521-48-2

Basic information

• Product Name: ISOXANTHOHUMOL
• Synonyms: ISOXANTHOHUMOL;4',7-DIHYDROXY-5-METHOXY-8-PRENYLFLAVANONE;2-(4-Hydroxyphenyl)-5-methoxy-7-hydroxy-8-(3-methyl-2-butenyl)-2,3-dihydro-4H-1-benzopyran-4-one;2,3-Dihydro-7-hydroxy-2-(4-hydroxyphenyl)-5-methoxy-8-(3-methyl-2-butenyl)-4H-1-benzopyran-4-one;2,3-Dihydro-7-hydroxy-2-(4-hydroxyphenyl)-5-methoxy-8-(3-methyl-2-buten-1-yl)-4H-1-benzopyran-4-one;4',7-Dihydroxy-5-methoxy-8-(3-methyl-2-butenyl)flavanone
• CAS NO: 521-48-2
• Molecular Formula: C₂₁H₂₂O₅
• Molecular Weight: 354.4
• Mol File: 521-48-2.mol
• Article Data: 12

Chemical Properties

• Boiling Point: 585.8±50.0 °C(Predicted)
• Appearance: /
• Density: 1.245±0.06 g/cm3(Predicted)
• Storage Temp.: 2-8°C
• Solubility: DMSO (Slightly), Methanol (Slightly)
• PKA: 7.90±0.40(Predicted)
• BRN: 10199264
• CAS DataBase Reference: ISOXANTHOHUMOL(CAS DataBase Reference)
• NIST Chemistry Reference: ISOXANTHOHUMOL(521-48-2)
• EPA Substance Registry System: ISOXANTHOHUMOL(521-48-2)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 521-48-2(Hazardous Substances Data)

Usage

Description

Isoxanthohumol is a natural, prenylated chalcone isolated from the hop plant, H. lupulus (hops). It has diverse biological activities, including antiproliferative, anti-inflammatory, and antiviral properties. In B16 and A375 melanoma cells, isoxanthohumol inhibits proliferation (IC50s = 22.15 and 22.9 μM in an MTT assay), slows cell division, and induces apoptosis. Isoxanthohumol reversibly inhibits Kv1.3 channels with an EC50 value of 7.8 μM in human Jurkat T cells using patch clamp electrophysiology. It has strong deterrent properties against the peach potato aphid. It has also been used as a marker of beer consumption. Isoxanthohumol is metabolized in the liver and intestine to 8-prenylnaringenin , a potent phytoestrogen.

Uses

Isoxanthohumol is a prenylated flavone isolated from hop. A chromane-like cyclic prenylflavonoids for neurological disorder therapy. Isoxanthohumol is a prenylated flavonoid phytoestrogen which is an apoptosis inducer in mature adipocytes

Upstream product

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

Downstream Products

• 72060-15-2 2'',3''-dihydroisoxanthohumol 
• 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 
• 906368-85-2 7,4'-di-triisopropylsilyloxy-8-prenylnaringenin 
• 936573-99-8 (+/-)-8-(3-Methylbutyl)naringenin 
• 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 

Relevant articles and documents

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

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

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

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.