117685-21-9

Upstream product

• 134-96-3 syringic aldehyde 
• 572-09-8 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide 
• 108-24-7 acetic anhydride 
• 6919-96-6 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide 
• 83-87-4 D-glucose pentaacetate 

Downstream Products

• 807629-91-0 C₂₃⁽¹³⁾C₂H₃₀O₁₄ 
• 133815-42-6 (2R,3S,4S,5R,6S)-2-(hydroxymethyl)-6-[4-(3-hydroxyprop-1-enyl)-2,6-dimethoxyphenoxy]oxane-3,4,5-triol 
• 1333206-28-2 C₂₄H₂₈BrFO₁₂ 
• 118-34-3 syringin 
• 203179-64-0 (2R,3R,4S,5R,6S)-2-(acetoxymethyl)-6-(4-((E)-3-hydroxyprop-1-en-1 -yl)-2,6-dimethoxyphenoxy)tetrahydro-2H-pyran-3,4,5-triyl triacetate 
• 203179-62-8 3,5-dimethoxy-4-(tetra-O-acetyl-β-D-glucopyranosyloxy)-trans-cinnamaldehyde 
• 66779-69-9 2,6-dimethoxy-4-formylphenyl β-D-glucopyranoside 

Relevant academic research and scientific papers

Synthesis and structure-activity relationship studies of cytotoxic cinnamic alcohol derivatives

Three series of di- and trisubstituted derivatives of cinnamic alcohol and its conjugated dienol analogues were designed and synthesised. The derivatives were screened for cytotoxicity against nine tumour cell lines: KB, A549, Hela, CNE, PC-3, BEL-7404, HL-60, BGC823 and P388D1. Most of the cinnamic alcohol derivatives showed cytotoxic activity. The compound 7-(4',5'-dichlorobenzyloxy)- 6,8-dihydroxycinnamic alcohol (55) exhibited significant cytotoxicity to seven human tumour cell lines on a micromolar range, especially with regard to the KB and P388D1 cell lines, showing IC50 values of 0.4 and 0.5μ M, respectively. The structure-activity relationships of the derivatives are discussed.

First synthesis of (1,2-13C2)-monolignol glucosides

The monolignol glucosides (1,2-13C2)-p-glucocoumaryl alcohol, (1,2-13C2)-coniferin and (1,2-13C 2)-syringin, and the glucosides of (1,2-13C 2)-p-coumaric, (1,2-13C2)-ferulic and (1,2-13C2)-sinapic acids were synthesized by condensation of the corresponding aldehydes with (1,2,3-13C3)-malonic acid. The free acids were converted to the acyl chlorides prior to their reduction to alcohols.

Coniferin and derivatives: A fast and easy synthesis via the aldehyde series using phase-transfer catalysis

Coniferin was synthesised in good yields (56% starting from vanillin) under mild conditions. A one-pot coupling of the glucosidation and Wittig- type reactions led to coniferaldehyde tetra-O-acetylglucoside, easily reduced into tetra-O-acetylconiferin by sodium borohydride. Similar procedures were used for the synthesis of syringin and the glucoside of 4-coumaryl alcohol.

NEW SYNTHESES OF PLANT ARYL GLYCOSIDES AS POTENTIAL GENE INDUCERS

Aryl β-D-glycopyranosides have been synthesized by coupling acetovanillone (4-hydroxy-3-methoxyacetophenone) with D-glucose, D-galactose, and maltose; acetosyringone (4-hydroxy-3,5-dimethoxyacetophenone) with D-glucose and D-galactose; syringaldehyde (3-methoxyvanillin) with D-glucose; and syringic acid (4-hydroxy-3,5-dimethoxybenzoic acid) with D-glucose.The Mauthner's procedure using peracetylated glycosyl bromides and phenolates in aqueous acetone afforded the acetylated β-D-glycosides, which were deacetylated.