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

isoxanthohumol
4H-1-benzopyran-4-one, 2,3-dihydro-7-hydroxy-2-(4-hydroxyphenyl)-5-methoxy-8-(3-methyl-2-buten-1-yl)-

Supplier Sponsors

Name:7-hydroxy-2-(4-hydroxyphenyl)-5-methoxy-8-(3-methylbut-2-enyl)-2,3-dihydrochromen-4-one
CAS Number: 70872-29-6Picture of molecule3D/inchi
FDA UNII: Search
Nikkaji Web:J120.928K
Beilstein Number:10199264
MDL:MFCD00238718
XlogP3-AA:4.10 (est)
Molecular Weight:354.40234000
Formula:C21 H22 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:
Google Scholar:Search
Google Books:Search
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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: 585.80 °C. @ 760.00 mm Hg (est)
Flash Point: 407.00 °F. TCC ( 208.60 °C. ) (est)
logP (o/w): 5.070 (est)
Soluble in:
 water, 1.946 mg/L @ 25 °C (est)
 
Organoleptic Properties:
Odor and/or flavor descriptions from others (if found).
 
Cosmetic Information:
None found
 
Suppliers:
BOC Sciences
For experimental / research use only.
Isoxanthohumol 0.98
Odor: characteristic
Use: Isoxanthohumol isolated from the roots of Sophora flavescens Ait. antiviral activity; antioxidant, anti-inflammatory, and antiangiogenic properties
ExtraSynthese
For experimental / research use only.
isoXanthohumol
Hopsteiner
isoXanthohumol
Santa Cruz Biotechnology
For experimental / research use only.
isoXanthohumol ≥98%
Sigma-Aldrich
For experimental / research use only.
isoXanthohumol
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 isoxanthohumol usage levels up to:
 not for fragrance use.
 
Recommendation for isoxanthohumol 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 :513197
National Institute of Allergy and Infectious Diseases:Data
WGK Germany:3
7-hydroxy-2-(4-hydroxyphenyl)-5-methoxy-8-(3-methylbut-2-enyl)-2,3-dihydrochromen-4-one
 
References:
 7-hydroxy-2-(4-hydroxyphenyl)-5-methoxy-8-(3-methylbut-2-enyl)-2,3-dihydrochromen-4-one
NIST Chemistry WebBook:Search Inchi
Pubchem (cid):513197
Pubchem (sid):135284376
 
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
CHEMBL:View
HMDB (The Human Metabolome Database):HMDB34048
FooDB:FDB012290
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:
4H-1-benzopyran-4-one, 2,3-dihydro-7-hydroxy-2-(4-hydroxyphenyl)-5-methoxy-8-(3-methyl-2-buten-1-yl)-
7-hydroxy-2-(4-hydroxyphenyl)-5-methoxy-8-(3-methyl-2-buten-1-yl)-2,3-dihydro-4H-chromen-4-one
7-hydroxy-2-(4-hydroxyphenyl)-5-methoxy-8-(3-methylbut-2-enyl)-2,3-dihydrochromen-4-one
 

Articles:

