevotella in diet-induced obese mice.

Journal: PloS one 20110101

Title: Quantification of xanthohumol, isoxanthohumol, 8-prenylnaringenin, and 6-prenylnaringenin in hop extracts and derived capsules using secondary standards.

Journal: Talanta 20101215

Title: Angiogenesis and inflammation signaling are targets of beer polyphenols on vascular cells.

Journal: Journal of cellular biochemistry 20101201

Title: 8-Prenylnaringenin is an inhibitor of multidrug resistance-associated transporters, P-glycoprotein and MRP1.

Journal: European journal of pharmacology 20101010

Title: Recovery and metabolism of xanthohumol in germ-free and human microbiota-associated rats.

Journal: Molecular nutrition & food research 20101001

Title: Disposition of hop prenylflavonoids in human breast tissue.

Journal: Molecular nutrition & food research 20100701

Title: Arsenic metabolism by human gut microbiota upon in vitro digestion of contaminated soils.

Journal: Environmental health perspectives 20100701

Title: Activation of transgenic estrogen receptor-beta by selected phytoestrogens in a stably transduced rat serotonergic cell line.

Journal: The Journal of steroid biochemistry and molecular biology 20100601

Title: A randomized, double-blind, placebo-controlled, cross-over pilot study on the use of a standardized hop extract to alleviate menopausal discomforts.

Journal: Phytomedicine : international journal of phytotherapy and phytopharmacology 20100501

Title: Development of a high-throughput LC/APCI-MS method for the determination of thirteen phytoestrogens including gut microbial metabolites in human urine and serum.

Journal: Journal of chromatography. B, Analytical technologies in the biomedical and life sciences 20100415

Title: Prenylation has a compound specific effect on the estrogenicity of naringenin and genistein.

Journal: The Journal of steroid biochemistry and molecular biology 20100101

Title: Through ageing, and beyond: gut microbiota and inflammatory status in seniors and centenarians.

Journal: PloS one 20100101

Title: Organogenic nodule formation in hop: a tool to study morphogenesis in plants with biotechnological and medicinal applications.

Journal: Journal of biomedicine & biotechnology 20100101

Title: Tissue culture and generation of autotetraploid plants of Sophora flavescens Aiton.

Journal: Pharmacognosy magazine 20100101

Title: Biotransformation of the phytoestrogen 8-prenylnaringenin.

Journal: Zeitschrift fur Naturforschung. C, Journal of biosciences 20100101

Title: Modulation of aflatoxin B1-mediated genotoxicity in primary cultures of human hepatocytes by diindolylmethane, curcumin, and xanthohumols.

Journal: Toxicological sciences : an official journal of the Society of Toxicology 20091201

Title: Anti-inflammatory and vascularprotective properties of 8-prenylapigenin.

Journal: European journal of pharmacology 20091012

Title: Flavonoid-induced autophagy in hormone sensitive breast cancer cells.

Journal: Fitoterapia 20090901

Title: Changes in gut microbiota control inflammation in obese mice through a mechanism involving GLP-2-driven improvement of gut permeability.

Journal: Gut 20090801

Title: Synthesis, biological evaluation of prenylflavonoids as vasorelaxant and neuroprotective agents.

Journal: Bioorganic & medicinal chemistry letters 20090615

Title: Dynamic residual complexity of natural products by qHNMR: solution stability of desmethylxanthohumol.

Journal: Planta medica 20090601

Title: 8-Prenylnaringenin inhibits epidermal growth factor-induced MCF-7 breast cancer cell proliferation by targeting phosphatidylinositol-3-OH kinase activity.

Journal: The Journal of steroid biochemistry and molecular biology 20090201

Title: An overview of conventional and emerging analytical methods for the determination of mycotoxins.

Journal: International journal of molecular sciences 20090101

Title: Validity and reproducibility of a self-administered semi-quantitative food-frequency questionnaire for estimating usual daily fat, fibre, alcohol, caffeine and theobromine intakes among Belgian post-menopausal women.

Journal: International journal of environmental research and public health 20090101

Title: Nitric oxide production by the human intestinal microbiota by dissimilatory nitrate reduction to ammonium.

Journal: Journal of biomedicine & biotechnology 20090101

Title: Time dependency of uterine effects of naringenin type phytoestrogens in vivo.

