Quaternium-22 (T3D3633)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesGene RegulationTargets (1)XML
Targets (1)
Record Information
Version2.0
Creation Date2009-11-28 22:56:28 UTC
Update Date2014-12-24 20:26:15 UTC
Accession NumberT3D3633
Identification
Common NameQuaternium-22
ClassSmall Molecule
DescriptionQuaternium-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. (5)
Compound Type
  • Amide
  • Amine
  • Cosmetic Toxin
  • Household Toxin
  • Organic Compound
  • Synthetic Compound
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
Synonym
3-(D-Gluconoylamino)propyl(2-hydroxyethyl)dimethylammonium chloride
g-Gluconamidopropyl dimethyl 2-hydroxyethyl ammonium chloride
gamma-Gluconamidopropyl dimethyl 2-hydroxyethyl ammonium chloride
N-(2-Hydroxyethyl)-N,N-dimethyl-3-{[(2R,3S,4R,5R)-2,3,4,5,6-pentahydroxyhexanoyl]amino}-1-propanaminium chloride
Chemical FormulaC13H29ClN2O7
Average Molecular Mass360.832 g/mol
Monoisotopic Mass360.166 g/mol
CAS Registry Number51812-80-7
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 IdentifierInChI=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 KeyInChIKey=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.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassFatty amides
Direct ParentN-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 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 Solubility17.9 g/LALOGPS
logP-3.3ALOGPS
logP-8.8ChemAxon
logS-1.3ALOGPS
pKa (Strongest Acidic)12ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count7ChemAxon
Polar Surface Area150.48 ŲChemAxon
Rotatable Bond Count11ChemAxon
Refractivity90.08 m³·mol⁻¹ChemAxon
Polarizability34.18 ųChemAxon
Number of Rings0ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-0913000000-51cb595f53b077209ed62019-02-22View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000t-3910000000-9b5d3bd67dcd806d80fa2019-02-22View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0005-4900000000-095fd691b9f4cd6a2b172019-02-22View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004l-6931000000-f0e68e6a174dd015ad732019-02-23View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-002f-9621000000-50236b272363d862372c2019-02-23View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-054o-9400000000-c74406f52d4d623f403a2019-02-23View Spectrum
Toxicity Profile
Route of ExposureOral (3) ; inhalation (3) ; dermal (4)
Mechanism of ToxicityWhile 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. (4, 5, 1, 2, 3)
MetabolismNitrosamines 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 ValuesNot Available
Lethal DoseNot 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). (6)
Uses/SourcesQuaternium-22 is a quaternary ammonium salt found in numerous cosmetics. (5)
Minimum Risk LevelNot Available
Health EffectsQuaternium-22 may react to produce nitrosamines, which are believed to be carcinogenic. (5)
SymptomsNot Available
TreatmentNot Available
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
DrugBank IDNot Available
HMDB IDNot Available
PubChem Compound ID40138
ChEMBL IDNot Available
ChemSpider IDNot Available
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
MSDSNot Available
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. Wikipedia. Nitrosamine. Last Updated 16 November 2009. [Link]
  5. Organic Natural Health (1998). Cancer Causing Toxic Chemical Ingredients in Cosmetic and Skin Care Products. [Link]
  6. International Agency for Research on Cancer (2014). IARC Monographs on the Evaluation of Carcinogenic Risks to Humans. [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. Organic Natural Health (1998). Cancer Causing Toxic Chemical Ingredients in Cosmetic and Skin Care Products. [Link]