<?xml version="1.0" encoding="UTF-8"?>
<compound>
  <version>1.0</version>
  <creation_date>2016-05-22 06:57:03 UTC</creation_date>
  <update_date>2026-05-14 19:50:50 UTC</update_date>
  <accession/>
  <common_name>(+)-gamma-Tocopherol</common_name>
  <class>SmallMolecule</class>
  <description>(+)-gamma-Tocopherol is an organic compound with the formula C28H48O2 and an average molecular weight of 416.68 g/mol. (+)-gamma-Tocopherol belongs to the quinone and hydroquinone lipids, a subclass of prenol lipids within the organic compounds. In industrial applications, the compound is used as a fragrance.

This substance is found in or released from several recorded sources, including household cleaning and consumer products such as other smoking requisites and non electric simulated smoking devices. It is also associated with food, food processing and cookware, specifically in the preparation of wine or sparkling wine, as well as electrical and electronic equipment including discharge lamps and antennas. Regarding health effects, (+)-gamma-Tocopherol has a therapeutic effect on prostate cancer (PMC3823537, PMC4670692) and is associated with prostate cancer in an inverse manner (PMC3823537).</description>
  <categories/>
  <types/>
  <synonyms/>
  <chemical_formula>C28H48O2</chemical_formula>
  <average_molecular_weight>416.6795</average_molecular_weight>
  <monisotopic_moleculate_weight>416.36543078</monisotopic_moleculate_weight>
  <iupac_name>(2R)-2,7,8-trimethyl-2-[(4R,8R)-4,8,12-trimethyltridecyl]-3,4-dihydro-2H-1-benzopyran-6-ol</iupac_name>
  <traditional_iupac>gamma-tocopherol</traditional_iupac>
  <cas_registry_number>54-28-4</cas_registry_number>
  <smiles>[H][C@@](C)(CCCC(C)C)CCC[C@@]([H])(C)CCC[C@]1(C)CCC2=C(O1)C(C)=C(C)C(O)=C2</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/t21-,22-,28-/m1/s1</inchi>
  <inchikey>QUEDXNHFTDJVIY-DQCZWYHMSA-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>
      <descriptor>tocopherol</descriptor>
      <descriptor>vitamin E</descriptor>
    </descriptors>
  </taxonomy>
  <status>Detected and Not Quantified</status>
  <origin/>
  <cellular_locations/>
  <biofluid_locations/>
  <tissue_locations/>
  <pathways/>
  <state/>
  <appearance/>
  <experimental_properties>
    <property>
      <kind>logp</kind>
      <value>9.99</value>
    </property>
  </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>(2R)-2,7,8-trimethyl-2-[(4R,8R)-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>[H][C@@](C)(CCCC(C)C)CCC[C@@]([H])(C)CCC[C@]1(C)CCC2=C(O1)C(C)=C(C)C(O)=C2</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/t21-,22-,28-/m1/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>QUEDXNHFTDJVIY-DQCZWYHMSA-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>54.12</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:0x00007f7281b06918&gt;</health_effects>
  <symptoms/>
  <treatment/>
  <drugbank_id>DB15394</drugbank_id>
  <hmdb_id/>
  <pubchem_compound_id>92729</pubchem_compound_id>
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  <biocyc_id/>
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  <wikipidia/>
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</compound>
