<?xml version="1.0" encoding="UTF-8"?>
<compound>
  <version>1.0</version>
  <creation_date>2010-04-08 22:10:56 UTC</creation_date>
  <update_date>2019-11-26 03:09:08 UTC</update_date>
  <accession>FDB013831</accession>
  <name>Retinol palmitate</name>
  <description>Nutrient, appearance control agent for colours and colour modifiers. Found in fish liver oils. Dietary supplement, permitted in infant formulas

Palmitate is an antioxidant and a vitamin A compound added to low fat milk and other dairy products to replace the vitamin content lost through the removal of milk fat. Palmitate is attached to the alcohol form of vitamin A, retinol, in order to make vitamin A stable in milk.[citation needed]; Retinyl palmitate is a synthetic alternate for retinyl acetate in vitamin A supplements, and is available in oily or dry forms. It is a common vitamin supplement, available in both oral and injectable forms for treatment of vitamin A deficiency, under the brand names Aquasol A, Palmitate A and many others. It is a pre-formed version of vitamin A, and can thus be realistically over-dosed, unlike beta-carotene.; Retinyl palmitate, or vitamin A palmitate, is a common vitamin supplement, with formula C36H60O2. It is available in both oral and injectable forms for treatment of vitamin A deficiency, under the brand names Aquasol and Palmitate. ; Retinyl palmitate is an alternate for retinyl acetate in vitamin A supplements, and is available in oily or dry forms. It is a pre-formed version of vitamin A, and can thus be realistically over-dosed, unlike beta-carotene.</description>
  <synonyms>
    <synonym>All-trans-retinol palmitate</synonym>
    <synonym>all-trans-Retinyl hexadecanoate</synonym>
    <synonym>all-trans-Retinyl hexadecanoic acid</synonym>
    <synonym>All-trans-retinyl palmitate</synonym>
    <synonym>all-trans-Retinyl palmitic acid</synonym>
    <synonym>All-trans-vitamin a palmitate</synonym>
    <synonym>Aquapalm</synonym>
    <synonym>Aquasol a</synonym>
    <synonym>Aquasol a (TN)</synonym>
    <synonym>Arovit</synonym>
    <synonym>Arovit (roche)</synonym>
    <synonym>Axerophthol palmitate</synonym>
    <synonym>Chocola a</synonym>
    <synonym>Chocola_a</synonym>
    <synonym>Del-vi-a</synonym>
    <synonym>Dispatabs tabs</synonym>
    <synonym>Ester found in fish liver oils</synonym>
    <synonym>Lutavit A 500 Plus</synonym>
    <synonym>O~15~-hexadecanoylretinol</synonym>
    <synonym>O~15~-palmitoylretinol</synonym>
    <synonym>Optovit a</synonym>
    <synonym>Optovit-a</synonym>
    <synonym>Palmitic acid, ester with retinol</synonym>
    <synonym>Retinol palmitate</synonym>
    <synonym>Retinol palmitate (6CI,7CI)</synonym>
    <synonym>Retinol palmitate (JP15)</synonym>
    <synonym>Retinol palmitic acid</synonym>
    <synonym>Retinol-palmitate</synonym>
    <synonym>Retinol, all-trans-, palmitate</synonym>
    <synonym>Retinol, hexadecanoate</synonym>
    <synonym>retinol, O~15~-(1-oxohexadecyl)-</synonym>
    <synonym>Retinol, palmitate, all-trans-</synonym>
    <synonym>Retinol, palmitate, all-trans- (8CI)</synonym>
    <synonym>Retinyl hexadecanoate</synonym>
    <synonym>Retinyl hexadecanoic acid</synonym>
    <synonym>Retinyl palmitate</synonym>
    <synonym>Retinyl palmitic acid</synonym>
    <synonym>Testavol s</synonym>
    <synonym>Trans-retinol palmitate</synonym>
    <synonym>Trans-retinyl palmitate</synonym>
    <synonym>Vi-dom-a</synonym>
    <synonym>Vitamin A palmitate</synonym>
    <synonym>Vitamin a palmitic acid</synonym>
    <synonym>Vitamin a solubilized</synonym>
    <synonym>Vitamin- a palmitate</synonym>
