111-64-8Relevant articles and documents
Chili pepper fruits: Presumed precursors of fatty acids characteristic for capsaicinoids
Thiele, Roland,Mueller-Seitz, Erika,Petz, Michael
, p. 4219 - 4224 (2008)
Capsaicin is a molecule unique to fruits from the genus Capsicum. It is responsible for the pungent sensation and displays valuable pharmacological properties. Despite the fruits' economic importance and decades of research, the regulation of the content of capsaicinoids in individual fruits is not completely elucidated, and no agricultural cultivation of chili of defined pungency is assured. Precursor candidates of the fatty acid moiety of the capsaicinoids, especially for the unique 8-methyl-trans-6-nonenoic acid, were examined. Thioesters, acyl-ACP and acyl-CoA, were isolated from the placenta of Capsicum fruits by means of DEAE-Sepharose chromatography, selectively converted to the corresponding N-butylamides, and analyzed by GC-MS. Fatty acid moieties characteristic for capsaicinoids were identified. In two different varieties (Capsicum chinense var. Habanero orange and Capsicum annuum var. Jalapeno) it was shown that the fatty acid pattern corresponds to the distribution pattern of the capsaicinoids formed up to this time. The acyl-thioester fractions contained already the 8-methyl-trans-6-nonenoic acid.
Synthesis, Physicochemical Properties, and Thermo-Oxidative Stability of Diesters of 5,7-Dimethyl-1,3-Adamantanediol and 5,7-Dimethyl-1,3-bis(Hydroxymethyl)adamantane
Ivleva,Baimuratov,Demidov,Lukashenko,Malinovskaya, Yu. A.,Klimochkin, Yu. N.,Tyshchenko,Kulikova,Pozdnyakov,Ovchinnikov,Rudyak
, p. 687 - 693 (2018)
A series of diesters on the basis of 5,7-dimethyl-1,3-adamantanediol and 5,7-dimethyl-1,3- bis(hydroxymethyl)adamantane and C3–C10 aliphatic acids have been synthesized and their physicochemical and thermo-oxidative properties have been studied. The properties of the esters obtained have been compared to those of trimethylolpropane and neopentyl glycol esters.
Reaction of long-chain vanillyl esters with ch-acids and 2-naphthylamine
Kozlov,Basalaeva,Dikusar
, p. 79 - 82 (2004)
The previously unknown4-(alkyl-11-oxo-7,8,9,10,11,12-hexahydrobenzo[a] acridin-12-yl)-and4-(alkyl-1,8-dioxo-2,3,4,5,6,7,8,9-octahydro-1H-xanthen-9-yl) -2-methoxyphenyl esters of aliphatic (C5-C7, C 12) carboxylic acids were synthesizedvia cascade heterocyclization of cyclohexane-1,3-dione and dimedone with 2-naphthylamine and long-chain vanillyl esters.
Synthesis, modelling and kinetic assays of potent inhibitors of purple acid phosphatase
Mohd-Pahmi, Siti Hajar,Hussein, Waleed M.,Schenk, Gerhard,McGeary, Ross P.
, p. 3092 - 3094 (2011)
Purple acid phosphatases (PAPs) are binuclear metallohydrolases that have been isolated from various mammals, plants, fungi and bacteria. In mammals PAP activity is associated with bone resorption and can lead to bone metabolic disorders such as osteoporosis; thus human PAP is an attractive target to develop anti-osteoporotic drugs. Based on a previous lead compound and rational drug design, acyl derivatives of α-aminonaphthylmethylphosphonic acid were synthesised and tested as PAP inhibitors. Kinetic analysis showed that they are good PAP inhibitors whose potencies improve with increasing acyl chain length. Maximum potency is reached when the number of carbons in the acyl chain is between 12 and 14. The most potent inhibitor of red kidney bean PAP is the dodecyl-derivative with Kic = 5 μM, while the most potent pig PAP inhibitor is the tetradecyl-derivative with Kic = 8 μM, the most potent inhibitor of a mammalian PAP yet reported.
Conformation, and Charge Tunneling through Molecules in SAMs
Belding, Lee,Root, Samuel E.,Li, Yuan,Park, Junwoo,Baghbanzadeh, Mostafa,Rojas, Edwin,Pieters, Priscilla F.,Yoon, Hyo Jae,Whitesides, George M.
, p. 3481 - 3493 (2021)
This paper demonstrates that the molecular conformation (in addition to the composition and structure) of molecules making up self-assembled monolayers (SAMs) influences the rates of charge tunneling (CT) through them, in molecular junctions of the form AuTS/S(CH2)2CONR1R2//Ga2O3/EGaIn, where R1 and R2 are alkyl chains of different length. The lengths of chains R1 and R2 were selected to influence the conformations and conformational homogeneity of the molecules in the monolayer. The conformations of the molecules influence the thickness of the monolayer (i.e. tunneling barrier width) and their rectification ratios at ±1.0 V. When R1 = H, the molecules are well ordered and exist predominantly in trans-extended conformations. When R1 is an alkyl group (e.g., R1 H), however, their conformations can no longer be all-trans-extended, and the molecules adopt more gauche dihedral angles. This change in the type of conformation decreases the conformational order and influences the rates of tunneling. When R1 = R2, the rates of CT decrease (up to 6.3×), relative to rates of CT observed through SAMs having the same total chain lengths, or thicknesses, when R1 = H. When R1 H R2, there is a weaker correlation (relative to that when R1 = H or R1 = R2) between current density and chain length or monolayer thickness, and in some cases the rates of CT through SAMs made from molecules with different R2 groups are different, even when the thicknesses of the SAMs (as determined by XPS) are the same. These results indicate that the thickness of a monolayer composed of insulating, amide-containing alkanethiols does not solely determine the rate of CT, and rates of charge tunneling are influenced by the conformation of the molecules making up the junction.
