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

xanthohumol
2-propen-1-one, 1-[2,4-dihydroxy-6-methoxy-3-(3-methyl-2-buten-1-yl)phenyl]-3-(4-hydroxyphenyl)-, (2E)-

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Name:(E)-1-[2,4-dihydroxy-6-methoxy-3-(3-methylbut-2-enyl)phenyl]-3-(4-hydroxyphenyl)prop-2-en-1-one
CAS Number: 6754-58-1Picture of molecule3D/inchi
FDA UNII: T4467YT1NT
Nikkaji Web:J1.438.271B
MDL:MFCD00210576
XlogP3-AA:5.10 (est)
Molecular Weight:354.40234000
Formula:C21 H22 O5
BioActivity Summary:listing
NMR Predictor:Predict (works with chrome, Edge or firefox)
Category:cosmetic agents
 
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: 576.00 to 577.00 °C. @ 760.00 mm Hg (est)
Flash Point: 398.00 °F. TCC ( 203.40 °C. ) (est)
logP (o/w): 5.172 (est)
Soluble in:
 water, 0.5131 mg/L @ 25 °C (est)
Insoluble in:
 water
 
Organoleptic Properties:
Odor and/or flavor descriptions from others (if found).
 
Cosmetic Information:
CosIng:cosmetic data
Cosmetic Uses: skin conditioning
 
Suppliers:
Alfa Biotechnology
For experimental / research use only.
Xanthohumol 98%
Axsyn
For experimental / research use only.
Xanthohumol
BOC Sciences
For experimental / research use only.
Xanthohumol >98%
Odor: characteristic
Use: Anti-inflammatory/antibacterial
Changsha Organic Herb
Hops Flower Extract 1% Xanthohumol
Hopsteiner
Xantho-Flav
ANTIOXIDANT
Indis NV
For experimental / research use only.
Xanthohumol
Sigma-Aldrich: Sigma
For experimental / research use only.
Xanthohumol from hop (Humulus lupulus) ≥96% (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:
Not determined
Dermal Toxicity:
Not determined
Inhalation Toxicity:
Not determined
 
Safety in Use Information:
Category:
cosmetic agents
Recommendation for xanthohumol usage levels up to:
 not for fragrance use.
 
Recommendation for xanthohumol flavor usage levels up to:
 not for flavor use.
 
Safety References:
European Food Safety Authority (EFSA) reference(s):

Xanthohumol in XERME®, a xanthohumol-enriched roasted malt extract, and protection of DNA from oxidative damage: evaluation of a health claim pursuant to Article 13(5) of Regulation (EC) No 1924/2006
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 :639665
National Institute of Allergy and Infectious Diseases:Data
WGK Germany:3
(E)-1-[2,4-dihydroxy-6-methoxy-3-(3-methylbut-2-enyl)phenyl]-3-(4-hydroxyphenyl)prop-2-en-1-one
Chemidplus:0006754581
 
References:
 (E)-1-[2,4-dihydroxy-6-methoxy-3-(3-methylbut-2-enyl)phenyl]-3-(4-hydroxyphenyl)prop-2-en-1-one
NIST Chemistry WebBook:Search Inchi
Pubchem (cid):639665
Pubchem (sid):135118027
 
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):C16417
HMDB (The Human Metabolome Database):HMDB37479
FooDB:FDB016545
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:
(E)-1-(2,4-dihydroxy-6-methoxy-3-(3-methyl-2-butenyl)phenyl)-3-(4-hydroxyphenyl)-2-propen-1-one
(E)-1-[2,4-dihydroxy-6-methoxy-3-(3-methylbut-2-enyl)phenyl]-3-(4-hydroxyphenyl)prop-2-en-1-one
2-propen-1-one, 1-[2,4-dihydroxy-6-methoxy-3-(3-methyl-2-buten-1-yl)phenyl]-3-(4-hydroxyphenyl)-, (2E)-
2-propen-1-one, 1-[2,4-dihydroxy-6-methoxy-3-(3-methyl-2-butenyl)phenyl]-3-(4-hydroxyphenyl)-, (2E)-
 

