Sodium laureth sulfate (T3D3630)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesGene RegulationTargets (3)XML
Targets (3)
Record Information
Version2.0
Creation Date2009-11-28 02:36:32 UTC
Update Date2014-12-24 20:26:15 UTC
Accession NumberT3D3630
Identification
Common NameSodium laureth sulfate
ClassSmall Molecule
DescriptionSodium laureth sulfate is a detergent and surfactant found in many personal care products (soaps, shampoos, toothpaste etc.). It is an inexpensive and very effective foaming agent made by mixing sulfuric acid, monododecyl ester, and sodium salt. Sodium laureth sulfate may cause eye or skin irritation. (6)
Compound Type
  • Cosmetic Toxin
  • Ester
  • Ether
  • Household Toxin
  • Lachrymator
  • Organic Compound
  • Synthetic Compound
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
Synonym
2-(Dodecyloxy)ethanol hydrogen sulfate sodium salt
2-(Dodecyloxy)ethyl sodium sulfate
Avirol 100E
Conco sulfate we
Cycloryl na
Dodecyl sodium ethoxysulfate
Elfan 242
Elfan NS 242
Elfan NS 243
Empicol ESB 3
Empicol ESB 30
Empimin KSN
Empimin KSN 27
Empimin KSN 60
Empimin KSN 70
Etoxon epa
Laureth-8 carboxylic acid sodium salt
Maprofix 60S
Maprofix es
PEG-12 Lauryl ether sulfate sodium salt
PEG-5 Lauryl ether sulfate sodium salt
PEG-7 Lauryl ether sulfate sodium salt
PEG-8 Lauryl ether sulfate sodium salt
Polyethylene glycol (5) lauryl ether sulfate sodium salt
Polyethylene Glycol (7) Lauryl Ether Sulfate Sodium Salt
Polyethylene glycol 400 lauryl ether sulfate sodium salt
Polyethylene glycol 600 lauryl ether sulfate sodium salt
Polyethylene glycol sulfate monododecyl ether sodium salt
Polyoxyethylene (12) lauryl ether sulfate sodium salt
Polyoxyethylene (5) lauryl ether sulfate sodium salt
Polyoxyethylene (7) lauryl ether sulfate sodium salt
Polyoxyethylene (8) lauryl ether sulfate sodium salt
Retzolate 60
Rewopol NL-2
Rhodapex esy
Sipon es
Sipon esy
Sipon LES 25
Sodium (lauryloxypolyethoxy)ethyl sulfate
Sodium 2-(dodecyloxy)ethyl sulfate
Sodium 2-(dodecyloxy)ethyl sulphate
Sodium 2-(lauryloxy)ethyl sulfate
Sodium dodeceth-1 sulfate
Sodium dodecylpoly(oxyethylene) sulfate
Sodium laureth sulfic acid
Sodium laureth sulphate
Sodium laureth sulphic acid
Sodium laureth-12 sulfate
Sodium laureth-3 sulfate
Sodium laureth-5 sulfate
Sodium laureth-7 sulfate
Sodium laureth-8 sulfate
Sodium lauryl ether sulfate
Sodium lauryl ethoxysulphate
Sodium lauryl oxyethyl sulfate
Sodium lauryl sulfate ethoxylate
Sodium laurylpoly(oxyethylene) sulfate
Sodium poly(oxyethylene) lauryl ether sulfate
Sodium polyethylene glycol (5) lauryl ether sulfate
Sodium polyethylene glycol (7) lauryl ether sulfate
Sodium polyethylene glycol 400 sulfate
Sodium polyethylene glycol 600 lauryl ether sulfate
Sodium polyoxyethylene (12) lauryl ether sulfate
Sodium polyoxyethylene (5) lauryl ether sulfate
Sodium polyoxyethylene (7) lauryl ether sulfate
Sodium polyoxyethylene (8) sulfate
Standapol ES 2
Standapol ES-3
Steol CS-460
Texapon N40
Zetesol LES 2
Chemical FormulaC14H29NaO5S
Average Molecular Mass332.432 g/mol
Monoisotopic Mass332.163 g/mol
CAS Registry Number9004-82-4
IUPAC Namesodium 2-(dodecyloxy)ethyl sulfate
Traditional Namesodium 2-(dodecyloxy)ethyl sulfate
SMILES[Na+].CCCCCCCCCCCCOCCOS([O-])(=O)=O
InChI IdentifierInChI=1S/C14H30O5S.Na/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);/q;+1/p-1
InChI KeyInChIKey=ASEFUFIKYOCPIJ-UHFFFAOYSA-M
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).
