199393-58-3

Basic information

• Product Name: 2′,4,4′-trimethoxymethoxy-6′-hydroxy-3′-prenylchalcone
• Synonyms: 2′,4,4′-trimethoxymethoxy-6′-hydroxy-3′-prenylchalcone
• CAS NO: 199393-58-3
• Molecular Weight: 472.535
• Mol File: 199393-58-3.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: 2′,4,4′-trimethoxymethoxy-6′-hydroxy-3′-prenylchalcone(CAS DataBase Reference)
• NIST Chemistry Reference: 2′,4,4′-trimethoxymethoxy-6′-hydroxy-3′-prenylchalcone(199393-58-3)
• EPA Substance Registry System: 2′,4,4′-trimethoxymethoxy-6′-hydroxy-3′-prenylchalcone(199393-58-3)

Safety Data

• Hazardous Substances Data: 199393-58-3(Hazardous Substances Data)

Upstream product

• 134955-29-6 2′,4,4′-trimethoxymethoxy-6′-hydroxychalcone 
• 6515-21-5 4-methoxymethoxy-benzaldehyde 
• 90632-20-5 1-[6-hydroxy-2,4-bis(methoxymethoxy)-3-(3-methylbut-2-en-1-yl)phenyl]ethanone 
• 65490-09-7 2'-hydroxy-4',6'-bis(methoxymethoxy)acetophenone 
• 160624-22-6 1-{2,4-bis(methoxymethoxy)-6-[(3-methylbut-2-en-1-yl)oxy]phenyl}ethanone 

Downstream Products

• 199393-59-4 4',5,7-tri(methoxymethoxy)-6-(3,3-dimethyl)allylflavanone 
• 68682-01-9 5,7,4'-trihydroxy-6-prenylflavanone 
• 115063-39-3 desmethylxanthohumol 
• 569-83-5 xanthohumol 

Relevant articles and documents

Synthesis and Antiproliferative Activity of Prenylated Chalcone Mannich Base Derivatives

Prenylated chalcones xanthohumol (1) and 2′-hydroxy-3,4,4′-trimethoxy-6′-O-prenyl chalcone (2) were synthesized through the Claisen–Schmidt condensation, O-prenylation, and Claisen rearrangement and deprotection respectively, using phloroglucinol and appropriate benzaldehydes as starting materials. Based on the Mannich reaction of prenylated chalcone 1 or 2 with various secondary amines and formaldehyde in acid alcohol solvent, 10 novel prenylated chalcone Mannich base derivatives 3a–3e and 4a–4e were synthesized. Furthermore, all synthetic compounds were evaluated for antiproliferative activities in vitro against four human cancer cell lines (Aspc-1, SUN-5, HepG-2, and HCT-116) by MTT assay. The results showed that most of them exhibit moderate to good antiproliferative activities against the four human cancer cells with IC50 values of 2.52 to 47.67 μM.

A facile synthesis of 6-C-prenylflavanones

The first total synthesis of two natural 6-C-prenylflavanones, (±)-6-C-prenyleriodoctyol (1) and 6-C-prenylnaringenin (2), using the acetophenone derivative 6 as the key intermediate is described. This new efficient synthetic approach was mainly based on