Home
Resources
Publications
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

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

H John, W Schlegel

Chem Phys Lipids. 1998 Oct;95(2):181-8.

PMID: 11458962

Abstract:

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 (1)max=232 nm and a molar absorptivity of about epsilon=26600 +/- 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: delta(R)G(o) = -1.42 +/- 0.07 kJ mol(-1), delta(R)H(o) = -3.50 +/- 0.9 kJ mol(-1), delta(R)S(o) = 7.0 +/- 3.0 J mol(-1)*K, delta(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).

Chemicals Related in the Paper:

Catalog Number	Product Name	Structure	CAS Number	Price
AP54397841	12(S)-Hydroxy-(5Z,8E,10E)-heptadecatrienoic acid		54397-84-1	Price

As a specialist in analytical chemical Products, Alfa Chemistry offers consumers a wealth of raw materials and a full range of technologies and services.

QUICK LINKS

HEADQUARTERS

Tel:

Fax:

Email: