<?xml version="1.0" encoding="UTF-8"?>
<compound>
  <version>1.0</version>
  <creation_date>2010-04-08 22:05:40 UTC</creation_date>
  <update_date>2019-11-26 02:58:31 UTC</update_date>
  <accession>FDB003135</accession>
  <name>Glycerol trioctanoate</name>
  <description>It is used in bakery products. Carrier for essential oils and flavours. Glycerol trioctanoate is found in cereals and cereal products.</description>
  <synonyms>
    <synonym>1,2,3-Propanetriol trioctanoate</synonym>
    <synonym>1,2,3-Propanetriol trioctanoic acid</synonym>
    <synonym>1,2,3-Propanetriyl octanoate, 9CI</synonym>
    <synonym>1,2,3-Tricapryloylglycerol</synonym>
    <synonym>1,2,3-Trioctanoylglycerol</synonym>
    <synonym>2,3-Bis(octanoyloxy)propyl octanoate</synonym>
    <synonym>Axona</synonym>
    <synonym>Caprylate triglyceride</synonym>
    <synonym>Caprylate, 1,2,3-propanetriyl ester</synonym>
    <synonym>Caprylic acid triglyceride</synonym>
    <synonym>Caprylic acid, 1,2,3-propanetriyl ester</synonym>
    <synonym>Caprylic triglyceride</synonym>
    <synonym>Caprylin</synonym>
    <synonym>Glycerin tricaprylate</synonym>
    <synonym>Glycerin tricaprylic acid</synonym>
    <synonym>Glycerol tricaprylate</synonym>
    <synonym>Glycerol tricaprylic acid</synonym>
    <synonym>Glycerol trioctanoic acid</synonym>
    <synonym>Glycerol trioctanoin</synonym>
    <synonym>Glyceryl tricaprylate</synonym>
    <synonym>Glyceryl tricaprylate-caprate</synonym>
    <synonym>Glyceryl tricaprylic acid</synonym>
    <synonym>Glyceryl trioctanoate</synonym>
    <synonym>Maceight</synonym>
    <synonym>Miglyol 808</synonym>
    <synonym>Octanoate triglyceride</synonym>
    <synonym>Octanoate, 1,1',1''-(1,2,3-propanetriyl) ester</synonym>
    <synonym>Octanoate, 1,2,3-propanetriyl ester</synonym>
    <synonym>Octanoic acid triglyceride</synonym>
    <synonym>Octanoic acid, 1,1',1''-(1,2,3-propanetriyl) ester</synonym>
    <synonym>Octanoic acid, 1,2,3-propanetriyl ester</synonym>
    <synonym>Octanoin, tri-</synonym>
    <synonym>Panacet 800</synonym>
    <synonym>Rato</synonym>
    <synonym>TG(8:0/8:0/8:0)</synonym>
    <synonym>Tri-octanoin</synonym>
    <synonym>Tricaprilin</synonym>
    <synonym>Tricaprylic glyceride</synonym>
    <synonym>Tricaprylin</synonym>
    <synonym>Tricapryloylglycerol</synonym>
    <synonym>Tricaprylyl glycerin</synonym>
    <synonym>Trioctanoin</synonym>
    <synonym>Trioctanoin oil</synonym>
    <synonym>Trioctanoylglyceride</synonym>
    <synonym>Trioctanoylglycerol</synonym>
  </synonyms>
  <chemical_formula>C27H50O6</chemical_formula>
  <average_molecular_weight>470.6823</average_molecular_weight>
  <monisotopic_moleculate_weight>470.360739332</monisotopic_moleculate_weight>
  <iupac_name>1,3-bis(octanoyloxy)propan-2-yl octanoate</iupac_name>
  <traditional_iupac>Rato</traditional_iupac>
  <cas_registry_number>538-23-8</cas_registry_number>
  <smiles>[H]C(COC(=O)CCCCCCC)(COC(=O)CCCCCCC)OC(=O)CCCCCCC</smiles>
  <inchi>InChI=1S/C27H50O6/c1-4-7-10-13-16-19-25(28)31-22-24(33-27(30)21-18-15-12-9-6-3)23-32-26(29)20-17-14-11-8-5-2/h24H,4-23H2,1-3H3</inchi>
  <inchikey>VLPFTAMPNXLGLX-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> 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.</description>
    <direct_parent>Triacylglycerols</direct_parent>
    <kingdom>Organic compounds</kingdom>
    <super_class>Lipids and lipid-like molecules</super_class>
    <class>Glycerolipids</class>
    <sub_class>Triradylcglycerols</sub_class>
    <molecular_framework>Aliphatic acyclic compounds</molecular_framework>
    <alternative_parents>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acid esters</alternative_parent>
      <alternative_parent>Fatty acid esters</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Tricarboxylic acids and derivatives</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Aliphatic acyclic compound</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Carboxylic acid ester</substituent>
      <substituent>Fatty acid ester</substituent>
      <substituent>Fatty acyl</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Triacyl-sn-glycerol</substituent>
      <substituent>Tricarboxylic acid or derivatives</substituent>
    </substituents>
    <external_descriptors>
      <external_descriptor>Triacylglycerols</external_descriptor>
      <external_descriptor>octanoate ester</external_descriptor>
      <external_descriptor>triglyceride</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <state>Solid</state>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>7.41</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-6.87</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>solubility</kind>
      <value>6.36e-05 g/l</value>
      <source>ALOGPS</source>
    </property>
  </predicted_properties>
  <experimental_properties>
    <property>
      <kind>melting_point</kind>
      <value>Mp 10°</value>
    </property>
  </experimental_properties>
  <property>
    <kind>logp</kind>
    <value>8.25</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>pka_strongest_basic</kind>
    <value>-6.6</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>iupac</kind>
    <value>1,3-bis(octanoyloxy)propan-2-yl octanoate</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>average_mass</kind>
    <value>470.6823</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>mono_mass</kind>
    <value>470.360739332</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>smiles</kind>
    <value>[H]C(COC(=O)CCCCCCC)(COC(=O)CCCCCCC)OC(=O)CCCCCCC</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>formula</kind>
    <value>C27H50O6</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>inchi</kind>
    <value>InChI=1S/C27H50O6/c1-4-7-10-13-16-19-25(28)31-22-24(33-27(30)21-18-15-12-9-6-3)23-32-26(29)20-17-14-11-8-5-2/h24H,4-23H2,1-3H3</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>inchikey</kind>
    <value>VLPFTAMPNXLGLX-UHFFFAOYSA-N</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>polar_surface_area</kind>
    <value>78.9</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>refractivity</kind>
    <value>130.87</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>polarizability</kind>
    <value>57.31</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>rotatable_bond_count</kind>
    <value>26</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>acceptor_count</kind>
    <value>3</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>donor_count</kind>
    <value>0</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>physiological_charge</kind>
    <value>0</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>formal_charge</kind>
    <value>0</value>
    <source>ChemAxon</source>
  </property>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>169123</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>563632</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>563633</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>563634</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2461927</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2461928</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2461929</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2612245</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2612246</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2612247</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2709071</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2709072</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2709073</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2719083</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2719084</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2719085</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3000499</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3000500</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3000501</spectrum_id>
    </spectrum>
  </spectra>
  <hmdb_id>HMDB11187</hmdb_id>
  <pubchem_compound_id/>
  <chemspider_id/>
  <kegg_id/>
  <chebi_id/>
  <biocyc_id/>
  <het_id/>
  <wikipidia/>
  <vmh_id/>
  <fbonto_id/>
  <foodb_id/>
  <general_references>
    <reference>#&lt;Reference:0x000055ce30784070&gt;</reference>
    <reference>#&lt;Reference:0x000055ce30783f08&gt;</reference>
    <reference>#&lt;Reference:0x000055ce30783cb0&gt;</reference>
    <reference>#&lt;Reference:0x000055ce307839b8&gt;</reference>
  </general_references>
  <foods>
    <food>
      <name>Anatidae</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Anatidae</name_scientific>
      <ncbi_taxonomy_id>8830</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Beefalo</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Bos taurus X Bison bison</name_scientific>
      <ncbi_taxonomy_id>297284</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Bison</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Bison bison</name_scientific>
