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Fatty acids and derivatives include saturated, unsaturated and branched-chain acids together with their esters. Fatty acids are carboxylic acids with hydrocarbon chains, and they form the acyl components of most membrane and storage lipids. Polyunsaturated examples are α-linolenic acid, an essential omega-3 fatty acid, and arachidonic acid, the omega-6 precursor of prostaglandins and leukotrienes. Nonadecanoic acid is an odd-chain saturated fatty acid that appears as a reference compound in lipid analysis. Fatty acid methyl esters (FAMEs), such as methyl oleate, are standard analytes in gas chromatography of lipids. 10-OAHSA belongs to the fatty acid esters of hydroxy fatty acids (FAHFAs), a lipid class found in mammalian adipose tissue. Dicarboxylic acids such as sebacic acid are listed as well.
Synonyms: Methyl docosahexaenoate; all cis-DHA methyl ester
Docosahexaenoic Acid methyl ester is a methylated docosahexaenoic acid analog which can be intercalated into membrane phospholipids without being oxidized or hydrolyzed.
Ethyl oleate, a fatty acid ester, is synthesized from the condensation of oleic acid and ethanol. It exhibits key biological activity as a prominent fatty acid ethyl ester in the bloodstream following alcohol consumption, and demonstrates low toxicity in rodent models. Ethyl oleate's pharmacokinetic profile closely resembles that of triacylglycerols, making it a valuable compound in studies of lipid metabolism. Additionally, it can enhance the drying process in food applications and serve as a liquid lipid component in nanostructured lipid carriers for drug delivery research.
Synonyms: Decanedioic acid; 1,10-Decanedioic acid; Acide sebacique; Decanedicarboxylic acid; n-Decanedioic acid; Sebacinsaure.
Decanedioic acid, a normal urinary acid, is found to be associated with carnitine-acylcarnitine translocase deficiency and medium chain acyl-CoA dehydrogenase deficiency.
Methyl oleate is a fatty acid methyl ester (FAME) that exhibits potential against extended spectrum β-lactamase (ESBL) production, along with notable anticancer and antibacterial activities. It significantly enhances antioxidant properties while adversely affecting the antiwear capacity of zinc dialkyldithiophosphate (ZDDP). Methyl oleate is a valuable compound for studying multi-drug resistant (MDR) pathogens that produce ESBL, making it relevant for research aimed at combating antibiotic resistance.
2-methylhexanoic acid is a medium-chain fatty acid and is used as flavouring.
Nonadecanoic acid is a 19-carbon saturated fatty acid that serves as a major component of secretions from Rhinotermes marginalis. It is derived from various biological sources, including fungi, plants, and marine sponges. This compound demonstrates inhibitory effects on fibrinolysis and plasmin activity, making it relevant in studies of coagulation. Additionally, nonadecanoic acid isolated from Streptomyces has shown potential as an anti-tumor agent and suppresses IL-12 production, highlighting its significance in cancer research and immunology.
Synonyms: Citraconsaeure; Kyselina citrakonova; Methyl-maleinsaeure; Methylmaleic acid
Citraconic acid belongs to the class of organic compounds known as methyl-branched fatty acids.
Synonyms: Immunocytophyt; Immunocytophyte; Vevodar
Arachidonic acid is an essential fatty acid and a major constituent of biomembranes.
Synonyms: ALA; C18:3 (9Z,12Z,15Z); C18:3 n-3
α-Linolenic acid sodium is an essential fatty acid that plays a crucial role in various biological processes. This compound modulates the PI3K/Akt signaling pathway, influencing thrombotic processes and offering potential therapeutic benefits. Additionally, α-Linolenic acid sodium exhibits anti-arrhythmic properties, making it relevant for research in cardiovascular diseases and cancer studies.
α-Linolenic acid is an essential fatty acid that cannot be synthesized by humans and is predominantly derived from sources such as Perilla frutescens. This compound influences thrombotic processes through modulation of the PI3K/Akt signaling pathway. Additionally, α-Linolenic acid exhibits anti-arrhythmic properties and is associated with research in cardiovascular diseases and cancer.
10-OAHSA is a fatty acid ester of hydroxy fatty acids (FAHFAs) that primarily targets glucose metabolism. This compound enhances glucose-stimulated insulin secretion (GSIS) at elevated glucose levels, suggesting a role in glucose homeostasis. Additionally, 10-OAHSA mitigates LPS-induced Tnf-α secretion in bone marrow-derived dendritic cells (BMDCs), indicating potential applications in immunological research and inflammation studies.
Crotonyl-CoA tetralithium is a high-energy acyl donor and an important derivative of CoA involved in the metabolism of fatty acids and amino acids. It serves as a substrate for p300's histone crotonyltransferase activity, influencing global and gene-specific histone crotonylation levels, and plays a role in the regulation of gene expression. Additionally, Crotonyl-CoA tetralithium is utilized in the NADPH-mediated reduction and carbon dioxide trapping catalyzed by crotonyl-CoA reductase/carboxylase, contributing to the formation of alkylmalonyl-CoA polyketide synthase extender units. This compound is valuable for studies related to the LPS-induced inflammatory response.
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Synonyms: EPA (metformin); Timnodonic acid (metformin)
Eicosapentaenoic Acid (EPA) functions as an omega-3 long-chain polyunsaturated fatty acid (ω-3 LC-PUFA) with significant biological activity. It exhibits a DNA demethylating capability, facilitating the re-expression of the tumor suppressor gene CCAAT/enhancer-binding protein δ (C/EBPδ). Additionally, EPA activates the RAS/ERK/C/EBPβ signaling pathway through H-Ras intron 1 CpG island demethylation in U937 leukemia cells, thereby enhancing cellular function. The compound also contributes to the relaxation of vascular smooth muscle cells and induces vasodilation, making it relevant for cardiovascular research.
