<?xml version="1.0" encoding="UTF-8"?>
<compound>
  <version>1.0</version>
  <creation_date>2010-04-08 22:05:58 UTC</creation_date>
  <update_date>2025-11-18 22:54:05 UTC</update_date>
  <accession>FDB003839</accession>
  <name>beta-Eudesmol</name>
  <description>Beta-Eudesmol, also known as beta-selinenol belongs to the class of organic compounds known as eudesmane, isoeudesmane or cycloeudesmane sesquiterpenoids. These are sesquiterpenoids with a structure based on the eudesmane skeleton. Sesquiterpenoids are terpenes that contain 15 carbon atoms and are comprised of three isoprene units. The biosynthesis of sesquiterpenes is known to occur mainly through the mevalonic acid pathway (MVA), in the cytosol. However, recent studies have found evidence of pathway crosstalk with the methyl-eritritol-phosphate (MEP) pathway in the plastid (PMID: 19932496, 17710406). Farnesyl diphosphate (FPP) is a key intermediate in the biosynthesis of cyclic sesquiterpenes. FPP undergoes several cyclization reactions to yield a diverse number of cyclic arrangements. Beta-eudesmol is a green and wood tasting compound that can be found in a number of food items such as common walnut, sweet basil, ginkgo nuts, burdock, and ginger (PMID: 18242187).</description>
  <synonyms>
    <synonym>&amp;beta;-eudesmol</synonym>
    <synonym>&amp;beta;-eudesmol (&amp;beta;-selinenol)</synonym>
    <synonym>&amp;beta;-selinenol</synonym>
    <synonym>beta-Eudesmol</synonym>
    <synonym>Beta-selinenol</synonym>
    <synonym>Eudesm-4(14)-en-11-ol</synonym>
    <synonym>Eudesm-4(14)-en-11-ol (8CI)</synonym>
  </synonyms>
  <chemical_formula>C15H26O</chemical_formula>
  <average_molecular_weight>222.3663</average_molecular_weight>
  <monisotopic_moleculate_weight>222.198365454</monisotopic_moleculate_weight>
  <iupac_name>2-[(2R,4aR,8aS)-4a-methyl-8-methylidene-decahydronaphthalen-2-yl]propan-2-ol</iupac_name>
  <traditional_iupac>β-eudesmol</traditional_iupac>
  <cas_registry_number>473-15-4</cas_registry_number>
  <smiles>CC(C)(O)[C@@H]1CC[C@@]2(C)CCCC(=C)[C@@H]2C1</smiles>
  <inchi>InChI=1S/C15H26O/c1-11-6-5-8-15(4)9-7-12(10-13(11)15)14(2,3)16/h12-13,16H,1,5-10H2,2-4H3/t12-,13+,15-/m1/s1</inchi>
  <inchikey>BOPIMTNSYWYZOC-VNHYZAJKSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as eudesmane, isoeudesmane or cycloeudesmane sesquiterpenoids. These are sesquiterpenoids with a structure based on the eudesmane skeleton.</description>
    <direct_parent>Eudesmane, isoeudesmane or cycloeudesmane sesquiterpenoids</direct_parent>
    <kingdom>Organic compounds</kingdom>
    <super_class>Lipids and lipid-like molecules</super_class>
    <class>Prenol lipids</class>
    <sub_class>Sesquiterpenoids</sub_class>
    <molecular_framework>Aliphatic homopolycyclic compounds</molecular_framework>
    <alternative_parents>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Tertiary alcohols</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Alcohol</substituent>
      <substituent>Aliphatic homopolycyclic compound</substituent>
      <substituent>Eudesmane, isoeudesmane or cycloeudesmane sesquiterpenoid</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Tertiary alcohol</substituent>
    </substituents>
    <external_descriptors>
      <external_descriptor>Eudesmanes</external_descriptor>
      <external_descriptor>carbobicyclic compound</external_descriptor>
      <external_descriptor>eudesmane sesquiterpenoid</external_descriptor>
      <external_descriptor>tertiary alcohol</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <state/>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>4.21</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-4.49</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>solubility</kind>
      <value>7.19e-03 g/l</value>
      <source>ALOGPS</source>
    </property>
  </predicted_properties>
  <experimental_properties>
  </experimental_properties>
  <property>
    <kind>logp</kind>
    <value>3.53</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>pka_strongest_acidic</kind>
    <value>19.32</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>pka_strongest_basic</kind>
    <value>-0.91</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>iupac</kind>
    <value>2-[(2R,4aR,8aS)-4a-methyl-8-methylidene-decahydronaphthalen-2-yl]propan-2-ol</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>average_mass</kind>
    <value>222.3663</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>mono_mass</kind>
    <value>222.198365454</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>smiles</kind>
    <value>CC(C)(O)[C@@H]1CC[C@@]2(C)CCCC(=C)[C@@H]2C1</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>formula</kind>
    <value>C15H26O</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>inchi</kind>
    <value>InChI=1S/C15H26O/c1-11-6-5-8-15(4)9-7-12(10-13(11)15)14(2,3)16/h12-13,16H,1,5-10H2,2-4H3/t12-,13+,15-/m1/s1</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>inchikey</kind>
    <value>BOPIMTNSYWYZOC-VNHYZAJKSA-N</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>polar_surface_area</kind>
    <value>20.23</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>refractivity</kind>
    <value>68.36</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>polarizability</kind>
    <value>27.56</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>rotatable_bond_count</kind>
    <value>1</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>acceptor_count</kind>
    <value>1</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::CMs</type>
      <spectrum_id>103782</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::EiMs</type>
