<?xml version="1.0" encoding="UTF-8"?>
<compound>
  <version>1.0</version>
  <creation_date>2010-04-08 22:13:20 UTC</creation_date>
  <update_date>2019-11-26 03:15:17 UTC</update_date>
  <accession>FDB017816</accession>
  <name>Dihydrocapsaicin</name>
  <description>Potential nutriceutical

Dihydrocapsaicin is a capsaicinoid and analog and congener of capsaicin in chili peppers (Capsicum). Like capsaicin it is an irritant. Dihydrocapsaicin accounts for about 22% of the total capsaicinoids mixture and has about the same pungency as capsaicin. Pure dihydrocapsaicin is a lipophilic colorless odorless crystalline to waxy compound. It is soluble in dimethyl sulfoxide and 100 % ethanol. Dihydrocapsaicin is found in many foods, some of which are green bell pepper, pepper (c. frutescens), pepper (c. annuum), and yellow bell pepper.</description>
  <synonyms>
    <synonym>6,7-Dihydrocapsaicin</synonym>
    <synonym>8-methyl dihydrocapsaicin</synonym>
    <synonym>8-Methyl-N-vanillyl-nonanamide</synonym>
    <synonym>8-METHYL-N-VANILLYLNONANAMIDE</synonym>
    <synonym>Dihydrocapsacine</synonym>
    <synonym>Dihydrocapsaicin</synonym>
    <synonym>N-((4-Hydroxy-3-methoxyphenyl)methyl)-8-methyl-nonanamide</synonym>
    <synonym>N-((4-Hydroxy-3-methoxyphenyl)methyl)-8-methylnonanamide</synonym>
    <synonym>N-(4-hydroxy-3-methoxybenzyl)-8-methylnonanamide</synonym>
    <synonym>Nonanamide, 8-methyl-N-vanillyl-</synonym>
    <synonym>Nonanamide, N-((4-hydroxy-3-methoxyphenyl)methyl)-8-methyl-</synonym>
  </synonyms>
  <chemical_formula>C18H29NO3</chemical_formula>
  <average_molecular_weight>307.4278</average_molecular_weight>
  <monisotopic_moleculate_weight>307.214743799</monisotopic_moleculate_weight>
  <iupac_name>N-[(4-hydroxy-3-methoxyphenyl)methyl]-8-methylnonanamide</iupac_name>
  <traditional_iupac>dihydrocapsaicin</traditional_iupac>
  <cas_registry_number>19408-84-5</cas_registry_number>
  <smiles>COC1=C(O)C=CC(CNC(=O)CCCCCCC(C)C)=C1</smiles>
  <inchi>InChI=1S/C18H29NO3/c1-14(2)8-6-4-5-7-9-18(21)19-13-15-10-11-16(20)17(12-15)22-3/h10-12,14,20H,4-9,13H2,1-3H3,(H,19,21)</inchi>
  <inchikey>XJQPQKLURWNAAH-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as methoxyphenols. Methoxyphenols are compounds containing a methoxy group attached to the benzene ring of a phenol moiety.</description>
    <direct_parent>Methoxyphenols</direct_parent>
    <kingdom>Organic compounds</kingdom>
    <super_class>Benzenoids</super_class>
    <class>Phenols</class>
    <sub_class>Methoxyphenols</sub_class>
    <molecular_framework>Aromatic homomonocyclic 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>Carboximidic acids</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Methoxybenzenes</alternative_parent>
      <alternative_parent>Organonitrogen compounds</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Phenoxy compounds</alternative_parent>
      <alternative_parent>Propargyl-type 1,3-dipolar organic compounds</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>1-hydroxy-2-unsubstituted benzenoid</substituent>
      <substituent>Alkyl aryl ether</substituent>
      <substituent>Anisole</substituent>
      <substituent>Aromatic homomonocyclic compound</substituent>
      <substituent>Carboximidic acid</substituent>
      <substituent>Carboximidic acid derivative</substituent>
      <substituent>Ether</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Methoxybenzene</substituent>
      <substituent>Methoxyphenol</substituent>
      <substituent>Monocyclic benzene moiety</substituent>
      <substituent>Organic 1,3-dipolar compound</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Phenol ether</substituent>
      <substituent>Phenoxy compound</substituent>
      <substituent>Propargyl-type 1,3-dipolar organic compound</substituent>
    </substituents>
    <external_descriptors>
      <external_descriptor>Capsaicinoids and derivatives</external_descriptor>
      <external_descriptor>N-acyl amines</external_descriptor>
      <external_descriptor>an alkaloid</external_descriptor>
      <external_descriptor>capsaicinoid</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <state/>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>4.56</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-4.33</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>solubility</kind>
      <value>1.44e-02 g/l</value>
      <source>ALOGPS</source>
    </property>
  </predicted_properties>
  <experimental_properties>
    <property>
      <kind>melting_point</kind>
      <value>Mp 65.5-65.8°</value>
    </property>
  </experimental_properties>
  <property>
    <kind>logp</kind>
    <value>4.11</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>pka_strongest_acidic</kind>
    <value>9.93</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>pka_strongest_basic</kind>
    <value>-0.52</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>iupac</kind>
    <value>N-[(4-hydroxy-3-methoxyphenyl)methyl]-8-methylnonanamide</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>average_mass</kind>
    <value>307.4278</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>mono_mass</kind>
    <value>307.214743799</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>smiles</kind>
    <value>COC1=C(O)C=CC(CNC(=O)CCCCCCC(C)C)=C1</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>formula</kind>
