Sodium laurylsulphate
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Sodium dodecyl sulfate (SDS) or sodium lauryl sulfate (SLS), sometimes written sodium laurilsulfate, is an
organic compound In chemistry, organic compounds are generally any chemical compounds that contain carbon-hydrogen or carbon-carbon bonds. Due to carbon's ability to catenate (form chains with other carbon atoms), millions of organic compounds are known. T ...
with the formula . It is an
anion An ion () is an atom or molecule with a net electrical charge. The charge of an electron is considered to be negative by convention and this charge is equal and opposite to the charge of a proton, which is considered to be positive by conve ...
ic surfactant used in many cleaning and hygiene products. This compound is the sodium
salt Salt is a mineral composed primarily of sodium chloride (NaCl), a chemical compound belonging to the larger class of salts; salt in the form of a natural crystalline mineral is known as rock salt or halite. Salt is present in vast quant ...
of the 12-carbon an
organosulfate Organosulfates are a class of organic compounds sharing a common functional group with the structure R-O-SO3−. The SO4 core is a sulfate group and the R group is any organic residue. All organosulfates are formally esters derived from alcohols ...
. Its
hydrocarbon In organic chemistry, a hydrocarbon is an organic compound consisting entirely of hydrogen and carbon. Hydrocarbons are examples of group 14 hydrides. Hydrocarbons are generally colourless and hydrophobic, and their odors are usually weak or ...
tail combined with a polar " headgroup" give the compound
amphiphilic An amphiphile (from the Greek αμφις amphis, both, and φιλíα philia, love, friendship), or amphipath, is a chemical compound possessing both hydrophilic (''water-loving'', polar) and lipophilic (''fat-loving'') properties. Such a compo ...
properties that make it useful as a detergent. SDS is also component of mixtures produced from inexpensive coconut and palm oils. SDS is a common component of many domestic cleaning, personal hygiene and cosmetic, pharmaceutical, and food products, as well as of industrial and commercial cleaning and product formulations.


Physicochemical properties

The
critical micelle concentration In colloidal and surface chemistry, the critical micelle concentration (CMC) is defined as the concentration of surfactants above which micelles form and all additional surfactants added to the system will form micelles. The CMC is an important c ...
(CMC) in water at 25 °C is 8.2 mM, and the
aggregation number An aggregation number is a description of the number of molecules present in a micelle once the critical micelle concentration (CMC) has been reached. In more detail, it has been defined as the average number of surfactant monomers in a spherical mi ...
at this concentration is usually considered to be about 62. The
micelle A micelle () or micella () (plural micelles or micellae, respectively) is an aggregate (or supramolecular assembly) of surfactant amphipathic lipid molecules dispersed in a liquid, forming a colloidal suspension (also known as associated coll ...
ionization fraction (α) is around 0.3 (or 30%).


Applications


Cleaning and hygiene

SDS is mainly used in detergents for laundry with many cleaning applications.Smulders, Eduard ; Rybinski, Wolfgang; Sung, Eric; Rähse, Wilfried; Steber, Josef; Wiebel, Frederike & Nordskog, Anette. (2002) "Laundry Detergents," in ''Ullmann's Encyclopedia of Industrial Chemistry,'' Weinheim: Wiley-VCH, It is a highly effective surfactant and is used in any task requiring the removal of oily stains and residues. For example, it is found in higher concentrations with industrial products including engine degreasers, floor cleaners, and car exterior cleaners. It is a component in hand soap, toothpastes, shampoos, shaving creams, and
bubble bath A bubble bath is a filled bathtub with a layer of surfactant foam on the surface of the water and consequently also the surfactant product used to produce the foam or soap. Less commonly, aerated or carbonated baths are called ''bubble baths''. ...
formulations, for its ability to create a foam (lather), for its surfactant properties, and in part for its thickening effect.


