EU/US Properties Organoleptics Cosmetics Suppliers Safety Safety in use Safety references References Other Blenders Uses Occurrence Synonyms Articles Notes
 

8-prenyl naringenin
sophoraflavanone B

Supplier Sponsors

Name:(2S)-5,7-dihydroxy-2-(4-hydroxyphenyl)-8-(3-methylbut-2-enyl)-2,3-dihydrochromen-4-one
CAS Number: 53846-50-7Picture of molecule3D/inchi
FDA UNII: 5L872SZR8X
Nikkaji Web:J607.005A
Beilstein Number:5611472
MDL:MFCD21364781
XlogP3-AA:4.30 (est)
Molecular Weight:340.37540000
Formula:C20 H20 O5
NMR Predictor:Predict (works with chrome, Edge or firefox)
Category:natural substances and extractives
 
US / EU / FDA / JECFA / FEMA / FLAVIS / Scholar / Patent Information:
Google Scholar:Search
Google Books:Search
Google Scholar: with word "volatile"Search
Google Scholar: with word "flavor"Search
Google Scholar: with word "odor"Search
Google Patents:Search
US Patents:Search
EU Patents:Search
Pubchem Patents:Search
PubMed:Search
NCBI:Search
 
Physical Properties:
Assay: 95.00 to 100.00
Food Chemicals Codex Listed: No
Boiling Point: 597.00 to 598.00 °C. @ 760.00 mm Hg (est)
Flash Point: 422.00 °F. TCC ( 216.40 °C. ) (est)
logP (o/w): 4.037 (est)
Soluble in:
 water, 1.546 mg/L @ 25 °C (est)
Insoluble in:
 water
 
Organoleptic Properties:
Odor and/or flavor descriptions from others (if found).
 
Cosmetic Information:
None found
 
Suppliers:
BOC Sciences
For experimental / research use only.
8-Flavaprenin 0.98
Odor: characteristic
Use: 8-Prenylnaringenin isolated from the herbs of Humulus lupulus. estrogenic activity
Coompo
For experimental / research use only.
8-Prenylnaringenin from Plants 98%
Hopsteiner
8-Prenylnaringenin
ANTIOXIDANT
Sigma-Aldrich
For experimental / research use only.
8-Prenylnaringenin
analytical standard
 
Safety Information:
 
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 8-prenyl naringenin usage levels up to:
 not for fragrance use.
 
Recommendation for 8-prenyl naringenin flavor usage levels up to:
 not for flavor use.
 
Safety References:
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 :480764
National Institute of Allergy and Infectious Diseases:Data
WGK Germany:3
(2S)-5,7-dihydroxy-2-(4-hydroxyphenyl)-8-(3-methylbut-2-enyl)-2,3-dihydrochromen-4-one
Chemidplus:C119737000
 
References:
 (2S)-5,7-dihydroxy-2-(4-hydroxyphenyl)-8-(3-methylbut-2-enyl)-2,3-dihydrochromen-4-one
NIST Chemistry WebBook:Search Inchi
Pubchem (cid):480764
Pubchem (sid):135301491
 
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):C18023
HMDB (The Human Metabolome Database):Search
FooDB:FDB012291
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
 hop
Search Trop Picture
 
Synonyms:
(2S)-5,7-dihydroxy-2-(4-hydroxyphenyl)-8-(3-methylbut-2-en-1-yl)-2,3-dihydro-4H-chromen-4-one
(2S)-5,7-dihydroxy-2-(4-hydroxyphenyl)-8-(3-methylbut-2-enyl)-2,3-dihydrochromen-4-one
(-)-(2S)-5,7-dihydroxy-2-(4-hydroxyphenyl)-8-(3-methylbut-2-enyl)chroman-4-one
(-)-(2S)-8-dimethylallylnaringenin
(S)-8-dimethylallylnaringenin
8-prenylnaringenin
 sophoraflavanone B
 

Articles:

