<?xml version="1.0" encoding="UTF-8"?>
<compound>
  <version>1.0</version>
  <creation_date>2016-05-19 02:29:02 UTC</creation_date>
  <update_date>2026-04-16 22:52:53 UTC</update_date>
  <accession/>
  <common_name>TOCOPHEROLS</common_name>
  <class>SmallMolecule</class>
  <description>TOCOPHEROLS (C28H48O2) is a compound with an average molecular weight of 416.68 g/mol. TOCOPHEROLS belongs to the quinone and hydroquinone lipids, a subclass of prenol lipids within the organic compounds. It serves as an industrial flavouring and nutrient, as well as an industrial and biological antioxidant (PMC9439934), and an environmental nutrient (PMC8373945).

The compound is found in or released from 23 recorded sources. These include vitamins in healthcare, pharmaceuticals, and veterinary products; food, food processing, and cookware such as the processing of fish and fermentation processes for beer, the preparation of malt, and the preparation of vinegar, wine, or sparkling wine; household cleaning and consumer products including soap detergents, bleaching agents, cigar cigarettes, non-electric simulated smoking devices, and other smoking requisites; building and construction materials such as sunshades, awnings, or outside screens; and electrical and electronic equipment including antennas, communication cables or conductors, cores yokes or armatures, and electrically stimulated smoking devices. Recorded exposure routes include oral, dental, topical, and cutaneous.

Health effects associated with TOCOPHEROLS include inflammation (PMC5796020), blood pressure (PMC9818577), arteriosclerosis (PMC9818577), high blood pressure (PMC13074123), hypertension (PMC13074123), and cancer (PMC13074123). Additionally, the compound has demonstrated therapeutic effects on obesity (PMC12897246), chronic inflammation (PMC10745369), and cancer (PMC10384004, PMC11643819, PMC12897246).</description>
  <categories/>
  <types/>
  <synonyms>
    <synonym>gamma-Tocopherol</synonym>
    <synonym>Gamma-Tocopherol</synonym>
  </synonyms>
  <chemical_formula>C28H48O2</chemical_formula>
  <average_molecular_weight>416.6795</average_molecular_weight>
  <monisotopic_moleculate_weight>416.36543078</monisotopic_moleculate_weight>
  <iupac_name>2,7,8-trimethyl-2-(4,8,12-trimethyltridecyl)-3,4-dihydro-2H-1-benzopyran-6-ol</iupac_name>
  <traditional_iupac>2,7,8-trimethyl-2-(4,8,12-trimethyltridecyl)-3,4-dihydro-1-benzopyran-6-ol</traditional_iupac>
  <cas_registry_number>1406-66-2</cas_registry_number>
  <smiles>CC(C)CCCC(C)CCCC(C)CCCC1(C)CCC2=CC(O)=C(C)C(C)=C2O1</smiles>
  <inchi>InChI=1S/C28H48O2/c1-20(2)11-8-12-21(3)13-9-14-22(4)15-10-17-28(7)18-16-25-19-26(29)23(5)24(6)27(25)30-28/h19-22,29H,8-18H2,1-7H3</inchi>
  <inchikey>QUEDXNHFTDJVIY-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <kingdom>Organic compounds</kingdom>
    <super_class>Lipids and lipid-like molecules</super_class>
    <class>Prenol lipids</class>
    <sub_class>Quinone and hydroquinone lipids</sub_class>
    <direct_parent>Tocopherols</direct_parent>
    <alternate_parents>
      <alternative_parent>1-benzopyrans</alternative_parent>
      <alternative_parent>1-hydroxy-2-unsubstituted benzenoids</alternative_parent>
      <alternative_parent>Alkyl aryl ethers</alternative_parent>
      <alternative_parent>Diterpenoids</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Oxacyclic compounds</alternative_parent>
    </alternate_parents>
    <substituents>
      <substituent>1-benzopyran</substituent>
      <substituent>1-hydroxy-2-unsubstituted benzenoid</substituent>
      <substituent>Alkyl aryl ether</substituent>
      <substituent>Aromatic heteropolycyclic compound</substituent>
      <substituent>Benzenoid</substituent>
      <substituent>Benzopyran</substituent>
      <substituent>Chromane</substituent>
      <substituent>Diterpenoid</substituent>
      <substituent>Ether</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organoheterocyclic compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Oxacycle</substituent>
      <substituent>Tocopherol</substituent>
    </substituents>
    <molecular_framework>Aromatic heteropolycyclic compounds</molecular_framework>
    <descriptors>
      <descriptor>vitamin E</descriptor>
    </descriptors>
  </taxonomy>
  <status>Detected and Not Quantified</status>
  <origin/>
  <cellular_locations/>
  <biofluid_locations/>
  <tissue_locations/>
  <pathways/>
  <state/>
  <appearance/>
  <experimental_properties/>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>8.81</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-7.75</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>solubility</kind>
      <value>7.37e-06 g/l</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>9.99</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>10.47</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-4.9</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>2,7,8-trimethyl-2-(4,8,12-trimethyltridecyl)-3,4-dihydro-2H-1-benzopyran-6-ol</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>416.6795</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>416.36543078</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>CC(C)CCCC(C)CCCC(C)CCCC1(C)CCC2=CC(O)=C(C)C(C)=C2O1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C28H48O2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C28H48O2/c1-20(2)11-8-12-21(3)13-9-14-22(4)15-10-17-28(7)18-16-25-19-26(29)23(5)24(6)27(25)30-28/h19-22,29H,8-18H2,1-7H3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>QUEDXNHFTDJVIY-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>29.46</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>130.33</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>54.13</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>12</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>1</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>
  </predicted_properties>
  <route_of_exposure/>
  <mechanism_of_toxicity/>
  <metabolism/>
  <toxicity/>
  <lethaldose/>
  <carcinogenicity/>
  <use_source/>
  <min_risk_level/>
  <health_effects>#&lt;HealthEffect::ActiveRecord_Associations_CollectionProxy:0x00007f7226260008&gt;</health_effects>
  <symptoms/>
  <treatment/>
  <drugbank_id>DB11251</drugbank_id>
  <hmdb_id/>
  <pubchem_compound_id>14986</pubchem_compound_id>
  <chembl_id/>
  <chemspider_id>14266</chemspider_id>
  <kegg_id/>
  <uniprot_id/>
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  <chebi_id/>
  <biocyc_id/>
  <ctd_id/>
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  <actor_id/>
  <pdb_id/>
  <wikipidia/>
  <general_references/>
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  </targets>
</compound>