    <synonym>Vitazyme a</synonym>
  </synonyms>
  <chemical_formula>C36H60O2</chemical_formula>
  <average_molecular_weight>524.8604</average_molecular_weight>
  <monisotopic_moleculate_weight>524.459331164</monisotopic_moleculate_weight>
  <iupac_name>(2E,4E,6Z,8E)-3,7-dimethyl-9-(2,6,6-trimethylcyclohex-1-en-1-yl)nona-2,4,6,8-tetraen-1-yl hexadecanoate</iupac_name>
  <traditional_iupac>(2E,4E,6Z,8E)-3,7-dimethyl-9-(2,6,6-trimethylcyclohex-1-en-1-yl)nona-2,4,6,8-tetraen-1-yl hexadecanoate</traditional_iupac>
  <cas_registry_number>79-81-2</cas_registry_number>
  <smiles>CCCCCCCCCCCCCCCC(=O)OC\C=C(/C)\C=C\C=C(\C)/C=C/C1=C(C)CCCC1(C)C</smiles>
  <inchi>InChI=1S/C36H60O2/c1-7-8-9-10-11-12-13-14-15-16-17-18-19-25-35(37)38-30-28-32(3)23-20-22-31(2)26-27-34-33(4)24-21-29-36(34,5)6/h20,22-23,26-28H,7-19,21,24-25,29-30H2,1-6H3/b23-20+,27-26+,31-22-,32-28+</inchi>
  <inchikey>VYGQUTWHTHXGQB-UMNZIDCRSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as wax monoesters. These are waxes bearing an ester group at exactly one position.</description>
    <direct_parent>Wax monoesters</direct_parent>
    <kingdom>Organic compounds</kingdom>
    <super_class>Lipids and lipid-like molecules</super_class>
    <class>Fatty Acyls</class>
    <sub_class>Fatty acid esters</sub_class>
    <molecular_framework>Aliphatic homomonocyclic compounds</molecular_framework>
    <alternative_parents>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acid esters</alternative_parent>
      <alternative_parent>Diterpenoids</alternative_parent>
      <alternative_parent>Fatty alcohol esters</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Retinoids</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Aliphatic homomonocyclic compound</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Carboxylic acid ester</substituent>
      <substituent>Diterpenoid</substituent>
      <substituent>Fatty alcohol ester</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Retinoid skeleton</substituent>
      <substituent>Wax monoester skeleton</substituent>
    </substituents>
    <external_descriptors>
    </external_descriptors>
  </taxonomy>
  <state>Solid</state>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>10.12</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-6.81</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>solubility</kind>
      <value>8.07e-05 g/l</value>
      <source>ALOGPS</source>
    </property>
  </predicted_properties>
  <experimental_properties>
    <property>
      <kind>melting_point</kind>
      <value>Mp 28-29°</value>
    </property>
  </experimental_properties>
  <property>
    <kind>logp</kind>
    <value>11.62</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>pka_strongest_basic</kind>
    <value>-7</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>iupac</kind>
    <value>(2E,4E,6Z,8E)-3,7-dimethyl-9-(2,6,6-trimethylcyclohex-1-en-1-yl)nona-2,4,6,8-tetraen-1-yl hexadecanoate</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>average_mass</kind>
    <value>524.8604</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>mono_mass</kind>
    <value>524.459331164</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>smiles</kind>
    <value>CCCCCCCCCCCCCCCC(=O)OC\C=C(/C)\C=C\C=C(\C)/C=C/C1=C(C)CCCC1(C)C</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>formula</kind>
    <value>C36H60O2</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>inchi</kind>
    <value>InChI=1S/C36H60O2/c1-7-8-9-10-11-12-13-14-15-16-17-18-19-25-35(37)38-30-28-32(3)23-20-22-31(2)26-27-34-33(4)24-21-29-36(34,5)6/h20,22-23,26-28H,7-19,21,24-25,29-30H2,1-6H3/b23-20+,27-26+,31-22-,32-28+</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>inchikey</kind>
