<?xml version="1.0" encoding="UTF-8"?>
<compound>
  <version>1.0</version>
  <creation_date>2010-04-08 22:10:01 UTC</creation_date>
  <update_date>2025-11-18 23:34:30 UTC</update_date>
  <accession>FDB012166</accession>
  <name>Racemethionine</name>
  <description>Flavouring ingredient; dietary supplement

Methionine is an alpha-amino acid with the chemical formula HO2CCH(NH2)CH2CH2SCH3. This essential amino acid is classified as nonpolar. Racemethionine is found in many foods, some of which are spinach, yellow bell pepper, saskatoon berry, and red beetroot.</description>
  <synonyms>
    <synonym>(+-)-Methionine</synonym>
    <synonym>(+/-)-2-Amino-4-(methylmercapto)butyric acid</synonym>
    <synonym>2-Amino-4-(methylmercapto)butyric acid</synonym>
    <synonym>2-Amino-4-(methylsulfanyl)butanoic acid</synonym>
    <synonym>2-amino-4-(methylthio)-Butyric acid</synonym>
    <synonym>2-Amino-4-(methylthio)butanoic acid</synonym>
    <synonym>2-Amino-4-(methylthio)butyric acid</synonym>
    <synonym>2-Amino-4-methylthiobutanoic acid</synonym>
    <synonym>alpha-Amino-gamma-(methylthio)butyric acid</synonym>
    <synonym>alpha-Amino-gamma-methylmercaptobutyric acid</synonym>
    <synonym>Butyric acid, 2-amino-4-(methylthio)-</synonym>
    <synonym>DL-2-Amino-4-(methylthio)-butyric acid</synonym>
    <synonym>DL-2-Amino-4-(methylthio)butanoic acid</synonym>
    <synonym>DL-2-Amino-4-(methylthio)butyric acid</synonym>
    <synonym>DL-2-Amino-4-methylthiobutanoic acid</synonym>
    <synonym>DL-Methionine</synonym>
    <synonym>FEMA 3301</synonym>
    <synonym>Methionine, DL-</synonym>
    <synonym>Racemethionine, USAN</synonym>
  </synonyms>
  <chemical_formula>C5H11NO2S</chemical_formula>
  <average_molecular_weight>149.211</average_molecular_weight>
  <monisotopic_moleculate_weight>149.051049291</monisotopic_moleculate_weight>
  <iupac_name>2-amino-4-(methylsulfanyl)butanoic acid</iupac_name>
  <traditional_iupac>methionine</traditional_iupac>
  <cas_registry_number>59-51-8</cas_registry_number>
  <smiles>CSCCC(N)C(O)=O</smiles>
  <inchi>InChI=1S/C5H11NO2S/c1-9-3-2-4(6)5(7)8/h4H,2-3,6H2,1H3,(H,7,8)</inchi>
  <inchikey>FFEARJCKVFRZRR-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as methionine and derivatives. Methionine and derivatives are compounds containing methionine or a derivative thereof resulting from reaction of methionine at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom.</description>
    <direct_parent>Methionine and derivatives</direct_parent>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic acids and derivatives</super_class>
    <class>Carboxylic acids and derivatives</class>
    <sub_class>Amino acids, peptides, and analogues</sub_class>
    <molecular_framework>Aliphatic acyclic compounds</molecular_framework>
    <alternative_parents>
      <alternative_parent>Alpha amino acids</alternative_parent>
      <alternative_parent>Amino acids</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>Monoalkylamines</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Sulfenyl compounds</alternative_parent>
      <alternative_parent>Thia fatty acids</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Aliphatic acyclic compound</substituent>
      <substituent>Alpha-amino acid</substituent>
      <substituent>Amine</substituent>
      <substituent>Amino acid</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Dialkylthioether</substituent>
      <substituent>Fatty acid</substituent>
      <substituent>Fatty acyl</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Methionine or derivatives</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Organosulfur compound</substituent>
      <substituent>Primary aliphatic amine</substituent>
      <substituent>Primary amine</substituent>
      <substituent>Sulfenyl compound</substituent>
      <substituent>Thia fatty acid</substituent>
      <substituent>Thioether</substituent>
    </substituents>
    <external_descriptors>
      <external_descriptor>alpha-amino acid</external_descriptor>
      <external_descriptor>sulfur-containing amino acid</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <state/>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-1.85</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-0.80</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>solubility</kind>
