Octadecanoids

Oleic acid (9-cis-Octadecenoic acid) is an abundant monounsaturated fatty acid. Oleic acid is a Na⁺/K⁺ ATPase activator.

Linoleic acid is a common polyunsaturated (PUFA) found in plant-based oils, nuts and seeds. Linoleic acid is a part of membrane phospholipids, and functions as a structural component to maintain a certain level of membrane fluidity of the transdermal water barrier of the epidermis. Linoleic acid induces red blood cells and hemoglobin damage via oxidative mechanism .

α-Linolenic acid (ALA (free base); C18:3 (9Z,12Z,15Z) (free base); C18:3 n-3 (free base)) is an essential fatty acid that cannot be synthesized by humans. α-Linolenic acid can affect the process of thrombotic through the modulation of PI3K/Akt signaling. α-Linolenic acid possess the anti-arrhythmic properties and is related to cardiovascular disease and cancer.

Gamma-linolenic acid (γ-Linolenic acid) is an orally active unsaturated fatty acid. Gamma-linolenic acid exerts anti-inflammatory effects by inhibiting the NF-κB pathway and the phosphorylation of ERK1/2 and JNK. At the same time, it exerts anticancer effects by inducing apoptosis (Apoptosis) in cancer cells. Additionally, Gamma-linolenic acid also has antioxidant and memory-improving effects. It holds promise for research in the fields of inflammation, neurology, and cancer diseases.

17-ODYA is a CYP450 ω-hydroxylase inhibitor. 17-ODYA is also a potent inhibitor (IC₅₀<100 nM) of the formation of 20-hydroxyeicosatetraenoic acid (20-HETE), epoxyeicosatrienoic acids and dihydroxyeicosatrienoic acids by rat renal cortical microsomes incubated with arachidonic acid. 17-ODYA completely attenuates the isoproterenol (ISO)-induced apoptosis, and necrosis in cultured cardiomyocytes. 17-ODYA is a click chemistry reagent, it contains an Alkyne group and can undergo copper-catalyzed azide-alkyne cycloaddition (CuAAc) with molecules containing Azide groups.

12-Hydroxystearic acid is a structurally simple and cost-effective low molecular weight organogelator, and its metal salts and derivatives find roles in many important applications.

(S)-Coriolic acid (13(S)-HODE), the product of 15-lipoxygenase (15-LOX) metabolism of linoleic acid, functions as the endogenous ligand to activate PPARγ. (S)-Coriolic acid is an important intracellular signal agent and is involved in cell proliferation and differentiation in various biological systems. (S)-Coriolic acid induces mitochondrial dysfunction and airway epithelial injury.

Linoleic acid is a critical component of polyunsaturated fatty acids. Linoleic acid reduces GSH-PX and T-SOD activities. Linoleic acid functions as a structural component to maintain a certain level of membrane fluidity of the transdermal water barrier of the epidermis. Linoleic acid can cause acute oxidative damage to red blood cells, ultimately leading to partial acute anemia. Linoleic acid can be used in the research of skin diseases associated with linoleic acid deficiency.

Elaidic acid is an orally active trans fatty acid. Elaidic acid enhances the stemness of colorectal cancer cells by activating the Wnt/ERK1/2 pathway, thereby promoting cell proliferation, invasion and metastasis, and inhibiting apoptosis. Elaidic acid also inhibits the growth of Lactobacillus and alters the cell surface hydrophobicity of Lactobacillus. Elaidic acid reduces basal 2-deoxyglucose uptake in muscle cells and adipocytes. Elaidic acid can be used in research on colorectal cancer, insulin and other related areas.

trans-Vaccenic acid is a naturally occurring trans fatty acid (TFA). trans-Vaccenic acid inhibits nasopharyngeal carcinoma (NPC) cell growth and induces apoptosis through the inhibition of Bad/Akt phosphorylation. trans-Vaccenic acid is a precursor for the synthesis of saturated fatty acid in the rumen and of conjugated Linoleic acid (CLA) at the tissue level. trans-Vaccenic acid exerts hypolipidemic effects in a rat model of obesity.

(±)-Jasmonic acid is an endogenous growth regulator closely related to plant resistance to abiotic stresses, used to activate defense responses to wounding, herbivory, and pathogen attacks. (±)-Jasmonic acid does not play an independent regulatory role, but works in a complex signaling network with other plant hormone signaling pathways. In addition, (±)-Jasmonic acid can also reduce chlorophyll levels in green and etiolated barley leaf segments and inhibit the elongation of rice seedlings.

10-Nitrooleic acid (CXA-10), a nitro fatty acid, has potential effects in disease states in which oxidative stress, inflammation, fibrosis, and/or direct tissue toxicity play significant roles.

Octadecanedioic acid is an endogenous metabolite. Octadecanedioic acid can be used in the research of Reye's syndrome.

cis-9,10-Epoxystearic acid (cis-9,10-Epoxyoctadecanoic acid) is an endogenous metabolite that can be found in plasma and urine.

9-Hydroxyoctadecanoic acid (9-HSA) is an HDAC1 inhibitor that inhibits ∼66.4% HDAC1 enzymatic activity at 5 μM. 9-Hydroxyoctadecanoic acid shows anticancer activity.

Bovinic acid is an orally active anti-inflammatory agent. Bovinic acid inhibits oxidative stress and ferroptosis by regulating the Keap1-Nrf2 signaling pathway. Bovinic acid exerts hepatoprotective effects against alcohol-associated liver disease. Bovinic acid can be used for the research of alcohol-associated liver disease.

(±)9,10-DiHOME is the racemate of 9,10-DiHOME.

9,10-Dihydroxystearic acid is an oxidation product of oleic acid. 9,10-Dihydroxystearic acid can improve glucose tolerance and insulin sensitivity in KKAy mice.

Ricinoleic acid (purity≥99%), a hydroxy fatty acid, is an attractive feedstock for the production of high-performance lubricants, cosmetics, polymers, surfactants, and coatings. Ricinoleic acid is the main active ingredient of Castor oil (HY-107799). Ricinoleic acid is the agonist for prostaglandin EP3 receptor (EP3 receptor) (EC₅₀ in MEG-01 is 0.5 μM), that causes laxative effects and uterine contraction. Ricinoleic acid exhibits antianxiety-like, anti-inflammatory and pro-inflammatory properties.

Stearidonic acid (6Z,9Z,12Z,15Z-Octadecatetraenoic acid) is an orally active polyunsaturated fatty acid found in blackcurrant seed oil. Stearidonic acid can inhibit 5-lipoxygenase and reduce leukotriene and 5-HETE synthesis. Stearidonic acid can increase the content of eicosapentaenoic acid (EPA) in red blood cells. Stearidonic acid can be used for the research of metabolic disease.