30403-01-1

Basic information

• Product Name: 1-[2,4-Dihydroxy-6-methoxy-3-(3-methyl-2-butenyl)phenyl]ethanone
• Synonyms: 1-[2,4-Dihydroxy-6-methoxy-3-(3-methyl-2-butenyl)phenyl]ethanone;Preremirol
• CAS NO: 30403-01-1
• Molecular Formula: C₁₄H₁₈O₄
• Molecular Weight: 250.29
• Mol File: 30403-01-1.mol
• Article Data: 4

Chemical Properties

• Melting Point: 169-170 °C
• Boiling Point: 403.5±35.0 °C(Predicted)
• Appearance: /
• Density: 1.150±0.06 g/cm3(Predicted)
• PKA: 8.15±0.28(Predicted)
• CAS DataBase Reference: 1-[2,4-Dihydroxy-6-methoxy-3-(3-methyl-2-butenyl)phenyl]ethanone(CAS DataBase Reference)
• NIST Chemistry Reference: 1-[2,4-Dihydroxy-6-methoxy-3-(3-methyl-2-butenyl)phenyl]ethanone(30403-01-1)
• EPA Substance Registry System: 1-[2,4-Dihydroxy-6-methoxy-3-(3-methyl-2-butenyl)phenyl]ethanone(30403-01-1)

Safety Data

• Hazardous Substances Data: 30403-01-1(Hazardous Substances Data)

Usage

Preparation

Preparation by reaction of prenyl bromide with 2,4-dihydroxy-6-methoxyacetophenone in the presence of methanolic potassium hydroxide (major product).

Upstream product

• 186581-53-3 diazomethane 
• 27364-71-2 2',4',6'-trihydroxy-3'-(3-methyl-2-butenyl)acetophenone 
• 90632-20-5 1-[6-hydroxy-2,4-bis(methoxymethoxy)-3-(3-methylbut-2-en-1-yl)phenyl]ethanone 
• 160624-22-6 1-{2,4-bis(methoxymethoxy)-6-[(3-methylbut-2-en-1-yl)oxy]phenyl}ethanone 
• 480-66-0 2,4,6-trihydroxyacetophenone 
• 450336-13-7 1-(2,6-dihydroxy-4-(methoxymethoxy)-3-(3-methylbut-2-en-1-yl)phenyl)ethanone 
• 65490-09-7 2'-hydroxy-4',6'-bis(methoxymethoxy)acetophenone 
• 450336-14-8 1-(2-hydroxy-6-methoxy-4-(methoxymethoxy)-3-(3-methylbut-2-enyl)phenyl)ethanone 

Downstream Products

• 116107-09-6 2',4'-Dihydroxy-6'-methoxy-3'-prenylchalcone 
• 143885-75-0 (2E)-1-(5-hydroxy-7-methoxy-2,2-dimethyl-2H-chromen-6-yl)-3-(4-methoxyphenyl)prop-2-en-1-one 
• 450336-11-5 (+/-)-5-methoxy-2-(4-methoxyphenyl)-8,8-dimethyl-2,3-dihydro-8H-pyrano[2,3-f]chromen-4-one 
• 33523-62-5 1-(2’-hydroxy-4’,6’-dimethoxy-3’-(3’’-methyl-2’’-buten-1’’-yl)phenyl)ethanone 
• 25983-76-0 isoevodionol 

Relevant articles and documents

Total Synthesis and in Vitro Anti-Tumor-Promoting Activities of Racemic Acetophenone Monomers from Acronychia trifoliolata

Six acetophenone derivatives, acronyculatins I (1), J (2), K (3), L (4), N (5), and O (6), were recently isolated from Acronychia trifoliolata, and the structure of the known acronyculatin B (7) was revised. Because of the limited quantities of isolated p

Natural and non-natural prenylated chalcones: Synthesis, cytotoxicity and anti-oxidative activity

A general strategy for the synthesis of 3′-prenylated chalcones was established and a series of prenylated hydroxychalcones, including the hop (Humulus lupulus L.) secondary metabolites xanthohumol (1), desmethylxanthohumol (2), xanthogalenol (3), and 4-methylxanthohumol (4) were synthesized. The influence of the A-ring hydroxylation pattern on the cytotoxic activity of the prenylated chalcones was investigated in a HeLa cell line and revealed that non-natural prenylated chalcones, like 2′,3,4′,5-tetrahydroxy-6′-methoxy-3′-prenylchalcone (9, IC50 3.2 ± 0.4 μM) as well as the phase 1 metabolite of xanthohumol (1), 3-hydroxyxanthohumol (8, IC50 2.5 ± 0.5 μM), were more active in comparison to 1 (IC50 9.4 ± 1.4 μM). A comparison of the cytotoxic activity of xanthohumol (1) and 3-hydroxyxanthohumol (8) with the non-prenylated analogs helichrysetin (12, IC50 5.2 ± 0.8) and 3-hydroxyhelichrysetin (13, IC50 14.8 ± 2.1) showed that the prenyl side chain at C-3′ has an influence on the cytotoxicity against HeLa cells only for the dihydroxylated derivative. This offers interesting synthetic possibilities for the development of more potent compounds. The ORAC activity of the synthesized compounds was also investigated and revealed the highest activity for compounds 12, 4′-methylxanthohumol (4), and desmethylxanthohumol (2), with 4.4 ± 0.6, 3.8 ± 0.4, and 3.8 ± 0.5 Trolox equivalents, respectively.