10340-22-4Relevant articles and documents
Structure-Odor Relationships of (Z)-3-Alken-1-ols, (Z)-3-Alkenals, and (Z)-3-Alkenoic Acids
Lorber, Katja,Zeh, Gina,Regler, Johanna,Buettner, Andrea
, p. 2334 - 2343 (2018)
(Z)-3-Unsaturated volatile acids, alcohols, and aldehydes are commonly found in foods and other natural sources, playing a vital role in the attractiveness of foods but also as compounds with chemocommunicative function in entomology. However, a systematic investigation of their smell properties, especially regarding humans, has not been carried out until today. To close this gap, the odor thresholds in air and odor qualities of homologous series of (Z)-3-alken-1-ols, (Z)-3-alkenals, and (Z)-3-alkenoic acids were determined by gas chromatography-olfactometry. It was found that the odor qualities in the series of the (Z)-3-alken-1-ols and (Z)-3-alkenals changed, with increasing chain length, from grassy, green to an overall fatty and citrus-like, soapy character. On the other hand, the odor qualities of the (Z)-3-alkenoic acids changed successively from cheesy, sweaty via plastic-like, to waxy in their homologous series. With regard to their odor potencies, the lowest thresholds in air were found for (Z)-3-hexenal, (Z)-3-octenoic acid, and (Z)-3-octenal.
Natural trienoic acids as anticancer agents: First stereoselective synthesis, cell cycle analysis, induction of apoptosis, cell signaling and mitochondrial targeting studies
D’yakonov, Vladimir A.,Makarov, Alexey A.,Dzhemileva, Lilya U.,Ramazanov, Ilfir R.,Makarova, Elina Kh.,Dzhemilev, Usein M.
, (2021)
The first Z-stereoselective method was developed for the synthesis of unsaturated acids containing a 1Z,5Z,9Z-triene moiety in 61–64% yields using the new Ti-catalyzed cross-coupling of oxygen-containing and aliphatic 1,2-dienes as the key synthetic step. It was shown for the first time that trienoic acids with non-methylene-interrupted Z-double bonds show moderate cytotoxic activities against tumor cell lines (Jurkat, K562, U937, HL60, HeLa), human embryonic kidney cells (Hek293), normal fibroblasts and human topoisomerase I (hTop1) inhibitory activity in vitro. The synthesized acids efficiently initiate apoptosis of Jurkat tumor cells, with the cell death mechanism being activated by the mitochondrial pathway. A probable mechanism of topoisomerase I inhibition was also hypothesized on the basis of in silico studies resorting to docking. The activation and inhibition of the most versatile intracellular signaling pathways (CREB, JNK, NFkB, p38, ERK1/2, Akt, p70S6K, STAT3 and STAT5 tyrosine kinases) responsible for cell proliferation and for initiation of apoptosis were studied by multiplex assay technology (Luminex xMAP).
CYCLOALKYL-CONTAINING CARBOXYLIC ACIDS AND USES THEREOF
-
Page/Page column 73; 75, (2021/06/26)
The present application discloses a compound of formula (I) or a salt thereof: (I) and compositions comprising such compound or salt thereof. The use of such compound, salt thereof or composition comprising same for treating anemia or leukopenia, fibrosis, cancer, hypertension and/or a metabolic condition in a subject is also disclosed.
NbCl5-Mg reagent system in regio-and stereoselective synthesis of (2Z)-alkenylamines and (3Z)-alkenylols from substituted 2-alkynylamines and 3-alkynylols
Dzhemilev, Usein M.,Gabdullin, Azat M.,Kadikova, Rita N.,Mozgovoj, Oleg S.,Ramazanov, Ilfir R.
supporting information, (2021/07/02)
The reduction of N,N-disubstituted 2-alkynylamines and substituted 3-alkynylols using the NbCl5 –Mg reagent system affords the corresponding dideuterated (2Z)-alkenylamine and (3Z)-alkenylol derivatives in high yields in a regio-and stereoselective manner through the deuterolysis (or hydrolysis). The reaction of substituted propargylamines and homopropargylic alcohols with the in situ generated low-valent niobium complex (based on the reaction of NbCl5 with magnesium metal) is an efficient tool for the synthesis of allylamines and homoallylic alcohols bearing a 1,2-disubstituted double bond. It was found that the well-known approach for the reduction of alkynes based on the use of the TaCl5-Mg reagent system does not work for 2-alkynylamines and 3-alkynylols. Thus, this article reveals a difference in the behavior of two reagent systems—NbCl5-Mg and TaCl5-Mg, in relation to oxygen-and nitrogen-containing alkynes. A regio-and stereoselective method was developed for the synthesis of nitrogen-containing E-β-chlorovinyl sulfides based on the reaction of 2-alkynylamines with three equivalents of methanesulfonyl chloride in the presence of stoichiometric amounts of niobium(V) chloride and magnesium metal in toluene.
