LIPID MAPS

(±)8(9)-DiHET is an oxylipin and a racemic mixture of the arachidonic acid metabolites 8(S),9(R)-DiHET and 8(R),9(S)-DiHET.¹ It is formed from arachidonic acid via an (±)8(9)-EET intermediate by epoxide hydrolases. (±)8(9)-DiHET (1 µM) induces cAMP production in primary human coronary artery smooth muscle cells.² Plasma levels of (±)8(9)-DiHET are increased in a mouse model of osteoarthritic pain induced by destabilization of the medial meniscus, an effect that can be reversed by the soluble epoxide hydrolase (sEH) inhibitor TPPU.³ Spinal cord levels of (±)8(9)-DiHET are also increased in a rat model of surgically-induced acute spinal cord injury (SCI).⁴

This information has been provided by Cayman Chemical

References

1. Oliw, E.H., Guengerich, F.P., and Oates, J.A. Oxygenation of arachidonic acid by hepatic monooxygenases. Isolation and metabolism of four epoxide intermediates. The Journal of Biological Chemistry 257(7), 3771-3781 (1982).

2. Matsumoto, N., Singh, N., Lee, K.S., et al. The epoxy fatty acid pathway enhances cAMP in mammalian cells through multiple mechanisms. Prostaglandins Other Lipid Mediat. 162, 106662 (2022).

3. Gowler, P.R.W., Turnbull, J., Shahtaheri, M., et al. Clinical and preclinical evidence for roles of soluble epoxide hydrolase in osteoarthritis knee pain. Arthritis Rheumatol. 74(4), 623-633 (2022).

4. Pang, Y., Liu, X., Zhao, C., et al. LC-MS/MS-based arachidonic acid metabolomics in acute spinal cord injury reveals the upregulation of 5-LOX and COX-2 products. Free Radic. Biol. Med. 193(Pt 1), 363-372 (2022).

References

Taxonomy Information

Curated from

NCBI taxonomy class

Reference

Homo sapiens (#9606)

Mammalia (#40674)

Lipidomics reveals a remarkable diversity of lipids in human plasma,
J Lipid Res, 2010

Pubmed ID: 20671299

DOI: 10.1194/jlr.M009449

String Representations

InChiKey (Click to copy)

DCJBINATHQHPKO-TYAUOURKSA-N

InChi (Click to copy)

InChI=1S/C20H34O4/c1-2-3-4-5-6-7-8-9-12-15-18(21)19(22)16-13-10-11-14-17-20(23)24/h6-7,9-10,12-13,18-19,21-22H,2-5,8,11,14-17H2,1H3,(H,23,24)/b7-6-,12-9-,13-10-

SMILES (Click to copy)

C(C(O)C(O)C/C=C\CCCC(=O)O)/C=C\C/C=C\CCCCC