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

Author(s):  
Kirsti Parikka ◽  
Kristiina Wähälä

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 semi-stabilized 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.

2009 ◽  
Vol 159 (21-22) ◽  
pp. 2240-2244 ◽  
Author(s):  
P. Berdyczko ◽  
W. Domagala ◽  
A. Czardybon ◽  
M. Lapkowski

Author(s):  
Brigid R. Heywood ◽  
S. Champ

Recent work on the crystallisation of inorganic crystals under compressed monomolecular surfactant films has shown that two dimensional templates can be used to promote the oriented nucleation of solids. When a suitable long alkyl chain surfactant is cast on the crystallisation media a monodispersied population of crystals forms exclusively at the monolayer/solution interface. Each crystal is aligned with a specific crystallographic axis perpendicular to the plane of the monolayer suggesting that nucleation is facilitated by recognition events between the nascent inorganic solid and the organic template.For example, monolayers of the long alkyl chain surfactant, stearic acid will promote the oriented nucleation of the calcium carbonate polymorph, calcite, on the (100) face, whereas compressed monolayers of n-eicosyl sulphate will induce calcite nucleation on the (001) face, (Figure 1 & 2). An extensive program of research has confirmed the general principle that molecular recognition events at the interface (including electrostatic interactions, geometric homology, stereochemical complementarity) can be used to promote the crystal engineering process.


2004 ◽  
Vol 69 (6) ◽  
pp. 1292-1300 ◽  
Author(s):  
Tahahiro Tani ◽  
Kazuki Sada ◽  
Masatsugu Ayabe ◽  
Yuya Iwashita ◽  
Takanori Kishida ◽  
...  

Crystal structure of hexylammonium anthracene-9-carboxylate was investigated. The salt was arranged by a one-dimensional hydrogen bond network to form a columnar structure in the crystalline state. This columnar structure should be the model of fibrous assemblies in the organogels of anthracene-9-carboxylate alkylammonium salts having a long alkyl chain.


2012 ◽  
Vol 137 (10) ◽  
pp. 104511 ◽  
Author(s):  
Tsuyoshi Yamaguchi ◽  
Ken-ichi Mikawa ◽  
Shinobu Koda ◽  
Kenta Fujii ◽  
Hitoshi Endo ◽  
...  

2006 ◽  
Vol 8 (9) ◽  
pp. 798 ◽  
Author(s):  
Juliusz Pernak ◽  
Marcin Smiglak ◽  
Scott T. Griffin ◽  
Whitney L. Hough ◽  
Timothy B. Wilson ◽  
...  

2011 ◽  
Vol 24 (3) ◽  
pp. 201-205 ◽  
Author(s):  
Marcin Rojkiewicz ◽  
Grzegorz Zięba ◽  
Anna Jarczyk ◽  
Piotr Kuś
Keyword(s):  

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