AMMONIUM LAURYL SULFATE

Details

Stereochemistry	ACHIRAL
Molecular Formula	C12H25O4S.H4N
Molecular Weight	283.428
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

[NH4+].CCCCCCCCCCCCOS([O-])(=O)=O

InChI

InChIKey=BTBJBAZGXNKLQC-UHFFFAOYSA-N

InChI=1S/C12H26O4S.H3N/c1-2-3-4-5-6-7-8-9-10-11-12-16-17(13,14)15;/h2-12H2,1H3,(H,13,14,15);1H3

HIDE SMILES / InChI

Molecular Formula	C12H26O4S
Molecular Weight	266.397
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Molecular Formula	H3N
Molecular Weight	17.0305
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/11899262

Sodium Lauryl Sulfate (SLS) is an anionic surfactant naturally derived from coconut and/or palm kernel oil. It usually consists of a mixture of sodium alkyl sulfates, mainly the lauryl. It is a widely used and inexpensive chemical found in many mainstream personal hygiene products such as shampoos, toothpastes, soaps, detergents and body wash. SLS is a detergent and surfactant, which essentially means that it breaks surface tension and separates molecules in order to allow better interaction between the product and your hair. It is also widely used as a skin irritant when testing products used to heal skin conditions. It was found that SLS represented a potential candidate for the use as a topical microbicide to prevent the sexual transmission of HIV-1, herpes, human papillomavirus and possibly other sexually transmitted pathogens. The mechanism of action of SLS involves the solubilization of the viral envelope and/or the denaturation of envelope and/or capsid proteins.

CNS Activity

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
virus envelope and/or capsid protein 3 Target ID: virus envelope and/or capsid protein Sources: https://www.ncbi.nlm.nih.gov/pubmed/11899262	Interacts 323

Conditions

Condition	Modality	Highest Phase	Product
Herpes simplex virus type 2 infection 4 Sources: https://www.ncbi.nlm.nih.gov/pubmed/11899262	Preventing	Preclinical	Unknown Approved Use Unknown
HIV-1 infection 151 Sources: https://www.ncbi.nlm.nih.gov/pubmed/11899262	Preventing	Preclinical	Unknown Approved Use Unknown
Human papilloma virus 3 Sources: https://www.ncbi.nlm.nih.gov/pubmed/11899262	Preventing	Preclinical	Unknown Approved Use Unknown
Acne 98 Sources: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=16d2264b-e00b-4a3a-9b52-2bf4ca33a73a	Inactive ingredient	Approved 8429	Clean Getaway Bag Approved Use Unknown

