19754-58-6Relevant academic research and scientific papers
PHEROMONES OF INSECTS AND THEIR ANALOGS. XXVIII. PRACTICAL SYNTHESIS OF TETRADECA-9Z,12E-DIEN-1-YL ACETATE - A COMPONENT OF THE SEX PHEROMONES OF INSECTS OF THE ORDER LEPIDOPTERA
Odinokov, V. N.,Dzhemilev, U. M.,Ishumuratov, G. Yu.,Botsman, L. P.,Ibragimov, A. G.,et al.
, p. 238 - 240 (1991)
Tetradeca-9Z,12E-dien-1-yl acetate, a sex pheromone of the Indian meal moth Plodia interpunctella has been synthesized from the readily available product of the hydrodimerization of butadiene - octa-1,7-diene.
Effect of perfluoroalkyl chain length on monolayer behavior of partially fluorinated oleic acid molecules at the air-water interface
Baba, Teruhiko,Takai, Katsuki,Takagi, Toshiyuki,Kanamori, Toshiyuki
, p. 31 - 39 (2013)
A series of oleic acid (OA) analogs containing terminal perfluoroalkyl groups (CF3, C2F5, n-C3F 7, n-C4F9 or n-C8F17) was synthesized to clarify how the fluorinated chain length affects the stability and molecular packing of liquid-expanded OA monolayers at the air-water interface. Although the substitution of terminal CF3 group for CH3 in OA had no effect on monolayer stability, further fluorination led to a gradual increase in monolayer stability at 25 ?C. Surface pressure-area isotherm revealed that partially fluorinated OA analogs form more expanded monolayers than OA at low surface pressures, and that the monolayer behavior of OA analogs with the even-carbon numbered fluorinated chain is almost the same as that of OA upon monolayer compression, whereas the behavior of OA analogs with the odd-carbon numbered fluorinated chain significantly differs from that of OA. These results indicate: (i) the terminal short part (at least C2 residue) in OA predominantly determines the liquid-expanded monolayer stability; (ii) the molecular packing state of OA may be perturbed by the substitution of a short odd-carbon numbered fluorinated chain; (iii) hence, OA analogs with even-carbon numbered chain are considered to be preferable as hydrophobic building blocks for the synthesis of fluorinated phospholipids.
Synthesis and characterization of partially fluorinated stearolic acid analogs: Effect of their fluorine content on the monolayer at the air-water interface
Takai, Katsuki,Takagi, Toshiyuki,Baba, Teruhiko,Kanamori, Toshiyuki
, p. 120 - 126 (2007)
Novel stearolic acid analogs (i.e., 9-octadecynoic acid analogs: 1a-d) containing the shorter perfluoroalkyl groups, CF3, C2F5, n-C3F7 or n-C4F9 group were synthesized. Equilibrium spreading pressures (πes) of their monolayers at the air-water interface were measured in order to demonstrate how the fluorine content has an effect on the stability of the fatty acid monolayers. As the fluorine content in stearolic acid molecule increased, its melting points was lowered indicating the solid bulk phase of stearolic acid became thermally unstable, while its monolayer stability evaluated by πe at 25 °C, dramatically increased and subsequently leveled off above a certain fluorine content. Under this condition, the replacement of at least five hydrogen atoms at the terminal hydrophobic segment in stearolic acid molecule by fluorine atoms (CF3CF2 group) was required to alter the bulk property of stearolic acid and exhibit the stabilization of monolayers, whereas further fluorination of stearolic acid had a minor effect on the monolayer stability. This behavior suggests the terminal fluorinated hydrophobic segment exclusively controls the interfacial stability of fatty acid monolayers.
THERAPY FOR DRY EYE (DE) AND MEIBOMIAN GLAND DYSFUNCTION (MGD) BASED ON THE REPLACEMENT OF O-ACYL-Ω-HYDROXY FATTY ACIDS (OAHFA)
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Page/Page column 26; 30; 32, (2020/09/19)
The present invention relates to a process for preparing a fatty acid, a fatty acid obtainable by said process, a composition comprising said fatty acid, an eye drop comprising said fatty acid and a method for treating dry eye disease or Meibomian gland d
Synthesis of site-specifically13C labeled linoleic acids
Offenbacher, Adam R.,Zhu, Hui,Klinman, Judith P.
supporting information, p. 4537 - 4540 (2016/09/23)
Soybean lipoxygenase-1 (SLO-1) catalyzes the C–H abstraction from the reactive carbon (C-11) in linoleic acid as the first and rate-determining step in the formation of alkylhydroperoxides. While previous labeling strategies have focused on deuterium labeling to ascertain the primary and secondary kinetic isotope effects for this reaction, there is an emerging interest and need for selectively enriched13C isotopologues. In this Letter, we present synthetic strategies for site-specific13C labeled linoleic acid substrates. We take advantage of a Corey–Fuchs formyl to terminal13C-labeled alkyne conversion, using13CBr4as the labeling source, to reduce the number of steps from a previous fatty acid13C synthetic labeling approach. The labeled linoleic acid substrates are useful as nuclear tunneling markers and for extracting active site geometries of the enzyme–substrate complex in lipoxygenase.
