1.0 2010-04-08 22:05:34 UTC 2019-11-26 02:58:07 UTC FDB002906 Glycerol tridodecanoate TG(12:0/12:0/12:0) or trilauric glyceride is a tridodecanoic acid triglyceride or medium chain triglyceride. Triglycerides (TGs) are also known as triacylglycerols or triacylglycerides, meaning that they are glycerides in which the glycerol is esterified with three fatty acid groups (i.e. fatty acid tri-esters of glycerol). TGs 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. TG(12:0/12:0/12:0), in particular, consists of one chain of dodecanoic acid at the C-1 position, one chain of dodecanoic acid at the C-2 position and one chain of dodecanoic acid at the C-3 position. 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. [HMDB]. Glycerol tridodecanoate is found in sweet bay. 1,2,3-Propanetriol tridodecanoate 1,2,3-Propanetriyl tridodecanoate 1,2,3-Tridodecanoylglycerol 1,2,3-Trilauroylglycerol 2,3-Bis(dodecanoyloxy)propyl laurate Dodecanoate 1,2,3-propanetriyl ester Dodecanoic acid 1,2,3-propanetriyl ester Dodecanoic acid, 1,1',1''-(1,2,3-propanetriyl) ester Dodecanoic acid, 1,2,3-propanetriyl ester Dodecanoic acid, 1,2,3-propantriyl ester Dodecanoic acid, tri-ester with glycerol Glycerin trilaate Glycerin trilaic acid Glycerin trilaurate Glycerin trilauric acid Glycerol trilaate Glycerol trilaic acid Glycerol trilaurate Glycerol trilauric acid Glyceryl tridodecanoate Glyceryl tridodecanoic acid Glyceryl trilaate Glyceryl trilaic acid Glyceryl trilaurate Glyceryl trilauric acid Laate triglyceride Laate triglycerin ester Laic acid triglyceride Laic acid triglycerin ester Lauric acid triglyceride Lauric acid triglycerin ester Laurin Laurin, tri- Propane-1,2,3-triyl trilaate Propane-1,2,3-triyl trilaic acid Propane-1,2,3-triyl trilaurate Propane-1,2,3-triyl trilauric acid TG 12:0/12:0/12:0 TG(12:0/12:0/12:0) Tri-laurin Tridodecanoin Tridodecanoyl glycerol Tridodecanoylglycerol Trilaurin Trilauroylglycerol C39H74O6 639.0013 638.5485401 1,3-bis(dodecanoyloxy)propan-2-yl dodecanoate 1,3-bis(dodecanoyloxy)propan-2-yl dodecanoate 538-24-9 [H]C(COC(=O)CCCCCCCCCCC)(COC(=O)CCCCCCCCCCC)OC(=O)CCCCCCCCCCC InChI=1S/C39H74O6/c1-4-7-10-13-16-19-22-25-28-31-37(40)43-34-36(45-39(42)33-30-27-24-21-18-15-12-9-6-3)35-44-38(41)32-29-26-23-20-17-14-11-8-5-2/h36H,4-35H2,1-3H3 VMPHSYLJUKZBJJ-UHFFFAOYSA-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 Triacylglycerols laurate ester triglyceride Solid logp 9.73 ALOGPS logs -7.70 ALOGPS solubility 1.27e-05 g/l ALOGPS melting_point Mp 46.5° logp 13.59 ChemAxon pka_strongest_basic -6.6 ChemAxon iupac 1,3-bis(dodecanoyloxy)propan-2-yl dodecanoate ChemAxon average_mass 639.0013 ChemAxon mono_mass 638.5485401 ChemAxon smiles [H]C(COC(=O)CCCCCCCCCCC)(COC(=O)CCCCCCCCCCC)OC(=O)CCCCCCCCCCC ChemAxon formula C39H74O6 ChemAxon inchi InChI=1S/C39H74O6/c1-4-7-10-13-16-19-22-25-28-31-37(40)43-34-36(45-39(42)33-30-27-24-21-18-15-12-9-6-3)35-44-38(41)32-29-26-23-20-17-14-11-8-5-2/h36H,4-35H2,1-3H3 ChemAxon inchikey VMPHSYLJUKZBJJ-UHFFFAOYSA-N ChemAxon polar_surface_area 78.9 ChemAxon refractivity 186.08 ChemAxon polarizability 82.63 ChemAxon rotatable_bond_count 38 ChemAxon acceptor_count 3 ChemAxon donor_count 0 