PubMed

Title	Date	PubMed
The state of the art of dynamic coatings.	2001	11296915
Microwave corneosurfametry and the short-duration dansyl chloride extraction test for rating concentrated irritant surfactants.	2001	11244229
Large-scale experiments for microbiological evaluation of measures for safeguarding sulfidic mine waste.	2001	11220178
Sodium dodecyl sulfate-freeze-fracture immunolabeling of gap junctions.	2001	11218657
Capillary electrophoresis of urinary normal and modified nucleosides of cancer patients.	2001	11217356
Zymography and reverse zymography for detecting MMPs, and TIMPs.	2001	11217315
Isolation of 2000-kDa complexes of N-methyl-D-aspartate receptor and postsynaptic density 95 from mouse brain.	2001 Apr	11279284
Pathological findings in cumulative irritation induced by SLS and croton oil in hairless mice.	2001 Apr	11260241
Films of collagen crosslinked by S-S bonds: preparation and characterization.	2001 Apr	11246954
Relaxed DM requirements during class II peptide loading and CD4+ T cell maturation in BALB/c mice.	2001 Apr 15	11290790
Enzyme-catalyzed and enzyme-triggered pathways in dioxygenation of 1-monolinoleoyl-rac-glycerol by potato tuber lipoxygenase.	2001 Apr 7	11295443
Spectrochemical investigations in molecularly organized solvent media: evaluation of pyridinium chloride as a selective fluorescence quenching agent of polycyclic aromatic hydrocarbons in aqueous carboxylate-terminated poly(amido) amine dendrimers and anionic micelles.	2001 Feb	11293719
Separation of basic, acidic and neutral compounds by capillary electrochromatography using uncharged monolithic capillary columns modified with anionic and cationic surfactants.	2001 Feb	11258767
Determination of alkylphenol ethoxylates by micellar electrokinetic chromatography with bile salts.	2001 Feb	11258765
The cold-shock stress response in Mycobacterium smegmatis induces the expression of a histone-like protein.	2001 Feb	11251819
Gamma radiation effects on alpha-lactalbumin: structural modifications.	2001 Feb	11233563
Adsorption of sodium lauryl sulfate onto arsenic-bearing ferrihydrite.	2001 Feb	11229002
Characterization of the laminated layer of in vitro cultivated Echinococcus vogeli metacestodes.	2001 Feb	11227903
Complex effects of papain on function and inhibitor sensitivity of the red cell anion exchanger AE1 suggest the presence of different transport subsites.	2001 Feb 1	11246420
Activation of ion-conducting pathways in the inner mitochondrial membrane - an unrecognized activity of fatty acid?	2001 Feb 23	11226416
A simple technique for the simultaneous determination of molecular weight and activity of superoxide dismutase using SDS-PAGE.	2001 Feb 26	11245894
Protein concentration of cerebrospinal fluid by precipitation with Pyrogallol Red prior to sodium dodecyl sulphate-polyacrylamide gel electrophoresis.	2001 Feb 26	11245891
[Calorimetric evaluation of directly compressed tablets].	2001 Jan	11242832
Laser-induced fluorescence detection at 266 nm in capillary electrophoresis. Polycyclic aromatic hydrocarbon metabolites in biota.	2001 Jan 12	11217036
Fabrication of polyester microchannels and their applications to capillary electrophoresis.	2001 Jan 12	11217035
Solute-solvent interactions in micellar electrokinetic chromatography. Selectivity of lithium dodecyl sulfate-lithium perfluorooctanesulfonate mixed-micellar buffers.	2001 Jan 12	11217033
Solute exchange between surfactant micelles by micelle fragmentation and fusion.	2001 Jan 29	11215796
[An amphiphilic substance inhibits the mollusk capacity to fliter phytoplankton cells from water].	2001 Jan-Feb	11236572
Effects of the incorporation of CHAPS into SDS micelles on neuropeptide-micelle binding: separation of the role of electrostatic interactions from hydrophobic interactions.	2001 Jun	11285556
Extension of A beta2M amyloid fibrils with recombinant human beta2-microglobulin.	2001 Mar	11293823
Subclinical, non-erythematous irritation with an open assay model (washing): sodium lauryl sulfate (SLS) versus sodium laureth sulfate (SLES).	2001 Mar	11278060
Soluble proteins of the nacre of the giant oyster Pinctada maxima and of the abalone Haliotis tuberculata: extraction and partial analysis of nacre proteins.	2001 Mar	11250534
Capillary electrophoretic separation, immunochemical recognition and analysis of the diastereomers quinine and quinidine and two quinidine metabolites in body fluids.	2001 Mar	11248471
Pitfalls of irritant patch testing using different test chamber sizes.	2001 Mar	11244137
Effect of patch type on the cumulative irritation potential of 4 test materials.	2001 Mar	11244136
Simple and rapid method for production of whole-virus antigen for serodiagnosis of caprine arthritis-encephalitis virus by enzyme-linked immunosorbent assay.	2001 Mar	11238221
Physico-chemical requirements for cellular uptake of pAntp peptide. Role of lipid-binding affinity.	2001 Mar	11231282
Isolation and partial characterization of the outer dense fibres and fibrous sheath from the sperm tail of a marsupial: the brushtail possum (Trichosurus vulpecula).	2001 Mar	11226063
The determination of draining lymph node cell cytokine mRNA levels in BALB/c mice following dermal sodium lauryl sulfate, dinitrofluorobenzene, and toluene diisocyanate exposure.	2001 Mar 15	11243917
A critical role for p38 mitogen-activated protein kinase in the maturation of human blood-derived dendritic cells induced by lipopolysaccharide, TNF-alpha, and contact sensitizers.	2001 Mar 15	11238627
Capillary electrophoretic determination of the constituents of Artemisiae Capillaris Herba.	2001 Mar 16	11293590
Analysis of sialo-N-glycans in glycoproteins as 1-phenyl-3-methyl-5-pyrazolone derivatives by capillary electrophoresis.	2001 Mar 2	11261727
Safety and immunogenicity of an intranasal Pseudomonas aeruginosa hybrid outer membrane protein F-I vaccine in human volunteers.	2001 Mar 21	11257350
Stabilisation of natural anthocyanins by micellar systems.	2001 Mar 23	11274803
Freezability of spermatozoa from Finn and Dorset rams in multiple semen extenders.	2001 Mar 30	11267804
Monoclonal antibodies against different epitopes of nonstructural protein sigmaNS of avian reovirus S1133.	2001 Mar 30	11259199
Identification and quantification of base and nucleoside markers in extracts of Ganoderma lucidum, Ganoderma japonicum and Ganoderma capsules by micellar electrokinetic chromatography.	2001 Mar 9	11269589
Structural and immunological similarities between high molecular weight zinc ion-dependent p-nitrophenylphosphatase and fructose-1,6-bisphosphate aldolase from bovine liver.	2001 Mar 9	11257525
Reduced levels of glutathione S-transferases in patch test reactions to dithranol and sodium lauryl sulphate as demonstrated by quantitative immunocytochemistry: evidence for oxidative stress in acute irritant contact dermatitis.	2001 Mar-Apr	11275802
Unusually stable and long-lived ligand-induced conformations of integrins.	2001 May 18	11278530

