ContaminantDB: Sodium lauroyl sarcosinate

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References Targets (2)XML

Record Information

Version

1.0

Creation Date

2009-11-20 01:20:47 UTC

Update Date

2026-04-16 22:49:59 UTC

Accession Number

CHEM002597

Identification

Common Name

Sodium lauroyl sarcosinate

Class

Small Molecule

Description

Sodium lauroyl 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 modified 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)

Contaminant Sources

HPV EPA Chemicals
T3DB toxins
ToxCast & Tox21 Chemicals

Contaminant Type

Amide
Amine
Cosmetic Toxin
Household Toxin
Lachrymator
Natural Compound
Organic Compound

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
Sodium lauroyl sarcosinic acid	Generator
4-Isopropylaminoantipyrine	MeSH
Gardol	MeSH
Lauroyl sarcosine	MeSH
Sarkosyl NL 30	MeSH
Sarkosyl, potassium salt	MeSH
N-Lauroylsarcosine	MeSH
Sarkosyl	MeSH
Sarkosyl L	MeSH
Sarkosyl, ammonium salt	MeSH
N-Lauroyl sarcosine	MeSH
N-Lauroylsarcosinate	MeSH
Sarcosyl NL	MeSH
Sodium N-laurylsarcosinate	MeSH

Chemical Formula

C₁₅H₂₈NNaO₃

Average Molecular Mass

293.378 g/mol

Monoisotopic Mass

293.197 g/mol

CAS Registry Number

137-16-6

IUPAC Name

sodium 2-(N-methyldodecanamido)acetate

Traditional Name

sodium lauroyl sarcosinate

SMILES

CCCCCCCCCCCC(=O)N(C)CC(=O)O[Na]

InChI Identifier

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 Key

KSAVQLQVUXSOCR-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.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

N-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 Framework

Aliphatic acyclic compounds

External Descriptors

Not Available

Biological Properties

Status

Detected and Not Quantified

Origin

Exogenous

Cellular Locations

Membrane

Biofluid Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Applications

Not Available

Biological Roles

Not Available

Chemical Roles

Not Available

Physical Properties

State

Solid

Appearance

White powder.

Experimental Properties

Property	Value
Melting Point	140°C
Boiling Point	Not Available
Solubility	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	0.016 g/L	ALOGPS
logP	4.51	ALOGPS
logP	3.51	ChemAxon
logS	-4.3	ALOGPS
pKa (Strongest Basic)	-0.76	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	46.61 Å²	ChemAxon
Rotatable Bond Count	13	ChemAxon
Refractivity	75.45 m³·mol⁻¹	ChemAxon
Polarizability	34.68 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0006-0190000000-b8040ab8a356a736ef69	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-01r6-8590000000-eb1d99ac0c1f4bfdd2b4	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-052f-9500000000-3cb4b0e5d9265b2d2dee	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0006-0090000000-fb9425d3738bccd8c3b3	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0udl-3590000000-c4fb362886b0453df33e	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-03yi-9700000000-a01af40f7d8015afa6a4	Spectrum

Toxicity Profile

Route of Exposure

Oral (4) ; inhalation (4) ; dermal (4)

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. (6, 7, 1, 2, 3, 4)

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. (1, 2, 8)

Toxicity Values

LD50: 175 mg/kg (Intravenous, Rat) (4) LD50: 2.1 g/kg (Oral, Mouse) (4)

Lethal Dose

Not Available

Carcinogenicity (IARC Classification)

No indication of carcinogenicity (not listed by IARC). (5)

Uses/Sources

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. (4)

Minimum Risk Level

Not Available

Health Effects

Acyl sarcosines may cause irritation to the skin and eyes. They may also react to produce N-nitrososarcosine, which is believed to be carcinogenic. (4)

Symptoms

Acyl sarcosines may cause irritation to the skin and eyes. (4)

Treatment

Not Available

Concentrations

Not Available

External Links

DrugBank ID

Not Available

HMDB ID

Not Available

FooDB ID

Not Available

Phenol Explorer ID

Not Available

KNApSAcK ID

Not Available

BiGG ID

Not Available

BioCyc ID

Not Available

METLIN ID

Not Available

PDB ID

Not Available

Wikipedia Link

Sodium lauroyl sarcosinate

Chemspider ID

Not Available

ChEBI ID

Not Available

PubChem Compound ID

8716

Kegg Compound ID

Not Available

YMDB ID

Not Available

ECMDB ID

Not Available

References

Synthesis Reference

Not Available

MSDS

Not Available

General References

Not Available

Sodium lauroyl sarcosinate (CHEM002597)

Structure for CHEM002597: Sodium lauroyl sarcosinate