      <value>2.39e+01 g/l</value>
      <source>ALOGPS</source>
    </property>
  </predicted_properties>
  <experimental_properties>
    <property>
      <kind>melting_point</kind>
      <value>Mp 281° dec.</value>
    </property>
  </experimental_properties>
  <property>
    <kind>logp</kind>
    <value>-2.2</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>pka_strongest_acidic</kind>
    <value>2.53</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>pka_strongest_basic</kind>
    <value>9.5</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>iupac</kind>
    <value>2-amino-4-(methylsulfanyl)butanoic acid</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>average_mass</kind>
    <value>149.211</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>mono_mass</kind>
    <value>149.051049291</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>smiles</kind>
    <value>CSCCC(N)C(O)=O</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>formula</kind>
    <value>C5H11NO2S</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>inchi</kind>
    <value>InChI=1S/C5H11NO2S/c1-9-3-2-4(6)5(7)8/h4H,2-3,6H2,1H3,(H,7,8)</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>inchikey</kind>
    <value>FFEARJCKVFRZRR-UHFFFAOYSA-N</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>polar_surface_area</kind>
    <value>63.32</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>refractivity</kind>
    <value>37.59</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>polarizability</kind>
    <value>15.61</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>0</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>formal_charge</kind>
    <value>0</value>
    <source>ChemAxon</source>
  </property>
  <pathways>
  </pathways>
  <spectra>
  </spectra>
  <hmdb_id>HMDB33951</hmdb_id>
  <pubchem_compound_id/>
  <chemspider_id/>
  <kegg_id/>
  <chebi_id>16811</chebi_id>
  <biocyc_id/>
  <het_id/>
  <wikipidia/>
  <vmh_id/>
  <fbonto_id/>
  <foodb_id/>
  <general_references>
    <reference>#&lt;Reference:0x0000558b62d24b30&gt;</reference>
    <reference>#&lt;Reference:0x0000558b62d24928&gt;</reference>
    <reference>#&lt;Reference:0x0000558b62d24770&gt;</reference>
    <reference>#&lt;Reference:0x0000558b62d24540&gt;</reference>
    <reference>#&lt;Reference:0x0000558b62d242c0&gt;</reference>
  </general_references>
  <foods>
    <food>
      <name>Barley</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Hordeum vulgare</name_scientific>
      <ncbi_taxonomy_id>4513</ncbi_taxonomy_id>
      <average_value>96.429865</average_value>
      <max_value>160.0</max_value>
      <min_value>32.85973034</min_value>
      <unit>mg/100 g</unit>
    </food>
    <food>
      <name>Broccoli</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Brassica oleracea var. italica</name_scientific>
      <ncbi_taxonomy_id>36774</ncbi_taxonomy_id>
      <average_value>40.095</average_value>
      <max_value>76.0</max_value>
      <min_value>4.19</min_value>
      <unit>mg/100 g</unit>
    </food>
    <food>
      <name>Carrot</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Daucus carota ssp. sativus</name_scientific>
      <ncbi_taxonomy_id>79200</ncbi_taxonomy_id>
      <average_value>7.655</average_value>
      <max_value>9.0</max_value>
      <min_value>6.31</min_value>
      <unit>mg/100 g</unit>
    </food>
    <food>
      <name>Cucumber</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Cucumis sativus</name_scientific>
      <ncbi_taxonomy_id>3659</ncbi_taxonomy_id>
      <average_value>6.75</average_value>
      <max_value>9.0</max_value>
      <min_value>4.5</min_value>
      <unit>mg/100 g</unit>
    </food>
    <food>
      <name>Dill</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Anethum graveolens</name_scientific>
      <ncbi_taxonomy_id>40922</ncbi_taxonomy_id>
      <average_value>32.59</average_value>
      <max_value>32.59</max_value>
      <min_value>32.59</min_value>
      <unit>mg/100 g</unit>
    </food>
    <food>
      <name>Eggplant</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Solanum melongena</name_scientific>
      <ncbi_taxonomy_id>4111</ncbi_taxonomy_id>