Patents

Sample Use Guides

In Vivo Use Guide

in rabbits

Route of Administration: Vaginal

In Vitro Use Guide

Sodium lauryl sulfate, a model substance in testing skin irritability was examined with regard to its effects on DNA synthesis and fine structure of human thymocytes incubated in vitro. At 5 h, incorporation of 3H-thymidine into DNA was inhibited with a discernable effect at 3 X 10(-4) M in serum-free medium and at 6 X 10(-4) M in medium to containing 15% serum. Sodium lauryl sulfate suppressed the incorporation of 3H-thymidine into DNA at 1.2 X 10(-3) M. No clear alterations in cell morphology were observed at 3 X 10(-4) M, whereas signs of irreversible cell damage, including pyknotic nuclei, were seen at 6 X 10(-4) M and complete disruption of most cells occurred at 1.2 X 10(-3) M. The results show that sodium lauryl sulfate inhibits DNA synthesis in human thymocytes and that there is a partial discrepancy between this inhibition and the adverse effects on the structural organization of the cell. It is proposed that the irritant effect of sodium lauryl sulfate in vivo is due to the breaking up of lymphoid or other cells and a consequent release of material that gives rise to an inflammatory response.

Substance Class	Chemical Created by `admin` on `Fri Dec 15 15:01:51 UTC 2023` Edited by `admin` on `Fri Dec 15 15:01:51 UTC 2023`
Record UNII	Q7AO2R1M0B
Record Status	`Validated (UNII)`
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Name

Type

Language

AMMONIUM LAURYL SULFATE

Official Name

English

AMMONIUM DODECYL SULFATE

Systematic Name

English

AMMONIUM LAURYL SULFATE [II]

Common Name

English

AMMONIUM LAURYL SULFATE [VANDF]

Common Name

English

PRESULIN

Brand Name

English

AMMONIUM LAURYL SULPHATE

Systematic Name

English

ALS

Common Name

English

AMMONIUM LAURYL SULFATE [HSDB]

Common Name

English

AMMONIUM LAURYL SULFATE [INCI]

Common Name

English

AMMONIUM DODECYL SULPHATE

Systematic Name

English

Classification Tree Code System Code

CFR

21 CFR 175.210