54397-84-1

Usage

Uses

1. Used in Pharmaceutical Research:
12(S)-HHT is used as a research compound for studying the COX pathway and its role in the biosynthesis of prostaglandins, thromboxanes, and leukotrienes. This helps in understanding the underlying mechanisms of various physiological and pathological processes.
2. Used in Biochemical Analysis:
12(S)-HHT is used as a biochemical marker to study the metabolism of arachidonic acid and its involvement in various biological processes. This aids in the identification of potential therapeutic targets for the treatment of diseases associated with altered arachidonic acid metabolism.
3. Used in Drug Development:
12(S)-HHT can be used as a lead compound in the development of new drugs targeting the COX pathway and related inflammatory processes. Understanding the structure and function of 12(S)-HHT can help in designing more effective and selective inhibitors or modulators of the COX pathway.
4. Used in Nutritional Science:
As a metabolite of arachidonic acid, 12(S)-HHT can be used to study the role of essential fatty acids in human health and nutrition. This can contribute to the development of dietary recommendations and supplementation strategies for maintaining optimal health.
5. Used in Analytical Chemistry:
12(S)-HHT can be used as a reference compound for the development and validation of analytical methods for the detection and quantification of arachidonic acid metabolites in biological samples. This is important for assessing the metabolic status of individuals and monitoring the effects of therapeutic interventions.

InChI:InChI=1/C17H28O3/c1-2-3-10-13-16(18)14-11-8-6-4-5-7-9-12-15-17(19)20/h5-8,11,14,16,18H,2-4,9-10,12-13,15H2,1H3,(H,19,20)/b7-5-,8-6+,14-11+/t16-/m0/s1

Upstream product

• 88765-27-9 (R)-1ξ-iodo-oct-1-en-3-ol 
• 128946-69-0 ester methylique du 12-HHT 
• 506-32-1 all cis 5,8,11,14-eicosatetraenoic acid 
• 79171-56-5 (5Z,8E,10E,12S)-12-hydroxy-5,8,10-heptadecatrienoic acid methyl ester 
• 73961-62-3 1-iodo-3(RS)-hydroxy-cis-octene 
• 53210-14-3 n-pentyl trimethylsilylethynyl ketone 
• 128899-38-7 (S )-1-(trimethylsilyl)oct -1-yn-3-ol 
• 192765-48-3 (3S)-3-(tert-butyl-diphenylsilyloxy)-oct-1-yne 
• 88765-26-8 (S)-1ξ-iodo-oct-1-en-3-ol 

Downstream Products

• 50683-78-8 12-(S)-hydroxy-(5E,8E,10E)-heptadecatrienoic acid 
• 103374-38-5 hydroxyheptadeca-5Z,8E,10E-trienoicacid 

Relevant academic research and scientific papers

Asymmetric synthesis of 12-hydroxyheptadecatrienoic acid and its 5,6-dihydro- and 14,15-dehydro-derivatives

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.

Synthesis of (S,5 Z,8 E,10 E)-12-hydroxyheptadeca-5,8,10-trienoic acid (12 S -HHT) and its analogues

Natural 12S-HHT and its analogues were synthesized for study of structure and activity relationship toward the BLT2 receptor. The Suzuki-Miyaura coupling was used for construction of the 8E,10E-diene moiety of 12S-HHT and analogues of (12R)- and 12-keto-t

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

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.

Spectrofluorimetric quantification of malondialdehyde for evaluation of cyclooxygenase-1/Thromboxane synthase inhibition

The in vitro assay developed by Hartmann and Ledergerber (1995) utilizing the spectrofluorimetric quantification of malondialdehyde after reaction with thiobarbituric acid was modified and used for further investigations. The human whole blood was replaced by a platelet suspension of pig blood, and calcium ionophore A23187 was used instead of collagen for inducing the arachidonic acid cascade. The modified assay represents a simple, time and cost saving method for the evaluation of cyclooxygenase- 1/thromboxane synthase inhibition. The reproducibility and comparability of results is given. Additional experiments allow classification of selective phospholipase A2, cyclooxygenase-1, and thromboxane synthase inhibitors. Further studies of malondialdehyde formation show that the cyclooxygenase and/or the thromboxane synthase are competitively inhibited by reaction products of the cyclooxygenase pathway by a negative feedback mechanism.