<?xml version="1.0" encoding="UTF-8"?>
<compound>
  <version>1.0</version>
  <creation_date>2009-11-20 01:20:47 UTC</creation_date>
  <update_date>2026-04-16 22:49:59 UTC</update_date>
  <accession>T3D3624</accession>
  <common_name>Sodium lauroyl sarcosinate</common_name>
  <class>SmallMolecule</class>
  <description>Sodium lauroyl sarcosinate (C15H28NNaO3) is an exogenous solid with an average molecular weight of 293.38 g/mol. Sodium lauroyl sarcosinate belongs to the amino acids, peptides, and analogues, a subclass of carboxylic acids and derivatives within the organic compounds.

In industrial applications, the compound serves as a surfactant, cleaning agent, foamant, and emulsifier. It is further utilized as an anti-static agent, viscosity modifier, and softener and conditioner. This substance is found in or released from several recorded sources, including household cleaning and consumer products such as soap dispensers and pipe accessories, as well as electrical and electronic equipment including cores yokes or armatures and antennas. It is also present in building and construction materials, specifically ceilings and floors.

Regarding biological interactions, one protein target is recorded: transient receptor potential cation channel subfamily A member 1 (TRPA1). Additionally, acyl sarcosines act as nitrosating agents and may react or decompose to cause nitrosamine contamination, specifically producing N-nitrososarcosine. Nitrosamines are believed to induce carcinogenic effects through the formation of DNA adducts at the O- and N-atoms.</description>
  <categories>
    <category>Household Toxin</category>
    <category>Natural Toxin</category>
  </categories>
  <types>
    <type>Organic Compound</type>
    <type>Amine</type>
    <type>Amide</type>
    <type>Cosmetic Toxin</type>
    <type>Lachrymator</type>
    <type>Household Toxin</type>
    <type>Natural Compound</type>
  </types>
  <synonyms>
    <synonym>(dodecanoyl(methyl)amino)acetic acid</synonym>
    <synonym>Gardol</synonym>
    <synonym>Hamposyl L-30</synonym>
    <synonym>Lauroylsarcosine sodium salt</synonym>
    <synonym>Maprosyl 30</synonym>
    <synonym>Medialan LL-99</synonym>
    <synonym>N-dodecanoyl-n-methylglycine sodium salt</synonym>
    <synonym>N-dodecanoyl-n-methylglycine, sodium salt</synonym>
    <synonym>N-lauroylsarcosine sodium</synonym>
    <synonym>N-lauroylsarcosine sodium salt</synonym>
    <synonym>N-lauroylsarcosine sodium salt solution</synonym>
    <synonym>N-Methyl-N-(1-oxododecyl)glycine sodium salt</synonym>
    <synonym>Sarcosyl</synonym>
    <synonym>Sarcosyl NL</synonym>
    <synonym>Sarcosyl NL 30</synonym>
    <synonym>Sarkosyl NL</synonym>
    <synonym>Sarkosyl NL 100</synonym>
    <synonym>Sarkosyl NL 30</synonym>
    <synonym>Sarkosyl NL 35</synonym>
    <synonym>Sarkosyl NL 97</synonym>
    <synonym>Sarkosyl NL-100</synonym>
    <synonym>Sarkosyl NL-30</synonym>
    <synonym>Sodium lauroyl sarcosinic acid</synonym>
    <synonym>Sodium lauroylsarcosinate</synonym>
    <synonym>Sodium lauroylsarcosine</synonym>
    <synonym>Sodium n-dodecanoyl-n-methylglycinate</synonym>
    <synonym>Sodium n-lauroylsarcosinate</synonym>
    <synonym>Sodium n-lauroylsarcosinate solution</synonym>
    <synonym>Sodium n-lauroylsarcosine</synonym>
    <synonym>Sodium [dodecanoyl(methyl)amino]acetate</synonym>
  </synonyms>
  <chemical_formula>C15H28NNaO3</chemical_formula>
  <average_molecular_weight>293.3775</average_molecular_weight>
  <monisotopic_moleculate_weight>293.196688442</monisotopic_moleculate_weight>
  <iupac_name>sodium 2-(N-methyldodecanamido)acetate</iupac_name>
  <traditional_iupac>sodium lauroyl sarcosinate</traditional_iupac>
  <cas_registry_number>137-16-6</cas_registry_number>
  <smiles>CCCCCCCCCCCC(=O)N(C)CC(=O)O[Na]</smiles>
  <inchi>InChI=1S/C15H29NO3.Na/c1-3-4-5-6-7-8-9-10-11-12-14(17)16(2)13-15(18)19;/h3-13H2,1-2H3,(H,18,19);/q;+1/p-1</inchi>
  <inchikey>KSAVQLQVUXSOCR-UHFFFAOYSA-M</inchikey>
  <taxonomy>
    <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>
    <direct_parent>N-acyl-alpha amino acids</direct_parent>
    <alternate_parents>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acid salts</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>N-acyl amines</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organic sodium salts</alternative_parent>
      <alternative_parent>Organic zwitterions</alternative_parent>
      <alternative_parent>Organonitrogen compounds</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Tertiary carboxylic acid amides</alternative_parent>
    </alternate_parents>
    <substituents>
      <substituent>Aliphatic acyclic compound</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxamide group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Carboxylic acid salt</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>N-acyl-alpha-amino acid</substituent>
      <substituent>N-acyl-amine</substituent>
      <substituent>Organic alkali metal salt</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organic salt</substituent>
      <substituent>Organic sodium salt</substituent>
      <substituent>Organic zwitterion</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Tertiary carboxylic acid amide</substituent>
    </substituents>
    <molecular_framework>Aliphatic acyclic compounds</molecular_framework>
    <descriptors/>
  </taxonomy>
  <status>Detected and Not Quantified</status>
  <origin>Exogenous</origin>
  <cellular_locations>
    <cellular_location>Membrane</cellular_location>
  </cellular_locations>
  <biofluid_locations/>
  <tissue_locations/>
  <pathways/>
  <state>Solid</state>
  <appearance>White powder.</appearance>
  <experimental_properties>