      <spectrum_id>1866</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>85854</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>85855</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>85856</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>148029</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>148030</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>148031</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1473378</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1473379</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>Burdock</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Arctium lappa</name_scientific>
      <ncbi_taxonomy_id>4217</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Common oregano</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Origanum vulgare</name_scientific>
      <ncbi_taxonomy_id>39352</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Common walnut</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Juglans regia</name_scientific>
      <ncbi_taxonomy_id>51240</ncbi_taxonomy_id>
      <average_value>2.1</average_value>
      <max_value>2.1</max_value>
      <min_value>2.1</min_value>
      <unit>mg/100 g</unit>
    </food>
    <food>
      <name>Dill</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Anethum graveolens</name_scientific>
      <ncbi_taxonomy_id>40922</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Ginger</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Zingiber officinale</name_scientific>
      <ncbi_taxonomy_id>94328</ncbi_taxonomy_id>
      <average_value>23.6</average_value>
      <max_value>23.6</max_value>
      <min_value>23.6</min_value>
      <unit>mg/100 g</unit>
    </food>
    <food>
      <name>Ginkgo nuts</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Ginkgo biloba</name_scientific>
      <ncbi_taxonomy_id>3311</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Orange mint</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Mentha aquatica</name_scientific>
      <ncbi_taxonomy_id>190902</ncbi_taxonomy_id>
      <average_value>1.75</average_value>
      <max_value>1.75</max_value>
      <min_value>1.75</min_value>
      <unit>mg/100 g</unit>
    </food>
    <food>
      <name>Sweet basil</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Ocimum basilicum</name_scientific>
      <ncbi_taxonomy_id>39350</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Sweet bay</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Laurus nobilis</name_scientific>
      <ncbi_taxonomy_id>85223</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>
      <average_value>15.05</average_value>
      <max_value>15.05</max_value>
      <min_value>15.05</min_value>
      <unit>mg/100 g</unit>
    </food>
  </foods>
  <flavors>
    <flavor>
      <name>green</name>
    </flavor>
    <flavor>
      <name>wood</name>
    </flavor>
  </flavors>
  <enzymes>
  </enzymes>
  <health_effects>
    <health_effect>
      <name>Anti Epstein-Barr virus</name>
      <id>245</id>
      <definition>A substance that destroys or inhibits replication of viruses.</definition>
    </health_effect>
    <health_effect>
      <name>Anti peptic</name>
      <id>512</id>
      <definition/>
    </health_effect>
    <health_effect>
      <name>Anti ulcer</name>
      <id>676</id>
      <definition>One of various classes of drugs with different action mechanisms used to treat or ameliorate peptic ulcer or irritation of the gastrointestinal tract.</definition>
    </health_effect>
    <health_effect>
      <name>Anti-anoxic</name>
      <id>119</id>
      <definition>Any substance introduced into a living organism with therapeutic or diagnostic purpose.</definition>
    </health_effect>
    <health_effect>
      <name>Anti-mutagenic</name>
      <id>451</id>
      <definition/>
    </health_effect>
    <health_effect>
      <name>Anti-salmonella</name>
      <id>591</id>
      <definition>A substance that kills or slows the growth of bacteria.</definition>
    </health_effect>
    <health_effect>
      <name>Antitumor promoter</name>
      <id>673</id>
      <definition>A substance that inhibits or prevents the proliferation of neoplasms.</definition>
    </health_effect>
    <health_effect>
      <name>Calcium antagonist</name>
      <id>748</id>
      <definition>Substance that attaches to and blocks cell receptors that normally bind naturally occurring substances.</definition>
    </health_effect>
    <health_effect>
      <name>Central nervous system inhibitor</name>
      <id>813</id>
      <definition>A class of drugs producing both physiological and psychological effects through a variety of mechanisms involving the central nervous system.</definition>
    </health_effect>
    <health_effect>
      <name>Hepatoprotective</name>
      <id>981</id>
      <definition>Any compound that is able to prevent damage to the liver.</definition>
    </health_effect>
    <health_effect>
      <name>Neurogenic</name>
      <id>1151</id>
      <definition/>
    </health_effect>
    <health_effect>
      <name>Pesticide</name>
      <id>1210</id>
      <definition>Strictly, a substance intended to kill pests. In common usage, any substance used for controlling, preventing, or destroying animal, microbiological or plant pests.</definition>
    </health_effect>
    <health_effect>
      <name>Sedative</name>
      <id>1311</id>
      <definition>A central nervous system depressant used to induce drowsiness or sleep or to reduce psychological excitement or anxiety.</definition>
    </health_effect>
  </health_effects>
</compound>