Articles:

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:Xanthohumol, a Prenylated Chalcone from Beer Hops, Acts as an α-Glucosidase Inhibitor in Vitro.
PubMed:Xanthohumol modulates inflammation, oxidative stress, and angiogenesis in type 1 diabetic rat skin wound healing.
PubMed:Human pharmacokinetics of xanthohumol, an antihyperglycemic flavonoid from hops.
PubMed:Xanthohumol modulates the expression of osteoclast-specific genes during osteoclastogenesis in RAW264.7 cells.
PubMed:Curcumin analogue identified as hyaluronan export inhibitor by virtual docking to the ABC transporter MRP5.
PubMed:Electrochemical versus spectrophotometric assessment of antioxidant activity of hop (Humulus lupulus L.) products and individual compounds.
PubMed:Simultaneous determination of prenylflavonoid and hop bitter acid in beer lee by HPLC-DAD-MS.
PubMed:Xanthohumol ameliorates atherosclerotic plaque formation, hypercholesterolemia, and hepatic steatosis in ApoE-deficient mice.
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:Differential regulation of detoxification enzymes in hepatic and mammary tissue by hops (Humulus lupulus) in vitro and in vivo.
PubMed:Xanthohumol and it's emerging anti-neoplastic effects: beyond it's role in breast carcinomas.
PubMed:Xanthohumol, a prenylated chalcone from Humulus lupulus L., inhibits cholesteryl ester transfer protein.
PubMed:Prenylated chalcone xanthohumol associates with histones in breast cancer cells--a novel target identified by a monoclonal antibody.
PubMed:Xanthohumol prevents carbon tetrachloride-induced acute liver injury in rats.
PubMed:Xanthohumol lowers body weight and fasting plasma glucose in obese male Zucker fa/fa rats.
PubMed:Neuroprotective effects of xanthohumol, a prenylated flavonoid from hops (Humulus lupulus), in ischemic stroke of rats.
PubMed:Pharmacokinetics of xanthohumol and metabolites in rats after oral and intravenous administration.
PubMed:Protective effects of xanthohumol against the genotoxicity of heterocyclic aromatic amines MeIQx and PhIP in bacteria and in human hepatoma (HepG2) cells.
PubMed:Xanthohumol uptake and intracellular kinetics in hepatocytes, hepatic stellate cells, and intestinal cells.
PubMed:Xanthohumol-supplemented beer modulates angiogenesis and inflammation in a skin wound healing model. Involvement of local adipocytes.
PubMed:Novel application of square-wave adsorptive-stripping voltammetry for the determination of xanthohumol in spent hops.
PubMed:Computational analysis for hepatic safety signals of constituents present in botanical extracts widely used by women in the United States for treatment of menopausal symptoms.
PubMed:Inhibitors of hyaluronan export from hops prevent osteoarthritic reactions.
PubMed:Xanthohumol, a prenylated flavonoid contained in beer, prevents the induction of preneoplastic lesions and DNA damage in liver and colon induced by the heterocyclic aromatic amine amino-3-methyl-imidazo[4,5-f]quinoline (IQ).
PubMed:Disposition of hop prenylflavonoids in human breast tissue.
PubMed:Xanthohumol, a prenylated chalcone from hops, modulates hepatic expression of genes involved in thyroid hormone distribution and metabolism.
PubMed:Xanthohumol feeding does not impair organ function and homoeostasis in mice.
PubMed:Recovery and metabolism of xanthohumol in germ-free and human microbiota-associated rats.
PubMed:Selective inhibition of prenylated flavonoids from Sophora flavescens against BACE1 and cholinesterases.
PubMed:Triggering of dendritic cell apoptosis by xanthohumol.
PubMed:Determination of xanthohumol in beer based on cloud point extraction coupled with high performance liquid chromatography.
PubMed:Xanthohumol, a chalcon derived from hops, inhibits hepatic inflammation and fibrosis.