Synthesis and Immobilization of Metal Nanoparticles Using Photoactive Polymer-Decorated Zeolite L Crystals and Their Application in Catalysis
Wissing, Maren,Niehues, Maximilian,Ravoo, Bart Jan,Studer, Armido
supporting information, p. 2245 - 2253 (2020/05/05)
A facile route to generate Au and Pd nanoparticles (NPs) on zeolite L crystals decorated with photoactive polymer brushes is described. The polymers used in this approach serve a dual role: Upon irradiation with UV light, they release highly reducing ketyl radicals in a Norrish-Type-I reaction. These radicals serve as one electron donors to reduce metal salts to the corresponding metal NPs. At the same time the polymer shell stabilizes the in situ generated metal NPs. It is shown that the zeolite-polymer-NP composites can be used as recyclable catalysts for the oxidation of benzylic alcohols to aldehydes and the stereoselective semihydrogenation of alkynes to Z-alkenes. The polymer shell in these hybrid catalysts protects the NPs from aggregation and also alters their catalytic properties. (Figure presented.).
COMPOUNDS AND COMPOSITIONS FOR INTRACELLULAR DELIVERY OF AGENTS
-
Paragraph 00956, (2019/01/08)
The disclosure features amino lipids and compositions involving the same. Nanoparticle compositions include an amino lipid as well as additional lipids such as phospholipids, structural lipids, PEG lipids, or a combination thereof. Nanoparticle compositions further including therapeutic and/or prophylactic agents such as RNA are useful in the delivery of therapeutic and/or prophylactic agents to mammalian cells or organs to, for example, regulate polypeptide, protein, or gene expression.
Influence of the chemical structure on odor qualities and odor thresholds in homologous series of alka-1,5-dien-3-ones, alk-1-en-3-ones, alka-1,5-dien-3-ols, and alk-1-en-3-ols
Lorber, Katja,Schieberle, Peter,Buettner, Andrea
, p. 1025 - 1031 (2014/03/21)
Odor qualities and odor thresholds in air in homologous series of synthesized alk-1-en-3-ols and alka-1,5-dien-3-ols and their corresponding ketones were evaluated by gas chromatography-olfactometry. In the series of the alk-1-en-3-ols and alk-1-en-3-ones the odor quality changed successively from pungent for the compounds with five carbon atoms via metallic, vegetable-like for the six- and seven-carbon odorants to mushroom-like for the compounds with eight and nine carbon atoms. With further increase in chain length the mushroom-like impression decreased and changed to citrus-like, soapy, or herb-like. In both series, two odor threshold minima were found for the six-carbon and also for the eight- and nine-carbon odorants, respectively. In contrast to this, the odor qualities in the series of the (Z)- and (E)-alka-1,5-dien-3-ols and their corresponding ketones did not change significantly with geranium-like, metallic odors and an increasing mushroom-like odor note with increasing chain length. The lowest thresholds were found for the eight- and nine-carbon (Z)-compounds, respectively.
Influence of the chemical structure on odor qualities and odor thresholds in homologous series of alka-1,5-dien-3-ones, alk-1-en-3-ones, alka-1,5-dien-3-ols, and alk-1-en-3-ols
Lorber, Katja,Schieberle, Peter,Buettner, Andrea
, p. 1025 - 1031 (2015/04/22)
Odor qualities and odor thresholds in air in homologous series of synthesized alk-1-en-3-ols and alka-1,5-dien-3-ols and their corresponding ketones were evaluated by gas chromatography-olfactometry. In the series of the alk-1-en-3-ols and alk-1-en-3-ones the odor quality changed successively from pungent for the compounds with five carbon atoms via metallic, vegetable-like for the six- and seven-carbon odorants to mushroom-like for the compounds with eight and nine carbon atoms. With further increase in chain length the mushroom-like impression decreased and changed to citrus-like, soapy, or herb-like. In both series, two odor threshold minima were found for the six-carbon and also for the eight- and nine-carbon odorants, respectively. In contrast to this, the odor qualities in the series of the (Z)- and (E)-alka-1,5-dien-3-ols and their corresponding ketones did not change significantly with geranium-like, metallic odors and an increasing mushroom-like odor note with increasing chain length. The lowest thresholds were found for the eight- and nine-carbon (Z)-compounds, respectively.
Ni-catalyzed stereoselective arylation of inert C-O bonds at low temperatures
Cornella, Josep,Martin, Ruben
supporting information, p. 6298 - 6301 (2014/01/17)
A Ni-catalyzed arylation of inert C-O bonds that operates at temperatures as low as -40 C is described. Unlike other methods for C-O bond cleavage utilizing organometallic species, this protocol operates at low temperatures, thus allowing the presence of sensitive functional groups with exquisite site-selectivity and stereoselectivity.
Highly selective hydrogenation of multiple carbon-carbon bonds promoted by nickel(0) nanoparticles
Alonso, Francisco,Osante, I?aki,Yus, Miguel
, p. 93 - 102 (2007/10/03)
A new method for the highly stereoselective cis semihydrogenation of internal alkynes, semihydrogenation of terminal alkynes, reduction of dienes to alkenes, and reduction of alkynes and alkenes to alkanes is described based on in situ generated both Ni(0) nanoparticles and molecular hydrogen.
