Linolein hydroperoxides are a mixture of 132 possible isomers of mono-, di-, and tri-hydroperoxides produced from the autoxidation of trilinolein. Autoxidation of linoleic acid containing triglycerides (for example, trilinolein) in vivo could result in the formation of these hydroperoxides. Unlike…

An alkaloid metabolite of nicotine as well as a major product of its pyrolysis; binds comparably to CYP2A6 and CYP2A13 (Kis = 7.5 and 5.6 µM, respectively), but appears to more effectively inactivate CYP2A6.

An 8-aza-9-oxo-15-hydroxy saturated analog of PGE2; selectively binds the EP4 receptor (Ki = 35 nM) relative to the EP1, EP2, and EP3 receptors (Ki = 3,000, 2,000, and >3,000 nM, respectively); stimulates cAMP formation in excised mouse ovaries.

The trans isomer of the 16:1 fatty acid palmitoleic acid.

The product of nitration of linoleate by NO-derived reactive species; activates PPARγ (Ki = 133 nM), inducing CD36 expression in macrophages, adipocyte differentiation, and glucose uptake; can also be metabolized to produce nitrite derivatives which in turn form NO, leading to increased cGMP production.

(±)12-HpETE is one of the six monohydroperoxy fatty acids produced by the non-enzymatic oxidation of arachidonic acid (Item No. 90010) and consists of an equal mixture of the R and S isomers. Reduction of the hydroperoxide yields the more stable hydroxyl fatty acid (±)12-HETE (Item…

An essential fatty acid and the most abundant ω-3 fatty acid in neural tissues, especially in the retina and brain; constitutes as much as 40% of the total PUFA pool in retinal and neuronal membranes; dietary supplementation via fish oil inhibits the progression of atherosclerosis and delays…

3-HPA is an analog of AM404, which is a selective inhibitor of carrier-mediated transport of AEA. 3-HPA is metabolized by both COX-1 and COX-2 and also selectively and irreversibly inhibits COX-2 with an IC50 value of 2 µM.

(±)15-HETE is one of the six monohydroxy fatty acids produced by the non-enzymatic oxidation of arachidonic acid. The biological activity of (±)15-HETE is similar to that of its constituent enantiomers (Item Nos. 34720 and 34710).

An ester of the free acid that is less water soluble, but more amenable for the formulation of stearidonate-containing diets and dietary supplements.

An aspirin-triggered lipoxin that inhibits LTB4-induced chemotaxis, adherence, and transmigration of the neutrophils with twice the potency of LXA4 demonstrating activity in the nM range.

An endogenous CB neurotransmitter that binds to both CB1 and CB2 receptors.

DGLA is a metabolite produced by chain elongation of the essential fatty acid γ-linolenic acid. Ethyl DGLA is an esterified version of the free acid which is less water soluble, but more ammenable for the formulation of DGLA-containing diets and dietary supplements. DGLA has been advanced as…

An analog of AEA that potentiates the activity of endogenous AEA by blocking its re-uptake into presynaptic neurons; selectively inhibits the carrier-mediated transport of AEA without affecting anandamide hydrolysis; inhibits the transport of AEA with an IC₅₀ value of 1 µM in rat…

Linoleic acid is an essential fatty acid and one of the most abundant PUFAs in the western diet. Deficiencies in linoleic acid are linked to defective wound healing, growth retardation, and dermatitis. Linoleic acid is metabolized by 15-LO in both plants and animals to form 9- and 13-HODE.

A DHA epoxygenase metabolite detected in rat brain and spinal cord, as well as human serum, that acts as a substrate for sEH (Km = 5.1 µM); demonstrates antihyperalgesic activity in inflammatory and neuropathic pain models and potently inhibits angiogenesis and tumor growth in in vitro assays.

Spontaneously hypertensive rats fed a diet which includes γ-tocotrienol show significant reduction of systolic blood pressure and an increase of nitric oxide synthase activity in blood vessels. γ-Tocotrienol at 20 µM induces apoptosis of malignant sympathoadrenal (+SA) murine…

A natural isothiocyanate which induces the expression of phase II detoxification enzymes and activates Nrf2, promoting the expression of antioxidant and phase II genes; acts as a quorum sensing inhibitor, blocking acyl-homoserine lactone signaling in P. aeruginosa without affecting growth…

(±)14(15)-EET-d11 contains 11 deuterium atoms at the 16, 16', 17, 17', 18, 18' ,19, 19' ,20, 20, and 20 positions. It is intended for use as an internal standard for the quantification of (±)14(15)-EET (Item No. 50651) by GC- or LC-MS.

A potent inhibitor of HCV infection (EC₅₀ = 17 nM) that displays low cytotoxicity of virally-infected human hepatoma Huh7.5.1 cells (CC₅₀ = 21.3 µM); displays good pharmacokinetics in mice when delivered intraperitoneally, with preferential liver distribution without…

A 5-series LO derived from EPA; contracts pulmonary parenchymal strips from guinea pig with similar potency to that of LXA4 and LXB4, yet does not exert the vasodilatory effects on aortic smooth muscle exhibited by LXA4 and LXB4.

A natural sesquiterpene that inhibits the proliferation of a wide range of tumors and enhances the effects of various chemotherapies; 10-40 µg/ml dose-dependently induces apoptosis and cell cycle arrest in the G2/M phase in HepG2 cells, upregulating Fas/FasL expression.

An EPA-containing MAG amide analog that inhibits the growth of human lung carcinoma A549 cells, producing 98.4% growth inhibition when applied at 3 µM; an analog of EPEA, a natural N-acylethanolamide that impacts aging and inflammation.

An elongation product of γ-linolenic acid (18:3), rapidly metabolized by fatty acid desaturases to produce arachidonic acid (20:4); metabolized through the cyclooxygenase pathway to produce 1-series prostaglandins; can reduce atopic dermatitis and atherosclerosis when added to the diet of mice.

A major CYP450 metabolite of arachidonic acid that is released from the kidney in response to angiotensin II; a potent vasodilator of renal preglomerular vessels; blocks 20-HETE-induced vasoconstriction of renal arterioles at 1 µM.

A potent anti-fungal antibiotic that can directly block nuclear transport by inhibiting the action of CRM1.

11β-PGF2α-d4 contains four deuterium atoms at the 3, 3', 4, and 4' positions. It is intended for use as an internal standard for the quantification of 11β-PGF2α by GC- or LC-MS.

A homolog of DHEA, characterized by the addition of an (R)-β-methyl group at the terminal ethanolamine carbon.

PPHP is a substrate for the measurement of peroxidase enzymes. PPHP has been used to quantitate the peroxidase activity of COX-1 and COX-2.

Docosatrienoic acid is a rare ω-3 fatty acid not readily detected in normal phospholipid PUFA pools. It inhibits [3H]-LTB4 binding to pig neutrophils at a concentration of 5 µM.

A substrate for cPLA₂.

5(S)-HETrE is produced by the action of 5-LO when mead acid is the substrate. There are no literature reports of the biological activity or further metabolic fate of 5(S)-HETrE.