521-48-2

Usage

Uses

Used in Pharmaceutical Applications:
Isoxanthohumol is used as a therapeutic agent for neurological disorders due to its chromane-like cyclic prenylflavonoids properties. It has demonstrated potential in treating various neurological conditions.
Used in Anticancer Applications:
Isoxanthohumol is used as an antiproliferative agent in the treatment of melanoma, specifically B16 and A375 melanoma cells. It inhibits cell proliferation, slows cell division, and induces apoptosis in these cells.
Used in Insect Deterrent Applications:
Isoxanthohumol is used as a strong deterrent against the peach potato aphid, providing a natural method for pest control in agriculture.
Used in Beer Consumption Analysis:
Isoxanthohumol is used as a marker for beer consumption, as it is metabolized in the liver and intestine to 8-prenylnaringenin, a potent phytoestrogen. This allows for the detection and analysis of beer intake in individuals.
Used in Drug Delivery Systems:
While not explicitly mentioned in the provided materials, due to its antiproliferative and apoptosis-inducing properties, isoxanthohumol could potentially be utilized in drug delivery systems to enhance the efficacy of cancer treatments and improve the delivery of therapeutic agents to target cells.

Upstream product

• 569-83-5 xanthoarnol 
• 569-83-5 xanthohumol 
• 334701-04-1 2-(4-acetoxyphenyl)-5-hydroxy-8-(3-methylbut-2-enyloxy)-4-oxochroman-7-yl acetate 
• 334701-03-0 4-(7-acetoxy-5-((3-methylbut-2-en-1-yl)oxy)-4-oxochroman-2-yl)phenyl acetate 
• 480-41-1 5,7-Dihydroxy-2-(4-hydroxy-phenyl)-chroman-4-on 
• 3162-03-6 2-(4-acetoxyphenyl)-5-hydroxy-4-oxochroman-7-yl acetate 
• 115063-39-3 desmethylxanthohumol 

Downstream Products

• 906368-84-1 7,4'-di-triisopropylsilyloxy-isoxanthohumol 
• 68634-20-8 4',5-dihydroxy-6'',6''-dimethyl-5'',6''-dihydro-4''H-pyrano[2'',3'':7,8]flavanone 
• 68682-02-0 5,7-Dihydroxy-2-(4-hydroxy-phenyl)-8-(3-methyl-but-2-enyl)-chroman-4-one 
• 569-83-5 xanthohumol 
• 68682-01-9 5,7,4'-trihydroxy-6-prenylflavanone 
• 68634-18-4 (+/-)-2,3,7,8-Tetrahydro-5-hydroxy-2-(4-hydroxyphenyl)-8,8-dimethyl-4H,6H-benzo<1,2-b:5,4-b'>dipyran-4-on 
• 936573-99-8 (+/-)-8-(3-Methylbutyl)naringenin 

Relevant academic research and scientific papers

Synthesis and antiproliferative activity of minor hops prenylflavonoids and new insights on prenyl group cyclization

Synthesis of minor prenylflavonoids found in hops and their non-natural derivatives were performed. The antiproliferative activity of the obtained compounds against some human cancer cell lines was investigated. Using xanthohumol isolated from spent hops

Analysis of the components of hard resin in hops (Humulus lupulus L.) and structural elucidation of their transformation products formed during the brewing process

The resins from hops (Humulus lupulus L.), which add the bitter taste to beer, are classified into two main subfractions, namely, soft and hard resins. α- and β-Acids in soft resin and their transformation during the wort boiling process are well-studied; however, other constituents in resins, especially hard resin, have been unidentified. In this study, we identified humulinones and hulupones as soft-resin components, in addition to 4′-hydroxyallohumulinones and tricyclooxyisohumulones A and B as hard-resin components. These compounds are all oxidation products derived from α- and β-acids. We also investigated compositional changes in the hard resin during the wort boiling process, which has a significant effect on the taste of the beer, by using model boiling experiments. The major changes were identified to be isomerization of 4′-hydroxyallohumulinones into 4′- hydroxyallo-cis-humulinones, followed by decomposition into cis-oxyhumulinic acids. These findings will be helpful in systematically evaluating and optimizing the effect of the hard resin on beer quality.

Prenylflavonoids from Humulus lupulus

Five flavonoids were isolated from the resin part of the female inflorescences of Humulus lupulus, together with four known hop flavonoids, i.e. xanthohumol, 2',4',6',4-tetrahydroxy-3'-C-prenylchalcone, iso- xanthohumol and 6-prenylnaringenin. The new hop

An efficient synthesis of the phytoestrogen 8-prenylnaringenin from isoxanthohumol with magnesium iodide etherate

Xanthohumol was isolated from supercritical carbon dioxide-spent hop and transformed into isoxanthohumol. The demethylation of isoxanthohumol with the best yield 93% occurred when MgI2 etherate in anhydrous THF was applied. Salts such as MgBrs

Neuroregenerative Potential of Prenyl- And Pyranochalcones: A Structure-Activity Study

Loss of neuronal tissue is a hallmark of age-related neurodegenerative diseases. Since adult neurogenesis has been confirmed in the human brain, great interest has arisen in substances stimulating the endogenous neuronal regeneration mechanism based on ad

Synthesis of xanthohumol and xanthohumol-d3from naringenin

A six-step synthesis of xanthohumol (1a) and its d3-derivative (1b) from easily accessible naringenin is reported. The prenyl side chain was introduced by Mitsunobu reaction followed by the europium-catalyzed Claisen rearrangement and base-mediated opening of chromanone gave access to an α,β-conjugated ketone system. Compound1bwas used as an internal standard in stable isotope dilution assays of1ain two Polish beers.

Chromane-like cyclic prenylflavonoids for the medical intervention in neurological disorders

The present invention relates to certain chromane-like cyclic prenylflavonoids, in particular the compounds of formulae (I), (II) and (III) as described and defined herein, for use in the treatment or prevention of a neurological disorder, as well as their use in promoting neuronal differentiation, neurite outgrowth and neuroprotection.

An efficient synthesis of the phytoestrogen 8-prenylnaringenin from xanthohumol by a novel demethylation process

8-Prenylnaringenin, a flavonoid, is the strongest known phytoestrogen (plant derived estrogen mimic) used in phytomedicinal applications. Starting from xanthohumol a byproduct of hops-extraction, 8-prenylnaringenin can be synthesized via isoxanthohumol. Of various demethylation procedures tested, the best yield (92%) is obtained by treatment with scandium trifluoromethanesulfonate and potassium iodide without any need of protection. The demethylation with AlBr3/collidine and of the TIPS protected isoxanthohumol provides good results too.

METHOD FOR PRODUCING NARINGENIN DERIVATIVES FROM XANTHOHUMOL

The invention relates to an efficient method for producing naringenin derivatives from xanthohumol or derivatives thereof. The method comprises, in particular, the production of isoxanthohumol, for example, even in an enantiomer-enriched form, from xanthohumol and subsequently demethylating isoxanthohumol according to specific procedures while obtaining corresponding naringenin derivatives such as 8-prenylnaringenin.

Production of hop extracts having oestrogenic and antiproliferative bioactivity

The invention relates to a method for the production of a hop extract enriched in prenylated flavonoids or derivatives thereof, whereby the method comprises the steps of subjecting a hop product to an isomerisation reaction in the presence of an amount of a base and to at least one extraction.