Journal: Molecular and cellular endocrinology 20081106

Title: In vivo estrogenic comparisons of Trifolium pratense (red clover) Humulus lupulus (hops), and the pure compounds isoxanthohumol and 8-prenylnaringenin.

Journal: Chemico-biological interactions 20081022

Title: Microbial metabolites of 8-prenylnaringenin, an estrogenic prenylflavanone.

Journal: Archives of pharmacal research 20081001

Title: Potent inhibition of human phosphodiesterase-5 by icariin derivatives.

Journal: Journal of natural products 20080901

Title: Direct determination of the estrogenic compounds 8-prenylnaringenin, zearalenone, alpha- and beta-zearalenol in beer by liquid chromatography-mass spectrometry.

Journal: Journal of chromatography. A 20080815

Title: Effects of long-term treatment with 8-prenylnaringenin and oral estradiol on the GH-IGF-1 axis and lipid metabolism in rats.

Journal: The Journal of endocrinology 20080801

Title: Comparison of the phytohormones genistein, resveratrol and 8-prenylnaringenin as agents for preventing osteoporosis.

Journal: Planta medica 20080601

Title: Determination of phytoestrogens in dietary supplements by LC-MS/MS.

Journal: Food additives & contaminants. Part A, Chemistry, analysis, control, exposure & risk assessment 20080501

Title: Pharmacognostic and pharmacological profile of Humulus lupulus L.

Journal: Journal of ethnopharmacology 20080328

Title: Cloning and characterization of naringenin 8-prenyltransferase, a flavonoid-specific prenyltransferase of Sophora flavescens.

Journal: Plant physiology 20080301

Title: Treatment of PC-3 and DU145 prostate cancer cells by prenylflavonoids from hop (Humulus lupulus L.) induces a caspase-independent form of cell death.

Journal: Phytotherapy research : PTR 20080201

Title: Screening of synthetic and plant-derived compounds for (anti)estrogenic and (anti)androgenic activities.

Journal: Analytical and bioanalytical chemistry 20080201

Title: Development of a screening assay for ligands to the estrogen receptor based on magnetic microparticles and LC-MS.

Journal: Combinatorial chemistry & high throughput screening 20080101

Title: Endocrine disruptors and the thyroid gland--a combined in vitro and in vivo analysis of potential new biomarkers.

Journal: Environmental health perspectives 20071201

Title: Microbial and dietary factors associated with the 8-prenylnaringenin producer phenotype: a dietary intervention trial with fifty healthy post-menopausal Caucasian women.

Journal: The British journal of nutrition 20071101

Title: Effects of the chemically synthesized flavanone 7-(O-prenyl)naringenin-4'-acetate on the estrogen signaling pathway in vivo and in vitro.

Journal: The Journal of steroid biochemistry and molecular biology 20071001

Title: Metabolism of isoflavones, lignans and prenylflavonoids by intestinal bacteria: producer phenotyping and relation with intestinal community.

Journal: FEMS microbiology ecology 20070801

Title: Binding of the hop (Humulus lupulus L.) chalcone xanthohumol to cytosolic proteins in Caco-2 intestinal epithelial cells.

Journal: Molecular nutrition & food research 20070701

Title: Ability of prenylflavanones present in hops to induce apoptosis in a human Burkitt lymphoma cell line.

Journal: Planta medica 20070701

Title: Resolution of diastereomeric flavonoid (1S)-(-)-camphanic acid esters via reversed-phase HPLC.

Journal: Phytochemistry 20070401

Title: pH-independent drug release of an extremely poorly soluble weakly acidic drug from multiparticulate extended release formulations.

Journal: European journal of pharmaceutics and biopharmaceutics : official journal of Arbeitsgemeinschaft fur Pharmazeutische Verfahrenstechnik e.V 20070101

Title: Modulation of breast cancer cell survival by aromatase inhibiting hop (Humulus lupulus L.) flavonoids.

Journal: The Journal of steroid biochemistry and molecular biology 20070101

Title: 8-Prenylnaringenin, inhibits estrogen receptor-alpha mediated cell growth and induces apoptosis in MCF-7 breast cancer cells.

Journal: The Journal of steroid biochemistry and molecular biology 20070101

Title: Subtle side-chain modifications of the hop phytoestrogen 8-prenylnaringenin result in distinct agonist/antagonist activity profiles for estrogen receptors alpha and beta.