    <property>
      <kind>melting_point</kind>
      <value>140°C</value>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>4.51</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-4.27</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>solubility</kind>
      <value>1.58e-02 g/l</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>3.51</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-0.76</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>sodium 2-(N-methyldodecanamido)acetate</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>293.3775</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>293.196688442</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>CCCCCCCCCCCC(=O)N(C)CC(=O)O[Na]</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C15H28NNaO3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C15H29NO3.Na/c1-3-4-5-6-7-8-9-10-11-12-14(17)16(2)13-15(18)19;/h3-13H2,1-2H3,(H,18,19);/q;+1/p-1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>KSAVQLQVUXSOCR-UHFFFAOYSA-M</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>46.61</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>75.45</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>34.68</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>13</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>0</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>
  </predicted_properties>
  <route_of_exposure>Oral (A2881) ; inhalation (A2881) ; dermal (A2881)</route_of_exposure>
  <mechanism_of_toxicity>While acyl sarcosines themselves are not toxic, they are nitrosating agents. Nitrosating agents may decompose and/or react to cause nitrosamine contamination. Nitrosamines are produced from secondary amines and amides in the presence of nitrite ions and are believed to be carcinogenic. The particular nitrosamine produced by acyl sarcosines is N-nitrososarcosine. Once in the body, nitrosamines are activated by cytochrome P-450 enzymes. They are then believed to induce their carcinogenic effects by forming DNA adducts at the N- and O-atoms. (L1889, L1890, A2878, A2879, A2880, A2881)</mechanism_of_toxicity>
  <metabolism>Acyl sarcosines can be absorbed following oral or dermal contact, while nitrosamines can enter the body via ingestion, inhalation, or dermal contact. Once in the body, nitrosamines are metabolized by cytochrome P-450 enzymes, which essentially activates them into carcinogens. Sarcosine is metabolized to glycine by the enzyme sarcosine dehydrogenase. (A2878, A2879, L1892)</metabolism>
  <toxicity>LD50: 175 mg/kg (Intravenous, Rat) (A2881)
LD50: 2.1 g/kg (Oral, Mouse) (A2881)</toxicity>
  <lethaldose/>
  <carcinogenicity>No indication of carcinogenicity (not listed by IARC). (L135)</carcinogenicity>
  <use_source>Acyl sarcosines are used as hair-conditioning agents and surfactant-cleansing agents in cosmetics, as well as to improve wetting and penetration of topical pharmaceutical products. Acyl sarcosines and their sodium salts are also used in the metal finishing and processing industries for their crystal modifying, anti-rust, and anti-corrosion properties. (A2881)</use_source>
  <min_risk_level/>
  <health_effects>#&lt;HealthEffect::ActiveRecord_Associations_CollectionProxy:0x00007f72261755a8&gt;</health_effects>
  <symptoms>Acyl sarcosines may cause irritation to the skin and eyes. (A2881)</symptoms>
  <treatment/>
  <drugbank_id/>
  <hmdb_id/>
  <pubchem_compound_id>23668817</pubchem_compound_id>
  <chembl_id>CHEMBL1903482</chembl_id>
  <chemspider_id>8392</chemspider_id>
  <kegg_id/>
  <uniprot_id/>
  <omim_id/>
  <chebi_id/>
  <biocyc_id/>
  <ctd_id/>
  <stitch_id/>
  <actor_id/>
  <pdb_id/>
  <wikipidia/>
  <general_references>
    <reference>
      <pubmed_id>17485391</pubmed_id>
    </reference>
    <reference>
      <pubmed_id>18218609</pubmed_id>
    </reference>
    <reference>
      <pubmed_id>15380096</pubmed_id>
    </reference>
    <reference>
      <pubmed_id>11358107</pubmed_id>
    </reference>
    <reference>
      <reference_text>International Agency for Research on Cancer (2014). IARC Monographs on the Evaluation of Carcinogenic Risks to Humans. : http://monographs.iarc.fr/index.php</reference_text>
    </reference>
    <reference>
      <reference_text>Wikipedia. Nitrosamine. Last Updated 16 November 2009.: http://en.wikipedia.org/wiki/Nitrosamine</reference_text>
    </reference>
    <reference>
      <reference_text>Organic Natural Health (1998). Cancer Causing Toxic Chemical Ingredients in Cosmetic and Skin Care Products.: http://www.health-report.co.uk/ingredients-directory.htm</reference_text>
    </reference>
    <reference>
      <reference_text>Wikipedia. Sarcosine. Last Updated 16 October 2009.: http://en.wikipedia.org/wiki/Sarcosine</reference_text>
    </reference>
  </general_references>
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    <target>
      <target_id>BE0004796</target_id>
      <mechanism_of_action>Acyl sarcosines are nitrosating agents and may decompose and/or react to cause nitrosamine contamination. The particular nitrosamine produced by acyl sarcosines is N-nitrososarcosine. Nitrosamines are believed to induce their carcinogenic effects by forming DNA adducts at the N- and O-atoms. (L1890, A2880, A2881)</mechanism_of_action>
      <constants/>
      <references>
        <reference>
          <reference_text>Organic Natural Health (1998). Cancer Causing Toxic Chemical Ingredients in Cosmetic and Skin Care Products.: http://www.health-report.co.uk/ingredients-directory.htm</reference_text>
        </reference>
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      <target_id>BE0001122</target_id>
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  </targets>
</compound>
