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9-Nitrooleate

Cayman Chemical Item Number 10008042

9-nitro-9-trans-Octadecenoic Acid (CAS 875685-44-2)

9-Nitrooleate (CAS 875685-44-2)

See more	Fatty Acids (267) NO Donors (26) Nuclear Receptors (86) PPAR (59) Reactive Probes (27) Nitric Oxide (101) Oxidative Injury (258)

Description

Nitrated unsaturated fatty acids, such as 10- and 12-nitrolinoleic acid (LNO₂), cholesteryl nitrolinoleate, and nitrohydroxylinoleate, represent a new class of endogenous lipid-derived signalling molecules. LNO₂ isomers serve as potent endogenous ligands for PPARγ and can also decompose or be metabolized to release nitric oxide.^1,2,3,4 9-Nitrooleic acid is one of two regioisomers of nitrooleic acid, the other being 10-nitrooleic acid (OA-NO₂; used for the mixture of isomers), which are formed by nitration of oleic acid in approximately equal proportions in vivo.⁵ Peroxynitrite, acidified nitrite, and myeloperoxidase in the presence of H₂O₂ and nitrite, all mediate the nitration of oleic acid. OA-NO₂ is found in human plasma as the free acid and esterified in phospholipids at concentrations of 619 ± 52 nM and 302 ± 369 nM, respectively. OA-NO₂ activates PPARγ approximately 7-fold at a concentration of 1 µM and effectively promotes differentiation 3T3-L1 preadipocytes to adipocytes at 3 µM.⁵

1 Lim, D.G., Sweeney, S., Bloodsworth, A., et al. Nitrolinoleate, a nitric oxide-derived mediator of cell function: Synthesis, characterization, and vasomotor activity. Proc Natl Acad Sci USA 99(25) 15941-15946 (2002).

2 Schopfer, F.J., Lin, Y., Baker, P.R.S., et al. Nitrolinoleic acid: An endogenous peroxisome proliferator-activated receptor g ligand. Proc Natl Acad Sci USA 102(7) 2340-2345 (2005).

3 Lima, E.S., Bonini, M.G., Augusto, O., et al. Nitrated lipids decompose to nitric oxide and lipid radicals and cause vasorelaxation. Free Radic Biol Med 39 532-539 (2005).

4 Baker, P.R.S., Schopfer, F.J., Sweeney, S., et al. Red cell membrane and plasma linoleic acid nitration products: Synthesis, clinical identification, and quantitation. Proc Natl Acad Sci USA 101(32) 11577-11582 (2004).

5 Baker, P.R., Lin, Y., Schopfer, F.J., et al. Fatty acid transduction of nitric oxide signaling. Multiple nitrated unsaturated acid derivatives exist in human blood and urine serve as endogenous peroxisome proliferator-activated receptor ligands. J Biol Chem 280(51) 42464-42475 (2005).

Synonyms	9-nitro-9-trans-Octadecenoic Acid
Formal Name	9-nitro-9E-octadecenoic acid
CAS Number	875685-44-2
Molecular Formula	C₁₈H₃₃NO₄
Formula Weight	327.5
Formulation	A solution in ethanol
Purity	>98%
λ_max	255 nm
Stability	1 year
Storage	-20°C
Shipping	Wet ice in continental US; may vary elsewhere
SMILES	Copy SMILES to clipboard CCCCCCCC/C=C([N+]([O-])=O)\CCCCCCCC(O)=O

Background Reading

Lim, D.G., Sweeney, S., Bloodsworth, A., et al. Nitrolinoleate, a nitric oxide-derived mediator of cell function: Synthesis, characterization, and vasomotor activity. Proc Natl Acad Sci USA 99(25) 15941-15946 (2002).

Schopfer, F.J., Lin, Y., Baker, P.R.S., et al. Nitrolinoleic acid: An endogenous peroxisome proliferator-activated receptor g ligand. Proc Natl Acad Sci USA 102(7) 2340-2345 (2005).

Lima, E.S., Bonini, M.G., Augusto, O., et al. Nitrated lipids decompose to nitric oxide and lipid radicals and cause vasorelaxation. Free Radic Biol Med 39 532-539 (2005).

Baker, P.R.S., Schopfer, F.J., Sweeney, S., et al. Red cell membrane and plasma linoleic acid nitration products: Synthesis, clinical identification, and quantitation. Proc Natl Acad Sci USA 101(32) 11577-11582 (2004).

Baker, P.R., Lin, Y., Schopfer, F.J., et al. Fatty acid transduction of nitric oxide signaling. Multiple nitrated unsaturated acid derivatives exist in human blood and urine serve as endogenous peroxisome proliferator-activated receptor ligands. J Biol Chem 280(51) 42464-42475 (2005).

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9-Nitrooleate is available in the following screening library:

Bio-active Lipid II Screening Library (96-Well)

Size	Price	Quantity	Subtotal
50 µg	$20.00		$0.00
100 µg	$38.00		$0.00
500 µg	$160.00		$0.00
1 mg	$280.00		$0.00
Bulk	Contact
		Cart Total	$0.00

Pricing updated 2012-02-12. Prices are subject to change without notice.

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Related Products

10-Nitrooleate

Oleic Acid

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