ContaminantDB: Cocoyl sarcosine

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

Record Information

Version

1.0

Creation Date

2009-11-19 22:48:32 UTC

Update Date

2026-04-06 14:58:24 UTC

Accession Number

CHEM002594

Identification

Common Name

Cocoyl sarcosine

Class

Small Molecule

Description

Cocoyl sarcosine is an N-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

T3DB toxins

Contaminant Type

Amide
Amine
Cosmetic Toxin
Household Toxin
Lachrymator
Natural Compound
Organic Compound

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Not Available

Chemical Formula

C₁₇H₃₃NO₃

Average Molecular Mass

299.449 g/mol

Monoisotopic Mass

299.246 g/mol

CAS Registry Number

783292-49-9

IUPAC Name

2-(N-methyltetradecanamido)acetic acid

Traditional Name

(N-methyltetradecanamido)acetic acid

SMILES

CCCCCCCCCCCCCC(=O)N(C)CC(O)=O

InChI Identifier

InChI=1S/C17H33NO3/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)

InChI Key

NGOZDSMNMIRDFP-UHFFFAOYSA-N

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
Monocarboxylic acid or derivatives
Carboxylic acid
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Carbonyl group
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

Liquid

Appearance

Yellow liquid.

Experimental Properties

Property	Value
Melting Point	22-28°C
Boiling Point	Not Available
Solubility	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	0.003 g/L	ALOGPS
logP	4.79	ALOGPS
logP	4.49	ChemAxon
logS	-5	ALOGPS
pKa (Strongest Acidic)	4.12	ChemAxon
pKa (Strongest Basic)	-0.76	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	57.61 Å²	ChemAxon
Rotatable Bond Count	14	ChemAxon
Refractivity	85.58 m³·mol⁻¹	ChemAxon
Polarizability	37.42 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	splash10-0udi-4169000000-0e6d5b83e83e08a4bf2c	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0f6x-9220000000-4432d304fb2b4e1bcf7b	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-006x-9300000000-1fb18f34daf29ff6295a	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0002-0090000000-6d058d6cc73de66233ff	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0f72-2090000000-9df25501e03259fb8b04	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-074u-9210000000-2e7b46bab8e183f96793	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: 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

Not Available

Chemspider ID

Not Available

ChEBI ID

Not Available

PubChem Compound ID

Not Available

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

Cocoyl sarcosine (CHEM002594)

Structure for CHEM002594: Cocoyl sarcosine