9(10)-Nitrooleate  (Synonyms: 9(10)-Nitrated oleic acid)

9 (10)-Nitrooleate (9(10)-Nitrated oleic acid) is an endogenous lipid signaling mediator with vasoprotective effects. 9 (10)-Nitrooleate enhances enzymatic activity and improves nitric oxide bioavailability by inducing phosphorylation of Akt and ERK1/2, regulating the multi-site phosphorylation status of eNOS and optimizing its interaction with Hsp90. 9 (10)-Nitrooleate also activates PPARα, PPARδ and PPARγ receptors, thereby regulating adipogenesis, glucose uptake and inflammation-related gene expression, and exhibits immunosuppressive effects by inhibiting neutrophil migration and cytokine secretion. 9 (10)-Nitrooleate is widely used in studies of sepsis and related inflammatory diseases^[1][2][3].

9(10)-Nitrooleate (3 μM; 2-16 h) activates Akt and ERK1/2 signaling in human umbilical vein endothelial cells, inducing peak threefold Akt phosphorylation at 2 h and sixfold ERK1/2 phosphorylation at 4 h^[1].
9(10)-Nitrooleate (3 μM; 2-16 h) modulates eNOS protein interactions in human umbilical vein endothelial cells, reducing eNOS/Cav-1 association and increasing eNOS/Hsp90 association to enhance eNOS activity^[1].
9(10)-Nitrooleate (1 μM; 2 days) significantly increases glucose uptake in differentiated 3T3-L1 adipocytes, with this effect partially dependent on PPARγ activation^[2].
9(10)-Nitrooleate (1-10 μM; 30 min) dose-dependently inhibits LPS-induced secretion of TNFα and IL-1β from normal murine peripheral blood PMNs^[3].

MedChemExpress (MCE) has not independently confirmed the accuracy of these methods. They are for reference only.

327.46

C₁₈H₃₃NO₄

1092676-99-7

Liquid

Colorless to light yellow

OC(CCCCCCC/C([N+]([O-])=O)=C\CCCCCCCC)=O.OC(CCCCCCC/C=C([N+]([O-])=O)\CCCCCCCC)=O

Room temperature in continental US; may vary elsewhere.

Solution, -20°C, 2 years

• [1]. Shin E, et al. Nitrooleate mediates nitric oxide synthase activation in endothelial cells. Lipids. 2014;49(5):457-466.  [Content Brief]

  [2]. Baker PR, et al. Fatty acid transduction of nitric oxide signaling: multiple nitrated unsaturated fatty acid derivatives exist in human blood and urine and serve as endogenous peroxisome proliferator-activated receptor ligands. J Biol Chem. 2005;280(51):42464-42475.  [Content Brief]

  [3]. Panati K, et al. The nitrated fatty acid, 10-nitrooleate inhibits the neutrophil chemotaxis via peroxisome proliferator-activated receptor gamma in CLP-induced sepsis in mice. Int Immunopharmacol. 2019;72:159-165.  [Content Brief]