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

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 potent anti-mitotic drug that is 100-fold more active than resveratrol at inhibiting the growth of human colon cancer Caco-2 cells; inhibits tubulin polymerization in a dose-dependent manner (IC₅₀ = 4 μM) and enzymes involved in the synthesis of the polyamines, putrescine, and spermidine.

A plant growth regulator involved in the signaling mechanisms for a variety of conditions including plant defense, wound healing, tuberization, fruit ripening, and senescence.

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…

Oleic acid is a monounsaturated fatty acid and is one of the major components of membrane phospholipids. Oleic acid contributes about 17% of the total fatty acids esterified to phosphatidylcholine, the major phospholipid class in porcine platelets. Oleic acid inhibits collagen-stimulated platelet…

EPA is an ω-3 fatty acid abundantly available in marine organisms. It is a poor substrate for COX-1. EPA has been shown to offer protection against coronary heart disease, thrombosis, ischemic brain injury, scaly dermatitis, and some inflammatory diseases.

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.

Keystone essential fatty acid that is converted by COX, LO, and epoxygenase enzymes into more than 150 potent metabolites in species ranging from fungi to plants to mammals.

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…

13(Z)-Docosenoic acid is a 22-carbon monounsaturated fatty acid. It is found predominantly in canola oil. 13(Z)-Docosenoic acid is metabolized to oleic acid in vivo. Diets rich in 13(Z)-docosenoic acid were shown to cause heart lipidosis in experimental animals. The C-1 amide of docosenoic acid has…

An uncommon, naturally occurring PUFA, inhibits the binding of [3H]-LTB4 to porcine neutrophil membranes with a Ki value of 3 µM.

A more lipid-soluble form of EPA.

A monounsaturated long chain fatty acid with potential antitumor and p53 inhibitory activity.

Ricinoleic acid is a naturally occurring 12-hydroxy fatty acid. It constitutes about 90% of the fatty acids in castor oil. Ricinoleic acid can serve as a substrate for the synthesis of conjugated linoleic acids. It is considered safe and non-toxic as a food constituent in humans, up to a daily…

Linoleic acid is a PUFA prevalent in the western diet. The peroxide free linoleic acid is protected from autoxidation by the antioxidant BHT (2,6-Di-tert-butyl-4-hydroxytoluene). Linoleic acid is also available without BHT (Item No. 90150).

Ricinoleic acid methyl ester is a neutral, more lipophilic form of the free acid that can be used as an analytical standard for ricinoleic acid.

A naturally occurring trans-fatty acid found in ruminant animals that is converted to 9(Z),11(E)-conjugated linoleic acid in mammals; reported to have beneficial antioxidant, anti-atherosclerotic, and antitumor activities.

Ethyl palmitoleate is a more lipophilic form of the free acid. It is one of the fatty acid ethyl esters that increase cytosolic Ca2+ concentration leading to pancreatic acinar cell injury due to excessive consumption of ethanol. Ethyl palmitoleate (10-100 µM) in addition to 850 mM ethanol…

An odoriferous component of musk that has been shown to exhibit anti-inflammatory effects by reducing the expression of proinflammatory cytokines both in vitro and in vivo; also reported to be both cardioprotective and neuroprotective during conditions of ischemia and to promote proliferation and…

Arachidonic acid is the keystone essential fatty acid at the origin of the arachidonic acid cascade. It is converted by cyclooxygenase, lipoxygenase, and epoxygenase enzymes into more than one hundred fifty different potent primary autacoid metabolites in species ranging from fungi to plants to…

An unsaturated diacylglycerol with linoleic acid (18:2) side-chains attached at both the C-1 and C-3 positions that is useful for lipid research.

The stabilized ethyl ester form of DHA; dietary intake enhances maze-learning in mice; in rats it increases fatty acid oxidation enzymes and in humans with peroxisomal disorders it improves vision, liver function, and muscle tone; may directly modulate the actions of enzymes involved in fatty acid metabolism.

Linoleic acid ethyl ester is a neutral, lipid-soluble form of linoleic acid.

Lauric acid ethyl ester is a more lipophilic and less toxic form of the free acid. It is one of the medium-chain fatty acid ethyl esters that is released during the anaerobic fermentation of Saccharomyces cerevisiae along with the free acid.

Myristic acid is a saturated fatty acid commonly found in animal and vegetable fats that is frequently used in cosmetics, soaps, perfumes, and flavorings. It increases LDL cholesterol making it one of the most hypercholesterolemic of the saturated fatty acids. Myristic acid ethyl ester is a more…

Arachidonic acid ethyl ester is a more lipophilic form of arachidonic acid that can be incorporated into dietary regimens or fed to cultured cells as a source of exogenous arachidonate. It is one of the fatty acid ethyl esters that increase cytosolic Ca2+ concentration leading to pancreatic acinar…

A more hydrophobic form of the free acid, a cytotoxic component from the fruit extract of S. repens.

LAEE is a neutral, more lipophilic form of the free acid that can be used as an exogenous source of α-linolenic acid (ALA). This ethanol metabolite may contribute to ethanol-induced hepatic fibrogenesis through stimulation of intracellular signaling pathways in hepatic stellate cells (HSC).…

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

A stabilized, lipid-soluble form of the free acid that has been used to produce biofuels as well as skin-conditioning agents, emulsion stabilizers, and surfactants in cosmetics.

A stabilized ethyl ester form of this ω-3 C20:5 PUFA; dietary EPA ethyl ester in rats increases fatty acid β-oxidation enzyme levels, down-regulates lipogenic genes, and decreases plasma cholesterol and triglyceride levels; blocks induced insulin resistance and corrects changes in…