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon Specdb::CMs 27946 Specdb::CMs 99952 Specdb::NmrOneD 4487 Specdb::NmrOneD 4614 Specdb::NmrOneD 275418 Specdb::NmrOneD 275419 Specdb::NmrOneD 275420 Specdb::NmrOneD 275421 Specdb::NmrOneD 275422 Specdb::NmrOneD 275423 Specdb::NmrOneD 275424 Specdb::NmrOneD 275425 Specdb::NmrOneD 275426 Specdb::NmrOneD 275427 Specdb::NmrOneD 275428 Specdb::NmrOneD 275429 Specdb::NmrOneD 275430 Specdb::NmrOneD 275431 Specdb::NmrOneD 275432 Specdb::NmrOneD 275433 Specdb::NmrOneD 275434 Specdb::NmrOneD 275435 Specdb::NmrOneD 275436 Specdb::NmrOneD 275437 Specdb::MsMs 613456 Specdb::MsMs 613457 Specdb::MsMs 613458 Specdb::MsMs 2427574 Specdb::MsMs 2427575 Specdb::MsMs 2427576 Specdb::MsMs 2749420 Specdb::MsMs 2749421 Specdb::MsMs 2749422 Specdb::MsMs 2804439 Specdb::MsMs 2804440 Specdb::MsMs 2804441 Specdb::MsMs 2849150 Specdb::MsMs 2849151 Specdb::MsMs 2849152 Specdb::MsMs 2874173 Specdb::MsMs 2874174 Specdb::MsMs 2874175 HMDB11188 #<Reference:0x0000561272f03ef0> #<Reference:0x0000561272f03c70> #<Reference:0x0000561272f03a68> #<Reference:0x0000561272f03860> #<Reference:0x0000561272f035e0> #<Reference:0x0000561272f033b0> #<Reference:0x0000561272f031a8> #<Reference:0x0000561272f02f78> #<Reference:0x0000561272f02d98> #<Reference:0x0000561272f02bb8> Anatidae Type 1 specific Anatidae 8830 Beefalo Type 1 specific Bos taurus X Bison bison 297284 Bison Type 1 specific Bison bison 9901 Buffalo Type 1 specific Bubalus bubalis 89462 Cattle (Beef, Veal) Type 1 specific Bos taurus 9913 Chicken Type 1 specific Gallus gallus 9031 Columbidae (Dove, Pigeon) Type 1 specific Columbidae 8930 Deer Type 1 specific Cervidae 9850 Domestic goat Type 1 specific Capra aegagrus hircus 9925 Domestic pig Type 1 specific Sus scrofa domestica 9825 Elk Type 1 specific Cervus canadensis 1574408 Emu Type 1 specific Dromaius novaehollandiae 8790 European rabbit Type 1 specific Oryctolagus 9984 Greylag goose Type 1 specific Anser anser 8843 Guinea hen Type 1 specific Numida meleagris 8996 Horse Type 1 specific Equus caballus 9796 Mallard duck Type 1 specific Anas platyrhynchos 8839 Mountain hare Type 1 specific Lepus timidus 62621 Mule deer Type 1 specific Odocoileus 9871 Ostrich Type 1 specific Struthio camelus 8801 Pheasant Type 1 specific Phasianus colchicus 9054 Quail Type 1 specific Phasianidae 9005 Rabbit Type 1 specific Leporidae 9979 Rock ptarmigan Type 1 specific Lagopus muta 64668 Sheep (Mutton, Lamb) Type 1 specific Ovis aries 9940 Squab Type 1 specific Columba 8931 Sweet bay Type 1 specific Laurus nobilis 85223 Turkey Type 1 specific Meleagris gallopavo 9103 Velvet duck Type 1 specific Melanitta fusca 371864 Wild boar Type 1 specific Sus scrofa 9823 2-acylglycerol O-acyltransferase 1 Q96PD6 MOGAT1 2-acylglycerol O-acyltransferase 2 Q3SYC2 MOGAT2 2-acylglycerol O-acyltransferase 3 Q86VF5 MOGAT3 Carnitine O-palmitoyltransferase 1, liver isoform P50416 CPT1A Carnitine O-palmitoyltransferase 1, muscle isoform Q92523 CPT1B Carnitine O-palmitoyltransferase 2, mitochondrial P23786 CPT2 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 Lysosomal acid lipase/cholesteryl ester hydrolase P38571 LIPA 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