T3DB: Ammonium laureth sulfate

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

Targets (1)

Record Information

Version

2.0

Creation Date

2009-11-19 01:38:02 UTC

Update Date

2014-12-24 20:26:13 UTC

Accession Number

T3D3619

Identification

Common Name

Ammonium laureth sulfate

Class

Small Molecule

Description

Ammonium laureth sulfate is a surfactant often found in shampoos. It can be mildly irritating. (4)

Compound Type

Cosmetic Toxin
Ester
Ether
Household Toxin
Organic Compound
Synthetic Compound

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Synonym
Ammonium laureth sulfic acid
Ammonium laureth sulphate
Ammonium laureth sulphic acid
Ammonium laureth-12 sulfate
Ammonium laureth-5 sulfate
Ammonium laureth-7 sulfate
Ammonium laureth-9 sulfate
Ammonium lauryl ether sulfate
Ammonium polyethylene glycol (450) lauryl ether sulfate
Ammonium polyoxyethylene (12) lauryl ether sulfate
Ammonium polyoxyethylene (5) lauryl ether sulfate
Ammonium polyoxyethylene (7) lauryl ether sulfate
PEG-(1-4) Lauryl ether sulfate, ammonium salt
PEG-12 Lauryl ether sulfate ammonium salt
PEG-5 Lauryl ether sulfate ammonium salt
PEG-7 Lauryl ether sulfate ammonium salt
PEG-9 Lauryl ether sulfate ammonium salt
Polyethylene glycol (5) lauryl ether sulfate ammonium salt
Polyethylene Glycol (7) Lauryl Ether Sulfate Ammonium Salt
Polyethylene glycol 450 lauryl ether sulfate ammonium salt
Polyethylene glycol 600 lauryl ether sulfate ammonium salt
Polyethylene glycol lauryl ether sulfate ammonium salt
Polyoxyethylene (1-4) lauryl ether sulfate ammonium salt
Polyoxyethylene (12) lauryl ether sulfate ammonium salt
Polyoxyethylene (5) lauryl ether sulfate ammonium salt
Polyoxyethylene (7) lauryl ether sulfate ammonium salt
Polyoxyethylene (9) lauryl ether sulfate ammonium salt
Sodium lauryl ether sulfate

Chemical Formula

C₁₄H₃₃NO₅S

Average Molecular Mass

327.481 g/mol

Monoisotopic Mass

327.208 g/mol

CAS Registry Number

32612-48-9

IUPAC Name

[2-(dodecyloxy)ethoxy]sulfonic acid amine

Traditional Name

2-(dodecyloxy)ethoxysulfonic acid amine

SMILES

N.CCCCCCCCCCCCOCCOS(O)(=O)=O

InChI Identifier

InChI=1S/C14H30O5S.H3N/c1-2-3-4-5-6-7-8-9-10-11-12-18-13-14-19-20(15,16)17;/h2-14H2,1H3,(H,15,16,17);1H3

InChI Key

InChIKey=OPVLOHUACNWTQT-UHFFFAOYSA-N

Chemical Taxonomy

Description

belongs to the class of organic compounds known as sulfuric acid monoesters. These are organic compounds containing the sulfuric acid monoester functional group, with the generic structure ROS(O)(=O)=O, (R=organyl group).

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Organic sulfuric acids and derivatives

Sub Class

Sulfuric acid esters

Direct Parent

Sulfuric acid monoesters

Alternative Parents

Substituents

Alkyl sulfate
Sulfate-ester
Sulfuric acid monoester
Ether
Dialkyl ether
Organic nitrogen compound
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
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
LogP	Not Available

Predicted Properties

Property	Value	Source
logP	4.37	ChemAxon
pKa (Strongest Acidic)	-1.7	ChemAxon
pKa (Strongest Basic)	-4.1	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	72.83 Å²	ChemAxon
Rotatable Bond Count	15	ChemAxon
Refractivity	79.98 m³·mol⁻¹	ChemAxon
Polarizability	36.87 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-004i-0009000000-de489830afe94a76ae9b	2016-06-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-004i-0009000000-de489830afe94a76ae9b	2016-06-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-004i-0009000000-de489830afe94a76ae9b	2016-06-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-004i-0009000000-52bb27867d9aa8ce2df3	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-004i-0009000000-52bb27867d9aa8ce2df3	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-004i-0009000000-52bb27867d9aa8ce2df3	2016-08-03	View Spectrum

Toxicity Profile

Route of Exposure

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

Mechanism of Toxicity

While ammonium laureth sulfate 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). (7)

Uses/Sources

Ammonium laureth sulfate is a surfactant often found in shampoos. (4)

Minimum Risk Level

Not Available

Health Effects

Ammonium laureth sulfate itself only causes mild irritation. However, it may react to produce nitrosamines, which are believed to be carcinogenic. (4, 6)

Symptoms

Ammonium laureth sulfate can cause mild irritation. (4)

Treatment

Not Available

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

External Links

DrugBank ID

Not Available

HMDB ID

Not Available

PubChem Compound ID

61913

ChEMBL ID

Not Available

ChemSpider ID

55774

KEGG ID

Not Available

UniProt ID

Not Available

OMIM ID

ChEBI ID

53474

BioCyc ID

Not Available

CTD ID

Not Available

Stitch ID

Not Available

PDB ID

Not Available

ACToR ID

Not Available

Wikipedia Link

Not Available

References

Synthesis Reference

Not Available

MSDS

T3D3619.pdf

General References

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 ]
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 ]
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 ]
Dead Sea Cosmetics (2009). Ingredient FAQs. [Link]
Wikipedia. Nitrosamine. Last Updated 16 November 2009. [Link]
Organic Natural Health (1998). Cancer Causing Toxic Chemical Ingredients in Cosmetic and Skin Care Products. [Link]
International Agency for Research on Cancer (2014). IARC Monographs on the Evaluation of Carcinogenic Risks to Humans. [Link]

Gene Regulation

Up-Regulated Genes

Not Available

Down-Regulated Genes

Not 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

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 ]
Organic Natural Health (1998). Cancer Causing Toxic Chemical Ingredients in Cosmetic and Skin Care Products. [Link]

Ammonium laureth sulfate (T3D3619)

Structure for T3D3619: Ammonium laureth sulfate

Targets

References