      <average_value>8.015</average_value>
      <max_value>10.0</max_value>
      <min_value>6.03</min_value>
      <unit>mg/100 g</unit>
    </food>
    <food>
      <name>Garden onion</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Allium cepa</name_scientific>
      <ncbi_taxonomy_id>4679</ncbi_taxonomy_id>
      <average_value>10.4</average_value>
      <max_value>12.0</max_value>
      <min_value>8.8</min_value>
      <unit>mg/100 g</unit>
    </food>
    <food>
      <name>Green bean</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Phaseolus vulgaris</name_scientific>
      <ncbi_taxonomy_id>3885</ncbi_taxonomy_id>
      <average_value>25.37</average_value>
      <max_value>28.0</max_value>
      <min_value>22.74</min_value>
      <unit>mg/100 g</unit>
    </food>
    <food>
      <name>Green bell pepper</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Capsicum annuum</name_scientific>
      <ncbi_taxonomy_id>4072</ncbi_taxonomy_id>
      <average_value>6.7</average_value>
      <max_value>7.0</max_value>
      <min_value>6.4</min_value>
      <unit>mg/100 g</unit>
    </food>
    <food>
      <name>Green zucchini</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Cucurbita pepo var. cylindrica</name_scientific>
      <ncbi_taxonomy_id/>
      <average_value>15.475</average_value>
      <max_value>18.0</max_value>
      <min_value>12.95</min_value>
      <unit>mg/100 g</unit>
    </food>
    <food>
      <name>Japanese pumpkin</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Cucurbita maxima</name_scientific>
      <ncbi_taxonomy_id>3661</ncbi_taxonomy_id>
      <average_value>7.55</average_value>
      <max_value>8.1</max_value>
      <min_value>7.0</min_value>
      <unit>mg/100 g</unit>
    </food>
    <food>
      <name>Nanking cherry</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Prunus tomentosa</name_scientific>
      <ncbi_taxonomy_id>105667</ncbi_taxonomy_id>
      <average_value>5.0</average_value>
      <max_value>5.0</max_value>
      <min_value>5.0</min_value>
      <unit>mg/100 g</unit>
    </food>
    <food>
      <name>Oat</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Avena sativa</name_scientific>
      <ncbi_taxonomy_id>4498</ncbi_taxonomy_id>
      <average_value>230.0</average_value>
      <max_value>230.0</max_value>
      <min_value>230.0</min_value>
      <unit>mg/100 g</unit>
    </food>
    <food>
      <name>Orange bell pepper</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Capsicum annuum</name_scientific>
      <ncbi_taxonomy_id>4072</ncbi_taxonomy_id>
      <average_value>10.0</average_value>
      <max_value>10.0</max_value>
      <min_value>10.0</min_value>
      <unit>mg/100 g</unit>
    </food>
    <food>
      <name>Parsnip</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Pastinaca sativa</name_scientific>
      <ncbi_taxonomy_id>4041</ncbi_taxonomy_id>
      <average_value>16.426369</average_value>
      <max_value>21.0</max_value>
      <min_value>11.85273803</min_value>
      <unit>mg/100 g</unit>
    </food>
    <food>
      <name>Potato</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Solanum tuberosum</name_scientific>
      <ncbi_taxonomy_id>4113</ncbi_taxonomy_id>
      <average_value>17.585</average_value>
      <max_value>26.0</max_value>
      <min_value>9.17</min_value>
      <unit>mg/100 g</unit>
    </food>
    <food>
      <name>Red beetroot</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Beta vulgaris var. rubra</name_scientific>
      <ncbi_taxonomy_id/>
      <average_value>8.0</average_value>
      <max_value>8.0</max_value>
      <min_value>8.0</min_value>
      <unit>mg/100 g</unit>
    </food>
    <food>
      <name>Red bell pepper</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Capsicum annuum</name_scientific>
      <ncbi_taxonomy_id>4072</ncbi_taxonomy_id>
      <average_value>7.575836</average_value>
      <max_value>10.0</max_value>
      <min_value>5.151671579</min_value>
      <unit>mg/100 g</unit>
    </food>
    <food>
      <name>Red raspberry</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Rubus idaeus</name_scientific>
      <ncbi_taxonomy_id>32247</ncbi_taxonomy_id>
      <average_value>0.206598</average_value>
      <max_value>0.206598462</max_value>