      <ncbi_taxonomy_id>9901</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Breakfast cereal</name>
      <food_type>Type 2</food_type>
      <category>specific</category>
      <name_scientific/>
      <ncbi_taxonomy_id/>
    </food>
    <food>
      <name>Buffalo</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Bubalus bubalis</name_scientific>
      <ncbi_taxonomy_id>89462</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Cattle (Beef, Veal)</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Bos taurus</name_scientific>
      <ncbi_taxonomy_id>9913</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Cereals and cereal products</name>
      <food_type>Unknown</food_type>
      <category>generic</category>
      <name_scientific/>
      <ncbi_taxonomy_id/>
    </food>
    <food>
      <name>Chicken</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Gallus gallus</name_scientific>
      <ncbi_taxonomy_id>9031</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Columbidae (Dove, Pigeon)</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Columbidae</name_scientific>
      <ncbi_taxonomy_id>8930</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Deer</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Cervidae</name_scientific>
      <ncbi_taxonomy_id>9850</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Domestic goat</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Capra aegagrus hircus</name_scientific>
      <ncbi_taxonomy_id>9925</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Domestic pig</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Sus scrofa domestica</name_scientific>
      <ncbi_taxonomy_id>9825</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Elk</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Cervus canadensis</name_scientific>
      <ncbi_taxonomy_id>1574408</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Emu</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Dromaius novaehollandiae</name_scientific>
      <ncbi_taxonomy_id>8790</ncbi_taxonomy_id>
    </food>
    <food>
      <name>European rabbit</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Oryctolagus</name_scientific>
      <ncbi_taxonomy_id>9984</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Greylag goose</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Anser anser</name_scientific>
      <ncbi_taxonomy_id>8843</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Guinea hen</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Numida meleagris</name_scientific>
      <ncbi_taxonomy_id>8996</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Horse</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Equus caballus</name_scientific>
      <ncbi_taxonomy_id>9796</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Mallard duck</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Anas platyrhynchos</name_scientific>
      <ncbi_taxonomy_id>8839</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Mountain hare</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Lepus timidus</name_scientific>
      <ncbi_taxonomy_id>62621</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Mule deer</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Odocoileus</name_scientific>
      <ncbi_taxonomy_id>9871</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Ostrich</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Struthio camelus</name_scientific>
      <ncbi_taxonomy_id>8801</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Pheasant</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Phasianus colchicus</name_scientific>
      <ncbi_taxonomy_id>9054</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Quail</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Phasianidae</name_scientific>
      <ncbi_taxonomy_id>9005</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Rabbit</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Leporidae</name_scientific>
      <ncbi_taxonomy_id>9979</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Rock ptarmigan</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Lagopus muta</name_scientific>
      <ncbi_taxonomy_id>64668</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Sheep (Mutton, Lamb)</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Ovis aries</name_scientific>
