155696-13-2

Upstream product

• 75-07-0 acetaldehyde 
• 439944-36-2 4-geranoyl-3,5-dimethoxybenzaldehyde 
• 5438-54-0 1,3-dimethoxy-2-[(prop-2-en-1-yl)oxy]benzene 
• 91-10-1 1,3-dimethoxy-2-hydroxy-benzene 
• 6138-90-5 trans-geranyl bromide 
• 4206-58-0 (E)-sinapinaldehyde 
• 439944-37-3 4-geranoylsinapic acid 
• 439944-28-2 4-geranyl sinapic acid methyl ester 
• 439944-32-8 4-geranoyl-3,5-dimethoxybenzoic acid methyl ester 
• 439944-35-1 4-geranoyl-3,5-dimethoxybenzyl alcohol 
• 530-59-6 trans-3,5-dimethoxy-4-hydroxycinnamic acid 
• 42041-51-0 methyl (E)-sinapate 
• 134-96-3 syringic aldehyde 
• 86-81-7 3,4,5-trimethoxy-benzaldehyde 

Downstream Products

• 77836-86-3 Nelumol A 

Relevant academic research and scientific papers

Modular synthesis of (E)-cinnamaldehydes directly from allylarenes via a metal-free DDQ-mediated oxidative process

An efficient synthesis of (E)-cinnamaldehydes by a metal-free DDQ-mediated oxidative transformation of allylarenes was developed. The protocol provides a practical method to prepare diverse (E)-cinnamaldehydes with broad functional group tolerance in good to excellent yields, including easy access to natural products randainal and geranyloxy sinapyl aldehyde from plant extracts. Finally, the mechanism of a single-electron transfer process was proposed.

Growth inhibitory activities of oxyprenylated and non-prenylated naturally occurring phenylpropanoids in cancer cell lines

A series of 25 selected oxyprenylated natural phenylpropanoids were synthesized, and their growth inhibitory activities were evaluated in vitro together with 14 other commercially available non-alkylated compounds belonging to the same chemical series. The compounds were tested on six human cancer cell lines using MTT colorimetric assays. The data reveal that of the six chemical groups (G) studied, coumarins (G1), cinnamic and benzoic acids (G2), chalcones (G3), acetophenones (G4), anthraquinones (G5), and cinnamaldehydes and cinnamyl alcohols (G6), G2-related compounds displayed the weakest growth inhibitory activities in vitro, whereas G5-related compounds displayed the highest activities. Quantitative videomicroscopy analyses were then carried out on human U373 glioblastoma cells, which are characterized by various levels of resistance to different pro-apoptotic stimuli. These analyses revealed that compounds 20 (4,2′,4′-trihydroxychalcone), and 30 and 31 (two cinnamaldehydes) were cytostatic and able to overcome the intrinsic resistance of U373 cancer cells to pro-apoptotic stimuli.

Design, synthesis, and SAR analysis of cytotoxic sinapyl alcohol derivatives

Five series totalling 51 of sinapyl alcohol derivatives were designed and synthesized. Their cytotoxicity analyses were performed on six human tumor cell lines such as PC-3, CNE, KB, A549, BEL-7404, and HeLa. Certain sinapyl alcohol derivatives showed significant cytotoxic activities. Compound 14d exhibited especially potent cytotoxicity against the BEL-7404 cell line with an IC 50 value of 0.7 μM, which showed more cytotoxic activity than the positive control, cisplatin. The structure-cytotoxicity relationships were discussed and the CoMFA analysis was performed using the cytotoxic data against HeLa cells as a template.

Syntheses of two cytotoxic sinapyl alcohol derivatives and isolation of four new related compounds from Ligularia nelumbifolia

Phytochemical reinvestigation on Ligularia nelumbifolia afforded four novel sinapyl alcohol analogues named nelumols B-E (1-4) and three known sinapyl alcohol derivatives (5-7). Their structures were elucidated by NMR techniques. Total syntheses of cytotoxic geranyloxy sinapyl alcohol (6) and geranyloxy sinapyl aldehyde (7) were carried out via two different paths. The 4-O-benzyl-substituted analogues (20 and 27) as well as the 4-O-(2-methylbutenyl) derivatives (34 and 35) were also synthesized. The cytotoxicities of 6 and 7 were measured using A-549, HL-60, and KB cancer cell lines.