1 linoleoyl glycerol

1-Myristoyl-2-linoleoyl-3-oleoyl-rac-glycerol, a triacylglycerol, features myristic acid, linoleic acid, and oleic acid at the sn-1, sn-2, and sn-3 positions, respectively. This compound is prevalent in mature human milk, infant formula fats, and butterfat.

1-Linoleoyl Glycerol (Monolinolein) is fatty acid glycerol that has been isolated from Saururus Chinensis roots. The (R)-1-Linoleoyl Glycerol and (S)-1-Linoleoyl Glycerol exhibit Lipoprotein-associated phospholipase A2 (Lp-PLA2) inhibitory activities with IC50 values of 45.0 and 52.0 μM, respectively.

1,2-Dioleoyl-3-linoleoyl-rac-glycerol (OOL) is a triglyceride featuring oleic acid at the sn-1 and sn-2 positions and linoleic acid at the sn-3 position. This compound is prevalent in several seed and vegetable oils, such as those from pumpkin seeds, olives, and sesame.

1-Palmitoyl-2-linoleoyl-3-stearoyl-rac-glycerol, a triacylglycerol, comprises palmitic acid (at the sn-1 position), linoleic acid (at the sn-2 position), and stearic acid (at the sn-3 position). This compound is present in mature human milk and various plant oils.

1-Stearoyl-3-linoleoyl-rac-glycerol, a diacylglycerol, incorporates stearic acid at the sn-1 position and linoleic acid at the sn-3 position. Its levels rise in a time-dependent manner throughout the ripening process of dry-cured sausages.

1-Oleoyl-2-palmitoyl-3-linoleoyl-rac-glycerol is a triacylglycerol comprising oleic acid [at the sn-1 position], palmitic acid [at the sn-2 position], and linoleic acid [at the sn-3 position], identified in bovine milk fat.

1-Myristoyl-2-linoleoyl-3-palmitoyl-rac-glycerol, a triacylglycerol comprising myristic, linoleic, and palmitic acids at the sn-1, sn-2, and sn-3 positions respectively, is present in palm and vegetable oils.

1-Linoleoyl-3-palmitoyl-rac-glycerol, a diacylglycerol, is characterized by the presence of linoleic acid (at the sn-1 position) and palmitic acid (at the sn-3 position). This compound has been detected in wheat bran extracts and in dry-cured Iberian ham, but not in its raw form.

1-Stearoyl-2-oleoyl-3-linoleoyl-rac-glycerol is a triacylglycerol consisting of stearic acid, oleic acid, and linoleic acid esterified at the sn-1, sn-2, and sn-3 positions, respectively. This compound is present in peanut and soybean oils as well as in ostrich and emu oils. Additionally, it serves as a substrate for soybean lipoxygenase in cell-free assays.

1,3-Distearoyl-2-linoleoyl glycerol, a triacylglycerol, features stearic acid at the sn-1 and sn-3 positions and linoleic acid at the sn-2 position. This compound is present in cocoa butter and in cocoa butter equivalents (CBEs) that include shea stearin and palm mid fraction.

1-Palmitoyl-2-elaidoyl-3-linoleoyl-rac-glycerol is a triacylglycerol composed of palmitic acid (at the sn-1 position), elaidic acid (at the sn-2 position), and linoleic acid (at the sn-3 position) respectively.

1-Linoleoyl-3-α-linolenoyl-rac-glycerol, a diacylglycerol, features linoleic acid at the sn-1 position and α-linolenic acid at the sn-3 position. This compound is identified in olive oil that has undergone lipase-catalyzed glycerolysis, utilizing immobilized lipase B derived from C. antarctica.

1,3-Dioleoyl-2-linoleoyl glycerol, a triacylglycerol, features oleic acid at the sn-1 and sn-3 positions and linoleic acid at the sn-2 position. This compound is a prominent species in butterfat and is present in A. trifoliata seed oil (ASO), along with smaller amounts in its physical blends and interesterified products.

1,3-Dipalmitoyl-2-linoleoyl glycerol is a triacylglycerol featuring palmitic acid at the sn-1 and sn-3 positions, and linoleic acid at the sn-2 position. Identified within the palm stearin fraction of palm oil and as a trace constituent in soybean germ oil, this compound exemplifies the structural diversity of fats and oils in both plant-based sources.

1,2-Dipalmitoyl-3-linoleoyl-rac-glycerol, a triacylglycerol, features palmitic acid at the sn-1 and sn-2 positions and linoleic acid at the sn-3 position. This compound is present in ostrich and emu oils as well as in bovine milk fat.

POL, a prevalent triglyceride component in various seed and vegetable oils such as olive, sesame, soybean, canola, corn, and hazelnut, is standardly utilized in the USP analysis of sesame oil for pharmaceutical applications.

