54397-84-1 Usage
Description
12(S)-HHT, also known as 12(S)-Hydroxyheptadecatrienoic acid, is an unusual product of the cyclooxygenase (COX) pathway and one of the primary metabolites of arachidonic acid in human platelets. It is biosynthesized by thromboxane synthase (TX synthase) from prostaglandin H2 (PGH2) concurrently with TXA2. The biological role of 12(S)-HHT is uncertain, but it is avidly oxidized to 12-oxoHTrE by porcine 15-hydroxy PGDH. Arachidonic acid, a precursor of 12(S)-HHT, is an essential fatty acid found in various animal tissues and is a constituent of animal phosphatides.
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.
Check Digit Verification of cas no
The CAS Registry Mumber 54397-84-1 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 5,4,3,9 and 7 respectively; the second part has 2 digits, 8 and 4 respectively.
Calculate Digit Verification of CAS Registry Number 54397-84:
(7*5)+(6*4)+(5*3)+(4*9)+(3*7)+(2*8)+(1*4)=151
151 % 10 = 1
So 54397-84-1 is a valid CAS Registry Number.
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
54397-84-1Relevant 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.
Spectrofluorimetric quantification of malondialdehyde for evaluation of cyclooxygenase-1/Thromboxane synthase inhibition
Dannhardt, Gerd,Flemmer, Linda,Hartmann, Rolf W.,Kleber, Alice,Schulze, Elfriede
, p. 359 - 364 (2007/10/03)
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.