PubMed:Limonoids and flavonoids from the flowers of Azadirachta indica var. siamensis, and their melanogenesis-inhibitory and cytotoxic activities.
PubMed:Inhibition of human cytochrome P450 enzymes by hops (Humulus lupulus) and hop prenylphenols.
PubMed:Herbal preparations for the menopause: beyond isoflavones and black cohosh.
PubMed:Analytical methods for quantitation of prenylated flavonoids from hops.
PubMed:Chroman-like cyclic prenylflavonoids promote neuronal differentiation and neurite outgrowth and are neuroprotective.
PubMed:[Comparative study on effect of 8-prenlynaringenin and narigenin on activity of osteoclasts cultured in vitro].
PubMed:Interaction of prenylated chalcones and flavanones from common hop with phosphatidylcholine model membranes.
PubMed:Human pharmacokinetics of xanthohumol, an antihyperglycemic flavonoid from hops.
PubMed:Microbial sulfation of 8-prenylnaringenin.
PubMed:Evaluation of estrogenic activity of licorice species in comparison with hops used in botanicals for menopausal symptoms.
PubMed:Effect of xanthohumol and 8-prenylnaringenin on MCF-7 breast cancer cells oxidative stress and mitochondrial complexes expression.
PubMed:Beer and beer compounds: physiological effects on skin health.
PubMed:Simultaneous determination of prenylflavonoid and hop bitter acid in beer lee by HPLC-DAD-MS.
PubMed:[Inhibitory effect of 8-prenylnaringenin on osteoclastogensis of bone marrow cells and bone resorption activity].
PubMed:Analytical condition setting a crucial step in the quantification of unstable polyphenols in acidic conditions: analyzing prenylflavanoids in biological samples by liquid chromatography-electrospray ionization triple quadruple mass spectrometry.
PubMed:Phytoestrogens in menopausal supplements induce ER-dependent cell proliferation and overcome breast cancer treatment in an in vitro breast cancer model.
PubMed:Hop extracts and hop substances in treatment of menopausal complaints.
PubMed:Differential regulation of detoxification enzymes in hepatic and mammary tissue by hops (Humulus lupulus) in vitro and in vivo.
PubMed:Method development and validation for ultra-high-pressure LC/MS/MS determination of hop prenylflavonoids in human serum.
PubMed:The prenyl group contributes to activities of phytoestrogen 8-prenynaringenin in enhancing bone formation and inhibiting bone resorption in vitro.
PubMed:A comparison of the anticancer properties of isoxanthohumol and 8-prenylnaringenin using in vitro models of colon cancer.
PubMed:Comparison between 8-prenylnarigenin and narigenin concerning their activities on promotion of rat bone marrow stromal cells' osteogenic differentiation in vitro.
PubMed:Antiproliferative activity and synthesis of 8-prenylnaringenin derivatives by demethylation of 7-O- and 4'-O-substituted isoxanthohumols.
PubMed:Prevention of disuse muscle atrophy by dietary ingestion of 8-prenylnaringenin in denervated mice.
PubMed:Transformation of 8-prenylnaringenin by Absidia coerulea and Beauveria bassiana.
PubMed:The influence of 8-prenylnaringenin on the activity of voltage-gated Kv1.3 potassium channels in human Jurkat T cells.
PubMed:The phytoestrogen 8-prenylnaringenin inhibits agonist-dependent activation of human platelets.
PubMed: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.
PubMed:Xanthohumol, a prenylated chalcone derived from hops, suppresses cancer cell invasion through inhibiting the expression of CXCR4 chemokine receptor.
PubMed:Hops (Humulus lupulus) inhibits oxidative estrogen metabolism and estrogen-induced malignant transformation in human mammary epithelial cells (MCF-10A).
PubMed:Production of monoclonal antibodies against hop-derived (Humulus lupulus L.) prenylflavonoids and the development of immunoassays.
PubMed:Production of 8-prenylnaringenin from isoxanthohumol through biotransformation by fungi cells.