1-O-Hexadecyl-Rac-Glycerol (1-O-Hexadecylglycerol) is a marine derived natural products found in Tritoniella belli.

1-Undecanoyl-rac-glycerol is a monoacylglycerol that contains undecanoic acid at the sn-1 position. It completely inhibits the growth of the bacteria B. cereus, B. subtilis, M. luteus, E. faecalis, and S. aureus when used at concentrations ranging from 250 to 1,500 mg/L.1 1-Undecanoyl-rac-glycerol (0.1 and 0.3 mg/ml) also has antifungal activity against K. marxianus, S. cerevisiae, and C. maltosa.2

1-Palmitoyl-2-stearoyl-3-oleoyl-rac-glycerol is a triacylglycerol that contains palmitic , stearic , and oleic acid at the sn-1, sn-2, and sn-3 positions, respectively. It has been detected in RAW 264.7 cells by neutral loss MS. Increased serum levels of 1-palmitoyl-2-stearoyl-3-oleoyl-rac-glycerol are a potential biomarker for non-alcoholic fatty liver disease (NAFLD).

1-Pentadecanoyl-rac-glycerol is a monoacylglycerol that contains pentadecanoic acid at the sn-1 position. It has been found in wheat bran extracts.1 1-Pentadecanoyl-rac-glycerol levels are increased in a HepaRG cell-based model of hepatic steatosis induced by BSA-conjugated palmitate.2 |1. Prinsen, P., Gutiérrez, A., Faulds, C.B., et al. Comprehensive study of valuable lipophilic phytochemicals in wheat bran. J. Agric. Food Chem. 62(7), 1664-1673 (2014).|2. Brown, M.V., Compton, S.A., Milburn, M.V., et al. Metabolomic signatures in lipid-loaded HepaRGs reveal pathways involved in steatotic progression. Obesity (Silver Spring) 21(12), E561-E570 (2013).

1-Oleoyl-2-palmitoyl-rac-glycerol (1,2-OP) is a diacylglycerol containing oleic acid at the sn-1 position and palmitic acid at the sn-2 position. It enhances the inhibition of superoxide anion production by cytochalasin B when used at a concentration of 10 μM. The concentration of 1,2-OP decreases from 25.7 to 11.15% during the dry-curing process of Iberian ham.

Phosphatidylethanolamines are important components of cell membranes and biochemical pathways of fatty acid synthesis. 1-Palmitoyl-2-linoleoyl PE (PLPE) is one of the many phosphatidylethanolamines that may be present in cellular membranes. It has been used in studies involving the biosynthesis of anandamide via the phospholipase A2 (PLA2) and lysoPLD pathways. PLPE can also be used as a specific substrate to assess the activity of sPLA2-IIA in the presence of other phospholipids.

1-Stearoyl-3-oleoyl-rac-glycerol is a diacylglycerol that contains stearic acid at the sn-1 position and oleic acid at the sn-3 position. Intermittent fasting decreases skeletal muscle and hepatic levels of 1-stearoyl-3-oleoyl-rac-glycerol in New Zealand obese (NZO) mice.1 The concentration of 1-stearoyl-3-oleoyl-rac-glycerol decreases from 4.59 to 1.88% during the dry-curing process of Iberian ham.2References1. Baumeier, C., Kaiser, D., Heeren, J., et al. Caloric restriction and intermittent fasting alter hepatic lipid droplet proteome and diacylglycerol species and prevent diabetes in NZO mice. Biochim. Biophys. Acta 1851(5), 566-576 (2015).2. Narváez-Rivas, M., Vicario, I.M., Constante, E.G., et al. Changes in the concentrations of free fatty acid, monoacylglycerol, and diacylglycerol in the subcutaneous fat of Iberian ham during the dry-curing process. J. Agric. Food Chem. 55(26), 10953-10961 (2007). 1-Stearoyl-3-oleoyl-rac-glycerol is a diacylglycerol that contains stearic acid at the sn-1 position and oleic acid at the sn-3 position. Intermittent fasting decreases skeletal muscle and hepatic levels of 1-stearoyl-3-oleoyl-rac-glycerol in New Zealand obese (NZO) mice.1 The concentration of 1-stearoyl-3-oleoyl-rac-glycerol decreases from 4.59 to 1.88% during the dry-curing process of Iberian ham.2 References1. Baumeier, C., Kaiser, D., Heeren, J., et al. Caloric restriction and intermittent fasting alter hepatic lipid droplet proteome and diacylglycerol species and prevent diabetes in NZO mice. Biochim. Biophys. Acta 1851(5), 566-576 (2015).2. Narváez-Rivas, M., Vicario, I.M., Constante, E.G., et al. Changes in the concentrations of free fatty acid, monoacylglycerol, and diacylglycerol in the subcutaneous fat of Iberian ham during the dry-curing process. J. Agric. Food Chem. 55(26), 10953-10961 (2007).