PubMed:Beer elicits vasculoprotective effects through Akt/eNOS activation.
PubMed:Pharmacokinetics of prenylated hop phenols in women following oral administration of a standardized extract of hops.
PubMed:Hop-derived prenylflavonoids are substrates and inhibitors of the efflux transporter breast cancer resistance protein (BCRP/ABCG2).
PubMed:Biological and chemical standardization of a hop (Humulus lupulus) botanical dietary supplement.
PubMed:Effects of xanthohumol-rich hop extract on the differentiation of preadipocytes.
PubMed:Mass spectrometry-based metabolomics approach to determine differential metabolites between regular and non-alcohol beers.
PubMed:[Non-alkaloid components from Sophora flavescens].
PubMed:Urinary isoxanthohumol is a specific and accurate biomarker of beer consumption.
PubMed:Inhibition of human cytochrome P450 enzymes by hops (Humulus lupulus) and hop prenylphenols.
PubMed:Antioxidant activity and spectroscopic data of isoxanthohomol oxime and related compounds.
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:Isoxanthohumol modulates angiogenesis and inflammation via vascular endothelial growth factor receptor, tumor necrosis factor alpha and nuclear factor kappa B pathways.
PubMed:A semi-automatic microextraction in packed sorbent, using a digitally controlled syringe, combined with ultra-high pressure liquid chromatography as a new and ultra-fast approach for the determination of prenylflavonoids in beers.
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: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:Antioxidant and antiproliferative activity of glycosides obtained by biotransformation of xanthohumol.
PubMed:Method development and validation for ultra-high-pressure LC/MS/MS determination of hop prenylflavonoids in human serum.
PubMed:Fungal metabolites of xanthohumol with potent antiproliferative activity on human cancer cell lines in vitro.
PubMed:A comparison of the anticancer properties of isoxanthohumol and 8-prenylnaringenin using in vitro models of colon cancer.
PubMed:Antiproliferative activity and synthesis of 8-prenylnaringenin derivatives by demethylation of 7-O- and 4'-O-substituted isoxanthohumols.
PubMed:Xanthohumol, a prenylated chalcone from Humulus lupulus L., inhibits cholesteryl ester transfer protein.
PubMed:Inverse Virtual Screening allows the discovery of the biological activity of natural compounds.
PubMed:Pitfalls in cell culture work with xanthohumol.
PubMed:Xanthohumol, a prenylated chalcone derived from hops, suppresses cancer cell invasion through inhibiting the expression of CXCR4 chemokine receptor.
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:Inhibition of TGF-β signaling, vasculogenic mimicry and proinflammatory gene expression by isoxanthohumol.
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:Disposition of hop prenylflavonoids in human breast tissue.
PubMed:Recovery and metabolism of xanthohumol in germ-free and human microbiota-associated rats.
PubMed:Xanthohumol and related prenylated flavonoids inhibit inflammatory cytokine production in LPS-activated THP-1 monocytes: structure-activity relationships and in silico binding to myeloid differentiation protein-2 (MD-2).
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: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:Oestrogenicity of prenylflavonoids from hops: activation of pro-oestrogens by intestinal bacteria.
PubMed:LC-MS/MS quantitation of hop-derived bitter compounds in beer using the ECHO technique.
PubMed:[Main flavonoids from Sophora flavescenes].
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:Inhibition of topoisomerase I activity and efflux drug transporters' expression by xanthohumol. from hops.
PubMed:Effect of xanthohumol and isoxanthohumol on 3T3-L1 cell apoptosis and adipogenesis.
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:Modulation of folate uptake in cultured human colon adenocarcinoma Caco-2 cells by dietary compounds.
PubMed:Characterization of flavonoids in the extract of Sophora flavescens Ait. by high-performance liquid chromatography coupled with diode-array detector and electrospray ionization mass spectrometry.
PubMed:Modulation of breast cancer cell survival by aromatase inhibiting hop (Humulus lupulus L.) flavonoids.
PubMed:Enantioseparation of isoxanthohumol in beer by hydroxypropyl-gamma-cyclodextrin-modified micellar electrokinetic chromatography.
PubMed:Binding of the hop (Humulus lupulus L.) chalcone xanthohumol to cytosolic proteins in Caco-2 intestinal epithelial cells.
PubMed:Acute and chronic effects of some dietary bioactive compounds on folic acid uptake and on the expression of folic acid transporters by the human trophoblast cell line BeWo.
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:Determination of xanthohumol in hops (Humulus lupulus L.) by nonaqueous CE.
PubMed:Microbial metabolism of the prenylated chalcone xanthohumol.
PubMed:Analysis of xanthohumol and isoxanthohumol in different hop products by liquid chromatography-diode array detection-electrospray ionization tandem mass spectrometry.
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: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:Glycosidase inhibitory flavonoids from Sophora flavescens.
PubMed:Enrichment of xanthohumol in the brewing process.
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:Beer constituents as potential cancer chemopreventive agents.
PubMed:Development of a radioimmunoassay for the quantitative determination of 8-prenylnaringenin in biological matrices.
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:Inhibition of endothelial cell functions by novel potential cancer chemopreventive agents.
PubMed:Xanthohumol and related prenylflavonoids from hops and beer: to your good health!
PubMed:Inhibition of peroxynitrite-mediated LDL oxidation by prenylated flavonoids: the alpha,beta-unsaturated keto functionality of 2'-hydroxychalcones as a novel antioxidant pharmacophore.
PubMed:A binary screening assay for pro-oestrogens in food: metabolic activation using hepatic microsomes and detection with oestrogen sensitive recombinant yeast cells.
PubMed:Cancer chemopreventive activity of Xanthohumol, a natural product derived from hop.
PubMed:Identification, quantitation and biological activity of phytoestrogens in a dietary supplement for breast enhancement.
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:Fate of xanthohumol and related prenylflavonoids from hops to beer.
PubMed:In vitro inhibition of human P450 enzymes by prenylated flavonoids from hops, Humulus lupulus.
PubMed:Antiproliferative and cytotoxic effects of prenylated flavonoids from hops (Humulus lupulus) in human cancer cell lines.
PubMed:Quantitative analysis of xanthohumol and related prenylflavonoids in hops and beer by liquid chromatography-tandem mass spectrometry.
 
Notes:
Isol. from hop (Humulus lupulus)
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