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Category: natural substances and extractives
US / EU / FDA / JECFA / FEMA / FLAVIS / Scholar / Patent Information:
Physical Properties:
| Assay: | 95.00 to 100.00 %
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| Food Chemicals Codex Listed: | No |
| Boiling Point: | 585.80 °C. @ 760.00 mm Hg (est)
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| Flash Point: | 407.00 °F. TCC ( 208.60 °C. ) (est)
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| logP (o/w): | 5.070 (est) |
| Soluble in: |
| | water, 1.946 mg/L @ 25 °C (est) |
Organoleptic Properties:
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| Odor and/or flavor descriptions from others (if found). |
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Cosmetic Information:
Suppliers:
Safety Information:
| Preferred SDS: View |
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| Hazards identification |
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| Classification of the substance or mixture |
| GHS Classification in accordance with 29 CFR 1910 (OSHA HCS) |
| None found. |
| GHS Label elements, including precautionary statements |
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| Pictogram | |
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| Hazard statement(s) |
| None found. |
| Precautionary statement(s) |
| None found. |
| Oral/Parenteral Toxicity: |
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Not determined
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| Dermal Toxicity: |
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Not determined
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| Inhalation Toxicity: |
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Not determined
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Safety in Use Information:
| Category: | natural substances and extractives |
| Recommendation for isoxanthohumol usage levels up to: | | | not for fragrance use.
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| Recommendation for isoxanthohumol flavor usage levels up to: |
| | not for flavor use.
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Safety References:
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:
Potential Blenders and core components note
Potential Uses:
Occurrence (nature, food, other): note
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. |
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