21662-16-8Relevant articles and documents
Synthesis and biological evaluation of a series of fatty acid amides from Echinacea
Moazami, Yasamin,Gulledge, Travis V.,Laster, Scott M.,Pierce, Joshua G.
, p. 3091 - 3094 (2015)
Abstract Alkylamides are lipophilic constituents of Echinacea and possess numerous biological activities. Although significant effort has been focused on the study of crude Echinacea extracts, very little is known regarding the activities of the individual constituents that make up these herbal treatments. Herein we explore the SAR of simple alkylamides found in Echinacea extracts with respect to their ability to decrease the production of the pro-inflammatory mediator TNF-α. Our results have revealed the key structural requirements for activity and provide lead compounds for further investigation of these poorly understood molecules.
Iron-Catalyzed ?±,?-Dehydrogenation of Carbonyl Compounds
Zhang, Xiao-Wei,Jiang, Guo-Qing,Lei, Shu-Hui,Shan, Xiang-Huan,Qu, Jian-Ping,Kang, Yan-Biao
supporting information, p. 1611 - 1615 (2021/03/03)
An iron-catalyzed α,β-dehydrogenation of carbonyl compounds was developed. A broad spectrum of carbonyls or analogues, such as aldehyde, ketone, lactone, lactam, amine, and alcohol, could be converted to their α,β-unsaturated counterparts in a simple one-step reaction with high yields.
ALKAMIDE COMPOUNDS AND USES THEREOF
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Page/Page column 75; 77; 78, (2019/04/27)
The present disclosure relates to alkamide compounds and compositions for treating allergic diseases, pain, or itch.
Pd(0) or Pd(II)-catalyzed ring-opening reactions of benzylidene- and alkylidenecyclopropyl ketones and aldehydes
Tang, Xiang-Ying,Shi, Min
supporting information; experimental part, p. 8863 - 8868 (2009/12/26)
Pd(0) catalyzed reactions of methylenecyclopropyl carbonyl compounds afforded a convenient method for the synthesis of conjugate (E,E)-1,3-diene derivatives 2 in good to excellent yields. Moreover, we also found that Pd(II)-catalyzed reactions of methylen
Chiral aggregates formed from methylated tetraenoic fatty acids: Formation of both antipodes of chiral aggregates from a single enantiomer and time-dependent stereomutation
Ma, Jianguo,Cheon, Hwan-Sung,Kishi, Yoshito
, p. 319 - 322 (2008/02/03)
(Chemical Equation Presented) Formation and behaviors of chiral aggregates of methylated tetraenoic fatty acids (TE-FAs) were reported. In the C-24 TE-FA series, the aggregate prepared by dispersing an ethanol stock solution of C-24 TE-FA 1b into sodium phosphate buffer gave a strong positive Cotton effect, whereas the aggregate prepared from a methanol stock solution gave a negative Cotton effect. In the C-20 TE-FA series, the aggregate prepared from an ethanol stock solution of C-20 TE-FA 2b exhibited time-dependent chirality inversion.
Aggregation behavior of tetraenoic fatty acids in aqueous solution
Wang, Yonghui,Ma, Jianguo,Cheon, Hwan-Sung,Kishi, Yoshito
, p. 1333 - 1336 (2008/04/05)
(Chemical Equation Presented) Why so blue? Unique blue-shifted UV absorptions were used to follow the aggregation of C24 tetraene fatty acids in aqueous solution. Aggregation takes place through three distinct states (i.e. K→T1→T2; see picture). It is suggested that all of these aggregates are lamellar-type in a local sense but differ in the packing mode of the fatty acid backbone.
Oxidation of unsaturated primary alcohols and ω-haloalkanols with 4-acetylamino-2,2,6,6-tetramethylpiperidine-1-oxoammonium tetrafluoroborate
Zakrzewski, Jerzy,Grodner, Jacek,Bobbitt, James M.,Karpinska, Monika
, p. 2491 - 2494 (2008/02/13)
Unsaturated primary alcohols and ω-haloalkanols, all applied in pheromone synthesis, are oxidized to the corresponding aldehydes using 4-acetylamino-2,2,6,6-tetramethylpiperidine- 1-oxoammonium tetrafluoroborate (1a). Three methods are compared with one another; oxidations with la and silica gel, oxidations with la in the presence of pyridine, and pyridinium chlorochromate (PCC). Georg Thieme Verlag Stuttgart.
Acid-catalyzed solvolysis of polyenol ethers. III. Effect of the alkoxy moiety
Nieuwenhuis, Saskia A. M.,Vertegaal, Louis B. J.,De Zoete, Marian C.,Van Der Gen, Arne
, p. 13207 - 13230 (2007/10/02)
The dependence of the solvolysis of polyenol ethers on the nature of the alkoxy moiety has been studied. A new reaction path, leading to the formation of ω-hydroxy (methoxy) substituted aldehydes and -esters, was established. The proposed reaction pathway (scheme 6) is initiated by an electron transfer from the polyenol ether to molecular oxygen, followed by combination of the two radicals to a peroxide zwitterion. Upon protonation, solvent adds to the ω-carbon atom of the polyene to give an intermediate that can either loose water to form an ester, or loose the alkoxy moiety to give an aldehyde. This mechanism is believed to be involved in the strong mutagenic activity displayed by many polyenol ethers, including the natural mutagen fecapentaene-12.
Acid-catalyzed solvolysis of polyenol ethers. II. Effect of the degree of unsaturation
Vertegaal,Van Der Gen
, p. 7301 - 7312 (2007/10/02)
The acid-catalyzed solvolysis of polyenol ethers of glycerol gradually changes with increasing unsaturation from the regular pattern into an anomalous one in which hydroxy- and methoxy-substituted aldehydes are formed.
New Functionalized Horner-Wadsworth-Emmons Reagents: Useful Building Blocks in the Synthesis of Polyunsaturated Aldehydes. A Short Synthesis of (+/-)-(E,E)-Coriolic Acid
Kann, Nina,Rein, Tobias,Akermark, Bjoern,Helquist, Paul
, p. 5312 - 5323 (2007/10/02)
The new Horner-Wadsworth-Emmons reagents 4 and 5 transform carbonyl compounds into 2,4-pentadienals and 3-methyl-2,4-pentadienals, respectively.Reagent 4 gives good yields of the desired products with a variety of aldehydes and ketones; reagent 5 generally gives good yields with aldehydes, but gives lower yields with ketones.The reactions proceed under mild conditions and give the products as predominantly 2E,4E isomers, with moderate to good stereoselectivity.In general, pure samples of the 2E,4E-dienals can be obtained after chromatography.Reagents 4 have been used in the key step in a short synthesis of (+/-)-13-hydroxy-9(E),11(E)-octadecanoic acid ((E,E)-coriolic aicd, 45).