PubMed:Biotransformation of the phytoestrogen 8-prenylnaringenin.
PubMed:Quantification of xanthohumol, isoxanthohumol, 8-prenylnaringenin, and 6-prenylnaringenin in hop extracts and derived capsules using secondary standards.
PubMed:The prenylflavonoid phytoestrogens 8-prenylnaringenin and isoxanthohumol diferentially suppress steroidogenesis in rat Leydig cells in ontogenesis.
PubMed:Inhibitors of hyaluronan export from hops prevent osteoarthritic reactions.
PubMed:Angiogenesis and inflammation signaling are targets of beer polyphenols on vascular cells.
PubMed:8-Prenylnaringenin is an inhibitor of multidrug resistance-associated transporters, P-glycoprotein and MRP1.
PubMed:Disposition of hop prenylflavonoids in human breast tissue.
PubMed:Activation of transgenic estrogen receptor-beta by selected phytoestrogens in a stably transduced rat serotonergic cell line.
PubMed:Recovery and metabolism of xanthohumol in germ-free and human microbiota-associated rats.
PubMed:Development of a high-throughput LC/APCI-MS method for the determination of thirteen phytoestrogens including gut microbial metabolites in human urine and serum.
PubMed:A randomized, double-blind, placebo-controlled, cross-over pilot study on the use of a standardized hop extract to alleviate menopausal discomforts.
PubMed:Xanthohumol inhibits IL-12 production and reduces chronic allergic contact dermatitis.
PubMed:Cosupplementation of isoflavones, prenylflavonoids, and lignans alters human exposure to phytoestrogen-derived 17beta-estradiol equivalents.
PubMed:Modulation of aflatoxin B1-mediated genotoxicity in primary cultures of human hepatocytes by diindolylmethane, curcumin, and xanthohumols.
PubMed:Prenylation has a compound specific effect on the estrogenicity of naringenin and genistein.
PubMed:Anti-inflammatory and vascularprotective properties of 8-prenylapigenin.
PubMed:Flavonoid-induced autophagy in hormone sensitive breast cancer cells.
PubMed:Oestrogenicity of prenylflavonoids from hops: activation of pro-oestrogens by intestinal bacteria.
PubMed:Dynamic residual complexity of natural products by qHNMR: solution stability of desmethylxanthohumol.
PubMed:8-Prenylnaringenin inhibits epidermal growth factor-induced MCF-7 breast cancer cell proliferation by targeting phosphatidylinositol-3-OH kinase activity.
PubMed:Microbial metabolites of 8-prenylnaringenin, an estrogenic prenylflavanone.
PubMed:Time dependency of uterine effects of naringenin type phytoestrogens in vivo.
PubMed:Direct determination of the estrogenic compounds 8-prenylnaringenin, zearalenone, alpha- and beta-zearalenol in beer by liquid chromatography-mass spectrometry.
PubMed:In vivo estrogenic comparisons of Trifolium pratense (red clover) Humulus lupulus (hops), and the pure compounds isoxanthohumol and 8-prenylnaringenin.
PubMed:Eubacterium limosum activates isoxanthohumol from hops (Humulus lupulus L.) into the potent phytoestrogen 8-prenylnaringenin in vitro and in rat intestine.
PubMed:Comparison of the phytohormones genistein, resveratrol and 8-prenylnaringenin as agents for preventing osteoporosis.
PubMed:Effects of long-term treatment with 8-prenylnaringenin and oral estradiol on the GH-IGF-1 axis and lipid metabolism in rats.
PubMed:Determination of phytoestrogens in dietary supplements by LC-MS/MS.
PubMed:Pharmacognostic and pharmacological profile of Humulus lupulus L.
PubMed:Development of a screening assay for ligands to the estrogen receptor based on magnetic microparticles and LC-MS.
PubMed:Cloning and characterization of naringenin 8-prenyltransferase, a flavonoid-specific prenyltransferase of Sophora flavescens.
PubMed:Aromatase inhibition by synthetic lactones and flavonoids in human placental microsomes and breast fibroblasts--a comparative study.
PubMed:Screening of synthetic and plant-derived compounds for (anti)estrogenic and (anti)androgenic activities.
