12-Hydroxyheptadecatrienoic acid

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 Edit this at Wikidata
  • InChI=1S/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
    Key: KUKJHGXXZWHSBG-WBGSEQOASA-N
  • 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
    Key: KUKJHGXXZWHSBG-WBGSEQOABE
  • CCCCC[C@@H](/C=C/C=C/C/C=C\CCCC(=O)O)O
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).

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 [pl], 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.[1][2] 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.

  1. ^ Wlodawer, P; Samuelsson, B (1973). "On the organization and mechanism of prostaglandin synthetase". The Journal of Biological Chemistry. 248 (16): 5673–8. doi:10.1016/S0021-9258(19)43558-8. PMID 4723909.
  2. ^ Hamberg, M; Samuelsson, B (1974). "Prostaglandin endoperoxides. Novel transformations of arachidonic acid in human platelets". Proceedings of the National Academy of Sciences of the United States of America. 71 (9): 3400–4. Bibcode:1974PNAS...71.3400H. doi:10.1073/pnas.71.9.3400. PMC 433780. PMID 4215079.