Journal: Journal of medicinal chemistry 20061214

Title: Anti-proliferative properties of prenylated flavonoids from hops (Humulus lupulus L.) in human prostate cancer cell lines.

Journal: Phytomedicine : international journal of phytotherapy and phytopharmacology 20061101

Title: The hop phytoestrogen, 8-prenylnaringenin, reverses the ovariectomy-induced rise in skin temperature in an animal model of menopausal hot flushes.

Journal: The Journal of endocrinology 20061101

Title: Pharmacokinetics and systemic endocrine effects of the phyto-oestrogen 8-prenylnaringenin after single oral doses to postmenopausal women.

Journal: British journal of clinical pharmacology 20060901

Title: Identification of human hepatic cytochrome P450 enzymes involved in the metabolism of 8-prenylnaringenin and isoxanthohumol from hops (Humulus lupulus L.).

Journal: Drug metabolism and disposition: the biological fate of chemicals 20060701

Title: A first prospective, randomized, double-blind, placebo-controlled study on the use of a standardized hop extract to alleviate menopausal discomforts.

Journal: Maturitas 20060520

Title: Effects of estrogenic xenobiotics on human and mouse spermatozoa.

Journal: Human reproduction (Oxford, England) 20060501

Title: Microsphere-based protease assays and screening application for lethal factor and factor Xa.

Journal: Cytometry. Part A : the journal of the International Society for Analytical Cytology 20060501

Title: In vitro studies of intestinal permeability and hepatic and intestinal metabolism of 8-prenylnaringenin, a potent phytoestrogen from hops (Humulus lupulus L.).

Journal: Pharmaceutical research 20060501

Title: Effect of hop (Humulus lupulus L.) flavonoids on aromatase (estrogen synthase) activity.

Journal: Journal of agricultural and food chemistry 20060419

Title: Prenylated flavonoids from the heartwood of Artocarpus communis with inhibitory activity on lipopolysaccharide-induced nitric oxide production.

Journal: Journal of natural products 20060401

Title: Effects of 8-prenylnaringenin on the hypothalamo-pituitary-uterine axis in rats after 3-month treatment.

Journal: The Journal of endocrinology 20060301

Title: Morphologic changes induced by oral long-term treatment with 8-prenylnaringenin in the uterus, vagina, and mammary gland of castrated rats.

Journal: Menopause (New York, N.Y.) 20060101

Title: Tissue specificity of 8-prenylnaringenin: protection from ovariectomy induced bone loss with minimal trophic effects on the uterus.

Journal: The Journal of steroid biochemistry and molecular biology 20051101

Title: Effect of phytoestrogens on gene expression of carbonic anhydrase II in rat uterus and liver.

Journal: The Journal of steroid biochemistry and molecular biology 20051101

Title: Regulation of osteoblastic phenotype and gene expression by hop-derived phytoestrogens.

Journal: The Journal of steroid biochemistry and molecular biology 20050901

Title: Activation of proestrogens from hops (Humulus lupulus L.) by intestinal microbiota; conversion of isoxanthohumol into 8-prenylnaringenin.

Journal: Journal of agricultural and food chemistry 20050810

Title: Xanthohumol isolated from Humulus lupulus Inhibits menadione-induced DNA damage through induction of quinone reductase.

Journal: Chemical research in toxicology 20050801

Title: Development of a radioimmunoassay for the quantitative determination of 8-prenylnaringenin in biological matrices.

Journal: Journal of agricultural and food chemistry 20050420

Title: Comparative study of oestrogenic properties of eight phytoestrogens in MCF7 human breast cancer cells.

Journal: The Journal of steroid biochemistry and molecular biology 20050401

Title: Metabolism of xanthohumol and isoxanthohumol, prenylated flavonoids from hops (Humulus lupulus L.), by human liver microsomes.

Journal: Journal of mass spectrometry : JMS 20050301

Title: Naringenin-type flavonoids show different estrogenic effects in mammalian and teleost test systems.

Journal: Biochemical and biophysical research communications 20050128

Title: Estrogens and congeners from spent hops (Humulus lupulus).

Journal: Journal of natural products 20041201

Title: Determination of unusual soya and non-soya phytoestrogen sources in beer, fish products and other foods.

Journal: Food additives and contaminants 20041001

Title: Two major metabolites of 8-prenylnaringenin are estrogenic in vitro.

