334701-03-0

Basic information

• Product Name: 4H-1-Benzopyran-4-one, 7-(acetyloxy)-2-[4-(acetyloxy)phenyl]-2,3-dihydro-5-[(3-methyl-2-butenyl) oxy]-
• CAS NO: 334701-03-0
• Molecular Formula: C24H24O7
• Molecular Weight: 424.45
• Mol File: 334701-03-0.mol
• Article Data: 5

Chemical Properties

• CAS DataBase Reference: 4H-1-Benzopyran-4-one, 7-(acetyloxy)-2-[4-(acetyloxy)phenyl]-2,3-dihydro-5-[(3-methyl-2-butenyl) oxy]-(CAS DataBase Reference)
• NIST Chemistry Reference: 4H-1-Benzopyran-4-one, 7-(acetyloxy)-2-[4-(acetyloxy)phenyl]-2,3-dihydro-5-[(3-methyl-2-butenyl) oxy]-(334701-03-0)
• EPA Substance Registry System: 4H-1-Benzopyran-4-one, 7-(acetyloxy)-2-[4-(acetyloxy)phenyl]-2,3-dihydro-5-[(3-methyl-2-butenyl) oxy]-(334701-03-0)

Safety Data

• Hazardous Substances Data: 334701-03-0(Hazardous Substances Data)

Upstream product

• 556-82-1 3-methyl-2-buten-1-ol 
• 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 

Downstream Products

• 68682-02-0 5,7-Dihydroxy-2-(4-hydroxy-phenyl)-8-(3-methyl-but-2-enyl)-chroman-4-one 
• 569-83-5 xanthohumol 
• 521-48-2 isoxanthohumol 
• 334701-04-1 2-(4-acetoxyphenyl)-5-hydroxy-8-(3-methylbut-2-enyloxy)-4-oxochroman-7-yl acetate 

Relevant articles and documents

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.

Ability of prenylflavanones present in hops to induce apoptosis in a human burkitt lymphoma cell line

The identification of effective cancer preventive compounds from hops has become an important issue in public health-related research. We compared the antiproliferative and apoptosis-inducing effects of side chain variants of prenylflavanones, e.g., 8-prenylnaringenin (7) and 8-geranylnaringenin (10), which have been identified in hops (Humulus lupulus), and their synthetic variations 8-furanmethylnaringenin (8) and 8-cinnamylnaringenin (9). These were accessible by a Mitsunobu reaction and Claisen rearrangement. Flavanones 9 and 10 showed cytotoxic and apoptotic activities. Apoptosis was induced in a mitochondrial dependent manner. 8-Cinnamylnaringenin (9) displayed noticeably improved apoptotic effects when compared to 8-prenylnaringenin. The potential of 8-prenylnaringenin (7) is shown in an ex vivo experiment on a multi-drug resistant leukaemia blast. Georg Thieme Verlag KG Stuttgart.

An efficient synthesis of the potent phytoestrogens 8-prenylnaringenin and 6-(1,1-dimethylallyl)naringenin by europium(III)-catalyzed Claisen rearrangement

Starting from commercially available naringenin (3), the flavanoids 8-prenylnaringenin (1) and 6-(1,1-dimethylallyl)naringenin (2) have been prepared in racemic form using prenyl ether 5 as a general intermediate. While a domino Claisen-Cope rearrangement of 5 was the key step in the synthesis of 1, the cytotoxic compound 2 was additionally secured via a europium(III)-catalyzed Claisen rearrangement of 5 at low temperature. Both 1 and 2 display strong estrogenic activities.