Synonyms: EPA sodium; Timnodonic acid sodium
Eicosapentaenoic Acid Sodium is an orally active omega-3 long-chain polyunsaturated fatty acid (LC-PUFA) that primarily targets DNA demethylation processes. This compound enhances the re-expression of the tumor suppressor gene CCAAT/enhancer-binding protein δ (C/EBPδ) and activates the RAS/ERK/C/EBPβ signaling pathway through H-Ras intron 1 CpG island demethylation in U937 leukemia cells. Additionally, Eicosapentaenoic Acid Sodium is known to promote relaxation of vascular smooth muscle cells, contributing to vasodilation. This makes it a valuable reagent for studies in cancer biology and cardiovascular research.
Isostearic acid is a branched-chain fatty acid known for its role in promoting IL-1 release and inducing apoptosis. Its potent inflammatory properties make it a valuable compound for studying mechanisms of inflammation and cell death. Isostearic acid is applicable in various fields, including pharmaceutical research, personal care formulations, and cosmetic product development.
(+)-Plakevulin A is an oxylipin derived from the Okinawan sponge Plakortis sp. Its primary mechanism involves the inhibition of DNA polymerases α and δ, which is crucial for DNA replication. This compound exhibits significant apoptotic activity and demonstrates potential anticancer properties, making it a valuable reagent for cancer research and studies focusing on DNA replication and repair mechanisms.
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Calendic acid, also known as 8(E),10(E),12(Z)-Octadecatrienoic acid, is a conjugated polyunsaturated fatty acid (PUFA) derived from Calendula officinalis seed oil. This compound exhibits significant anticancer properties, making it a valuable tool in cancer research. Its unique structure and biological activity provide insights into potential therapeutic applications and mechanisms of action in tumor biology.
Synonyms: Carnitine palmitoyltransferase 2
CPT2 (Carnitine palmitoyltransferase 2) is an enzyme involved in fatty acid oxidation and serves as a prognostic biomarker for colorectal cancer (CRC). Overexpression of CPT2 activates phosphorylated p53, leading to increased p53 levels, which inhibits tumor proliferation and promotes apoptosis. Its deficiency is associated with inherited disorders affecting long-chain fatty acid oxidation in skeletal muscle. Additionally, decreased levels of CPT2 correlate with the progression of various cancers, highlighting its potential significance in cancer research.
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Cinnamic acid sodium is a sodium salt of cinnamic acid that primarily acts as an aromatic fatty acid. It exhibits notable neuroprotective and anti-inflammatory properties, making it a valuable compound for research in neurodegenerative diseases and inflammatory conditions. Its low toxicity profile further supports its application in various biological studies and therapeutic explorations.
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Synonyms: 9-cis-Octadecenoic acid triethanolamine; 9Z-Octadecenoic acid triethanolamine
Oleic acid triethanolamine is a monounsaturated fatty acid that acts as a Na+/K+ ATPase activator. This compound plays a critical role in cellular processes by influencing membrane fluidity and signaling pathways. It is widely utilized in biological research to study lipid metabolism, cell signaling, and the physiological effects of fatty acids on various tissues.
Synonyms: 19,20-DHEA epoxide; 19,20-Epoxy docosapentaenoic acid ethanolamide; 19,20-EDP-EA
(±)19(20)-EDP ethanolamide, a derivative of ω-3 endocannabinoids, acts primarily through the modulation of interleukin signaling pathways. This compound exhibits significant anti-inflammatory properties, particularly in neuroinflammation studies, and demonstrates antiangiogenic effects on vascular endothelial cells. Additionally, it induces vasodilation in coronary arteries, making it a valuable tool for research focused on cytokine interactions and vascular biology.
Synonyms: Behenic acid
Docosanoic acid, also known as behenic acid, is a long-chain saturated fatty acid that primarily targets p53, inhibiting the double-stranded DNA (dsDNA) binding activity of its DNA binding domain with a Kd of 12 nM. This compound is particularly relevant in research exploring the role of p53 in cellular processes and cancer biology. Although docosanoic acid has low bioavailability, it has been noted to influence cholesterol levels in humans, making it of interest for studies related to lipid metabolism.
(2E)-4-Hydroperoxy-2-nonenal is a reactive aldehyde product formed during the lipid peroxidation of ω-6 polyunsaturated fatty acids. It serves as a significant biomarker for oxidative stress and is utilized in research to study the effects of oxidative damage on cellular components. This compound plays a crucial role in understanding lipid peroxidation processes and their implications in various biological systems.
Synonyms: 9-trans-Hexadecenoic acid; trans-Palmitoleic acid
Palmitelaidic acid, also known as 9-trans-Hexadecenoic acid, is the trans isomer of palmitoleic acid, a crucial fatty acid in metabolic and cellular studies. This compound serves as a valuable tool in research focusing on lipid metabolism and the role of unsaturated fatty acids in various biological processes. Its presence in serum and tissues highlights its significance in understanding fatty acid profiles and their implications in health and disease.
Synonyms: DL-α-Aminocaprylic acid; DL-2-Aminocaprylic acid
2-Aminooctanoic acid, also known as DL-α-Aminocaprylic acid, targets fatty acids and possesses an amino functional group that facilitates direct coupling with antimicrobial peptides (AMP) derived from lactoferrin B. This coupling enhances the antibacterial activity of the resulting conjugates, making it a valuable reagent for studies in antimicrobial research and peptide synthesis. Its applications extend to the development of potent antibacterial agents and the exploration of peptide-related therapeutic strategies.
