12-Hydroxyheptadecatrienoic acid
| Names | |
|---|---|
| Preferred IUPAC name
(5Z,8E,10E,12S)-12-Hydroxyheptadeca-5,8,10-trienoic acid | |
| Identifiers | |
3D model (JSmol) |
|
| ChemSpider | |
| ECHA InfoCard | 100.161.462 |
PubChem CID |
|
CompTox Dashboard (EPA) |
|
| |
| |
| Properties | |
| C17H28O3 | |
| Molar mass | 280.408 g·mol−1 |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references | |
12-Hydroxyheptadecatrienoic acid (also termed 12-HHT, 12(S)-hydroxyheptadeca-5Z,8E,10E-trienoic acid, or 12(S)-HHTrE) is a 17 carbon metabolite of the 20 carbon polyunsaturated fatty acid, arachidonic acid. 12-HHT is less ambiguously termed 12-(S)-hydroxy-5Z,8E,10E-heptadecatrienoic acid to indicate the S stereoisomerism of its 12-hydroxyl residue and the Z, E, and E cis–trans isomerism of its three double bonds. 12-HHT was discovered and structurally defined in 1973 by Paulina Wlodawer, Bengt Samuelsson, and Mats Hamberg. It was identified as a product of arachidonic acid metabolism made by microsomes isolated from sheep seminal vesicle glands and by intact human platelets. 12-HHT was for many years thought to be merely a biologically inactive byproduct of prostaglandin synthesis. More recent studies, however, have attached potentially important activity to it.