    <value>VYGQUTWHTHXGQB-UMNZIDCRSA-N</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>polar_surface_area</kind>
    <value>26.3</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>refractivity</kind>
    <value>171.51</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>polarizability</kind>
    <value>70.21</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>rotatable_bond_count</kind>
    <value>21</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>acceptor_count</kind>
    <value>1</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>
    <pathway>
      <name>Retinol Metabolism</name>
      <smpdb_id>SMP00074</smpdb_id>
      <kegg_map_id>map00830</kegg_map_id>
    </pathway>
  </pathways>
  <spectra>
  </spectra>
  <hmdb_id>HMDB03648</hmdb_id>
  <pubchem_compound_id/>
  <chemspider_id/>
  <kegg_id/>
  <chebi_id>17616</chebi_id>
  <biocyc_id/>
  <het_id/>
  <wikipidia/>
  <vmh_id/>
  <fbonto_id/>
  <foodb_id/>
  <general_references>
    <reference>#&lt;Reference:0x000055ce33197678&gt;</reference>
    <reference>#&lt;Reference:0x000055ce331974c0&gt;</reference>
    <reference>#&lt;Reference:0x000055ce33197308&gt;</reference>
    <reference>#&lt;Reference:0x000055ce33197128&gt;</reference>
    <reference>#&lt;Reference:0x000055ce33196f70&gt;</reference>
    <reference>#&lt;Reference:0x000055ce33196db8&gt;</reference>
    <reference>#&lt;Reference:0x000055ce33196c00&gt;</reference>
    <reference>#&lt;Reference:0x000055ce33196a48&gt;</reference>
    <reference>#&lt;Reference:0x000055ce33196890&gt;</reference>
    <reference>#&lt;Reference:0x000055ce331966d8&gt;</reference>
    <reference>#&lt;Reference:0x000055ce33196520&gt;</reference>
    <reference>#&lt;Reference:0x000055ce33196368&gt;</reference>
    <reference>#&lt;Reference:0x000055ce331961b0&gt;</reference>
    <reference>#&lt;Reference:0x000055ce33195ff8&gt;</reference>
    <reference>#&lt;Reference:0x000055ce33195e40&gt;</reference>
    <reference>#&lt;Reference:0x000055ce33195c88&gt;</reference>
    <reference>#&lt;Reference:0x000055ce33195ad0&gt;</reference>
    <reference>#&lt;Reference:0x000055ce33195918&gt;</reference>
    <reference>#&lt;Reference:0x000055ce33195760&gt;</reference>
    <reference>#&lt;Reference:0x000055ce331955a8&gt;</reference>
  </general_references>
  <foods>
    <food>
      <name>Fats and oils</name>
      <food_type>Unknown</food_type>
      <category>generic</category>
      <name_scientific/>
      <ncbi_taxonomy_id/>
    </food>
    <food>
      <name>Fishes</name>
      <food_type>Unknown</food_type>
      <category>generic</category>
      <name_scientific/>
      <ncbi_taxonomy_id/>
    </food>
    <food>
      <name>Wild celery</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Apium graveolens</name_scientific>
      <ncbi_taxonomy_id>4045</ncbi_taxonomy_id>
    </food>
  </foods>
  <flavors>
  </flavors>
  <enzymes>
    <enzyme>
      <name>Acyl-CoA wax alcohol acyltransferase 1</name>
      <uniprot_id>Q58HT5</uniprot_id>
      <uniprot_name/>
      <gene_name>AWAT1</gene_name>
    </enzyme>
    <enzyme>
      <name>Acyl-CoA wax alcohol acyltransferase 2</name>
      <uniprot_id>Q6E213</uniprot_id>
      <uniprot_name/>
      <gene_name>AWAT2</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>Lecithin retinol acyltransferase</name>
      <uniprot_id>O95237</uniprot_id>
      <uniprot_name/>
      <gene_name>LRAT</gene_name>
    </enzyme>
  </enzymes>
  <health_effects>
  </health_effects>
</compound>