PubMed:Anti-obesity effects of xanthohumol plus guggulsterone in 3T3-L1 adipocytes.
PubMed:Inhibition of suicidal erythrocyte death by xanthohumol.
PubMed:Xanthohumol from hop (Humulus lupulus L.) is an efficient inhibitor of monocyte chemoattractant protein-1 and tumor necrosis factor-alpha release in LPS-stimulated RAW 264.7 mouse macrophages and U937 human monocytes.
PubMed:Fundamentals and health benefits of xanthohumol, a natural product derived from hops and beer.
PubMed:LC-MS/MS quantitation of hop-derived bitter compounds in beer using the ECHO technique.
PubMed:Xanthohumol influences preadipocyte differentiation: implication of antiproliferative and apoptotic effects.
PubMed:Antimutagenicity of hops (Humulus lupulus L.): bioassay-directed fractionation and isolation of xanthohumol.
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:Microbial and dietary factors associated with the 8-prenylnaringenin producer phenotype: a dietary intervention trial with fifty healthy post-menopausal Caucasian women.
PubMed:Relevance of organic farming and effect of climatological conditions on the formation of alpha-acids, beta-acids, desmethylxanthohumol, and xanthohumol in hop (Humulus lupulus L.).
PubMed:Effect of hop (Humulus lupulus L.) flavonoids on aromatase (estrogen synthase) activity.
PubMed:Optimization of conditions for supercritical fluid extraction of flavonoids from hops (Humulus lupulus L.).
PubMed:Xanthohumol kills B-chronic lymphocytic leukemia cells by an apoptotic mechanism.
PubMed:Xanthohumol, a new all-rounder?
PubMed:Xanthohumol, the chalcone from beer hops (Humulus lupulus L.), is the ligand for farnesoid X receptor and ameliorates lipid and glucose metabolism in KK-A(y) mice.
PubMed:Enrichment of xanthohumol in the brewing process.
PubMed:Broad spectrum anti-infective potential of xanthohumol from hop (Humulus lupulus L.) in comparison with activities of other hop constituents and xanthohumol metabolites.
PubMed:A safety study of oral xanthohumol administration and its influence on fertility in Sprague Dawley rats.
PubMed:In vitro phase II metabolism of xanthohumol by human UDP-glucuronosyltransferases and sulfotransferases.
PubMed:Xanthohumol stimulates iodide uptake in rat thyroid-derived FRTL-5 cells.
PubMed:Xanthohumol does not affect the composition of rat intestinal microbiota.
PubMed:Biosynthetic (14)C-labelling of xanthohumol in hop cones.
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:Xanthohumol induces apoptosis in cultured 40-16 human colon cancer cells by activation of the death receptor- and mitochondrial pathway.
PubMed:In vitro free radical and ONOO- scavengers from Sophora flavescens.
PubMed:Cloning and molecular analysis of the regulatory factor HlMyb1 in hop (Humulus lupulus L.) and the potential of hop to produce bioactive prenylated flavonoids.
PubMed:Development of a radioimmunoassay for the quantitative determination of 8-prenylnaringenin in biological matrices.
PubMed:Formation and accumulation of alpha-acids, beta-acids, desmethylxanthohumol, and xanthohumol during flowering of hops (Humulus lupulus L.).
PubMed:Identification, quantitation and biological activity of phytoestrogens in a dietary supplement for breast enhancement.
PubMed:Influence of prenylated and non-prenylated flavonoids on liver microsomal lipid peroxidation and oxidative injury in rat hepatocytes.
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:Antioxidant and prooxidant actions of prenylated and nonprenylated chalcones and flavanones in vitro.
PubMed:Fate of xanthohumol and related prenylflavonoids from hops to beer.
PubMed:Antiproliferative and cytotoxic effects of prenylated flavonoids from hops (Humulus lupulus) in human cancer cell lines.
 
Notes:
Isol. from Humulus lupulus (hops)
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