77836-86-3

Usage

Uses

Used in Plant Structural Integrity:
O-geranylsinapyl alcohol is used as a key component in maintaining the structural integrity and rigidity of plant tissues, ensuring their stability and resistance to external factors.
Used in Plant Defense Mechanisms:
It serves as a vital element in the defense mechanisms of plants against environmental stresses and pathogens, helping protect the plant from potential harm.
Used in Bio-based Materials Development:
O-geranylsinapyl alcohol is used as a starting material in the development of bio-based materials, capitalizing on its abundance in plant biomass and potential for sustainable applications.
Used in Biofuels Production:
It is utilized as a resource in the production of biofuels, offering an alternative and renewable energy source due to its presence in plant biomass.

InChI:InChI=1/C21H30O4/c1-16(2)8-6-9-17(3)11-13-25-21-19(23-4)14-18(10-7-12-22)15-20(21)24-5/h7-8,10-11,14-15,22H,6,9,12-13H2,1-5H3/b10-7+,17-11+

Upstream product

• 439944-32-8 4-geranoyl-3,5-dimethoxybenzoic acid methyl ester 
• 439944-35-1 4-geranoyl-3,5-dimethoxybenzyl alcohol 
• 439944-36-2 4-geranoyl-3,5-dimethoxybenzaldehyde 
• 530-59-6 trans-3,5-dimethoxy-4-hydroxycinnamic acid 
• 42041-51-0 methyl (E)-sinapate 
• 439944-37-3 4-geranoylsinapic acid 
• 439944-28-2 4-geranyl sinapic acid methyl ester 
• 155696-13-2 Nelumal A 

Downstream Products

• 155696-13-2 Nelumal A 

Relevant academic research and scientific papers

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.

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.

SINAPYL ALCOHOL DERIVATIVES AND OTHER CONSTITUENTS FROM LIGULARIA NELUMBIFOLIA

Three novel sinapyl alcohol derivatives together with two other new constituents were isolated from the roots of Ligularia nelumbifolia.Their structures were elucidated by high field 1D and 2D NMR techniques and chemical transformations. - Key words: Ligu