<?xml version="1.0" encoding="UTF-8"?>
<compound>
  <version>1.0</version>
  <creation_date>2010-04-08 22:09:10 UTC</creation_date>
  <update_date>2025-11-18 23:19:55 UTC</update_date>
  <accession>FDB010527</accession>
  <name>Zingerone</name>
  <description>Reputed pungent principle of ginger (Zingiber officinale). Flavour material used in imitation fruit flavours, ginger beer, ginger ale etcand is also present in cranberry, raspberry and mango. Zingerone is found in many foods, some of which are pot marjoram, fruits, ginger, and herbs and spices.</description>
  <synonyms>
    <synonym>(0)-Paradol</synonym>
    <synonym>(4-Hydroxy-3-methoxyphenyl)ethyl methyl ketone</synonym>
    <synonym>[0]-Paradol</synonym>
    <synonym>[0]Paradol</synonym>
    <synonym>2-(4-Hydroxy-3-methoxyphenyl)ethyl methyl ketone</synonym>
    <synonym>2-Butanone, 4-(4-hydroxy-3-methoxyphenyl)-</synonym>
    <synonym>3-Methoxy-4-hydroxybenzylacetone</synonym>
    <synonym>4-(3-Methoxy-4-hydroxyphenyl)-2-butanone</synonym>
    <synonym>4-(3-Methoxy-4-hydroxyphenyl)butan-2-one</synonym>
    <synonym>4-(4-hydroxy-3-methoxy-phenyl)-butan-2-one</synonym>
    <synonym>4-(4-Hydroxy-3-methoxyphenyl)-2-butanone</synonym>
    <synonym>4-(4-Hydroxy-3-methoxyphenyl)-2-butanone, 9CI, 8CI</synonym>
    <synonym>4-(4-Hydroxy-3-methoxyphenyl)butan-2-one</synonym>
    <synonym>4-Hydroxy-3-methoxybenzylacetone</synonym>
    <synonym>FEMA 3124</synonym>
    <synonym>Gingerone</synonym>
    <synonym>Vanillyl acetone</synonym>
    <synonym>Vanillylacetone</synonym>
    <synonym>Zingerone</synonym>
    <synonym>Zingherone</synonym>
    <synonym>Zingiberone</synonym>
  </synonyms>
  <chemical_formula>C11H14O3</chemical_formula>
  <average_molecular_weight>194.2271</average_molecular_weight>
  <monisotopic_moleculate_weight>194.094294314</monisotopic_moleculate_weight>
  <iupac_name>4-(4-hydroxy-3-methoxyphenyl)butan-2-one</iupac_name>
  <traditional_iupac>zingerone</traditional_iupac>
  <cas_registry_number>122-48-5</cas_registry_number>
  <smiles>COC1=C(O)C=CC(CCC(C)=O)=C1</smiles>
  <inchi>InChI=1S/C11H14O3/c1-8(12)3-4-9-5-6-10(13)11(7-9)14-2/h5-7,13H,3-4H2,1-2H3</inchi>
  <inchikey>OJYLAHXKWMRDGS-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>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Ketones</alternative_parent>
      <alternative_parent>Methoxybenzenes</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Phenoxy 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>Carbonyl group</substituent>
      <substituent>Ether</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Ketone</substituent>
      <substituent>Methoxybenzene</substituent>
      <substituent>Methoxyphenol</substituent>
      <substituent>Monocyclic benzene moiety</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Phenol ether</substituent>
      <substituent>Phenoxy compound</substituent>
    </substituents>
    <external_descriptors>
      <external_descriptor>Zingiber derived compounds</external_descriptor>
      <external_descriptor>ketone</external_descriptor>
      <external_descriptor>monomethoxybenzene</external_descriptor>
      <external_descriptor>phenols</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <state/>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>2.02</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-2.53</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>solubility</kind>
      <value>5.67e-01 g/l</value>
      <source>ALOGPS</source>
    </property>
  </predicted_properties>
  <experimental_properties>
    <property>
      <kind>melting_point</kind>
      <value>Mp 41°</value>
    </property>
  </experimental_properties>
  <property>
    <kind>logp</kind>
    <value>1.92</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>pka_strongest_acidic</kind>
    <value>9.95</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>pka_strongest_basic</kind>
    <value>-4.9</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>iupac</kind>
    <value>4-(4-hydroxy-3-methoxyphenyl)butan-2-one</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>average_mass</kind>
    <value>194.2271</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>mono_mass</kind>
    <value>194.094294314</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>smiles</kind>
    <value>COC1=C(O)C=CC(CCC(C)=O)=C1</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>formula</kind>
    <value>C11H14O3</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>inchi</kind>
    <value>InChI=1S/C11H14O3/c1-8(12)3-4-9-5-6-10(13)11(7-9)14-2/h5-7,13H,3-4H2,1-2H3</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>inchikey</kind>
    <value>OJYLAHXKWMRDGS-UHFFFAOYSA-N</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>polar_surface_area</kind>
    <value>46.53</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>refractivity</kind>
    <value>53.96</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>polarizability</kind>
    <value>20.95</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>rotatable_bond_count</kind>
    <value>4</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::MsIr</type>
      <spectrum_id>5582</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsIr</type>
      <spectrum_id>5583</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsIr</type>
