ISOXANTHOHUMOL

Base Information

• Chemical Name: ISOXANTHOHUMOL
• CAS No.: 521-48-2
• Molecular Formula: C21H22O5
• Molecular Weight: 354.403
• Hs Code.: 2932999099
• Mol file: 521-48-2.mol

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

Chemical Property of ISOXANTHOHUMOL

Chemical Property:

• Boiling Point: 585.8±50.0 °C(Predicted)
• PKA: 7.90±0.40(Predicted)
• PSA: 75.99000
• Density: 1.245±0.06 g/cm3(Predicted)
• LogP: 4.32160
• Storage Temp.: 2-8°C
• Solubility.: DMSO (Slightly), Methanol (Slightly)

Purity/Quality:

98%Min ^*data from raw suppliers

Isoxanthohumol ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• 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

Technology Process of ISOXANTHOHUMOL

There total 9 articles about ISOXANTHOHUMOL which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 99.0%

4-(7-acetoxy-5-methoxy-8-(3-methylbut-2-en-1-yl)-4-oxochroman-2-yl)phenyl acetate → isoxanthohumol (521-48-2,70872-29-6)

Guidance literature:

With potassium hydroxide; In methanol; for 1h;

DOI:10.1039/d1ra05443k

Reference yield: 83.8%

xanthohumol (569-83-5,6754-58-1) → isoxanthohumol (521-48-2,70872-29-6)

Guidance literature:

With sodium hydroxide;

DOI:10.1016/j.tet.2008.07.072

Reference yield:

xanthoarnol (569-83-5) → isoxanthohumol (521-48-2,70872-29-6)

Guidance literature:

With sodium hydroxide;

upstream raw materials:

xanthoarnol

xanthohumol

desmethylxanthohumol

2-(4-acetoxyphenyl)-5-hydroxy-4-oxochroman-7-yl acetate

Downstream raw materials:

2'',3''-dihydroisoxanthohumol

(+/-)-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

4',5-dihydroxy-6'',6''-dimethyl-5'',6''-dihydro-4''H-pyrano[2'',3'':7,8]flavanone

Refernces

• 1、 Taniguchi, Yoshimasa,Taniguchi, Harumi,Yamada, Makiko,Matsukura, Yasuko,Koizumi, Hideki,Furihata, Kazuo,Shindo, Kazutoshi. "Analysis of the components of hard resin in hops (Humulus lupulus L.) and structural elucidation of their transformation products formed during the brewing process". . p. 11602 - 11612. Retrieved 2014.
• 2、 Anio?, Miros?aw,Szymańska, Katarzyna,Zo?nierczyk, Anna. "An efficient synthesis of the phytoestrogen 8-prenylnaringenin from isoxanthohumol with magnesium iodide etherate". . p. 9544 - 9547. Retrieved 2008.
• 3、 Andrusiak, Joanna,Mylkie, Kinga,Wysocka, Ma?gorzata,?cianowski, Jacek,Wolan, Andrzej,Budny, Marcin. "Synthesis of xanthohumol and xanthohumol-d3from naringenin". . p. 28934 - 28939. Retrieved 2021/09/22.