<?xml version="1.0" encoding="UTF-8"?>
<compound>
  <version>1.0</version>
  <creation_date>2016-05-25 02:53:11 UTC</creation_date>
  <update_date>2026-04-14 17:04:02 UTC</update_date>
  <accession/>
  <common_name>Ferulic acid</common_name>
  <class>SmallMolecule</class>
  <description>Ferulic acid (C10H10O4) is a compound with an average molecular weight of 194.18 g/mol. Ferulic acid belongs to the hydroxycinnamic acids and derivatives, a subclass of cinnamic acids and derivatives within the organic compounds. It is categorized under the superclass of phenylpropanoids and polyketides.

The compound serves as an industrial additive (PMC10048273) and acts as an antioxidant for both industrial and biological applications (PMC10048273, PMC10224177, PMC10573426, PMC12562121, PMC3595371, PMC9607127, PMC9786992, PMC8253632). Ferulic acid has been recorded in 11 sources, including building and construction ceilings, electrical and electronic equipment coils, and household cleaning and consumer products such as soap dispensers. It is also found in food, food processing, and cookware, specifically in the preparation of vinegar, wort, malt, wine or sparkling wine, and molasses and the treatment of molasses.

Biologically, ferulic acid targets 12 proteins, acting as an inhibitor of O-methyltransferase, Est1e, Endo-1,4-beta-xylanase Z (xynZ), and Endo-1,4-beta-xylanase Y (xynY). The compound is used as a treatment for skin cancer (PMC3595371) and exhibits therapeutic effects on cancer (PMC9786992), ischemic stroke (PMC8253632), inflammation (PMC13316579), and depression (PMC10831359).</description>
  <categories/>
  <types/>
  <synonyms>
    <synonym>ferulate</synonym>
    <synonym>trans-Ferulic acid</synonym>
  </synonyms>
  <chemical_formula>C10H10O4</chemical_formula>
  <average_molecular_weight>194.184</average_molecular_weight>
  <monisotopic_moleculate_weight>194.057908808</monisotopic_moleculate_weight>
  <iupac_name>(2E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoic acid</iupac_name>
  <traditional_iupac>ferulic acid</traditional_iupac>
  <cas_registry_number>537-98-4</cas_registry_number>
  <smiles>COC1=C(O)C=CC(\C=C\C(O)=O)=C1</smiles>
  <inchi>InChI=1S/C10H10O4/c1-14-9-6-7(2-4-8(9)11)3-5-10(12)13/h2-6,11H,1H3,(H,12,13)/b5-3+</inchi>
  <inchikey>KSEBMYQBYZTDHS-HWKANZROSA-N</inchikey>
  <taxonomy>
    <kingdom>Organic compounds</kingdom>
    <super_class>Phenylpropanoids and polyketides</super_class>
    <class>Cinnamic acids and derivatives</class>
    <sub_class>Hydroxycinnamic acids and derivatives</sub_class>
    <direct_parent>Hydroxycinnamic acids</direct_parent>
    <alternate_parents>
      <alternative_parent>1-hydroxy-2-unsubstituted benzenoids</alternative_parent>
      <alternative_parent>Alkyl aryl ethers</alternative_parent>
      <alternative_parent>Anisoles</alternative_parent>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Cinnamic acids</alternative_parent>
      <alternative_parent>Coumaric acids and derivatives</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Methoxybenzenes</alternative_parent>
      <alternative_parent>Methoxyphenols</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Phenoxy compounds</alternative_parent>
      <alternative_parent>Styrenes</alternative_parent>
    </alternate_parents>
    <substituents>
      <substituent>1-hydroxy-2-unsubstituted benzenoid</substituent>
      <substituent>Alkyl aryl ether</substituent>
      <substituent>Anisole</substituent>
      <substituent>Aromatic homomonocyclic compound</substituent>
      <substituent>Benzenoid</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Cinnamic acid</substituent>
      <substituent>Coumaric acid or derivatives</substituent>
      <substituent>Ether</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Hydroxycinnamic acid</substituent>
      <substituent>Methoxybenzene</substituent>
      <substituent>Methoxyphenol</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>Monocyclic benzene moiety</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Phenol</substituent>
      <substituent>Phenol ether</substituent>
      <substituent>Phenoxy compound</substituent>
      <substituent>Styrene</substituent>
    </substituents>
    <molecular_framework>Aromatic homomonocyclic compounds</molecular_framework>
    <descriptors>
      <descriptor>Coniferyl alcohol derivatives</descriptor>
      <descriptor>ferulic acids</descriptor>
    </descriptors>
  </taxonomy>
  <status>Detected and Not Quantified</status>
  <origin/>
  <cellular_locations/>
  <biofluid_locations/>
  <tissue_locations/>
  <pathways/>
  <state/>
  <appearance/>
  <experimental_properties/>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>1.58</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-2.33</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>solubility</kind>
      <value>9.06e-01 g/l</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>1.67</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>3.77</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-4.9</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(2E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>194.184</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>194.057908808</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>COC1=C(O)C=CC(\C=C\C(O)=O)=C1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C10H10O4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C10H10O4/c1-14-9-6-7(2-4-8(9)11)3-5-10(12)13/h2-6,11H,1H3,(H,12,13)/b5-3+</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>KSEBMYQBYZTDHS-HWKANZROSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>66.76</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>51.5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>19.18</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <route_of_exposure/>
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  <metabolism/>
  <toxicity/>
  <lethaldose/>
  <carcinogenicity/>
  <use_source/>
  <min_risk_level/>
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  <symptoms/>
  <treatment/>
  <drugbank_id>DB07767</drugbank_id>
  <hmdb_id/>
  <pubchem_compound_id>445858</pubchem_compound_id>
  <chembl_id/>
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  <biocyc_id/>
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