<?xml version="1.0" encoding="UTF-8"?>
<compound>
  <version>1.0</version>
  <creation_date>2010-04-08 22:06:51 UTC</creation_date>
  <update_date>2025-11-18 23:00:03 UTC</update_date>
  <accession>FDB005790</accession>
  <name>Oryzanol</name>
  <description>Oryzanol belongs to cycloartanols and derivatives class of compounds. Those are steroids containing a cycloartanol moiety. Oryzanol is practically insoluble (in water) and a very weakly acidic compound (based on its pKa). Oryzanol can be found in barley, which makes oryzanol a potential biomarker for the consumption of this food product. Rice bran oil is the oil extracted from the hard outer brown layer of rice after chaff (rice husk). It is known for its high smoke point of 232 °C (450 °F) and mild flavor, making it suitable for high-temperature cooking methods such as stir frying and deep frying. It is popular as a cooking oil in several Asian countries, including Bangladesh, Japan, India and China .</description>
  <synonyms>
    <synonym>Gamma oryzanol [jan]</synonym>
    <synonym>Gamma-orizanol</synonym>
    <synonym>Gamma-oryzanol</synonym>
    <synonym>Gammariza</synonym>
    <synonym>Hi-z</synonym>
    <synonym>Oliver</synonym>
    <synonym>OZ</synonym>
    <synonym>triacontane 3-(4-hydroxy-3-methoxyphenyl)-2-propenate</synonym>
  </synonyms>
  <chemical_formula>C40H58O4</chemical_formula>
  <average_molecular_weight>602.8861</average_molecular_weight>
  <monisotopic_moleculate_weight>602.433510344</monisotopic_moleculate_weight>
  <iupac_name>(1S,3R,6S,12S,15R,16R)-7,7,12,16-tetramethyl-15-(6-methylhept-5-en-2-yl)pentacyclo[9.7.0.0¹,³.0³,⁸.0¹²,¹⁶]octadecan-6-yl (2E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate</iupac_name>
  <traditional_iupac>(1S,3R,6S,12S,15R,16R)-7,7,12,16-tetramethyl-15-(6-methylhept-5-en-2-yl)pentacyclo[9.7.0.0¹,³.0³,⁸.0¹²,¹⁶]octadecan-6-yl (2E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate</traditional_iupac>
  <cas_registry_number>11042-64-1</cas_registry_number>
  <smiles>COC1=C(O)C=CC(\C=C\C(=O)O[C@H]2CC[C@]34C[C@]33CC[C@]5(C)[C@H](CC[C@@]5(C)C3CCC4C2(C)C)C(C)CCC=C(C)C)=C1</smiles>
  <inchi>InChI=1S/C40H58O4/c1-26(2)10-9-11-27(3)29-18-20-38(7)33-16-15-32-36(4,5)34(19-21-39(32)25-40(33,39)23-22-37(29,38)6)44-35(42)17-13-28-12-14-30(41)31(24-28)43-8/h10,12-14,17,24,27,29,32-34,41H,9,11,15-16,18-23,25H2,1-8H3/b17-13+/t27?,29-,32?,33?,34+,37-,38+,39-,40+/m1/s1</inchi>
  <inchikey>FODTZLFLDFKIQH-AEUNZGHWSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as cycloartanols and derivatives. These are steroids containing a cycloartanol moiety.</description>
    <direct_parent>Cycloartanols and derivatives</direct_parent>
    <kingdom>Organic compounds</kingdom>
    <super_class>Lipids and lipid-like molecules</super_class>
    <class>Steroids and steroid derivatives</class>
    <sub_class>Cycloartanols and derivatives</sub_class>
    <molecular_framework>Aromatic homopolycyclic compounds</molecular_framework>
    <alternative_parents>
      <alternative_parent>1-hydroxy-2-unsubstituted benzenoids</alternative_parent>
      <alternative_parent>Alkyl aryl ethers</alternative_parent>
      <alternative_parent>Anisoles</alternative_parent>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Cinnamic acid esters</alternative_parent>
      <alternative_parent>Coumaric acids and derivatives</alternative_parent>
      <alternative_parent>Enoate esters</alternative_parent>
      <alternative_parent>Fatty acid esters</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Methoxybenzenes</alternative_parent>
      <alternative_parent>Methoxyphenols</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Phenoxy compounds</alternative_parent>
      <alternative_parent>Steroid esters</alternative_parent>
      <alternative_parent>Styrenes</alternative_parent>
      <alternative_parent>Triterpenoids</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>1-hydroxy-2-unsubstituted benzenoid</substituent>
      <substituent>9b,19-cyclo-lanostane-skeleton</substituent>
      <substituent>Alkyl aryl ether</substituent>
      <substituent>Alpha,beta-unsaturated carboxylic ester</substituent>
      <substituent>Anisole</substituent>
      <substituent>Aromatic homopolycyclic compound</substituent>
      <substituent>Benzenoid</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Carboxylic acid ester</substituent>
      <substituent>Cinnamic acid ester</substituent>
      <substituent>Cinnamic acid or derivatives</substituent>
      <substituent>Coumaric acid or derivatives</substituent>