PubMed:Inhibition of topoisomerase I activity and efflux drug transporters' expression by xanthohumol. from hops.
PubMed:Treatment of PC-3 and DU145 prostate cancer cells by prenylflavonoids from hop (Humulus lupulus L.) induces a caspase-independent form of cell death.
PubMed:Ability of prenylflavanones present in hops to induce apoptosis in a human Burkitt lymphoma cell line.
PubMed:8-Prenylnaringenin, inhibits estrogen receptor-alpha mediated cell growth and induces apoptosis in MCF-7 breast cancer cells.
PubMed:Modulation of breast cancer cell survival by aromatase inhibiting hop (Humulus lupulus L.) flavonoids.
PubMed:Effects of the chemically synthesized flavanone 7-(O-prenyl)naringenin-4'-acetate on the estrogen signaling pathway in vivo and in vitro.
PubMed:Binding of the hop (Humulus lupulus L.) chalcone xanthohumol to cytosolic proteins in Caco-2 intestinal epithelial cells.
PubMed:Microbial and dietary factors associated with the 8-prenylnaringenin producer phenotype: a dietary intervention trial with fifty healthy post-menopausal Caucasian women.
PubMed:Metabolism of isoflavones, lignans and prenylflavonoids by intestinal bacteria: producer phenotyping and relation with intestinal community.
PubMed:Resolution of diastereomeric flavonoid (1S)-(-)-camphanic acid esters via reversed-phase HPLC.
PubMed:Antihyperglycemic activity and chemical constituents of Eysenhardtia platycarpa.
PubMed:Subtle side-chain modifications of the hop phytoestrogen 8-prenylnaringenin result in distinct agonist/antagonist activity profiles for estrogen receptors alpha and beta.
PubMed:The hop phytoestrogen, 8-prenylnaringenin, reverses the ovariectomy-induced rise in skin temperature in an animal model of menopausal hot flushes.
PubMed:Microbial metabolism of the prenylated chalcone xanthohumol.
PubMed:Pharmacokinetics and systemic endocrine effects of the phyto-oestrogen 8-prenylnaringenin after single oral doses to postmenopausal women.
PubMed:pH-independent drug release of an extremely poorly soluble weakly acidic drug from multiparticulate extended release formulations.
PubMed:Morphologic changes induced by oral long-term treatment with 8-prenylnaringenin in the uterus, vagina, and mammary gland of castrated rats.
PubMed:The prenylflavonoid isoxanthohumol from hops (Humulus lupulus L.) is activated into the potent phytoestrogen 8-prenylnaringenin in vitro and in the human intestine.
PubMed:In vitro studies of intestinal permeability and hepatic and intestinal metabolism of 8-prenylnaringenin, a potent phytoestrogen from hops (Humulus lupulus L.).
PubMed:Anti-proliferative properties of prenylated flavonoids from hops (Humulus lupulus L.) in human prostate cancer cell lines.
PubMed:Identification of human hepatic cytochrome P450 enzymes involved in the metabolism of 8-prenylnaringenin and isoxanthohumol from hops (Humulus lupulus L.).
PubMed:Effect of hop (Humulus lupulus L.) flavonoids on aromatase (estrogen synthase) activity.
PubMed:Effects of 8-prenylnaringenin on the hypothalamo-pituitary-uterine axis in rats after 3-month treatment.
PubMed:Effects of estrogenic xenobiotics on human and mouse spermatozoa.
PubMed:A first prospective, randomized, double-blind, placebo-controlled study on the use of a standardized hop extract to alleviate menopausal discomforts.
PubMed:Effect of phytoestrogens on gene expression of carbonic anhydrase II in rat uterus and liver.
PubMed:Tissue specificity of 8-prenylnaringenin: protection from ovariectomy induced bone loss with minimal trophic effects on the uterus.
PubMed:Xanthohumol isolated from Humulus lupulus Inhibits menadione-induced DNA damage through induction of quinone reductase.
PubMed:Activation of proestrogens from hops (Humulus lupulus L.) by intestinal microbiota; conversion of isoxanthohumol into 8-prenylnaringenin.