      <spectrum_id>5584</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>2998</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>42865</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>148963</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>96423</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>96424</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>96425</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>160902</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>160903</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>160904</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2744517</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2744518</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2744519</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2937055</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2937056</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2937057</spectrum_id>
    </spectrum>
  </spectra>
  <hmdb_id>HMDB32590</hmdb_id>
  <pubchem_compound_id/>
  <chemspider_id/>
  <kegg_id/>
  <chebi_id/>
  <biocyc_id/>
  <het_id/>
  <wikipidia/>
  <vmh_id/>
  <fbonto_id/>
  <foodb_id/>
  <general_references>
    <reference>#&lt;Reference:0x000055ce32113568&gt;</reference>
    <reference>#&lt;Reference:0x000055ce321133b0&gt;</reference>
    <reference>#&lt;Reference:0x000055ce321131f8&gt;</reference>
  </general_references>
  <foods>
    <food>
      <name>Fruits</name>
      <food_type>Unknown</food_type>
      <category>generic</category>
      <name_scientific/>
      <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>1.015</average_value>
      <max_value>1.015</max_value>
      <min_value>1.015</min_value>
      <unit>mg/100 g</unit>
    </food>
    <food>
      <name>Herbs and Spices</name>
      <food_type>Unknown</food_type>
      <category>generic</category>
      <name_scientific/>
      <ncbi_taxonomy_id/>
    </food>
    <food>
      <name>Pot marjoram</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Origanum onites</name_scientific>
      <ncbi_taxonomy_id>452416</ncbi_taxonomy_id>
      <average_value>10.5</average_value>
      <max_value>10.5</max_value>
      <min_value>10.5</min_value>
      <unit>mg/100 g</unit>
    </food>
  </foods>
  <flavors>
    <flavor>
      <name>animal</name>
    </flavor>
    <flavor>
      <name>clove</name>
    </flavor>
    <flavor>
      <name>ginger</name>
    </flavor>
    <flavor>
      <name>phenolic</name>
    </flavor>
    <flavor>
      <name>spicy</name>
    </flavor>
    <flavor>
      <name>sweet</name>
    </flavor>
    <flavor>
      <name>vanilla</name>
    </flavor>
    <flavor>
      <name>woody</name>
    </flavor>
  </flavors>
  <enzymes>
  </enzymes>
  <health_effects>
    <health_effect>
      <name>5-lipoxygenase inhibitor</name>
      <id>10</id>
      <definition>A compound or agent that combines with an enzyme in such a manner as to prevent the normal substrate-enzyme combination and the catalytic reaction.</definition>
    </health_effect>
    <health_effect>
      <name>Adrenergic</name>
      <id>31</id>
      <definition>Any agent that acts on an adrenergic receptor or affects the life cycle of an adrenergic transmitter.</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-atherosclerotic</name>
      <id>138</id>
      <definition>A drug used for the treatment or prevention of cardiac arrhythmias. Anti-arrhythmia drugs may affect the polarisation-repolarisation phase of the action potential, its excitability or refractoriness, or impulse conduction or membrane responsiveness within cardiac fibres.</definition>
    </health_effect>
    <health_effect>
      <name>Anti-inflammatory</name>
      <id>370</id>
      <definition>A substance that reduces or suppresses inflammation.</definition>
    </health_effect>
    <health_effect>
      <name>Anti-mutagenic</name>
      <id>451</id>
      <definition/>
    </health_effect>
    <health_effect>
      <name>Anti-oxidant</name>
      <id>502</id>
      <definition>A substance that opposes oxidation or inhibits reactions brought about by dioxygen or peroxides. In European countries, E-numbers for permitted antioxidant food additives are from E 300 to E 324.</definition>
    </health_effect>
    <health_effect>
      <name>Cardiotonic</name>
      <id>771</id>
      <definition>A drug used for the treatment or prevention of cardiac arrhythmias. Anti-arrhythmia drugs may affect the polarisation-repolarisation phase of the action potential, its excitability or refractoriness, or impulse conduction or membrane responsiveness within cardiac fibres.</definition>
    </health_effect>
    <health_effect>
      <name>Cyclooxygenase inhibitor</name>
      <id>849</id>
      <definition>A compound or agent that combines with cyclooxygenases (EC 1.14.99.1) and thereby prevents its substrate-enzyme combination with arachidonic acid and the formation of icosanoids, prostaglandins, and thromboxanes.</definition>
    </health_effect>
    <health_effect>
      <name>Hypotensive</name>
      <id>1021</id>
      <definition/>
    </health_effect>
    <health_effect>
      <name>Name</name>
      <id>936</id>
      <definition>A substance, extract, or preparation for diffusing or imparting an agreeable or attractive smell.</definition>
    </health_effect>
    <health_effect>
      <name>Paralytic</name>
      <id>1196</id>
      <definition/>
    </health_effect>
    <health_effect>
      <name>Perfumery</name>
      <id>1206</id>
      <definition>A substance, extract, or preparation for diffusing or imparting an agreeable or attractive smell.</definition>
    </health_effect>
    <health_effect>
      <name>Secretogogue</name>
      <id>1308</id>
      <definition/>
    </health_effect>
    <health_effect>
      <name>Vasodilator</name>
      <id>1413</id>
      <definition>A drug used to cause dilation of the blood vessels.</definition>
    </health_effect>
  </health_effects>
</compound>
