<?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>2026-09-18 18:02:35 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:0x0000558be9610e70&gt;</reference>
    <reference>#&lt;Reference:0x0000558be9610cb8&gt;</reference>
    <reference>#&lt;Reference:0x0000558be9610b00&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>
    <enzyme>
      <name>Cytochrome P450 2A6</name>
      <uniprot_id>P11509</uniprot_id>
      <uniprot_name>CP2A6_HUMAN</uniprot_name>
      <gene_name>CYP2A6</gene_name>
    </enzyme>
    <enzyme>
      <name>Glutathione peroxidase 1</name>
      <uniprot_id>P07203</uniprot_id>
      <uniprot_name/>
      <gene_name>GPX1</gene_name>
    </enzyme>
    <enzyme>
      <name>Mitochondrial 2-oxodicarboxylate carrier</name>
      <uniprot_id>Q9BQT8</uniprot_id>
      <uniprot_name/>
      <gene_name>SLC25A21</gene_name>
    </enzyme>
    <enzyme>
      <name>Peroxidase (Pseudotsuga menziesii)</name>
      <uniprot_id>P85957</uniprot_id>
      <uniprot_name>PER_PSEMZ</uniprot_name>
      <gene_name/>
    </enzyme>
  </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 bacterial</name>
      <id>145</id>
      <definition>A substance that kills or slows the growth of bacteria.</definition>
    </health_effect>
    <health_effect>
      <name>Anti carcinogenic</name>
      <id>161</id>
      <definition>A substance that inhibits or prevents the proliferation of neoplasms.</definition>
    </health_effect>
    <health_effect>
      <name>Anti coagulant</name>
      <id>191</id>
      <definition>An agent that prevents blood clotting.</definition>
    </health_effect>
    <health_effect>
      <name>Anti emetic</name>
      <id>253</id>
      <definition>A drug used to prevent nausea or vomiting. An antiemetic may act by a wide range of mechanisms: it might affect the medullary control centres (the vomiting centre and the chemoreceptive trigger zone) or affect the peripheral receptors.</definition>
    </health_effect>
    <health_effect>
      <name>Anti hyperglycemic</name>
      <id>343</id>
      <definition/>
    </health_effect>
    <health_effect>
      <name>Anti hyperlipidemic</name>
      <id>348</id>
      <definition>Any substance introduced into a living organism with therapeutic or diagnostic purpose.</definition>
    </health_effect>
    <health_effect>
      <name>Anti microbial</name>
      <id>436</id>
      <definition>A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans.</definition>
    </health_effect>
    <health_effect>
      <name>Anti peroxidative</name>
      <id>520</id>
      <definition/>
    </health_effect>
    <health_effect>
      <name>Anti thrombotic</name>
      <id>650</id>
      <definition>Drug that acts on blood and blood-forming organs and those that affect the hemostatic system.</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-angiogenic</name>
      <id>115</id>
      <definition>An agent and endogenous substances that antagonize or inhibit the development of new blood vessels.</definition>
    </health_effect>
    <health_effect>
      <name>Anti-apoptotic</name>
      <id>125</id>
      <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-cancer</name>
      <id>159</id>
      <definition>A substance that inhibits or prevents the proliferation of neoplasms.</definition>
    </health_effect>
    <health_effect>
      <name>Anti-diabetic</name>
      <id>228</id>
      <definition>Any substance introduced into a living organism with therapeutic or diagnostic purpose.</definition>
    </health_effect>
    <health_effect>
      <name>Anti-diarrheic</name>
      <id>229</id>
      <definition>Any drug found useful in the symptomatic treatment of diarrhoea.</definition>
    </health_effect>
    <health_effect>
      <name>Anti-infective</name>
      <id>368</id>
      <definition>Any substance introduced into a living organism with therapeutic or diagnostic purpose.</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>Anti-Parkinsonian</name>
      <id>509</id>
      <definition>A drug used in the treatment of Parkinson's disease.</definition>
    </health_effect>
    <health_effect>
      <name>Antitumor</name>
      <id>672</id>
      <definition>A substance that inhibits or prevents the proliferation of neoplasms.</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>Cytotoxic</name>
      <id>859</id>
      <definition>A role played by the molecular entity or part thereof which causes the development of a pathological process.</definition>
    </health_effect>
    <health_effect>
      <name>Flavor</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>Hypotensive</name>
      <id>1021</id>
      <definition/>
    </health_effect>
    <health_effect>
      <name>Immunomodulator</name>
      <id>1031</id>
      <definition>Biologically active substance whose activity affects or plays a role in the functioning of the immune system.</definition>
    </health_effect>
    <health_effect>
      <name>Inhibitor</name>
      <id>1432</id>
      <definition>A substance that diminishes the rate of a chemical reaction.</definition>
    </health_effect>
    <health_effect>
      <name>Lipolytic</name>
      <id>1074</id>
      <definition/>
    </health_effect>
    <health_effect>
      <name>Neuroprotective</name>
      <id>1158</id>
      <definition>Any compound that can be used for the treatment of neurodegenerative disorders.</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>Platelet aggregation inhibitor</name>
      <id>1434</id>
      <definition>A drug or agent which antagonizes or impairs any mechanism leading to blood platelet aggregation, whether during the phases of activation and shape change or following the dense-granule release reaction and stimulation of the prostaglandin-thromboxane system.</definition>
    </health_effect>
    <health_effect>
      <name>Quorum-Sensing-Inhibitor</name>
      <id>1443</id>
      <definition/>
    </health_effect>
    <health_effect>
      <name>Radioprotective</name>
      <id>1279</id>
      <definition>Any pharmaceutical compound containing a radioisotope.</definition>
    </health_effect>
    <health_effect>
      <name>Secretogogue</name>
      <id>1308</id>
      <definition/>
    </health_effect>
    <health_effect>
      <name>Ulcerprotective</name>
      <id>2113</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>
