73436-02-9

Basic information

• Product Name: (E)-1-(3-((E)-3,7-dimethylocta-2,6-dienyl)-2,4,6-trihydroxyphenyl)-3-phenylprop-2-en-1-one
• Synonyms: (E)-1-(3-((E)-3,7-dimethylocta-2,6-dienyl)-2,4,6-trihydroxyphenyl)-3-phenylprop-2-en-1-one
• CAS NO: 73436-02-9
• Molecular Weight: 392.495
• Mol File: 73436-02-9.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: (E)-1-(3-((E)-3,7-dimethylocta-2,6-dienyl)-2,4,6-trihydroxyphenyl)-3-phenylprop-2-en-1-one(CAS DataBase Reference)
• NIST Chemistry Reference: (E)-1-(3-((E)-3,7-dimethylocta-2,6-dienyl)-2,4,6-trihydroxyphenyl)-3-phenylprop-2-en-1-one(73436-02-9)
• EPA Substance Registry System: (E)-1-(3-((E)-3,7-dimethylocta-2,6-dienyl)-2,4,6-trihydroxyphenyl)-3-phenylprop-2-en-1-one(73436-02-9)

Safety Data

• Hazardous Substances Data: 73436-02-9(Hazardous Substances Data)

Upstream product

• 261758-70-7 4',6'-dimethoxymethoxy-2'-hydroxy-3'-(1-geranyl)chalcone 
• 102-92-1 Cinnamoyl chloride 
• 108-73-6 3,5-dihydroxyphenol 
• 6138-90-5 trans-geranyl bromide 
• 82451-30-7 2',4',6'-trihydroxychalcone 
• 328946-43-6 1-{3-[(2E)-3,7-dimethylocta-2,6-dien-1-yl]-2-hydroxy-4,6-bis(methoxymethoxy)phenyl}ethanone 
• 43230-44-0 1-{3-[(2E)-3,7-dimethylocta-2,6-dien-1-yl]-2,4,6-trihydroxyphenyl}ethanone 

Downstream Products

• 67832-08-0 (+/-)-5,7-Dihydroxy-6-(1''-geranyl)flavanone 

Relevant articles and documents

Hits-to-lead optimization of the natural compound 2,4,6-trihydroxy-3-geranyl-acetophenone (thga) as a potent lox inhibitor: Synthesis, structure-activity relationship (sar) study, and computational assignment

A new series of 2,4,6-trihydroxy-3-geranyl-acetophenone (tHGA) analogues were synthesized and evaluated for their lipoxygenase (LOX) inhibitory activity. Prenylated analogues 4a-g (half maximal inhibitory concentration (IC50) values ranging from 35 μM to 95 μM) did not exhibit better inhibitory activity than tHGA (3a) (IC50 value: 23.6 μM) due to the reduction in hydrophobic interaction when the alkyl chain length was reduced. One geranylated analogue, 3d, with an IC50 value of 15.3 μM, exhibited better LOX inhibitory activity when compared to tHGA (3a), which was in agreement with our previous findings. Kinetics study showed that the most active analogue (3e) and tHGA (3a) acted as competitive inhibitors. The combination of in silico approaches of molecular docking and molecular dynamic simulation revealed that the lipophilic nature of these analogues further enhanced the LOX inhibitory activity. Based on absorption, distribution, metabolism, excretion, and toxicity (ADMET) and toxicity prediction by komputer assisted technology (TOPKAT) analyses, all geranylated analogues (3a-g) showed no hepatotoxicity effect and were biodegradable, which indicated that they could be potentially safe drugs for treating inflammation.

A facile synthetic approach to prenylated flavanones: First total syntheses of (±)-bonannione A and (±)-sophoraflavanone A

A facile and efficient approach for the syntheses of both C-8 and C-6 prenylated flavonoids has been developed that features a highly regioselective prenylation of 2,4,6-trihydroxyacetophenone and regioselective cyclization of prenylated polyhydroxy chalcones. Thus, the first efficient total syntheses of (±)sophoraflavanone A (1) and (±)-bonannione A (2), two naturally occurring geranylated flavanones with antibacterial activities, have been achieved starting from the key intermediate 3 via regioselective cyclization of geranylated tetrahydroxychalcone 4.