131119-10-3Relevant academic research and scientific papers
Enzymatic synthesis of a capsinoid by the acylation of vanillyl alcohol with fatty acid derivatives catalyzed by lipases
Kobata, Kenji,Kawaguchi, Manami,Watanabe, Tatsuo
, p. 319 - 327 (2002)
Capsinoids are a novel group of compounds produced by the Capsicum plant. We synthesized a capsinoid by the lipase-catalyzed esterification of vanillyl alcohol with fatty acid derivatives in an organic solvent. The use of seven out of 17 commercially available lipases, especially Novozym 435, was applicable to the synthesis of vanillyl nonanoate, a model compound of capsinoids. The yield of vanillyl nonanoate under the optimum conditions of 50 mM vanillyl alcohol and 50 mM methyl nonanoate in 500 μl of dioxane, using 20 mg of Novozym 435 and 50 mg of 4 A° molecular sieves at 25°C, was 86% in 20 h. Several capsinoid homologues having various acyl chain lengths (C6-C18) were synthesized at 64-86% yields from the corresponding fatty acid methyl ester. The natural capsinoids, capsiate and dihydrocapsiate, were obtained by a 400-fold-scale reaction at these optimum conditions in 60% and 59% isolated yields, respectively.
Stability of capsinoid in various solvents
Sutoh,Kobata,Watanabe
, p. 4026 - 4030 (2001)
To investigate the stability of capsinoid in solvents, the quantitative change of vanillyl nonanoate, a synthetic model capsinoid, in various solvents was measured by HPLC. Vanillyl nonanoate was stable in nonpolar solvents, whereas it was labile in polar solvents. In particular, vanillyl nonanoate tended to decompose in protic solvents such as alcohol and water. Structures of the decomposition products from vanillyl nonanoate in methanol and ethanol were determined to be methyl and ethyl vanillyl ethers, respectively. To clarify the decomposition mechanism of capsinoid, six analogues of vanillyl nonanoate were tested. The stability of the analogues in organic solvents suggested that the hydroxyl group in the para-position of the benzene ring largely contributes to the decomposition of capsinoid.
Application of hansch's model to capsaicinoids and capsinoids: A study using the quantitative structure-activity relationship. A novel method for the synthesis of capsinoids
Barbero, Gerardo F.,Molinillo, Jose M. G.,Varela, Rosa M.,Palma, Miguel,MacIas, Francisco A.,Barroso, Carmelo G.
, p. 3342 - 3349 (2011/07/30)
We describe a synthetic approach for two families of compounds, the capsaicinoids and capsinoids, as part of a study of the quantitative relationship between structure and activity. A total of 14 capsaicinoids of increasing lateral chain lengths, from 2 to 16 carbon atoms, were synthesized. In addition, 14 capsinoids with identical lateral chains, as well as capsiate and dihydrocapsiate, have been synthesized, and a new method for the synthesis of these compounds has been developed. The yields range from 48.35 to 98.98%. It has been found that the synthetic capsaicinoids and capsinoids present a lipophilia similar to those of the natural compounds and present similar biological activity. The bioactivity of the synthetic capsaicinoids and capsinoids decreases proportionally to the degree of difference in lipophilia (higher or lower) compared to the natural compounds. Biological activity was determined using the etiolated wheat (Triticum aestlvum L.) coleoptiles bioassay and by comparing results of the synthesis with those presented by their counterpart natural compounds. The bioactivities found correlated directly to the lipophilic properties of the synthesized compounds.
METHOD FOR THE CHEMICAL SYNTHESIS OF CAPSINOIDS
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Page/Page column 7, (2010/03/02)
Method for the chemical synthesis of capsinoids, natural compounds with proven biological activity, from vanillin, comprising the protection of the alcohol group thereof, reduction of the aldehyde to alcohol, esterification of same and deprotection of the first protected alcohol group. In this way, the desired compounds are generated with high purity and said compounds can be easily separated with no mixing owing to the competitive esterification on the aromatic ring.
Cerium(III) chloride-promoted chemoselective esterification of phenolic alcohols
Torregiani, Elisabetta,Seu, Gianfranco,Minassi, Alberto,Appendino, Giovanni
, p. 2193 - 2196 (2007/10/03)
A mild and operationally simple method for the chemoselective esterification of phenolic alcohols is described. The reaction overcomes the tyranny of protection, and capitalizes on the activation of acyl halides with cerium(III) chloride to selectively esterify alcohol hydroxyls in the presence of phenolic ones. The generality of the reaction was demonstrated with a series of phenolic alcohols of dietary relevance (vanillol, hydroxytyrosol, epicatechin), providing an expeditious entry into a series of compounds of relevance for biomedical research, some of which previously available only by enzymatic methods.
Chemoselective Esterification of Phenolic Acids and Alcohols
Appendino, Giovanni,Minassi, Alberto,Daddario, Nives,Bianchi, Federica,Tron, Gian Cesare
, p. 3839 - 3841 (2007/10/03)
(Matrix Presented) The Mitsunobu reaction can distinguish between alcohol and phenol hydroxyls in esterification reactions, providing an expeditious and broadly applicable entry into various phenolics and polyphenolics of biomedical and nutritional relevance.
Analogues of capsaicin with agonist activity as novel analgesic agents; structure-activity studies. 2. The amide bond 'B-region'
Walpole,Wrigglesworth,Bevan,Campbell,Dray,James,Masdin,Perkins,Winter
, p. 2373 - 2380 (2007/10/02)
A series of compounds incorporating replacements for the amide bond 'B- region' moiety of capsaicin have been synthesized, including vanillylamides and esters, homovanillic acid amides and esters, ureas, and thioureas. These have been tested in an in vitr