1-Heptadecanoyl-rac-glycerol is a monoacylglycerol that contains heptadecanoic acid at the sn-1 position. It is active against the bacteria E. aerogens, E. cloacae, P. mirabilis, and S. faecalis (MIC = 78 μg/ml for all).1 1-Heptadecanoyl-rac-glycerol has been found in T. africana, I. sonorae, and wheat bran.1,2,3 |1. Kuete, V., Metuno, R., Ngameni, B., et al. Antimicrobial activity of the methanolic extracts and compounds from Treculia africana and Treculia acuminata (Moraceae). S. Afr. J. Bot. 74(1), 111-115 (2008).|2. Fernández-Galicia, E., Calada, F., Roman-Romos, R., et al. Monoglycerides and fatty acids from Ibervillea sonorae root: Isolation and hypoglycemic activity. Planta Med. 73(3), 236-240 (2007).|3. Prinsen, P., Gutiérrez, A., Faulds, C.B., et al. Comprehensive study of valuable lipophilic phytochemicals in wheat bran. J. Agric. Food Chem. 62(7), 1664-1673 (2014).

1-Palmitoyl-sn-glycerol 3-phosphate (1-P-GPA), an endogenous metabolite, is utilized in the research of non-alcoholic fatty liver disease [1].

1-Palmitoyl-2-oleoyl-3-arachidonoyl-rac-glycerol is a triacylglycerol that contains palmitic acid , oleic acid , and arachidonic acid at the sn-1, sn-2, and sn-3 positions, respectively. It has been found in lipid extracts from whole rat retina.1

1-Stearoyl-2-linoleoyl-sn-glycero-3-phosphocholine is an endogenous metabolite.

Diacylglycerols (DAG) are generated through the hydrolysis of membrane phospholipids and function as lipid second messengers by activating protein kinase C (PKC) and modulating cell growth and apoptosis. Additionally, they act as precursors for DAG kinases in the synthesis of phosphatidic acid, a crucial lipid messenger. The compound 1-NBD-decanoyl-2-decanoyl-sn-glycerol incorporates a nitrobenzoxadiazole (NBD) fluorophore at the ω-end of its terminal decanoyl chain, using the structure of 1,2-didecanoyl-sn-glycerol as a model for diacylglycerol. This molecule is expected to exhibit excitation and emission peaks at roughly 470/541 nm, paralleling those of various NBD-labeled phospholipids. Fluorescently labeled lipids, such as this, are instrumental in exploring their interactions with proteins, their uptake by cells and liposomes, and in developing assays for lipid metabolism research.

1-Palmitoyl-2-arachidoyl-3-oleoyl-rac-glycerol, a triacylglycerol, incorporates palmitic acid, arachidic acid, and oleic acid at the sn-1, sn-2, and sn-3 positions, respectively, and is identified in cod liver oil.

1-Palmitoyl-2-oleoyl-rac-glycerol, a diacylglycerol, features palmitic acid at the sn-1 position and oleic acid at the sn-2 position. Detected in crude sunflower lecithin, its levels elevate in RINm5F rat insulinoma cells following treatment with oleate, elaidate, or trans-vaccenate.

1-Stearoyl-rac-glycerol is a monoacylglycerol that contains stearic acid at the sn-1 position. 1-Stearoyl-rac-glycerol levels are decreased in tumor tissue in a mouse model of azoxymethane-induced colorectal carcinogenesis. 1-Stearoyl-rac-glycerol has been used in the composition of transfersomes for transdermal delivery of doxorubicin in rats, leading to doxorubicin accumulation in lymph nodes, spleen, and heart.

1-O-Octadecyl-2-O-methyl-sn-glycerol is a metabolite of a phosphotidylinositol ether lipid analog (PIA). PIAs are known to target the pleckstrin homology domain of the serine/threonine kinase Akt and to induce apoptosis in cancer cell lines with high levels of endogenous Akt activity.

1-Linoleoyl lysophosphatidic acid (1-linoleoyl LPA), a glycerophospholipid with linoleic acid at its sn-1 position, acts as an LPA2 receptor agonist and is the predominant LPA form in both mouse and human plasma. This compound preferentially boosts intracellular calcium in Sf9 cells expressing the LPA2 receptor (EC50 = ~10 nM), compared to those with LPA1 and LPA3 receptors (EC50s = ~200 and ~80 nM, respectively). Notably, 1-linoleoyl LPA serum concentrations are elevated in mice with NCTC clone 2472 tumors, while its plasma levels are reduced in primary progressive multiple sclerosis patients—unlike in those with relapsing-remitting multiple sclerosis—and inversely associate with the severity of neurological deficits.

