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Record Information
Version2.0
Creation Date2009-11-20 01:11:44 UTC
Update Date2014-12-24 20:26:14 UTC
Accession NumberT3D3623
Identification
Common NameSodium cocoyl sarcosinate
ClassSmall Molecule
DescriptionSodium cocoyl sarcosinate is an sodium salt of an acyl derivative of sarcosine, which is a natural amino acid found in muscles and other body tissues. Acyl sarcosines are considered modifiŽed fatty acids in which the hydrocarbon chains are interrupted by an amidomethyl group in the alpha position. They 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. (8, 4)
Compound Type
  • Amide
  • Amine
  • Cosmetic Toxin
  • Household Toxin
  • Lachrymator
  • Natural Compound
  • Organic Compound
Chemical Structure
Thumb
Synonyms
Synonym
Sodium cocoyl sarcosinic acid
Sodium N-cocoyl sarcosinate
Chemical FormulaC17H32NNaO3
Average Molecular Mass321.431 g/mol
Monoisotopic Mass321.228 g/mol
CAS Registry Number61791-59-1
IUPAC Namesodium 2-(N-methyltetradecanamido)acetate
Traditional Namesodium 2-(N-methyltetradecanamido)acetate
SMILESCCCCCCCCCCCCCC(=O)N(C)CC(=O)O[Na]
InChI IdentifierInChI=1S/C17H33NO3.Na/c1-3-4-5-6-7-8-9-10-11-12-13-14-16(19)18(2)15-17(20)21;/h3-15H2,1-2H3,(H,20,21);/q;+1/p-1
InChI KeyInChIKey=KHCOJQDJOCNUGV-UHFFFAOYSA-M
Chemical Taxonomy
Description belongs to the class of organic compounds known as n-acyl-alpha amino acids. N-acyl-alpha amino acids are compounds containing an alpha amino acid which bears an acyl group at its terminal nitrogen atom.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentN-acyl-alpha amino acids
Alternative Parents
Substituents
  • N-acyl-alpha-amino acid
  • N-acyl-amine
  • Tertiary carboxylic acid amide
  • Carboxamide group
  • Carboxylic acid salt
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Organic alkali metal salt
  • Organic zwitterion
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Organic oxide
  • Organopnictogen compound
  • Carbonyl group
  • Organic oxygen compound
  • Organic salt
  • Organic sodium salt
  • Organic nitrogen compound
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External DescriptorsNot Available
Biological Properties
StatusDetected and Not Quantified
OriginExogenous
Cellular Locations
  • Membrane
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateSolid
AppearanceWhite powder.
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
LogPNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.0021 g/LALOGPS
logP5.32ALOGPS
logP4.3ChemAxon
logS-5.2ALOGPS
pKa (Strongest Basic)-0.76ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area46.61 ŲChemAxon
Rotatable Bond Count15ChemAxon
Refractivity84.65 m³·mol⁻¹ChemAxon
Polarizability38.92 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-0149000000-0175c9159de53b78f308JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0h99-9554000000-faa159f27a70d21b5e33JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9600000000-d761daa0cfbbf3695246JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-0009000000-9b06f1daf74eeec78f55JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0ff0-4986000000-e9e17e559ba95ea486cfJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-08fr-7920000000-f9ba4041b8d817ede8dcJSpectraViewer
Toxicity Profile
Route of ExposureOral (4) ; inhalation (4) ; dermal (4)
Mechanism of ToxicityWhile 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. (6, 7, 1, 2, 3, 4)
MetabolismAcyl 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. (1, 2, 8)
Toxicity ValuesLD50: 4.2 g/kg (Oral, Rat) (4)
Lethal DoseNot Available
Carcinogenicity (IARC Classification)No indication of carcinogenicity (not listed by IARC). (5)
Uses/SourcesAcyl 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. (4)
Minimum Risk LevelNot Available
Health EffectsAcyl sarcosines may cause irritation to the skin and eyes. They may also react to produce N-nitrososarcosine, which is believed to be carcinogenic. (4)
SymptomsAcyl sarcosines may cause irritation to the skin and eyes. (4)
TreatmentNot Available
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
DrugBank IDNot Available
HMDB IDNot Available
PubChem Compound ID23687235
ChEMBL IDNot Available