The (5Z)-5-Pentacosenoic and 5-Pentacosynoic Acids Inhibit the HIV-1 Reverse Transcriptase
Moreira, Lizabeth Giménez,Orellano, Elsie A.,Rosado, Karolyna,Guido, Rafael V. C.,Andricopulo, Adriano D.,Soto, Gabriela Ortiz,Rodríguez, José W.,Sanabria-Ríos, David J.,Carballeira, Néstor M.
, p. 1043 - 1050 (2015/10/05)
The natural fatty acids (5Z)-5-pentacosenoic and (9Z)-9-pentacosenoic acids were synthesized for the first time in eight steps starting from either 4-bromo-1-butanol or 8-bromo-1-butanol and in 20-58 % overall yields, while the novel fatty acids 5-pentacosynoic and 9-pentacosynoic acids were also synthesized in six steps and in 34-43 % overall yields. The ?5 acids displayed the best IC50's (24-38 μM) against the HIV-1 reverse transcriptase (RT) enzyme, comparable to nervonic acid (IC50 = 12 μM). The ?9 acids were not as effective towards HIV-RT with the (9Z)-9-pentacosenoic acid displaying an IC50 = 54 μM and the 9-pentacosynoic acid not inhibiting the enzyme at all. Fatty acid chain length and position of the unsaturation was important for the observed inhibition. None of the synthesized fatty acids were toxic (IC50 > 500 μM) towards peripheral blood mononuclear cells. Molecular modeling studies indicated the structural determinants underlying the biological activity of the most potent compounds. These results provide new insights into the structural requirements that must be present in fatty acids so as to enhance their inhibitory potential towards HIV-RT.
Long-chain triazolyl acids as inhibitors of osteoclastogenesis
Marshall, Andrew J.,Lin, Jian-Ming,Grey, Andrew,Reid, Ian R.,Cornish, Jillian,Denny, William A.
, p. 4112 - 4119 (2013/07/27)
Saturated fatty acids (e.g., palmitic acid) are known to moderately inhibit the development of osteoclasts in vitro. In pursuit of more effective inhibitors of osteoclastogenesis we explored two new classes of palmitic acid analogues containing either an ether or triazolyl group at various positions along the chain. The compounds were evaluated for their ability to inhibit the formation of osteoclasts in primary mouse bone marrow cultures. The oxyacids were generally prepared by condensation of the appropriate alkyl halides and diols, followed by Jones oxidation. The triazolyl acids were prepared by copper-catalysed click chemistry between alkyl azides and acetylenic acids, or with the appropriately-protected azides and alkynes, followed by deprotection and oxidation. The oxyacids were little more effective than palmitic acid, but the triazolyl analogues were much more effective osteoclastogenesis inhibitors, especially when the triazole was distant from the acid unit.
SELF-ASSEMBLED MONOLAYERS AND METHODS FOR USING THE SAME IN BIOSENSING APPLICATIONS
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Page/Page column 9; 16-17, (2013/02/27)
Cross-linked amphiphile constructs that form self-assembled monolayers (SAMs) on metal surfaces such as gold surfaces are disclosed. These new SAMs generate well packed and highly oriented monolayer films on gold surfaces. A method for using the SAMs in t
Improved synthesis of (9Z)-9,13-tetradecadien-11-ynal, the sex pheromone of the avocado seed moth, Stenoma catenifer
Zou, Yunfan,Millar, Jocelyn G.
body text, p. 1336 - 1337 (2010/04/29)
The terminal dienyne of (9Z)-9,13-tetradecadien-11-ynal, the sex pheromone of the avocado seed moth, Stenoma catenifer, was constructed by coupling a vinyl iodide precursor with commercially available 1-buten-3-yne with Pd catalysis, resulting in a short and efficient synthesis of the pheromone.
Synthesis of photoactivatable analogues of lysophosphatidic acid and covalent labeling of plasma proteins
Li, Zaiguo,Baker, Daniel L.,Tigyi, Gabor,Bittman, Robert
, p. 629 - 635 (2007/10/03)
Lysophosphatidic acids hearing a benzophenone group in either the sn-1 or sn-2 chain of an oleoyl-type ester or oleyl-type ether chain and 32P in the phosphate group were synthesized. The benzophenone moiety was introduced by selective hydrobor
