<?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 23:00:10 UTC</update_date>
  <accession>FDB005824</accession>
  <name>2-Hydroxy-4-methoxybenzaldehyde</name>
  <description>2-hydroxy-4-methoxybenzaldehyde, also known as 4-methoxysalicylaldehyde or 2-hydroxy-P-anisaldehyde, is a member of the class of compounds known as methoxyphenols. Methoxyphenols are compounds containing a methoxy group attached to the benzene ring of a phenol moiety. 2-hydroxy-4-methoxybenzaldehyde is slightly soluble (in water) and a very weakly acidic compound (based on its pKa). 2-hydroxy-4-methoxybenzaldehyde is a vanillin tasting compound found in black walnut, which makes 2-hydroxy-4-methoxybenzaldehyde a potential biomarker for the consumption of this food product. 2-hydroxy-4-methoxybenzaldehyde is a chemical compound and an isomer of vanillin. Urolithin M7, one of the urolithins, has also been synthesized from 2-hydroxy-4-methoxybenzaldehyde using the inverse electron-demand Diels–Alder reaction .</description>
  <synonyms>
    <synonym>2-Hydroxy-4-methoxybenzaldehyde</synonym>
    <synonym>2-Hydroxy-p-anisaldehyde</synonym>
    <synonym>4-Methoxysalicyaldehyde</synonym>
    <synonym>4-Methoxysalicylaldehyde</synonym>
    <synonym>4-o-methylresorcylaldehyde</synonym>
    <synonym>Benzaldehyde, 2-hydroxy-4-methoxy-</synonym>
    <synonym>ghl.PD_Mitscher_leg0.298</synonym>
    <synonym>O-hydroxy-p-methoxybenzaldehyde</synonym>
    <synonym>p-Anisaldehyde, 2-hydroxy-</synonym>
    <synonym>Salicylaldehyde, 4-methoxy-</synonym>
  </synonyms>
  <chemical_formula>C8H8O3</chemical_formula>
  <average_molecular_weight>152.1473</average_molecular_weight>
  <monisotopic_moleculate_weight>152.047344122</monisotopic_moleculate_weight>
  <iupac_name>2-hydroxy-4-methoxybenzaldehyde</iupac_name>
  <traditional_iupac>2-hydroxy-4-methoxybenzaldehyde</traditional_iupac>
  <cas_registry_number>673-22-3</cas_registry_number>
  <smiles>COC1=CC(O)=C(C=O)C=C1</smiles>
  <inchi>InChI=1S/C8H8O3/c1-11-7-3-2-6(5-9)8(10)4-7/h2-5,10H,1H3</inchi>
  <inchikey>WZUODJNEIXSNEU-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>1-hydroxy-4-unsubstituted benzenoids</alternative_parent>
      <alternative_parent>Alkyl aryl ethers</alternative_parent>
      <alternative_parent>Anisoles</alternative_parent>
      <alternative_parent>Benzoyl derivatives</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Hydroxybenzaldehydes</alternative_parent>
      <alternative_parent>Methoxybenzenes</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Phenoxy compounds</alternative_parent>
      <alternative_parent>Vinylogous acids</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>1-hydroxy-2-unsubstituted benzenoid</substituent>
      <substituent>1-hydroxy-4-unsubstituted benzenoid</substituent>
      <substituent>Aldehyde</substituent>
      <substituent>Alkyl aryl ether</substituent>
      <substituent>Anisole</substituent>
      <substituent>Aromatic homomonocyclic compound</substituent>
      <substituent>Aryl-aldehyde</substituent>
      <substituent>Benzaldehyde</substituent>
      <substituent>Benzoyl</substituent>
      <substituent>Ether</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Hydroxybenzaldehyde</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>
      <substituent>Vinylogous acid</substituent>
    </substituents>
    <external_descriptors>
    </external_descriptors>
  </taxonomy>
  <state/>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>1.31</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-1.47</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>solubility</kind>
      <value>5.19e+00 g/l</value>
      <source>ALOGPS</source>
    </property>
  </predicted_properties>
  <experimental_properties>
  </experimental_properties>
  <property>
    <kind>logp</kind>
    <value>1.87</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>pka_strongest_acidic</kind>
    <value>8.31</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>pka_strongest_basic</kind>
    <value>-4.8</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>iupac</kind>
    <value>2-hydroxy-4-methoxybenzaldehyde</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>average_mass</kind>
    <value>152.1473</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>mono_mass</kind>
    <value>152.047344122</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>smiles</kind>
    <value>COC1=CC(O)=C(C=O)C=C1</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>formula</kind>
    <value>C8H8O3</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>inchi</kind>
    <value>InChI=1S/C8H8O3/c1-11-7-3-2-6(5-9)8(10)4-7/h2-5,10H,1H3</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>inchikey</kind>
    <value>WZUODJNEIXSNEU-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>41.09</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>polarizability</kind>
    <value>14.87</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>rotatable_bond_count</kind>
    <value>2</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::CMs</type>
      <spectrum_id>90761</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>95955</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>95956</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>95957</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>160338</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>160339</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>160340</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>Black walnut</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Juglans nigra</name_scientific>
      <ncbi_taxonomy_id>16719</ncbi_taxonomy_id>
      <average_value>2400.0</average_value>
      <max_value>2400.0</max_value>
      <min_value>2400.0</min_value>
      <unit>mg/100 g</unit>
    </food>
  </foods>
  <flavors>
    <flavor>
      <name>vanillin</name>
    </flavor>
  </flavors>
  <enzymes>
  </enzymes>
  <health_effects>
  </health_effects>
</compound>