      <ncbi_taxonomy_id>9940</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Squab</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Columba</name_scientific>
      <ncbi_taxonomy_id>8931</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Turkey</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Meleagris gallopavo</name_scientific>
      <ncbi_taxonomy_id>9103</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Velvet duck</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Melanitta fusca</name_scientific>
      <ncbi_taxonomy_id>371864</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Wild boar</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Sus scrofa</name_scientific>
      <ncbi_taxonomy_id>9823</ncbi_taxonomy_id>
    </food>
  </foods>
  <flavors>
    <flavor>
      <name>odorless</name>
    </flavor>
  </flavors>
  <enzymes>
    <enzyme>
      <name>2-acylglycerol O-acyltransferase 1</name>
      <uniprot_id>Q96PD6</uniprot_id>
      <uniprot_name/>
      <gene_name>MOGAT1</gene_name>
    </enzyme>
    <enzyme>
      <name>2-acylglycerol O-acyltransferase 2</name>
      <uniprot_id>Q3SYC2</uniprot_id>
      <uniprot_name/>
      <gene_name>MOGAT2</gene_name>
    </enzyme>
    <enzyme>
      <name>2-acylglycerol O-acyltransferase 3</name>
      <uniprot_id>Q86VF5</uniprot_id>
      <uniprot_name/>
      <gene_name>MOGAT3</gene_name>
    </enzyme>
    <enzyme>
      <name>Diacylglycerol O-acyltransferase 1</name>
      <uniprot_id>O75907</uniprot_id>
      <uniprot_name/>
      <gene_name>DGAT1</gene_name>
    </enzyme>
    <enzyme>
      <name>Diacylglycerol O-acyltransferase 2</name>
      <uniprot_id>Q96PD7</uniprot_id>
      <uniprot_name/>
      <gene_name>DGAT2</gene_name>
    </enzyme>
    <enzyme>
      <name>Endothelial lipase</name>
      <uniprot_id>Q9Y5X9</uniprot_id>
      <uniprot_name/>
      <gene_name>LIPG</gene_name>
    </enzyme>
    <enzyme>
      <name>Gastric triacylglycerol lipase</name>
      <uniprot_id>P07098</uniprot_id>
      <uniprot_name/>
      <gene_name>LIPF</gene_name>
    </enzyme>
    <enzyme>
      <name>Glycerol-3-phosphate acyltransferase 3</name>
      <uniprot_id>Q53EU6</uniprot_id>
      <uniprot_name/>
      <gene_name>AGPAT9</gene_name>
    </enzyme>
    <enzyme>
      <name>Hepatic triacylglycerol lipase</name>
      <uniprot_id>P11150</uniprot_id>
      <uniprot_name/>
      <gene_name>LIPC</gene_name>
    </enzyme>
    <enzyme>
      <name>Inactive pancreatic lipase-related protein 1</name>
      <uniprot_id>P54315</uniprot_id>
      <uniprot_name/>
      <gene_name>PNLIPRP1</gene_name>
    </enzyme>
    <enzyme>
      <name>Lipoprotein lipase</name>
      <uniprot_id>P06858</uniprot_id>
      <uniprot_name/>
      <gene_name>LPL</gene_name>
    </enzyme>
    <enzyme>
      <name>Liver carboxylesterase 1</name>
      <uniprot_id>P23141</uniprot_id>
      <uniprot_name/>
      <gene_name>CES1</gene_name>
    </enzyme>
    <enzyme>
      <name>Monoglyceride lipase</name>
      <uniprot_id>Q99685</uniprot_id>
      <uniprot_name/>
      <gene_name>MGLL</gene_name>
    </enzyme>
    <enzyme>
      <name>Pancreatic lipase-related protein 2</name>
      <uniprot_id>P54317</uniprot_id>
      <uniprot_name/>
      <gene_name>PNLIPRP2</gene_name>
    </enzyme>
    <enzyme>
      <name>Pancreatic lipase-related protein 3</name>
      <uniprot_id>Q17RR3</uniprot_id>
      <uniprot_name/>
      <gene_name>PNLIPRP3</gene_name>
    </enzyme>
    <enzyme>
      <name>Pancreatic triacylglycerol lipase</name>
      <uniprot_id>P16233</uniprot_id>
      <uniprot_name/>
      <gene_name>PNLIP</gene_name>
    </enzyme>
    <enzyme>
      <name>Patatin-like phospholipase domain-containing protein 2</name>
      <uniprot_id>Q96AD5</uniprot_id>
      <uniprot_name/>
      <gene_name>PNPLA2</gene_name>
    </enzyme>
    <enzyme>
      <name>Patatin-like phospholipase domain-containing protein 3</name>
      <uniprot_id>Q9NST1</uniprot_id>
      <uniprot_name/>
      <gene_name>PNPLA3</gene_name>
    </enzyme>
    <enzyme>
      <name>Patatin-like phospholipase domain-containing protein 4</name>
      <uniprot_id>P41247</uniprot_id>
      <uniprot_name/>
      <gene_name>PNPLA4</gene_name>
    </enzyme>
    <enzyme>
      <name>Protein disulfide-isomerase</name>
      <uniprot_id>P07237</uniprot_id>
      <uniprot_name/>
      <gene_name>P4HB</gene_name>
    </enzyme>
  </enzymes>
  <health_effects>
  </health_effects>
</compound>