      <min_value>0.206598462</min_value>
      <unit>mg/100 g</unit>
    </food>
    <food>
      <name>Romaine lettuce</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Lactuca sativa L. var. longifolia</name_scientific>
      <ncbi_taxonomy_id/>
      <average_value>9.4</average_value>
      <max_value>15.0</max_value>
      <min_value>3.8</min_value>
      <unit>mg/100 g</unit>
    </food>
    <food>
      <name>Rye</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Secale cereale</name_scientific>
      <ncbi_taxonomy_id>4550</ncbi_taxonomy_id>
      <average_value>150.0</average_value>
      <max_value>150.0</max_value>
      <min_value>150.0</min_value>
      <unit>mg/100 g</unit>
    </food>
    <food>
      <name>Saskatoon berry</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Amelanchier alnifolia</name_scientific>
      <ncbi_taxonomy_id>32219</ncbi_taxonomy_id>
      <average_value>3.6</average_value>
      <max_value>7.0</max_value>
      <min_value>0.2</min_value>
      <unit>mg/100 g</unit>
    </food>
    <food>
      <name>Spinach</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Spinacia oleracea</name_scientific>
      <ncbi_taxonomy_id>3562</ncbi_taxonomy_id>
      <average_value>16.1</average_value>
      <max_value>26.0</max_value>
      <min_value>6.2</min_value>
      <unit>mg/100 g</unit>
    </food>
    <food>
      <name>Sunburst squash (pattypan squash)</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Cucurbita pepo var. clypeata</name_scientific>
      <ncbi_taxonomy_id/>
      <average_value>17.1</average_value>
      <max_value>20.0</max_value>
      <min_value>14.2</min_value>
      <unit>mg/100 g</unit>
    </food>
    <food>
      <name>Swiss chard</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Beta vulgaris ssp. cicla</name_scientific>
      <ncbi_taxonomy_id>1527200</ncbi_taxonomy_id>
      <average_value>19.0</average_value>
      <max_value>19.0</max_value>
      <min_value>19.0</min_value>
      <unit>mg/100 g</unit>
    </food>
    <food>
      <name>Turnip</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Brassica rapa var. rapa</name_scientific>
      <ncbi_taxonomy_id>51350</ncbi_taxonomy_id>
      <average_value>4.19</average_value>
      <max_value>7.0</max_value>
      <min_value>1.38</min_value>
      <unit>mg/100 g</unit>
    </food>
    <food>
      <name>Wheat</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Triticum</name_scientific>
      <ncbi_taxonomy_id>4564</ncbi_taxonomy_id>
      <average_value>385.833686</average_value>
      <max_value>480.0</max_value>
      <min_value>260.0</min_value>
      <unit>mg/100 g</unit>
    </food>
    <food>
      <name>White cabbage</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Brassica oleracea L. var. capitata L. f. alba DC.</name_scientific>
      <ncbi_taxonomy_id/>
      <average_value>9.365</average_value>
      <max_value>9.73</max_value>
      <min_value>9.0</min_value>
      <unit>mg/100 g</unit>
    </food>
    <food>
      <name>Yellow bell pepper</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Capsicum annuum</name_scientific>
      <ncbi_taxonomy_id>4072</ncbi_taxonomy_id>
      <average_value>6.0</average_value>
      <max_value>7.0</max_value>
      <min_value>5.0</min_value>
      <unit>mg/100 g</unit>
    </food>
    <food>
      <name>Yellow wax bean</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Phaseolus vulgaris</name_scientific>
      <ncbi_taxonomy_id>3885</ncbi_taxonomy_id>
      <average_value>28.75</average_value>
      <max_value>29.5</max_value>
      <min_value>28.0</min_value>
      <unit>mg/100 g</unit>
    </food>
    <food>
      <name>Yellow zucchini</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Cucurbita pepo var. cylindrica</name_scientific>
      <ncbi_taxonomy_id/>
      <average_value>14.38</average_value>
      <max_value>18.0</max_value>
      <min_value>10.76</min_value>
      <unit>mg/100 g</unit>
    </food>
  </foods>
  <flavors>
    <flavor>
      <name>acidic</name>
    </flavor>
    <flavor>
      <name>mild</name>
    </flavor>
    <flavor>
      <name>sulfurous</name>
    </flavor>
  </flavors>
  <enzymes>
  </enzymes>
  <health_effects>
  </health_effects>
</compound>
