96215-83-7

Upstream product

• 96215-87-1 1-(3,5-Dimethoxy-phenyl)-nonadecanol-⁽¹⁾ 
• 877-88-3 3,5-dimethoxybenzyl bromide 
• 92206-73-0 1-octadecylmagnesium bromide 
• 7311-34-4 3,5-dimethoxybenzaldehdye 
• 51241-55-5 n-octadecyllithium 
• 705-76-0 3,5-dimethoxybenzyl alcohol 
• 17213-57-9 3,5-dimethoxybenzoyl chloride 
• 112-89-0 1-Bromooctadecane 

Downstream Products

• 96376-24-8 5-Nonadecyl-resorcin-diacetat 
• 70110-59-7 1,3-dihydroxy-5-heneicosylbenzene 

Relevant academic research and scientific papers

An expedient synthesis of 5-n-alkylresorcinols and novel 5-n-alkylresorcinol haptens

The first synthesis of bioactive long alkyl chain 5-n-alkylresorcinols, present in whole grain products, by a novel modification of the Wittig reaction is described. All the main long chain 5-n-alkylresorcinols present in rye and wheat, including C23 and C25 analogues and haptens, which have not been previously prepared, were synthesised. Microwave-promoted reactions of a semistabilized ylid and alkanals in water gave good yields in both pressurized and open systems. An alternative microwave-promoted synthesis starting from non-stabilized alkyltriphenylphosphonium salts and 3,5-dimethoxybenzaldehyde worked as well. Aqueous media were suitable for the reactions even if the starting materials were not soluble in water. The 5-n-alkylresorcinols are potential biomarkers of whole grain intake, and the new hapten derivatives of 5-n-alkylresorcinols will open the way for the immunochemical detection techniques of alkylresorcinols.

Cereal grain resorcinolic lipids: mono and dienoic homologues are present in rye grains

Analyses (UV, IR, 1H-NMR, MS) of the main phenolic fraction isolated by sequential separation on normal-phase and argentation chromatography on silica gel confirmed the presence of monoenoic and dienoic homologues of 1,3-dihydroxy-5-n-alkylbenzene in acet

Properties of mixed monolayers and bilayers of long-chain 5-n-alkylresorcinols and dipalmitoylphosphatidylcholine

5-n-Alkylresorcinols with different chain length are known to occur in different plants and procaryonts, for example in the cysts of the Azotobacter genus. To study the monolayer and bilayer behaviour of these amphiphilic compounds, we synthesized three analogues with different chain length, namely 5-n-octadecylresorcinol (18AR), 5-n-nonadecylresorcinol (19AR) and 5-n-heneicosylresorcinol (21AR). The pure alkylresorcinols form stable monolayers, 18AR and 19AR, show a phase transition from a liquid-condensed to a liquid-expanded state at temperatures between 20 and 40°C and at lateral pressures below 15 dyn/cm. In mixtures with dipalmitoylphosphatidylcholine (DPPC), monolayer isobars at higher lateral pressures (20-30 dyn/cm) show an increase in the transition temperature to values greater than 50°C for the liquid-condensed to liquid-expanded state of DPPC when the alkylresorcinol content is increased. Particularly in the liquid-expanded state, alkylresorcinols show a strong condensing effect on DPPC monolayers. 18AR/DPPC monolayers at a pressure of 5 dyn/cm show indications of an azeotropic behaviour. A similar increase in transition temperature is observed by differential scanning calorimetry (DSC) and differential scanning densitometry (DSD) in DPPC/alkylresorcinol bilayers. The transition enthalpy decreases with increasing alkylresorcinol content. All alkylresorcinols seem to be completely miscible with DPPC up to at least 50 mol%. The DSD data indicate a slight condensing effect of the alkylresorcinols on the liquid-crystalline phase of DPPC.