PubMed:Comparison of the in vitro estrogenic activities of compounds from hops (Humulus lupulus) and red clover (Trifolium pratense).
PubMed:Regulation of osteoblastic phenotype and gene expression by hop-derived phytoestrogens.
PubMed:Comparative study of oestrogenic properties of eight phytoestrogens in MCF7 human breast cancer cells.
PubMed:Development of a radioimmunoassay for the quantitative determination of 8-prenylnaringenin in biological matrices.
PubMed:Determination of unusual soya and non-soya phytoestrogen sources in beer, fish products and other foods.
PubMed:Metabolism of xanthohumol and isoxanthohumol, prenylated flavonoids from hops (Humulus lupulus L.), by human liver microsomes.
PubMed:Phytochemical-induced changes in gene expression of carcinogen-metabolizing enzymes in cultured human primary hepatocytes.
PubMed:Estrogens and congeners from spent hops (Humulus lupulus).
PubMed:Naringenin-type flavonoids show different estrogenic effects in mammalian and teleost test systems.
PubMed:Two major metabolites of 8-prenylnaringenin are estrogenic in vitro.
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:Uterine effects of the phytoestrogen 6-(1,1-dimethylallyl)naringenin in rats.
PubMed:Xanthohumol and related prenylflavonoids from hops and beer: to your good health!
PubMed:Toxicity and cell cycle effects of synthetic 8-prenylnaringenin and derivatives in human cells.
PubMed:8-prenylnaringenin, a novel phytoestrogen, inhibits angiogenesis in vitro and in vivo.
PubMed:Regulation of gene expression by 8-prenylnaringenin in uterus and liver of Wistar rats.
PubMed:Prediction of ligand binding affinity and orientation of xenoestrogens to the estrogen receptor by molecular dynamics simulations and the linear interaction energy method.
PubMed:Metabolism of 8-prenylnaringenin, a potent phytoestrogen from hops (Humulus lupulus), by human liver microsomes.
PubMed:Antiandrogenic activity of the phytoestrogens naringenin, 6-(1,1-dimethylallyl)naringenin and 8-prenylnaringenin.
PubMed:Phytoestrogens: recent developments.
PubMed:"Bust enhancing" herbal products.
PubMed:8-Prenyl naringenin is a potent ERalpha selective phytoestrogen present in hops and beer.
PubMed:A binary screening assay for pro-oestrogens in food: metabolic activation using hepatic microsomes and detection with oestrogen sensitive recombinant yeast cells.
PubMed:Analysis of estrogenic activity of foodstuffs and cigarette smoke condensates using a yeast estrogen screening method.
PubMed: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.
PubMed:17beta-Estradiol and environmental estrogens significantly affect mammalian sperm function.
PubMed:Estrogenic activity of the phytoestrogens naringenin, 6-(1,1-dimethylallyl)naringenin and 8-prenylnaringenin.
PubMed:Oestrogenic activity of the hop phyto-oestrogen, 8-prenylnaringenin.
PubMed:Identification, quantitation and biological activity of phytoestrogens in a dietary supplement for breast enhancement.
PubMed:8-Prenylnaringenin, the phytoestrogen in hops and beer, upregulates the function of the E-cadherin/catenin complex in human mammary carcinoma cells.
PubMed:The endocrine activities of 8-prenylnaringenin and related hop (Humulus lupulus L.) flavonoids.
PubMed:Prenylflavonoids from hops inhibit the metabolic activation of the carcinogenic heterocyclic amine 2-amino-3-methylimidazo[4, 5-f]quinoline, mediated by cDNA-expressed human CYP1A2.
PubMed:In vitro inhibition of human P450 enzymes by prenylated flavonoids from hops, Humulus lupulus.
PubMed:Determination of the hop-derived phytoestrogen, 8-prenylnaringenin, in beer by gas chromatography/mass spectrometry.
PubMed:Identification of a potent phytoestrogen in hops (Humulus lupulus L.) and beer.
 
Notes:
None found
Please share your Comments.
Email Address:
Top of Page Home
Copyright © 1980-2021 The Good Scents Company (tgsc) ™ Disclaimer Privacy Policy