      <substituent>Cycloartane-skeleton</substituent>
      <substituent>Cycloartanol-skeleton</substituent>
      <substituent>Enoate ester</substituent>
      <substituent>Ether</substituent>
      <substituent>Fatty acid ester</substituent>
      <substituent>Fatty acyl</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Hydroxycinnamic acid or derivatives</substituent>
      <substituent>Methoxybenzene</substituent>
      <substituent>Methoxyphenol</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>Monocyclic benzene moiety</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Phenol</substituent>
      <substituent>Phenol ether</substituent>
      <substituent>Phenoxy compound</substituent>
      <substituent>Steroid ester</substituent>
      <substituent>Styrene</substituent>
      <substituent>Triterpenoid</substituent>
    </substituents>
    <external_descriptors>
    </external_descriptors>
  </taxonomy>
  <state/>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>8.54</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-7.65</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>solubility</kind>
      <value>1.36e-05 g/l</value>
      <source>ALOGPS</source>
    </property>
  </predicted_properties>
  <experimental_properties>
  </experimental_properties>
  <property>
    <kind>logp</kind>
    <value>10.12</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>pka_strongest_acidic</kind>
    <value>9.87</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>pka_strongest_basic</kind>
    <value>-4.9</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>iupac</kind>
    <value>(1S,3R,6S,12S,15R,16R)-7,7,12,16-tetramethyl-15-(6-methylhept-5-en-2-yl)pentacyclo[9.7.0.0¹,³.0³,⁸.0¹²,¹⁶]octadecan-6-yl (2E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>average_mass</kind>
    <value>602.8861</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>mono_mass</kind>
    <value>602.433510344</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>smiles</kind>
    <value>COC1=C(O)C=CC(\C=C\C(=O)O[C@H]2CC[C@]34C[C@]33CC[C@]5(C)[C@H](CC[C@@]5(C)C3CCC4C2(C)C)C(C)CCC=C(C)C)=C1</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>formula</kind>
    <value>C40H58O4</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>inchi</kind>
    <value>InChI=1S/C40H58O4/c1-26(2)10-9-11-27(3)29-18-20-38(7)33-16-15-32-36(4,5)34(19-21-39(32)25-40(33,39)23-22-37(29,38)6)44-35(42)17-13-28-12-14-30(41)31(24-28)43-8/h10,12-14,17,24,27,29,32-34,41H,9,11,15-16,18-23,25H2,1-8H3/b17-13+/t27?,29-,32?,33?,34+,37-,38+,39-,40+/m1/s1</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>inchikey</kind>
    <value>FODTZLFLDFKIQH-AEUNZGHWSA-N</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>polar_surface_area</kind>
    <value>55.76</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>refractivity</kind>
    <value>180.04</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>polarizability</kind>
    <value>74.83</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>rotatable_bond_count</kind>
    <value>9</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>acceptor_count</kind>
    <value>3</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>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>93345</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>93346</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>93347</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>157092</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>157093</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>157094</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3602135</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3602136</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3602137</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3602138</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3602139</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3602140</spectrum_id>
    </spectrum>
  </spectra>
  <hmdb_id/>
  <pubchem_compound_id/>
  <chemspider_id/>
  <kegg_id/>
  <chebi_id/>
  <biocyc_id/>
  <het_id/>
  <wikipidia/>
  <vmh_id/>
  <fbonto_id/>
  <foodb_id/>
  <general_references>
  </general_references>
  <foods>
    <food>
      <name>Barley</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Hordeum vulgare</name_scientific>
      <ncbi_taxonomy_id>4513</ncbi_taxonomy_id>
    </food>
  </foods>
  <flavors>
  </flavors>
  <enzymes>
  </enzymes>
  <health_effects>
  </health_effects>
</compound>
