isoxanthohumol

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

CAS: 70872-29-6 C21 H22 O5 MW: 354.40234000

Identification

Nameisoxanthohumol
IUPAC7-hydroxy-2-(4-hydroxyphenyl)-5-methoxy-8-(3-methylbut-2-enyl)-2,3-dihydrochromen-4-one
CAS Number70872-29-6
FDA UNIISearch
Molecular FormulaC21 H22 O5
Molecular Weight354.40234000
MDL NumberMFCD00238718
Nikkaji NumberJ120.928K
Beilstein10199264

Regulatory

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)

No sensory data available

Safety Information

Oral/Parenteral ToxicityNot determined
Dermal ToxicityNot determined
Inhalation ToxicityNot determined

GHS Classification

['GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)', 'GHS Label elements, including precautionary statements']

Safety in Use

Categorynatural substances and extractives
Recommendation for isoxanthohumol usage levels up tonot for fragrance use.
Recommendation for isoxanthohumol flavor usage levels up tonot for flavor use.

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Potential Uses

None Found

Natural Occurrence

hop

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 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.