    <value>C18H29NO3</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>inchi</kind>
    <value>InChI=1S/C18H29NO3/c1-14(2)8-6-4-5-7-9-18(21)19-13-15-10-11-16(20)17(12-15)22-3/h10-12,14,20H,4-9,13H2,1-3H3,(H,19,21)</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>inchikey</kind>
    <value>XJQPQKLURWNAAH-UHFFFAOYSA-N</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>polar_surface_area</kind>
    <value>58.56</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>refractivity</kind>
    <value>89.2</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>polarizability</kind>
    <value>36.55</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>rotatable_bond_count</kind>
    <value>10</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>acceptor_count</kind>
    <value>3</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>donor_count</kind>
    <value>2</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::EiMs</type>
      <spectrum_id>1874</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>5645</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>45832</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>171065</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>65430</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>65431</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>65432</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>122832</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>122833</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>122834</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>374833</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>439155</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>439454</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>439456</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>439458</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>439618</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>439619</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>439620</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>439621</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>448102</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>449496</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>449499</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>449502</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>449691</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>449692</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>449693</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>449694</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>449695</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>449696</spectrum_id>
    </spectrum>
  </spectra>
  <hmdb_id>HMDB38457</hmdb_id>
  <pubchem_compound_id/>
  <chemspider_id/>
  <kegg_id/>
  <chebi_id>46932</chebi_id>
  <biocyc_id/>
  <het_id/>
  <wikipidia/>
  <vmh_id/>
  <fbonto_id/>
  <foodb_id/>
  <general_references>
    <reference>#&lt;Reference:0x000055ce32513780&gt;</reference>
  </general_references>
  <foods>
    <food>
      <name>Green bell pepper</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Capsicum annuum</name_scientific>
      <ncbi_taxonomy_id>4072</ncbi_taxonomy_id>
      <average_value>16442.575</average_value>
      <max_value>32800.0</max_value>
      <min_value>85.15</min_value>
      <unit>mg/100 g</unit>
    </food>
    <food>
      <name>Orange bell pepper</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Capsicum annuum</name_scientific>
      <ncbi_taxonomy_id>4072</ncbi_taxonomy_id>
      <average_value>16442.575</average_value>
      <max_value>32800.0</max_value>
      <min_value>85.15</min_value>
      <unit>mg/100 g</unit>
    </food>
    <food>
      <name>Pepper</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Capsicum annuum</name_scientific>
      <ncbi_taxonomy_id>4072</ncbi_taxonomy_id>
      <average_value>16442.575</average_value>
      <max_value>32800.0</max_value>
      <min_value>85.15</min_value>
      <unit>mg/100 g</unit>
    </food>
    <food>
      <name>Pepper (C. frutescens)</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Capsicum annuum var. annuum</name_scientific>
      <ncbi_taxonomy_id>40321</ncbi_taxonomy_id>
      <average_value>85.15</average_value>
      <max_value>85.15</max_value>
      <min_value>85.15</min_value>
      <unit>mg/100 g</unit>
    </food>
    <food>
      <name>Red bell pepper</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Capsicum annuum</name_scientific>
      <ncbi_taxonomy_id>4072</ncbi_taxonomy_id>
      <average_value>16442.575</average_value>
      <max_value>32800.0</max_value>
      <min_value>85.15</min_value>
      <unit>mg/100 g</unit>
    </food>
    <food>
      <name>Yellow bell pepper</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Capsicum annuum</name_scientific>
      <ncbi_taxonomy_id>4072</ncbi_taxonomy_id>
      <average_value>16442.575</average_value>
      <max_value>32800.0</max_value>
      <min_value>85.15</min_value>
      <unit>mg/100 g</unit>
    </food>
  </foods>
  <flavors>
  </flavors>
  <enzymes>
  </enzymes>
  <health_effects>
    <health_effect>
      <name>Hypocholesterolemic</name>
      <id>1016</id>
      <definition/>
    </health_effect>
  </health_effects>
</compound>
