(±)9(10)-DiHOME

(±)9(10)-DiHOME is the diol form of (±)9(10)-EpOME (Cay-52400), a cytochrome P450-derived epoxide of linoleic acid (Cay-90150, Cay-90150.1, Cay-21909) also known as leukotoxin. It is formed from 9(10)-EpOME by soluble epoxide hydrolase (sEH) in neutrophils. It is toxic to Sf21 cells expressing sEH and to lacZ-expressing control cells, unlike leukotoxin, which is only toxic to cells containing sEH. A mixture of 9(10)- and 12(13)-DiHOME induces cell death in rabbit renal proximal tubule cells concomitant with mitochondrial respiration dysfunction and induces lung injury, respiratory distress, and mortality in mice. 9(10)-DiHOME is a toxic lipid mediator involved in acute respiratory distress syndrome (ARDS), a common and often fatal complication in severe burn victims. Levels of 9(10)-DiHOME are increased in bronchoalveolar lavage fluid (BALF) from women, but not men, with chronic obstructive pulmonary disease (COPD). BALF levels are also increased in patients with allergic asthma following allergen exposure compared to patients without allergic asthma. It has been used as a plasma biomarker for sEH activity in vivo.Formal Name: (±)9,10-dihydroxy-12Z-octadecenoic acid. CAS Number: 263399-34-4. Synonyms: Leukotoxin diol. Molecular Formula: C18H34O4. Formula Weight: 314.5. Purity: >98%. Formulation: (Request formulation change), A solution in methyl acetate. Solubility: DMF: 20 mg/ml, DMSO: 20 mg/ml, Ethanol: 20 mg/ml, PBS (pH 7.2): 10 µg/ml. SMILES: O[C@H](C/C=C\CCCCC)[C@H](O)CCCCCCCC(O)=O. InChi Code: InChI=1S/C18H34O4/c1-2-3-4-5-7-10-13-16(19)17(20)14-11-8-6-9-12-15-18(21)22/h7,10,16-17,19-20H,2-6,8-9,11-15H2,1H3,(H,21,22)/b10-7-/t16-,17-/m1/s1. InChi Key: XEBKSQSGNGRGDW-GJWDQICYSA-N. Side Chain Carbon Sum: 18:1.