ContaminantDB: Quaternium-15

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

Record Information

Version

1.0

Creation Date

2009-11-24 01:14:16 UTC

Update Date

2016-11-09 01:08:54 UTC

Accession Number

CHEM002601

Identification

Common Name

Quaternium-15

Class

Small Molecule

Description

Quaternium-15 is a quaternary ammonium salt used as a preservative in many cosmetics and industrial substances. It acts as a formaldehyde releaser. It can cause contact dermatitis in sensitive individuals. It's toxicity is also due to it's ability to react and release formaldehyde and nitrosamines, both of which are believed to be carcinogenic. (7, 8)

Contaminant Sources

Clean Air Act Chemicals
HPV EPA Chemicals
IARC Carcinogens Group 1
STOFF IDENT Compounds
T3DB toxins

Contaminant Type

Amine
Cosmetic Toxin
Household Toxin
Industrial/Workplace Toxin
Organic Compound
Organochloride
Synthetic Compound

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
Dowicil 200	MeSH
1-(3-Chloroallyl)-hexaminium chloride	MeSH
Quaternium-15	MeSH

Chemical Formula

C₉H₁₆Cl₂N₄

Average Molecular Mass

251.160 g/mol

Monoisotopic Mass

250.075 g/mol

CAS Registry Number

4080-31-3

IUPAC Name

1-[(2E)-3-chloroprop-2-en-1-yl]-1,3,5,7-tetraazatricyclo[3.3.1.1³,⁷]decan-1-ium chloride

Traditional Name

1-[(2E)-3-chloroprop-2-en-1-yl]-1,3,5,7-tetraazatricyclo[3.3.1.1³,⁷]decan-1-ium chloride

SMILES

[Cl-].[H]\C(Cl)=C(\[H])C[N+]12CN3CN(CN(C3)C1)C2

InChI Identifier

InChI=1S/C9H16ClN4.ClH/c10-2-1-3-14-7-11-4-12(8-14)6-13(5-11)9-14;/h1-2H,3-9H2;1H/q+1;/p-1/b2-1+;

InChI Key

UKHVLWKBNNSRRR-TYYBGVCCSA-M

Chemical Taxonomy

Description

belongs to the class of organic compounds known as 1,3,5-triazinanes. These are triazinanes having three nitrogen ring atoms at the 1-, 3-, and 5- positions.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Triazinanes

Sub Class

1,3,5-triazinanes

Direct Parent

1,3,5-triazinanes

Alternative Parents

Substituents

1,3,5-triazinane
Tetraalkylammonium salt
Aminal
Vinyl chloride
Azacycle
Vinyl halide
Chloroalkene
Haloalkene
Organic nitrogen compound
Organic salt
Organic chloride salt
Hydrocarbon derivative
Organonitrogen compound
Organochloride
Organohalogen compound
Organopnictogen compound
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic 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

Biological Roles

Chemical Roles

Not Available

Physical Properties

State

Solid

Appearance

White powder.

Experimental Properties

Property	Value
Melting Point	Not Available
Boiling Point	Not Available
Solubility	304 mg/mL at 25°C

Predicted Properties

Property	Value	Source
Water Solubility	39.7 g/L	ALOGPS
logP	-2.7	ALOGPS
logP	-2.7	ChemAxon
logS	-0.8	ALOGPS
pKa (Strongest Basic)	3.7	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	9.72 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	66.87 m³·mol⁻¹	ChemAxon
Polarizability	22.05 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	Yes	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-0390000000-b38b08aeb969e9ff8719	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0udi-0790000000-8e57ee50cfe260ac8b09	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-000i-0900000000-afef158b3f0192f3f0c1	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0002-0290000000-25e47eb7f91df97fdac2	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-004i-0910000000-e9a64b5202ea552d0e3f	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-056r-1910000000-8ccab74df13e292c71c4	Spectrum

Toxicity Profile

Route of Exposure

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

Mechanism of Toxicity

Quaternium-15 is a formaldehyde releaser. It is likely that formaldehyde toxicity occurs when intracellular levels saturate formaldehyde dehydrogenase activity, allowing the unmetabolized intact molecule to exert its effects. Formaldehyde is known to form cross links between protein and DNA and undergo metabolic incorporation into macromolecules (DNA, RNA, and proteins). Quaternium-15 is also 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, 7, 1, 2, 3, 8)

Metabolism

Formaldehyde may be absorbed following inhalation, oral, or dermal exposure. It is an essential metabolic intermediate in all cells and is produced during the normal metabolism of serine, glycine, methionine, and choline and also by the demethylation of N-, S-, and O-methyl compounds. Exogenous formaldehyde is metabolized to formate by the enzyme formaldehyde dehydrogenase at the initial site of contact. After oxidation of formaldehyde to formate, the carbon atom is further oxidized to carbon dioxide or incorporated into purines, thymidine, and amino acids via tetrahydrofolatedependent one-carbon biosynthetic pathways. Formaldehyde is not stored in the body and is excreted in the urine (primarily as formic acid), incorporated into other cellular molecules, or exhaled as carbon dioxide. Nitrosamines can also 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. (5, 1, 2)

Toxicity Values

LD50: 500 mg/kg (Oral, Rat) (9) LD50: 565 mg/kg (Dermal, Rabbit) (9)

Lethal Dose

Not Available

Carcinogenicity (IARC Classification)

1, carcinogenic to humans (for formaldehyde). (4)

Uses/Sources

Quaternium-15 is used as a preservative in many cosmetics and industrial substances. (8)

Minimum Risk Level

Not Available

Health Effects

Quaternium-15 releases formaldehyde, a known human carcinogen. It may also react to produce nitrosamines, which are believed to be carcinogenic. Quaternium-15 is also an allergen, and can cause contact dermatitis in susceptible individuals. Many of those with an allergy to quaternium-15 are also allergic to formaldehyde. It is the single most often found cause of allergic contact dermatitis of the hands. (5, 7, 8)

Symptoms

Quaternium-15 can cause contact dermatitis in sensitive individuals. (8)

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

Quaternium-15

Chemspider ID

Not Available

ChEBI ID

Not Available

PubChem Compound ID

6433396

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-15 (CHEM002601)

Structure for CHEM002601: Quaternium-15