Journal: The Journal of steroid biochemistry and molecular biology 20040901

Title: Uterine effects of the phytoestrogen 6-(1,1-dimethylallyl)naringenin in rats.

Journal: Planta medica 20040701

Title: 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.

Journal: The Journal of steroid biochemistry and molecular biology 20040701

Title: Phytochemical-induced changes in gene expression of carcinogen-metabolizing enzymes in cultured human primary hepatocytes.

Journal: Xenobiotica; the fate of foreign compounds in biological systems 20040701

Title: Toxicity and cell cycle effects of synthetic 8-prenylnaringenin and derivatives in human cells.

Journal: Pharmacology 20040501

Title: Xanthohumol and related prenylflavonoids from hops and beer: to your good health!

Journal: Phytochemistry 20040501

Title: 8-prenylnaringenin, a novel phytoestrogen, inhibits angiogenesis in vitro and in vivo.

Journal: Journal of cellular physiology 20040401

Title: Prediction of ligand binding affinity and orientation of xenoestrogens to the estrogen receptor by molecular dynamics simulations and the linear interaction energy method.

Journal: Journal of medicinal chemistry 20040212

Title: Metabolism of 8-prenylnaringenin, a potent phytoestrogen from hops (Humulus lupulus), by human liver microsomes.

Journal: Drug metabolism and disposition: the biological fate of chemicals 20040201

Title: Regulation of gene expression by 8-prenylnaringenin in uterus and liver of Wistar rats.

Journal: Planta medica 20040101

Title: Prenylated flavanones isolated from flowers of Azadirachta indica (the neem tree) as antimutagenic constituents against heterocyclic amines.

Journal: Journal of agricultural and food chemistry 20031022

Title: Antiandrogenic activity of the phytoestrogens naringenin, 6-(1,1-dimethylallyl)naringenin and 8-prenylnaringenin.

Journal: Planta medica 20030901

Title: Antifungal agents from the roots of Cudrania cochinchinensis against Candida, Cryptococcus, and Aspergillus species.

Journal: Journal of natural products 20030801

Title: Phytoestrogens: recent developments.

Journal: Planta medica 20030701

Title: 'Bust enhancing' herbal products.

Journal: Obstetrics and gynecology 20030601

Title: Efficient production and capture of 8-prenylnaringenin and leachianone G-biosynthetic intermediates of sophoraflavanone G--by the addition of cork tissue to cell suspension cultures of Sophora flavescens.

Journal: Phytochemistry 20030401

Title: Analysis of estrogenic activity of foodstuffs and cigarette smoke condensates using a yeast estrogen screening method.

Journal: Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association 20030401

Title: 8-Prenyl naringenin is a potent ERalpha selective phytoestrogen present in hops and beer.

Journal: The Journal of steroid biochemistry and molecular biology 20030201

Title: 17beta-Estradiol and environmental estrogens significantly affect mammalian sperm function.

Journal: Human reproduction (Oxford, England) 20030101

Title: A binary screening assay for pro-oestrogens in food: metabolic activation using hepatic microsomes and detection with oestrogen sensitive recombinant yeast cells.

Journal: Food additives and contaminants 20021201

Title: Influence of flavonoids and vitamins on the MMP- and TIMP-expression of human dermal fibroblasts after UVA irradiation.

Journal: Photochemical & photobiological sciences : Official journal of the European Photochemistry Association and the European Society for Photobiology 20021001

Title: Estrogenic activity of the phytoestrogens naringenin, 6-(1,1-dimethylallyl)naringenin and 8-prenylnaringenin.

Journal: Planta medica 20020501

Title: Oestrogenic activity of the hop phyto-oestrogen, 8-prenylnaringenin.

Journal: Reproduction (Cambridge, England) 20020201

Title: Identification, quantitation and biological activity of phytoestrogens in a dietary supplement for breast enhancement.

Journal: Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association 20011201

Title: 8-Prenylnaringenin, the phytoestrogen in hops and beer, upregulates the function of the E-cadherin/catenin complex in human mammary carcinoma cells.

Journal: European journal of cell biology 20010901

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Tags:68682-02-0 Molecular Formula|68682-02-0 MDL|68682-02-0 SMILES|68682-02-0 5,7-Dihydroxy-2-(4-hydroxyphenyl)-8-(3-methylbut-3-en-1-yl)chroman-4-one