Potent anticonvulsant urea derivatives of constitutional isomers of valproic acid
Shimshoni, Jakob Avi,Bialer, Meir,Wlodarczyk, Bogdan,Finnell, Richard H.,Yagen, Boris
, p. 6419 - 6427 (2007)
Valproic acid (VPA) is a major antiepileptic drug (AED); however, its use is limited by two life-threatening side effects: teratogenicity and hepatotoxicity. Several constitutional isomers of VPA and their amide and urea derivatives were synthesized and evaluated in three different anticonvulsant animal models and a mouse model for AED-induced teratogenicity. The urea derivatives of three VPA constitutional isomers propylisopropylacetylurea, diisopropylacetylurea, and 2-ethyl-3-methyl-pentanoylurea displayed a broad spectrum of anticonvulsant activity in rats with a clear superiority over their corresponding amides and acids. Enanatiomers of propylisopropylacetylurea and propylisopropylacetamide revealed enantioselective anticonvulsant activity, whereas only enantiomers of propylisopropylacetylurea displayed enantioselective teratogenicity. These potent urea derivatives caused neural tube defects, but only at doses markedly exceeding their effective dose, whereas VPA showed no separation between its anticonvulsant activity and teratogenicity. The broad spectrum of anticonvulsant activity of the urea derivatives coupled with their wide safety margin make them potential candidates to become new, potent AEDs.
Assessment of intermolecular N-H.F and N-H.Cl hydrogen bonding in stabilising hetero- and homodimers in solution
Liu, Yan-Hua,Xu, Xiao-Na,Zhao, Xin,Li, Zhan-Ting
, p. 310 - 320 (2015)
This paper describes the first assessment of intermolecular weak N-H.F and N-H.Cl hydrogen bonding in stabilising hetero- and homodimers in solution. Aromatic amide and urea monomers have been designed and synthesised. The association constants of the heterodimers formed by two complementary monomers and the homodimers formed by self-complementary monomers have been determined by using 1H titration and dilution experiments. The results show that both N-H.F and N-H.Cl hydrogen bonds are able to stabilise the corresponding dimers to a measurable extent, even though the stability of the dimers is generally low.
Copper-Catalyzed Bromination of C(sp3)?H Bonds Distal to Functional Groups
Liu, Tao,Myers, Michael C.,Yu, Jin-Quan
, p. 306 - 309 (2017)
Selective bromination of γ-methylene C(sp3)?H bonds of aliphatic amides and δ-methylene C(sp3)?H bonds of nosyl-protected alkyl amines are developed using NBS as the brominating reagent and catalytic amount of CuII/phenanthroline complexes as the catalyst. Aryl and benzylic C?H bonds at other locations remain intact during this directed radical abstraction reaction.
Polymorphism in 'L' shaped lipids: structure of N-, O-diacylethanolamines with mixed acyl chains
Tarafdar, Pradip K.,Swamy, Musti J.
, p. 25 - 33 (2009)
Although solid state polymorphism in lipids has been established by spectroscopic and calorimetric studies long ago, only in a few cases crystal structures of different polymorphs of the same compound have been reported, possibly due to difficulties in obtaining high quality single crystals of individual polymorphs. Recent studies show that N-, O-diacylethanolamines (DAEs) can be derived by the O-acylation of the stress-related lipids, the N-acylethanolamines under physiological conditions. In this study, two DAEs with mixed acyl chains, namely N-palmitoyl, O-octanoylethanolamine and N-palmitoyl, O-decanoylethanolamine have been synthesized and their three-dimensional structures were determined. Both the compounds were found to adopt 'L' shaped structures and exist in two polymorphic forms, α and β. In the α form a mixed-type chain packing has been observed whereas in the β form the chain packing is symmetric. Similar polymorphic forms are likely to exist in other 'L' shaped lipids such as 1,3-diacylglycerols and ceramides, where polymorphism has been detected earlier, but three-dimensional structures - which can give precise information about the packing at atomic resolution - have not been reported.
Pyrene-derived novel one- and two-component organogelators
Babu,Sangeetha,Vijaykumar,Maitra, Uday,Rissanen, Kari,Raju
, p. 1922 - 1932 (2003)
A new class of alkyl-chainappended pyrene derivatives 4 - 14 were synthesized and evaluated for their gelation abilities. Depending on the nature of the linking group, these compounds gelated a number of organic solvents, either in the presence or in the absence of the acceptor molecule 2,4,7-trinitrofluorenone (TNF). Compounds with ester, ether, or alkyl linkages gelated a number of hydroxylic and hydrocarbon solvents by means of a charge-transfer interaction with TNF, while compounds with amide, urethane and urea linkers formed gels on their own in a variety of solvents by means of π-π stacking and hydrogen-bonding interactions. The X-ray crystal structure of urethane (S)-12 showed hydrogen-bonding and stacking features, as suggested by the model. The gels obtained were investigated by spectroscopic and electron microscopic techniques which provided structural insights.
