<?xml version="1.0" encoding="UTF-8"?>
<compound>
  <version>1.0</version>
  <creation_date>2016-05-19 03:17:28 UTC</creation_date>
  <update_date>2026-05-14 17:47:22 UTC</update_date>
  <accession/>
  <common_name>cis-12-Hydroxy-9-octadecenoic acid</common_name>
  <class>SmallMolecule</class>
  <description>cis-12-Hydroxy-9-octadecenoic acid belongs to the fatty acids and conjugates, a subclass of fatty acyls within the organic compounds. This lipid-like molecule has the chemical formula C18H34O3 and an average molecular weight of 298.47 g/mol.

The compound is found in or released from 20 recorded sources across several categories. Within electrical and electronic equipment, it is associated with antennas, communication cables or conductors, cores yokes or armatures, emergency protective devices, and loudspeakers, among four other sources. In the sector of food, food processing, and cookware, it is linked to food contact materials and the preparation of malt, vinegar, wine or sparkling wine, and wort, as well as one additional source. It is also found in household cleaning and consumer products, specifically in ash trays, soap dispensers, and tobacco product cases. Furthermore, it is present in building and construction materials such as floors and tents or canopies. Recorded exposure routes for this compound include inhalation, oral, and touch.</description>
  <categories/>
  <types/>
  <synonyms>
    <synonym>(9Z,12R)-12-Hydroxyoctadec-9-enoic acid</synonym>
    <synonym>Ricinoleic acid</synonym>
  </synonyms>
  <chemical_formula>C18H34O3</chemical_formula>
  <average_molecular_weight>298.467</average_molecular_weight>
  <monisotopic_moleculate_weight>298.250794955</monisotopic_moleculate_weight>
  <iupac_name>(9Z,12R)-12-hydroxyoctadec-9-enoic acid</iupac_name>
  <traditional_iupac>ricinoleic acid</traditional_iupac>
  <cas_registry_number>141-22-0</cas_registry_number>
  <smiles>[H]\C(CCCCCCCC(O)=O)=C(/[H])C[C@]([H])(O)CCCCCC</smiles>
  <inchi>InChI=1S/C18H34O3/c1-2-3-4-11-14-17(19)15-12-9-7-5-6-8-10-13-16-18(20)21/h9,12,17,19H,2-8,10-11,13-16H2,1H3,(H,20,21)/b12-9-/t17-/m1/s1</inchi>
  <inchikey>WBHHMMIMDMUBKC-QJWNTBNXSA-N</inchikey>
  <taxonomy>
    <kingdom>Organic compounds</kingdom>
    <super_class>Lipids and lipid-like molecules</super_class>
    <class>Fatty Acyls</class>
    <sub_class>Fatty acids and conjugates</sub_class>
    <direct_parent>Long-chain fatty acids</direct_parent>
    <alternate_parents>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Hydroxy fatty acids</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
      <alternative_parent>Unsaturated fatty acids</alternative_parent>
    </alternate_parents>
    <substituents>
      <substituent>Alcohol</substituent>
      <substituent>Aliphatic acyclic compound</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Hydroxy fatty acid</substituent>
      <substituent>Long-chain fatty acid</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Secondary alcohol</substituent>
      <substituent>Unsaturated fatty acid</substituent>
    </substituents>
    <molecular_framework>Aliphatic acyclic compounds</molecular_framework>
    <descriptors>
      <descriptor>(9Z)-12-hydroxyoctadec-9-enoic acid</descriptor>
      <descriptor>Hydroxy fatty acids</descriptor>
      <descriptor>Other Octadecanoids</descriptor>
      <descriptor>Unsaturated fatty acids</descriptor>
    </descriptors>
  </taxonomy>
  <status>Detected and Not Quantified</status>
  <origin/>
  <cellular_locations/>
  <biofluid_locations/>
  <tissue_locations/>
  <pathways/>
  <state/>
  <appearance/>
  <experimental_properties>
    <property>
      <kind>logp</kind>
      <value>5.4</value>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>6.14</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-5.07</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>solubility</kind>
      <value>2.54e-03 g/l</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>5.4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>4.99</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-1.3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(9Z,12R)-12-hydroxyoctadec-9-enoic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>298.467</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>298.250794955</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>[H]\C(CCCCCCCC(O)=O)=C(/[H])C[C@]([H])(O)CCCCCC</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C18H34O3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C18H34O3/c1-2-3-4-11-14-17(19)15-12-9-7-5-6-8-10-13-16-18(20)21/h9,12,17,19H,2-8,10-11,13-16H2,1H3,(H,20,21)/b12-9-/t17-/m1/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>WBHHMMIMDMUBKC-QJWNTBNXSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>57.53</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>89.07</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>37.85</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>15</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>-1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <route_of_exposure/>
  <mechanism_of_toxicity/>
  <metabolism/>
  <toxicity/>
  <lethaldose/>
  <carcinogenicity/>
  <use_source/>
  <min_risk_level/>
  <health_effects>#&lt;HealthEffect::ActiveRecord_Associations_CollectionProxy:0x00007f72238b35c0&gt;</health_effects>
  <symptoms/>
  <treatment/>
  <drugbank_id>DB02955</drugbank_id>
  <hmdb_id/>
  <pubchem_compound_id>643684</pubchem_compound_id>
  <chembl_id/>
  <chemspider_id>558800</chemspider_id>
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  <wikipidia/>
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</compound>