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassOrganic sulfuric acids and derivatives
Sub ClassSulfuric acid esters
Direct ParentSulfuric acid monoesters
Alternative Parents
Substituents
  • Alkyl sulfate
  • Sulfate-ester
  • Sulfuric acid monoester
  • Organic alkali metal salt
  • Ether
  • Dialkyl ether
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organic sodium salt
  • Organic salt
  • Organooxygen compound
  • 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
Solubility0.187 mg/mL at 25°C
LogPNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.0076 g/LALOGPS
logP4.04ALOGPS
logP4.37ChemAxon
logS-4.6ALOGPS
pKa (Strongest Acidic)-1.7ChemAxon
pKa (Strongest Basic)-4.1ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area75.66 ŲChemAxon
Rotatable Bond Count15ChemAxon
Refractivity78.86 m³·mol⁻¹ChemAxon
Polarizability36.56 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
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, Positivesplash10-001j-6936000000-449907010ea90ea7115d2019-02-23View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0002-9810000000-154cf486ff8fa68c0d452019-02-23View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00kb-8910000000-01ed8b46b3b1cc4a27012019-02-23View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-0309000000-d0dfa979e5680f7701822019-02-23View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001i-5923000000-ca79024f8d00cdaf579b2019-02-23View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-001i-9400000000-d84fd0d37a5caece94c92019-02-23View Spectrum
Toxicity Profile
Route of ExposureOral (3) ; inhalation (3) ; dermal (4)
Mechanism of ToxicityWhile sodium 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. Sodium laureth sulfate may also be contaminated with low levels of 1,4-dioxane, another believed carcinogen. (4, 5, 1, 2, 3, 6)
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). (7)
Uses/SourcesSodium laureth sulfate is a detergent and surfactant found in many personal care products (soaps, shampoos, toothpaste etc.). (6)
Minimum Risk LevelNot Available
Health EffectsSodium laureth sulfate may cause skin and eye irritation, as well as increase the frequency of canker sores when used in toothpaste. It may also react to produce nitrosamines or contain low levels of 1,4-dioxane, both of which are believed to be carcinogenic. (5, 6)
SymptomsSodium laureth sulfate may cause skin and eye irritation, as well as increase the frequency of canker sores when used in toothpaste. (6)
TreatmentNot Available
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
DrugBank IDNot Available
HMDB IDNot Available
PubChem Compound ID23665884
ChEMBL IDNot Available
ChemSpider ID23146
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 LinkSodium_laureth_sulfate
References
Synthesis ReferenceNot Available
MSDST3D3630.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. Wikipedia. Sodium laureth sulfate. Last Updated 21 November 2009. [Link]
  7. 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]
Target Details
2. Transient receptor potential cation channel subfamily A member 1
General Function:
Temperature-gated cation channel activity
Specific Function:
Receptor-activated non-selective cation channel involved in detection of pain and possibly also in cold perception and inner ear function (PubMed:25389312, PubMed:25855297). Has a central role in the pain response to endogenous inflammatory mediators and to a diverse array of volatile irritants, such as mustard oil, cinnamaldehyde, garlic and acrolein, an irritant from tears gas and vehicule exhaust fumes (PubMed:25389312, PubMed:20547126). Is also activated by menthol (in vitro)(PubMed:25389312). Acts also as a ionotropic cannabinoid receptor by being activated by delta(9)-tetrahydrocannabinol (THC), the psychoactive component of marijuana (PubMed:25389312). May be a component for the mechanosensitive transduction channel of hair cells in inner ear, thereby participating in the perception of sounds. Probably operated by a phosphatidylinositol second messenger system (By similarity).
Gene Name:
TRPA1
Uniprot ID:
O75762
Molecular Weight:
127499.88 Da
References
  1. Nilius B, Prenen J, Owsianik G: Irritating channels: the case of TRPA1. J Physiol. 2011 Apr 1;589(Pt 7):1543-9. doi: 10.1113/jphysiol.2010.200717. Epub 2010 Nov 15. [21078588 ]
Target Details
3. Estrogen receptor
General Function:
Zinc ion binding
Specific Function:
Nuclear hormone receptor. The steroid hormones and their receptors are involved in the regulation of eukaryotic gene expression and affect cellular proliferation and differentiation in target tissues. Ligand-dependent nuclear transactivation involves either direct homodimer binding to a palindromic estrogen response element (ERE) sequence or association with other DNA-binding transcription factors, such as AP-1/c-Jun, c-Fos, ATF-2, Sp1 and Sp3, to mediate ERE-independent signaling. Ligand binding induces a conformational change allowing subsequent or combinatorial association with multiprotein coactivator complexes through LXXLL motifs of their respective components. Mutual transrepression occurs between the estrogen receptor (ER) and NF-kappa-B in a cell-type specific manner. Decreases NF-kappa-B DNA-binding activity and inhibits NF-kappa-B-mediated transcription from the IL6 promoter and displace RELA/p65 and associated coregulators from the promoter. Recruited to the NF-kappa-B response element of the CCL2 and IL8 promoters and can displace CREBBP. Present with NF-kappa-B components RELA/p65 and NFKB1/p50 on ERE sequences. Can also act synergistically with NF-kappa-B to activate transcription involving respective recruitment adjacent response elements; the function involves CREBBP. Can activate the transcriptional activity of TFF1. Also mediates membrane-initiated estrogen signaling involving various kinase cascades. Isoform 3 is involved in activation of NOS3 and endothelial nitric oxide production. Isoforms lacking one or several functional domains are thought to modulate transcriptional activity by competitive ligand or DNA binding and/or heterodimerization with the full length receptor. Essential for MTA1-mediated transcriptional regulation of BRCA1 and BCAS3. Isoform 3 can bind to ERE and inhibit isoform 1.
Gene Name:
ESR1
Uniprot ID:
P03372
Molecular Weight:
66215.45 Da
Binding/Activity Constants
TypeValueAssay TypeAssay Source
AC502.32 uMACEA_T47D_80hr_PositiveACEA Biosciences
AC509.97 uMOT_ERa_EREGFP_0480Odyssey Thera
References
  1. Sipes NS, Martin MT, Kothiya P, Reif DM, Judson RS, Richard AM, Houck KA, Dix DJ, Kavlock RJ, Knudsen TB: Profiling 976 ToxCast chemicals across 331 enzymatic and receptor signaling assays. Chem Res Toxicol. 2013 Jun 17;26(6):878-95. doi: 10.1021/tx400021f. Epub 2013 May 16. [23611293 ]