<?xml version="1.0" encoding="UTF-8"?>
<compound>
  <version>1.0</version>
  <creation_date>2010-04-08 22:12:14 UTC</creation_date>
  <update_date>2025-11-19 01:43:52 UTC</update_date>
  <accession>FDB016108</accession>
  <name>(±)-2-Hydroxy-4-(methylthio)butanoic acid</name>
  <description>Animal and poultry feed additive</description>
  <synonyms>
    <synonym>(+-)-2-Hydroxy-4-(methylthio)butyric acid</synonym>
    <synonym>2-Hydroxy-4-(methylthio) butanoic acid</synonym>
    <synonym>2-Hydroxy-4-(methylthio)-butanoic acid</synonym>
    <synonym>2-Hydroxy-4-(methylthio)-butyric acid</synonym>
    <synonym>2-Hydroxy-4-(methylthio)butanoic acid</synonym>
    <synonym>2-Hydroxy-4-(methylthio)butyric acid</synonym>
    <synonym>4857-44-7 (calcium[2:1] salt)</synonym>
    <synonym>Alimet</synonym>
    <synonym>Alpha-hydroxy-gamma-(methylmercapto)butyric acid</synonym>
    <synonym>Alpha-hydroxy-gamma-(methylthio)butyric acid</synonym>
    <synonym>Alpha-hydroxy-gamma-methylmercaptobutyric acid</synonym>
    <synonym>Butanoic acid, 2-hydroxy-4-(methylthio)-</synonym>
    <synonym>Butyric acid, 2-hydroxy-4-(methylthio)-</synonym>
    <synonym>Desmeninol</synonym>
    <synonym>Desmeninol [inn]</synonym>
    <synonym>Gamma-(methylthio)-alpha-hydroxybutyric acid</synonym>
    <synonym>Methionine hydroxy analog</synonym>
    <synonym>MHA</synonym>
    <synonym>Mha acid</synonym>
    <synonym>Mha-fa</synonym>
  </synonyms>
  <chemical_formula>C5H10O3S</chemical_formula>
  <average_molecular_weight>150.196</average_molecular_weight>
  <monisotopic_moleculate_weight>150.035064876</monisotopic_moleculate_weight>
  <iupac_name>2-hydroxy-4-(methylsulfanyl)butanoic acid</iupac_name>
  <traditional_iupac>methionine hydroxy analog</traditional_iupac>
  <cas_registry_number>120-91-2</cas_registry_number>
  <smiles>CSCCC(O)C(O)=O</smiles>
  <inchi>InChI=1S/C5H10O3S/c1-9-3-2-4(6)5(7)8/h4,6H,2-3H2,1H3,(H,7,8)</inchi>
  <inchikey>ONFOSYPQQXJWGS-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as thia fatty acids. These are fatty acid derivatives obtained by insertion of a sulfur atom at specific positions in the chain.</description>
    <direct_parent>Thia fatty acids</direct_parent>
    <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>
    <molecular_framework>Aliphatic acyclic compounds</molecular_framework>
    <alternative_parents>
      <alternative_parent>Alpha hydroxy acids and derivatives</alternative_parent>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Dialkylthioethers</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>Monosaccharides</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
      <alternative_parent>Sulfenyl compounds</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Alcohol</substituent>
      <substituent>Aliphatic acyclic compound</substituent>
      <substituent>Alpha-hydroxy acid</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Dialkylthioether</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Hydroxy acid</substituent>
      <substituent>Hydroxy fatty acid</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>Monosaccharide</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organosulfur compound</substituent>
      <substituent>Secondary alcohol</substituent>
      <substituent>Sulfenyl compound</substituent>
      <substituent>Thia fatty acid</substituent>
      <substituent>Thioether</substituent>
    </substituents>
    <external_descriptors>
    </external_descriptors>
  </taxonomy>
  <state/>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-0.40</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-0.56</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>solubility</kind>
      <value>4.09e+01 g/l</value>
      <source>ALOGPS</source>
    </property>
  </predicted_properties>
  <experimental_properties>
    <property>
      <kind>melting_point</kind>
      <value>Mp 250° (Zn salt)</value>
    </property>
  </experimental_properties>
  <property>
    <kind>logp</kind>
    <value>0.18</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>pka_strongest_acidic</kind>
    <value>4.03</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>pka_strongest_basic</kind>
    <value>-3.8</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>iupac</kind>
    <value>2-hydroxy-4-(methylsulfanyl)butanoic acid</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>average_mass</kind>
    <value>150.196</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>mono_mass</kind>
    <value>150.035064876</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>smiles</kind>
    <value>CSCCC(O)C(O)=O</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>formula</kind>
    <value>C5H10O3S</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>inchi</kind>
    <value>InChI=1S/C5H10O3S/c1-9-3-2-4(6)5(7)8/h4,6H,2-3H2,1H3,(H,7,8)</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>inchikey</kind>
    <value>ONFOSYPQQXJWGS-UHFFFAOYSA-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>35.93</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>polarizability</kind>
    <value>15.09</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>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>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>19568</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>45245</spectrum_id>
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    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>171972</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>94653</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
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    <spectrum>
      <type>Specdb::MsMs</type>
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    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>158724</spectrum_id>
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      <type>Specdb::MsMs</type>
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    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>158726</spectrum_id>
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    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2236238</spectrum_id>
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    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2238412</spectrum_id>
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    <spectrum>
      <type>Specdb::MsMs</type>
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      <type>Specdb::MsMs</type>
      <spectrum_id>2338782</spectrum_id>
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      <spectrum_id>2338784</spectrum_id>
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      <type>Specdb::MsMs</type>
      <spectrum_id>2623976</spectrum_id>
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    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2623978</spectrum_id>
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    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>138970</spectrum_id>
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      <type>Specdb::NmrOneD</type>
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      <spectrum_id>138987</spectrum_id>
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      <spectrum_id>138989</spectrum_id>
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    <spectrum>
      <type>Specdb::MsIr</type>
      <spectrum_id>7386</spectrum_id>
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      <type>Specdb::MsIr</type>
      <spectrum_id>7387</spectrum_id>
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    <spectrum>
      <type>Specdb::MsIr</type>
      <spectrum_id>7388</spectrum_id>
    </spectrum>
  </spectra>
  <hmdb_id>HMDB37115</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:0x000055ce32287660&gt;</reference>
  </general_references>
  <foods>
  </foods>
  <flavors>
  </flavors>
  <enzymes>
  </enzymes>
  <health_effects>
  </health_effects>
</compound>
