121818-29-9Relevant articles and documents
Selective terminal olefin oxidation of n-3 polyunsaturated fatty acids
Kato,Hirukawa,Namiki
, p. 1475 - 1478 (1992)
Through the action of N-bromosuccinimide in aqueous glyme, terminal double bond of n-3 fatty acids was selectively converted to the corresponding bromohydrin. This evidence suggests the tight conformation of the n-3 fatty acids in aqueous medium.
Control Mechanism for Carbon-Chain Length in Polyunsaturated Fatty-Acid Synthases
Hayashi, Shohei,Naka, Mai,Ikeuchi, Kenshin,Ohtsuka, Makoto,Kobayashi, Kota,Satoh, Yasuharu,Ogasawara, Yasushi,Maruyama, Chitose,Hamano, Yoshimitsu,Ujihara, Tetsuro,Dairi, Tohru
, p. 6605 - 6610 (2019)
Polyunsaturated fatty acids (PUFAs) such as docosahexaenoic acid (DHA) and eicosapentaenoic acid (EPA) are essential fatty acids. PUFA synthases are composed of three to four subunits and each create a specific PUFA without undesirable byproducts. However, detailed biosynthetic mechanisms for controlling final product profiles have been obscure. Here, the bacterial DHA and EPA synthases were carefully dissected by in vivo and in vitro experiments. In vitro analysis with two KS domains (KSA and KSC) and acyl-acyl carrier protein (ACP) substrates showed that KSA accepted short- to medium-chain substrates while KSC accepted medium- to long-chain substrates. Unexpectedly, condensation from C18 to C20, the last elongation step in EPA biosynthesis, was catalyzed by KSA domains in both EPA and DHA synthases. Conversely, condensation from C20 to C22, the last elongation step for DHA biosynthesis, was catalyzed by the KSC domain in DHA synthase. KSC domains therefore determine the chain lengths.
ALL-CIS-3,6,9,12,15-OCTADECAPENTAENOIC ACID FROM THE UNICELLULAR ALGA GYMNODINIUM KOWALEVSKII
Kuklev, D. V.,Aizdaicher, N. A.,Imbs, A. B.,Bezuglov, V. V.,Latyshev, N. A.
, p. 2401 - 2404 (1992)
All-cis-3,6,9,12,15-octadecapentaenoic acid (18:5n-3) was isolated from total lipids of the cultivated microalga Gymnodinium kowalevskii.Its structure was confirmed by GC-MS, 1HNMR, IR and synthesis using a modified method of iodolactonization from 22:6n-3. Key Word Index - Gymnodinium kowalevskii; Gymnodiniaceae; unicellular algae; marine lipids; octadecapentaenoic acid; synthesis.
Synthesis of long chain n-3 and n-6 fatty acids having a photoactive conjugated tetraene group
Kuklev, Dmitry V.,Smith, William L.
, p. 145 - 158 (2004)
Fatty acids of the n-3 and n-6 families containing a photoactive conjugated tetraene group near the carboxylate were prepared from several naturally occurring fatty acids by sequential iodolactonization and treatment with excess 1,8-diazabicyclo[5.4.0]undec-7-ene. The new conjugated fatty acids include 5E,7E,9E,11Z,14Z- and 5E,7E,9E,11E,14Z-eicosapentaenoic acids derived from arachidonic acid; 5E,7E,9E,11Z,14Z,17Z- and 5E,7E,9E,11E,14Z,17Z-eicosahexaenoic acids from eicosapentaenoic acid; and 4E,6E,8E,10Z,13Z,16Z,19Z- and 4E,6E,8E,10E,13Z,16Z,19Z-docosaheptaenoic acids from docosahexaenoic acid. All of the newly synthesized fatty acids were characterized by UV, 1H NMR and mass spectroscopy. These new products represent the first examples of directed conjugation of methylene interrupted double bond systems. The products can be synthesized in gram quantities and in high yields (>50%). Interestingly, it did not prove possible to synthesize fatty acids having a triene group near the carboxyl group even using mild conditions and different synthetic approaches. Once initiated, the isomerization always continued until a tetraene group was formed. Because of the sensitivity of the tetraene group to light, these fatty acids have the potential for being used in tracking fatty acid movements in cells employing fluorescence techniques and in UV light-induced cross linking to membrane proteins.
PROCESSES IN THE PREPARATION OF POLYUNSATURATED KETONE COMPOUNDS
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, (2019/12/04)
A process comprising the following steps: a-i) treating a polyunsaturated ester with a base in a solvent of lower alcohol and water to form the corresponding polyunsaturated acid; a-ii) treating the product from step a-i), especially the crude product, with a halolactonization agent in the solvent of lower alcohol and water, to form the corresponding polyunsaturated halolactone; and a-iii) treating the product from step a-ii), especially the crude product, with a reagent in the solvent of lower alcohol and water to convert the polyunsaturated halolactone to the corresponding polyunsaturated epoxide lower alkyl ester.
Trans Lipid Library: Synthesis of Docosahexaenoic Acid (DHA) Monotrans Isomers and Regioisomer Identification in DHA-Containing Supplements
Menounou, Georgia,Giacometti, Giorgia,Scanferlato, Roberta,Dambruoso, Paolo,Sansone, Anna,Tueros, Itziar,Amézaga, Javier,Chatgilialoglu, Chryssostomos,Ferreri, Carla
, p. 191 - 200 (2018/03/25)
Docosahexaenoic acid (DHA) is a semiessential polyunsaturated fatty acid (PUFA) for eukaryotic cells that is found in natural sources such as fish and algal oils and widely used as an ingredient for omega-3 containing foods or supplements. DHA effects are
PROCESS FOR THE PREPARATION OF A POLYUNSATURATED KETONE COMPOUND
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Page/Page column 21; 22, (2015/02/19)
The invention relates to the manufacture of certain polyunsaturated compounds employing a particular application of the Mitsonobu reaction in the presence of at least one anti-oxidant. We have found a method of making a pharmaceutically-acccptable polyunsaturated ester or thioester compound directly, which can ultimately be converted to the advantageous ketone compounds, in which unwanted oxidation and cis/trans isomerization are substantially reduced or eliminated using particular Mitsonobu chemistry.
Concise syntheses of three ω-3 polyunsaturated fatty acids
Jakobsen, Martin Gjerde,Vik, Anders,Hansen, Trond Vidar
supporting information, p. 5837 - 5839 (2013/01/13)
The synthesis of the three ω-3 polyunsaturated fatty acids, eicosatetraenoic acid (3), docosapentaenoic acid (4), and stearidonic acid (5) has been achieved using eicosapentaenoic acid or docosahexaenoic acid as the starting materials.
Synthesis of polyconjugated fatty acids
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Page 3; 12-13, (2010/02/10)
The present invention relates to fatty acids. In particular, the present invention provides polyconjugated fatty acids, and methods of their synthesis and their use.
