U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ACHIRAL
Molecular Formula C12H25O4S.Na
Molecular Weight 288.379
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of SODIUM LAURYL SULFATE

SMILES

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

InChI

InChIKey=DBMJMQXJHONAFJ-UHFFFAOYSA-M
InChI=1S/C12H26O4S.Na/c1-2-3-4-5-6-7-8-9-10-11-12-16-17(13,14)15;/h2-12H2,1H3,(H,13,14,15);/q;+1/p-1

HIDE SMILES / InChI

Molecular Formula C12H25O4S
Molecular Weight 265.39
Charge -1
Count
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Molecular Formula Na
Molecular Weight 22.9898
Charge 1
Count
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description

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 TargetPharmacologyConditionPotency

Conditions

ConditionModalityTargetsHighest PhaseProduct
Preventing
Unknown
Preventing
Unknown
Preventing
Unknown
Inactive ingredient
Clean Getaway Bag

PubMed

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
Record UNII
368GB5141J
Record Status Validated (UNII)
Record Version