9(10)-Nitrooleate
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.
For research use only. We do not sell to patients.
- CAS No.: 1092676-99-7
- Formula: C18H33NO4
- Molecular Weight:327.46
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Storage:
Solution, -20°C, 2 years
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Biological Activity
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Chemical Information
- Purity & Documentation
- References
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Help & FAQs
Biological Activity
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PPARα |
PPARγ |
PPARβ/δ |
eNOS |
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.
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Cell Line:human umbilical vein endothelial cells (HUVEC)
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Concentration:3 μM
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Incubation Time:2, 4, 8, 16 h
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Result:Increased phosphorylation of eNOS-Ser1177 at 2-4 h, gradually increased phosphorylation of eNOS-Ser633 through 16 h, and gradually increased dephosphorylation of eNOS at Ser113 and Thr495, despite decreasing total eNOS protein expression.\n
Induced threefold phosphorylation of Akt-Ser473 at 2 h, followed by sixfold phosphorylation of ERK1/2 (P44-Thr202/P42-Tyr204) at 4 h, with both kinases gradually returning to basal levels after peak induction.
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Cell Line:3T3-L1 preadipocyte
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Concentration:1-3 μM
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Incubation Time:14 days
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Result:Induced ~60% of 3T3-L1 preadipocyte differentiation at 3 μM, as measured by oil red O staining for intracellular lipid accumulation.
Upregulated expression of adipocyte-specific markers PPARγ2 and aP2.
Chemical Information
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CAS No. 1092676-99-7
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Appearance Liquid
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Molecular Weight 327.46
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Formula C18H33NO4
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Color Colorless to light yellow
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SMILES
OC(CCCCCCC/C([N+]([O-])=O)=C\CCCCCCCC)=O.OC(CCCCCCC/C=C([N+]([O-])=O)\CCCCCCCC)=O
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Synonyms
9(10)-Nitrated oleic acid
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Shipping
Room temperature in continental US; may vary elsewhere.
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Storage
Solution, -20°C, 2 years
Purity & Documentation
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Data Sheet (274 KB)
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SDS (252 KB)
- English - EN (252 KB)
- Français - FR (252 KB)
- Deutsch - DE (252 KB)
- Norwegian - NO (252 KB)
- Español - ES (252 KB)
- Swedish - SV (252 KB)
- Italian - IT (252 KB)
- Portuguese - PT (252 KB)
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Handling Instructions (2659 KB)
References
[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]
Calculators
Concentration (start) × Volume (start) = Concentration (final) × Volume (final)
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