1.0 2010-04-08 22:05:34 UTC 2019-11-26 02:58:08 UTC FDB002910 Glycerol trioleate Constituent of olive oil and other vegetable oils TG(18:1(9Z)/18:1(9Z)/18:1(9Z)) or Triolein is a monoacid triglyceride. Triglycerides (TGs) are also known as triacylglycerols or triacylglycerides. TGs are fatty acid triesters of glycerol and may be divided into three general types with respect to their acyl substituents. They are simple or monoacid if they contain only one type of fatty acid, diacid if they contain two types of fatty acids and triacid if three different acyl groups. Chain lengths of the fatty acids in naturally occurring triglycerides can be of varying lengths and saturations but 16, 18 and 20 carbons are the most common. TGs are the main constituent of vegetable oil and animal fats. TGs are major components of very low density lipoprotein (VLDL) and chylomicrons, play an important role in metabolism as energy sources and transporters of dietary fat. They contain more than twice the energy (9 kcal/g) of carbohydrates and proteins. In the intestine, triglycerides are split into glycerol and fatty acids (this process is called lipolysis) (with the help of lipases and bile secretions), which can then move into blood vessels. The triglycerides are rebuilt in the blood from their fragments and become constituents of lipoproteins, which deliver the fatty acids to and from fat cells among other functions. Various tissues can release the free fatty acids and take them up as a source of energy. Fat cells can synthesize and store triglycerides. When the body requires fatty acids as an energy source, the hormone glucagon signals the breakdown of the triglycerides by hormone-sensitive lipase to release free fatty acids. As the brain cannot utilize fatty acids as an energy source, the glycerol component of triglycerides can be converted into glucose for brain fuel when it is broken down. (www.cyberlipid.org, www.wikipedia.org); ; TAGs can serve as fatty acid stores in all cells, but primarily in adipocytes of adipose tissue. The major building block for the synthesis of triacylglycerides, in non-adipose tissue, is glycerol. Adipocytes lack glycerol kinase and so must use another route to TAG synthesis. Specifically, dihydroxyacetone phosphate (DHAP), which is produced during glycolysis, is the precursor for TAG synthesis in adipose tissue. DHAP can also serve as a TAG precursor in non-adipose tissues, but does so to a much lesser extent than glycerol. The use of DHAP for the TAG backbone depends on whether the synthesis of the TAGs occurs in the mitochondria and ER or the ER and the peroxisomes. The ER/mitochondria pathway requires the action of glycerol-3-phosphate dehydrogenase to convert DHAP to glycerol-3-phosphate. Glycerol-3-phosphate acyltransferase then esterifies a fatty acid to glycerol-3-phosphate thereby generating lysophosphatidic acid. The ER/peroxisome reaction pathway uses the peroxisomal enzyme DHAP acyltransferase to acylate DHAP to acyl-DHAP which is then reduced by acyl-DHAP reductase. The fatty acids that are incorporated into TAGs are activated to acyl-CoAs through the action of acyl-CoA synthetases. Two molecules of acyl-CoA are esterified to glycerol-3-phosphate to yield 1,2-diacylglycerol phosphate (also known as phosphatidic acid). The phosphate is then removed by phosphatidic acid phosphatase (PAP1), to generate 1,2-diacylglycerol. This diacylglycerol serves as the substrate for addition of the third fatty acid to make TAG. Intestinal monoacylglycerols, derived from dietary fats, can also serve as substrates for the synthesis of 1,2-diacylglycerols.; Triolein is a triglyceride and unsaturated fat formed from oleic acid. Glycerol trioleate is found in fats and oils, almond, and peach. (9Z)-1,1',1''-(1,2,3-propanetriyl) ester 9-Octadecenoate (9Z)-1,1',1''-(1,2,3-propanetriyl) ester 9-octadecenoic acid (9Z)-1,2,3-propanetriyl ester 9-Octadecenoate (9Z)-1,2,3-propanetriyl ester 9-Octadecenoic acid (Z)-1,2,3-propanetriyl ester 9-Octadecenoate (Z)-1,2,3-propanetriyl ester 9-Octadecenoic acid (Z)-9-Octadecenoate, 1,2,3-propanetriyl ester (Z)-9-Octadecenoic acid, 1,2,3-propanetriyl ester 1,2,3-Propanetriol tri(9-octandecenoate) 1,2,3-Propanetriyl trioleate 1,2,3-Tri-(9Z-octadecenoyl)-glycerol 1,2,3-tri-(9Z-octadecenoyl)-sn-glycerol 1,2,3-Tri(cis-9-octadecenoyl)glycerol 2,3-Bis[(9E)-9-octadecenoyloxy]propyl (9E)-9-octadecenoate 9-Octadecenoic acid (9Z)-, 1,2,3-propanetriyl ester 9-Octadecenoic