Quaternium-52 (T3D3636)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesGene RegulationTargets (1)XML
Targets (1)
Record Information
Version2.0
Creation Date2009-11-28 22:58:33 UTC
Update Date2014-12-24 20:26:15 UTC
Accession NumberT3D3636
Identification
Common NameQuaternium-52
ClassSmall Molecule
DescriptionQuaternium-52 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
  • Cosmetic Toxin
  • Ether
  • Household Toxin
  • Organic Compound
  • Synthetic Compound
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
Synonym
tris[2-(2-hydroxyethoxy)ethyl]-octadecyl-ammonium phosphate
Chemical FormulaC30H64NO10P
Average Molecular Mass629.804 g/mol
Monoisotopic Mass629.427 g/mol
CAS Registry Number58069-11-7
IUPAC Nametris[2-(2-hydroxyethoxy)ethyl](octadecyl)azanium phosphate
Traditional Nametris[2-(2-hydroxyethoxy)ethyl](octadecyl)azanium phosphate
SMILES[O-]P([O-])([O-])=O.CCCCCCCCCCCCCCCCCC[N+](CCOCCO)(CCOCCO)CCOCCO
InChI IdentifierInChI=1S/C30H64NO6.H3O4P/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-31(19-25-35-28-22-32,20-26-36-29-23-33)21-27-37-30-24-34;1-5(2,3)4/h32-34H,2-30H2,1H3;(H3,1,2,3,4)/q+1;/p-3
InChI KeyInChIKey=GUIWIPNQQLZJIE-UHFFFAOYSA-K
Chemical Taxonomy
Description belongs to the class of organic compounds known as organic phosphoric acids and derivatives. These are organic compounds containing phosphoric acid or a derivative thereof.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassOrganic phosphoric acids and derivatives
Sub ClassNot Available
Direct ParentOrganic phosphoric acids and derivatives
Alternative Parents
Substituents
  • Organic phosphoric acid derivative
  • Quaternary ammonium salt
  • Tetraalkylammonium salt
  • Ether
  • Dialkyl ether
  • Organic oxide
  • Hydrocarbon derivative
  • Organic salt
  • Alcohol
  • Primary alcohol
  • Organooxygen compound
  • Organonitrogen compound
  • Organic nitrogen compound
  • Amine
  • Organopnictogen compound
  • Organic oxygen compound
  • Organic anion
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External DescriptorsNot Available
Biological Properties
StatusDetected and Not Quantified
OriginExogenous
Cellular Locations
  • Cytoplasm
  • Extracellular
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
Applications
Biological RolesNot Available
Chemical Roles
Physical Properties
StateSolid
AppearanceWhite powder.
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
LogPNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.0012 g/LALOGPS
logP2.98ALOGPS
logP1.36ChemAxon
logS-5.8ALOGPS
pKa (Strongest Acidic)14.64ChemAxon
pKa (Strongest Basic)-2.7ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area88.38 ŲChemAxon
Rotatable Bond Count32ChemAxon
Refractivity166.2 m³·mol⁻¹ChemAxon
Polarizability70.04 ųChemAxon
Number of Rings0ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
SpectraNot Available
Toxicity Profile
Route of ExposureOral (3) ; inhalation (3) ; dermal (4)
Mechanism of ToxicityWhile quaternium-52 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-52 is a quaternary ammonium salt found in numerous cosmetics. (5)
Minimum Risk LevelNot Available
Health EffectsQuaternium-52 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 ID174876
ChEMBL IDNot Available
ChemSpider ID152496
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
MSDST3D3636.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. 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]