ContaminantDB: Quaternium-22

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References Targets (1)XML

Record Information

Version

1.0

Creation Date

2009-11-28 22:56:28 UTC

Update Date

2026-04-02 23:01:09 UTC

Accession Number

CHEM002604

Identification

Common Name

Quaternium-22

Class

Small Molecule

Description

Quaternium-22 is a quaternary ammonium salt found in numerous cosmetics. Its toxicity is due to its ability to act as a nitrosating agent, releasing potentially carcinogenic nitrosamines. (6)

Contaminant Sources

T3DB toxins

Contaminant Type

Amide
Amine
Cosmetic Toxin
Household Toxin
Organic Compound
Synthetic Compound

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Not Available

Chemical Formula

C₁₃H₂₉ClN₂O₇

Average Molecular Mass

360.832 g/mol

Monoisotopic Mass

360.166 g/mol

CAS Registry Number

51812-80-7

IUPAC Name

(2-hydroxyethyl)dimethyl[3-(2,3,4,5,6-pentahydroxyhexanamido)propyl]azanium chloride

Traditional Name

(2-hydroxyethyl)dimethyl[3-(2,3,4,5,6-pentahydroxyhexanamido)propyl]azanium chloride

SMILES

[Cl-].C[N+](C)(CCO)CCCNC(=O)C(O)C(O)C(O)C(O)CO

InChI Identifier

InChI=1S/C13H28N2O7.ClH/c1-15(2,6-7-16)5-3-4-14-13(22)12(21)11(20)10(19)9(18)8-17;/h9-12,16-21H,3-8H2,1-2H3;1H

InChI Key

FVEWVVDBRQZLSJ-UHFFFAOYSA-N

Chemical Taxonomy

Description

belongs to the class of organic compounds known as n-acyl amines. N-acyl amines are compounds containing a fatty acid moiety linked to an amine group through an ester linkage.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty amides

Direct Parent

N-acyl amines

Alternative Parents

Substituents

N-acyl-amine
Monosaccharide
Tetraalkylammonium salt
Quaternary ammonium salt
Secondary carboxylic acid amide
Secondary alcohol
Carboxamide group
1,2-aminoalcohol
Polyol
Carboxylic acid derivative
Alkanolamine
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Organic chloride salt
Organic salt
Organic zwitterion
Primary alcohol
Organooxygen compound
Organonitrogen compound
Carbonyl group
Amine
Alcohol
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	Not Available
Boiling Point	Not Available
Solubility	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	17.9 g/L	ALOGPS
logP	-3.3	ALOGPS
logP	-8.8	ChemAxon
logS	-1.3	ALOGPS
pKa (Strongest Acidic)	12	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	7	ChemAxon
Polar Surface Area	150.48 Å²	ChemAxon
Rotatable Bond Count	11	ChemAxon
Refractivity	90.08 m³·mol⁻¹	ChemAxon
Polarizability	34.18 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	0	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	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	splash10-0002-0913000000-51cb595f53b077209ed6	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-000t-3910000000-9b5d3bd67dcd806d80fa	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0005-4900000000-095fd691b9f4cd6a2b17	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-004l-6931000000-f0e68e6a174dd015ad73	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-002f-9621000000-50236b272363d862372c	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-054o-9400000000-c74406f52d4d623f403a	Spectrum

Toxicity Profile

Route of Exposure

Oral (3) ; inhalation (3) ; dermal (5)

Mechanism of Toxicity

While quaternium-22 itself is not toxic, it is a nitrosating agent. 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. 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. (5, 6, 1, 2, 3)

Metabolism

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. (1, 2)

Toxicity Values

Not Available

Lethal Dose

Not Available

Carcinogenicity (IARC Classification)

Not listed by IARC. Certain nitrosamines are classified by IARC as either probably or possibly carcinogenic to humans (Groups 2A and 2B, respectively). (4)

Uses/Sources

Quaternium-22 is a quaternary ammonium salt found in numerous cosmetics. (6)

Minimum Risk Level

Not Available

Health Effects

Quaternium-22 may react to produce nitrosamines, which are believed to be carcinogenic. (6)

Symptoms

Not Available

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

21960603

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

Quaternium-22 (CHEM002604)

Structure for CHEM002604: Quaternium-22