31823-43-5Relevant articles and documents
[6, 7, 10, 11-13C4]-labelled leukotriene B4 synthesis: Standard for mass spectrometry determination and metabolic studies
Treilhou, Michel,Couderc, Francois
, p. 737 - 745 (2001)
The mass spectrometry quantification and metabolic studies of leukotriene B4 (LTB4) in biological fluids require standards labelled with stable isotopes. This paper describes the synthesis of LTB4 labelled with 13C in positions 6, 7, 10 and 11 (1). These labelled carbons come from 13C2-acetylene. A labelled LTB4 is obtained with an isotopic enrichment of 99%. Copyright
A new efficient synthesis of (58,12S)-DiHETE
Chemin,Alami,Linstrumelle
, p. 2681 - 2684 (1992)
An efficient synthesis of (5S,12S)-diHETE was realized by a Pd-Cu catalysed coupling of the chiral synthons 3 and 4 which were easily obtained by the kinetic resolution of the corresponding racemates using the Sharpless reagent.
A convergent strategy toward linear Cis-skipped polyenes
Sandri, Jacqueline,Soto, Thierry,Gras, Jean-Louis,Viala, Jacques
, p. 6611 - 6612 (1997)
An easy preparation of symmetric Cis-skipped polyenic hydrocarbons 1 to 5 combining the controlled classical Wittig reaction or the oxidative dimerization of phosphoranes is described.
An Efficient Stereocontrolled Synthesis of 12(R)-HETE and 12(S)-HETE
Chemin, Denis,Gueugnot, Sylvie,Linstrumelle, Gerard
, p. 4369 - 4378 (1992)
An efficient synthesis of 12(R) and 12(S) HETEs was realized by assembly of the easily obtainable synthons: optically pure iodo-alcohols 3(R) and 3(S) with the ester 4, followed by reduction with activated zinc.
Synthesis of 7-thiaarachidonic acid as a mechanistic probe of prostaglandin H synthase-2
McGinley, Chris M.,Jacquot, Cyril,van der Donk, Wilfred A.
, p. 4049 - 4052 (2007)
The mechanism by which prostaglandin synthase converts arachidonic acid to prostaglandin G2, creating five new chiral centers in the process, is still incompletely understood. The first radical intermediate has been characterized by EPR spectroscopy but subsequent proposed intermediates have not succumbed to detection. We report the synthesis of 7-thiaarachidonic acid designed to stabilize one of the proposed radical intermediates, which may allow its detection.
Catalytic asymmetric synthesis of Leukotriene B4
Yang, Pengfei,Zhong, Jiangchun,Ji, Kaijie,Yin, Jingwei,Li, Shuoning,Wei, Siyuan,Zhou, Yun,Wang, Lifeng,Wang, Min,Bian, Qinghua
, p. 1596 - 1601 (2017/10/20)
Leukotriene B4 1 was prepared from two chiral synthons 8 and 14. The chiral secondary alcohols of 8 and 14 were constructed by BINOL/Ti(OiPr)4 catalyzed enantioselective alkynylzinc addition to aldehydes.
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.