acid (Z)-, 1,2,3-propanetriyl ester 9-Octadecenoic acid 1,2,3-propanetriyl ester 9-Octadecenoic acid, 1,2,3-propanetriyl ester Actor LO 1 Aldo to Edenor nhti-g Emerest 2423 Emery 2423 Emery oleic acid ester 2230 Estol 1433 Glycerin trioleate Glycerin trioleic acid Glycerol trioleate Glycerol trioleic acid Glycerol triolein Glycerol, tri(cis-9-octadecenoate) Glycerol, tri(cis-9-octadecenoic acid) Glyceryl trioleate Glyceryl trioleic acid Glyceryl-1,2,3-trioleate Glyceryl-1,2,3-trioleic acid Kaolube 190 Kemester 1000 Oleate triglyceride Oleic acid triglyceride Oleic triglyceride Olein Olein, tri- Oleyl triglyceride Priolube 1435 propane-1,2,3-triyl (9Z,9'Z,9''Z)tris-octadec-9-enoate Propane-1,2,3-triyl (9Z,9'z,9''z)tris-octadec-9-enoic acid Radia 7363 Raoline SN-glyceryl trioleate TG(18:1(9Z)/18:1(9Z)/18:1(9Z)) TG(18:1(9Z)/18:1(9Z)/18:1(9Z))[iso] Tri-olein Triglyceride ooo Triolein triolein C18:1 Triolein glyceryl trioleate Triolein, [9,10-3H(N)]- Trioleoylglyceride Trioleoylglycerol C57H104O6 885.4321 884.78329106 3-[(9E)-octadec-9-enoyloxy]-2-[(9Z)-octadec-9-enoyloxy]propyl (9E)-octadec-9-enoate 3-[(9E)-octadec-9-enoyloxy]-2-[(9Z)-octadec-9-enoyloxy]propyl (9E)-octadec-9-enoate 122-32-7 CCCCCCCC\C=C\CCCCCCCC(=O)OCC(COC(=O)CCCCCCC\C=C\CCCCCCCC)OC(=O)CCCCCCC\C=C/CCCCCCCC InChI=1S/C57H104O6/c1-4-7-10-13-16-19-22-25-28-31-34-37-40-43-46-49-55(58)61-52-54(63-57(60)51-48-45-42-39-36-33-30-27-24-21-18-15-12-9-6-3)53-62-56(59)50-47-44-41-38-35-32-29-26-23-20-17-14-11-8-5-2/h25-30,54H,4-24,31-53H2,1-3H3/b28-25+,29-26+,30-27- PHYFQTYBJUILEZ-BSCDBXJPSA-N belongs to the class of organic compounds known as triacylglycerols. These are glycerides consisting of three fatty acid chains covalently bonded to a glycerol molecule through ester linkages. Triacylglycerols Organic compounds Lipids and lipid-like molecules Glycerolipids Triradylcglycerols Aliphatic acyclic compounds Carbonyl compounds Carboxylic acid esters Fatty acid esters Hydrocarbon derivatives Organic oxides Tricarboxylic acids and derivatives Aliphatic acyclic compound Carbonyl group Carboxylic acid derivative Carboxylic acid ester Fatty acid ester Fatty acyl Hydrocarbon derivative Organic oxide Organic oxygen compound Organooxygen compound Triacyl-sn-glycerol Tricarboxylic acid or derivatives Liquid logp 10.82 ALOGPS logs -8.16 ALOGPS solubility 6.14e-06 g/l ALOGPS melting_point Mp 5° logp 20.51 ChemAxon pka_strongest_basic -6.6 ChemAxon iupac 3-[(9E)-octadec-9-enoyloxy]-2-[(9Z)-octadec-9-enoyloxy]propyl (9E)-octadec-9-enoate ChemAxon average_mass 885.4321 ChemAxon mono_mass 884.78329106 ChemAxon smiles CCCCCCCC\C=C\CCCCCCCC(=O)OCC(COC(=O)CCCCCCC\C=C\CCCCCCCC)OC(=O)CCCCCCC\C=C/CCCCCCCC ChemAxon formula C57H104O6 ChemAxon inchi InChI=1S/C57H104O6/c1-4-7-10-13-16-19-22-25-28-31-34-37-40-43-46-49-55(58)61-52-54(63-57(60)51-48-45-42-39-36-33-30-27-24-21-18-15-12-9-6-3)53-62-56(59)50-47-44-41-38-35-32-29-26-23-20-17-14-11-8-5-2/h25-30,54H,4-24,31-53H2,1-3H3/b28-25+,29-26+,30-27- ChemAxon inchikey PHYFQTYBJUILEZ-BSCDBXJPSA-N ChemAxon polar_surface_area 78.9 ChemAxon refractivity 272.25 ChemAxon polarizability 118.51 ChemAxon rotatable_bond_count 53 ChemAxon acceptor_count 3 ChemAxon donor_count 0 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon HMDB05453 #<Reference:0x000055ac40ade958> #<Reference:0x000055ac40ade7a0> Almond Type 1 specific Prunus dulcis 3755 Fats and oils Unknown generic Milk (Cow) Type 2 specific 284.9 738.0 7.6 uM Peach Type 1 specific Prunus persica 3760 2-acylglycerol O-acyltransferase 1 Q96PD6 MOGAT1 2-acylglycerol O-acyltransferase 2 Q3SYC2 MOGAT2 2-acylglycerol O-acyltransferase 3 Q86VF5 MOGAT3 Diacylglycerol O-acyltransferase 1 O75907 DGAT1 Diacylglycerol O-acyltransferase 2 Q96PD7 DGAT2 Endothelial lipase Q9Y5X9 LIPG Gastric triacylglycerol lipase P07098 LIPF Glycerol-3-phosphate acyltransferase 3 Q53EU6 AGPAT9 Hepatic triacylglycerol lipase P11150 LIPC Inactive pancreatic lipase-related protein 1 P54315 PNLIPRP1 Lipoprotein lipase P06858 LPL Liver carboxylesterase 1 P23141 CES1 Monoglyceride lipase Q99685 MGLL Pancreatic lipase-related protein 2 P54317 PNLIPRP2 Pancreatic lipase-related protein 3 Q17RR3 PNLIPRP3 Pancreatic triacylglycerol lipase P16233 PNLIP Patatin-like phospholipase domain-containing protein 2 Q96AD5 PNPLA2 Patatin-like phospholipase domain-containing protein 3 Q9NST1 PNPLA3 Patatin-like phospholipase domain-containing protein 4 P41247 PNPLA4 Protein disulfide-isomerase P07237 P4HB anti aggregant 94