64234-42-0Relevant articles and documents
Asymmetric synthesis of 12-hydroxyheptadecatrienoic acid and its 5,6-dihydro- and 14,15-dehydro-derivatives
Kobayashi, Yuichi,Morita, Masao,Ogawa, Narihito,Kondo, Daiki,Tojo, Toshifumi
, p. 10667 - 10673 (2016/11/30)
Natural 12-hydroxyheptadecatrienoic acid (12-HHT) with an S configuration was synthesised by a Suzuki-Miyaura coupling of C10-C17 iodo alcohol with C1-C9 vinylborane. The iodo alcohol was synthesised by utilising Sharpless asymmetric epoxidation of the corresponding trimethylsilyl alcohol. The method yielded more than 100 mg of 12-HHT. Similarly, syntheses of 5,6-dihydro- and 14,15-dehydro derivatives of 12-HHT, known as HHD and HHTE, respectively, were completed in a stereoselective manner.
Thermodynamic and structural characterization of cis-trans isomerization of 12-(S)-hydroxy-(5Z, 8E,10E)-heptadecatrienoic acid by high-performance liquid chromatography and gaschromatography-mass spectrometry
John,Schlegel
, p. 181 - 188 (2007/10/03)
It is shown that 12-(S)-hydroxy-(5Z,8E,10E)-heptadecatrienoic acid (5-cis-HHT) - a physiological metabolite of arachidonic acid-is acid-catalyzed converted into a less polar substance with its maximum UV-absorption at λ(max)=232 nm and a molar absorptivity of about ε=26 600±200 M-1 cm-1. Using a reversed-phase high-performance liquid chromatographic (HPLC) method this equilibrium reaction (K(c)=1.78±0.05 at pH 1.10 and 298 K) could be thermodynamicly characterized as a pH dependent, exergonic and exothermic reaction according to kinetics of a first order reaction (at pH 1.10 and 298 K: Δ(R)G°=-1.42±0.07 kJ mol-1, Δ(R)H°=-3.50±0.9 kJ mol-1, Δ(R)S°=-7.0±3.0 J mol-1*K, Δ(R)H(f)(≠)=100.0±4.0 kJ mol-1). Kinetic data for several pH-values and temperatures are presented. These data and structural characterization by gaschromatography-mass spectrometry (GC/MS) lead to the conclusion that 5-cis-HHT is isomerized to 12-(S)-hydroxy-(5E,8E,10E)-heptadecatrienoic acid (5-trans-HHT). Copyright (C) 1998 Elsevier Science Ireland Ltd.