ChemSpider ID108568
KEGG IDNot Available
UniProt IDNot Available
OMIM ID
ChEBI IDNot Available
BioCyc IDNot Available
CTD IDNot Available
Stitch IDNot Available
PDB IDNot Available
ACToR IDNot Available
Wikipedia LinkNot Available
References
Synthesis ReferenceNot Available
MSDST3D3623.pdf
General References
  1. Oyama T, Sugio K, Uramoto H, Iwata T, Onitsuka T, Isse T, Nozoe T, Kagawa N, Yasumoto K, Kawamoto T: Increased cytochrome P450 and aryl hydrocarbon receptor in bronchial epithelium of heavy smokers with non-small cell lung carcinoma carries a poor prognosis. Front Biosci. 2007 May 1;12:4497-503. [17485391 ]
  2. Sasaki S, Sata F, Katoh S, Saijo Y, Nakajima S, Washino N, Konishi K, Ban S, Ishizuka M, Kishi R: Adverse birth outcomes associated with maternal smoking and polymorphisms in the N-Nitrosamine-metabolizing enzyme genes NQO1 and CYP2E1. Am J Epidemiol. 2008 Mar 15;167(6):719-26. doi: 10.1093/aje/kwm360. Epub 2008 Jan 23. [18218609 ]
  3. Drablos F, Feyzi E, Aas PA, Vaagbo CB, Kavli B, Bratlie MS, Pena-Diaz J, Otterlei M, Slupphaug G, Krokan HE: Alkylation damage in DNA and RNA--repair mechanisms and medical significance. DNA Repair (Amst). 2004 Nov 2;3(11):1389-407. [15380096 ]
  4. Lanigan RS: Final report on the safety assessment of Cocoyl Sarcosine, Lauroyl Sarcosine, Myristoyl Sarcosine, Oleoyl Sarcosine, Stearoyl Sarcosine, Sodium Cocoyl Sarcosinate, Sodium Lauroyl Sarcosinate, Sodium Myristoyl Sarcosinate, Ammonium Cocoyl Sarcosinate, and Ammonium Lauroyl Sarcosinate. Int J Toxicol. 2001;20 Suppl 1:1-14. [11358107 ]
  5. International Agency for Research on Cancer (2014). IARC Monographs on the Evaluation of Carcinogenic Risks to Humans. [Link]
  6. Wikipedia. Nitrosamine. Last Updated 16 November 2009. [Link]
  7. Organic Natural Health (1998). Cancer Causing Toxic Chemical Ingredients in Cosmetic and Skin Care Products. [Link]
  8. Wikipedia. Sarcosine. Last Updated 16 October 2009. [Link]
Gene Regulation
Up-Regulated GenesNot Available
Down-Regulated GenesNot Available

Targets

1. DNA
General Function:
Used for biological information storage.
Specific Function:
DNA contains the instructions needed for an organism to develop, survive and reproduce.
Molecular Weight:
2.15 x 1012 Da
References
  1. Drablos F, Feyzi E, Aas PA, Vaagbo CB, Kavli B, Bratlie MS, Pena-Diaz J, Otterlei M, Slupphaug G, Krokan HE: Alkylation damage in DNA and RNA--repair mechanisms and medical significance. DNA Repair (Amst). 2004 Nov 2;3(11):1389-407. [15380096 ]
  2. Lanigan RS: Final report on the safety assessment of Cocoyl Sarcosine, Lauroyl Sarcosine, Myristoyl Sarcosine, Oleoyl Sarcosine, Stearoyl Sarcosine, Sodium Cocoyl Sarcosinate, Sodium Lauroyl Sarcosinate, Sodium Myristoyl Sarcosinate, Ammonium Cocoyl Sarcosinate, and Ammonium Lauroyl Sarcosinate. Int J Toxicol. 2001;20 Suppl 1:1-14. [11358107 ]
  3. Organic Natural Health (1998). Cancer Causing Toxic Chemical Ingredients in Cosmetic and Skin Care Products. [Link]
General Function:
Temperature-gated cation channel activity
Specific Function:
Receptor-activated non-selective cation channel involved in detection of pain and possibly also in cold perception and inner ear function (PubMed:25389312, PubMed:25855297). Has a central role in the pain response to endogenous inflammatory mediators and to a diverse array of volatile irritants, such as mustard oil, cinnamaldehyde, garlic and acrolein, an irritant from tears gas and vehicule exhaust fumes (PubMed:25389312, PubMed:20547126). Is also activated by menthol (in vitro)(PubMed:25389312). Acts also as a ionotropic cannabinoid receptor by being activated by delta(9)-tetrahydrocannabinol (THC), the psychoactive component of marijuana (PubMed:25389312). May be a component for the mechanosensitive transduction channel of hair cells in inner ear, thereby participating in the perception of sounds. Probably operated by a phosphatidylinositol second messenger system (By similarity).
Gene Name:
TRPA1
Uniprot ID:
O75762
Molecular Weight:
127499.88 Da
References
  1. Nilius B, Prenen J, Owsianik G: Irritating channels: the case of TRPA1. J Physiol. 2011 Apr 1;589(Pt 7):1543-9. doi: 10.1113/jphysiol.2010.200717. Epub 2010 Nov 15. [21078588 ]