1-Palmitoyl-3-stearoyl-rac-glycerol, a diacylglycerol, features palmitic acid at the sn-1 position and stearic acid at the sn-3 position. This compound appears in palm-based diacylglycerols derived from palm stearin, palm mid fraction, palm oil, and palm olein, as well as in extracts of wheat bran and brewer’s spent grain.

1-Palmitoyl-2-lauroyl-rac-glycerol, a diacylglycerol, features palmitic acid at the sn-1 position and lauric acid at the sn-2 position.

1-Palmitoyl-2-stearoyl-3-butyryl-rac-glycerol is a triacylglycerol that incorporates palmitic acid, stearic acid, and butyric acid at the sn-1, sn-2, and sn-3 positions, respectively. This compound serves as a substrate to establish the stereospecificity and typoselectivity of lipases.

1-Palmitoyl-2-Linoleoyl-sn-glycero-3-phosphatidylcholine (PC) is a phospholipid characterized by the incorporation of palmitic (16:0) and linoleic (18:2) acids at the sn-1 and sn-2 positions, respectively. It is utilized in the creation of micelles, liposomes, and various artificial membranes, playing a significant role in research on lipid peroxidation.

1-Stearoyl-2-arachidonoyl-sn-glycerol (DAG) is a diacylglycerol (DAG) substrate that can be hydrolyzed to 2-arachidonic acid glycerol. 1-Stearoyl-2-arachidonoyl-sn-glycerol activates PKC, induces Ca2+ influx, and can induce tracheal smooth muscle contraction.

Glycerol 1-(26-hydroxyhexacosanoate) has weak activities antiplasmodial

1-Arachidoyl-2-palmitoyl-3-oleoyl-rac-glycerol, a triacylglycerol, incorporates arachidic, palmitic, and oleic acids at the sn-1, sn-2, and sn-3 positions, respectively. It is present in butterfat and exhibits elevated liver levels in Plin5-overexpressing mice subjected to a high-fat diet.

1-Palmitoyl-3-oleoyl-rac-glycerol, a diacylglycerol featuring palmitic acid at the sn-1 position and oleic acid at the sn-3 position, serves as a substrate for diacylglycerol acyltransferase (DAGAT) in myotubes.

1-Oleoyl-3-arachidoyl-rac-glycerol is a diacylglycerol with oleic acid at the sn-1 position and arachidic acid at the sn-3 position.

1-Palmitoyl-2-oleoyl-3-stearoyl-rac-glycerol, a primary triacylglycerol in cocoa butter, features palmitic acid (at the sn-1 position), oleic acid (at the sn-2 position), and stearic acid (at the sn-3 position).

1-Palmitoyl-d9-2-palmitoyl-sn-glycerol serves as an internal standard for quantifying 1,2-dipalmitoyl-sn-glycerol using GC or LC-MS techniques. This diacylglycerol, featuring palmitic acid at both the sn-1 and sn-2 positions, stimulates protein kinase C (PKC) activity by 15% at a 25 μM concentration. Additionally, 1,2-dipalmitoyl-sn-glycerol encourages rapid growth in Frankia, a genus of Gram-positive bacteria.

1-Arachidonoyl-d8-rac-glycerol (1-AG-d8) serves as an internal standard for 1-AG quantification via GC or LC-MS. As a weak CB1 receptor agonist, 1-AG exhibits potential pharmacological effects. Notably, 1-AG, an isomer of 2-AG, is more stable, avoiding the rapid in vitro and in vivo isomerization that diminishes 2-AG's cannabinergic efficacy due to conversion to 1-AG (also known as 1(3)-AG), a common impurity in synthetic 2-AG formulations.

2-Arachidonoyl glycerol (2-AG), a natural endocannabinoid ligand for the CB1 receptor, was isolated from porcine brain and characterized. Its congener, 2-linoleoyl glycerol (2-LG), which has a linoleoyl group instead of an arachidonoyl group, also exists alongside 2-AG in vivo. While 2-LG exhibits low intrinsic activity, it enhances the activity of 2-AG and other endocannabinoids through an entourage effect, attributed to the inhibition of breakdown and reuptake pathways that typically decrease endocannabinoid levels post-release.

1-Palmitoyl-2-oleoyl-3-linolenoyl-rac-glycerol is a triacylglycerol comprising palmitic acid, oleic acid, and α-linolenic acid esterified at the sn-1, sn-2, and sn-3 positions, respectively.

1-Arachidoyl-rac-glycerol, a monoacylglycerol, features arachidic acid at the sn-1 position and has been detected in pork muscle.

1-Myristoyl-3-elaidoyl-rac-glycerol is a diacylglycerol comprising myristic acid and elaidic acid at the sn-1 and sn-3 positions, respectively.

1-Stearoyl-2-palmitoyl-3-oleoyl-rac-glycerol is a triacylglycerol comprising stearic acid (at the sn-1 position), palmitic acid (at the sn-2 position), and oleic acid (at the sn-3 position), identified in bovine milk.