Food additive

Sodium dodecyl sulfate, appearing as its synonym ''sodium lauryl sulfate'' (SLS), is considered a generally recognized as safe (GRAS) ingredient for food use according to the
USFDA The United States Food and Drug Administration (FDA or US FDA) is a federal agency of the Department of Health and Human Services. The FDA is responsible for protecting and promoting public health through the control and supervision of food s ...
(21 CFR 172.822). It is used as an emulsifying agent and whipping aid. As an emulsifier in or with egg whites the United States Code of Federal Regulations require that it must not exceed 1,000 parts per million (0.1%) in egg white solids or 125 parts per million (0.0125%) in frozen or liquid egg whites and as a whipping agent for the preparation of marshmallows it must not exceed 0.5% of the weight of gelatine. SLS is reported to temporarily diminish perception of sweetness.


Laboratory applications

SDS is used in cleaning procedures, and is commonly used as a component for lysing cells during
RNA extraction RNA extraction is the purification of RNA from biological samples. This procedure is complicated by the ubiquitous presence of ribonuclease enzymes in cells and tissues, which can rapidly degrade RNA. Several methods are used in molecular biology ...
and/or
DNA extraction The first isolation of deoxyribonucleic acid (DNA) was done in 1869 by Friedrich Miescher. Currently, it is a routine procedure in molecular biology or forensic analyses. For the chemical method, many different kits are used for extraction, and s ...
, and for denaturing proteins in preparation for electrophoresis in the
SDS-PAGE SDS-PAGE (sodium dodecyl sulfate–polyacrylamide gel electrophoresis) is a Discontinuous electrophoresis, discontinuous electrophoretic system developed by Ulrich K. Laemmli which is commonly used as a method to separate proteins with molecular m ...
technique. In the case of SDS-PAGE, the compound works by disrupting non-covalent bonds in the proteins, and so denaturing them, i.e. causing the protein molecules to lose their native conformations and shapes. By binding to proteins at a ratio of one SDS molecule per 2 amino acid residues, the negatively charged detergent provides all proteins with a similar net negative charge and therefore a similar charge-to-mass ratio. In this way, the difference in mobility of the polypeptide chains in the gel can be attributed solely to their length as opposed to both their native charge and shape. This separation based on the size of the polypeptide chain simplifies the analysis of protein molecules.


Pharmaceutical applications

Sodium lauryl sulfate is a widely used in the pharmaceutical field as an ionic solubilizer and emulsifier that is suitable for applications in liquid dispersions, solutions, emulsions and micro emulsions, tablets, foams and semi-solids such as creams, lotions and gels. Additionally, SLS aids in tablet wettability, as well as lubrication during manufacturing. Brand names of pharma-grade SLS include Kolliphor SLS and Kolliphor SLS Fine.


Miscellaneous applications

SLS is used in an improved technique for preparing brain tissues for study by optical microscopy. The technique, which has been branded as CLARITY, was the work of Karl Deisseroth and coworkers at Stanford University, and involves infusion of the organ with an
acrylamide Acrylamide (or acrylic amide) is an organic compound with the chemical formula CH2=CHC(O)NH2. It is a white odorless solid, soluble in water and several organic solvents. From the chemistry perspective, acrylamide is a vinyl-substituted primary ...
solution to bind the macromolecules of the organ (
protein Proteins are large biomolecules and macromolecules that comprise one or more long chains of amino acid residues. Proteins perform a vast array of functions within organisms, including catalysing metabolic reactions, DNA replication, res ...
s, nucleic acids, etc.), followed by thermal polymerization to form a "brain–hydrogel" (a mesh interspersed throughout the tissue to fix the macromolecules and other structures in space), and then by lipid removal using SDS to eliminate
light scattering Scattering is a term used in physics to describe a wide range of physical processes where moving particles or radiation of some form, such as light or sound, are forced to deviate from a straight trajectory by localized non-uniformities (including ...
with minimal protein loss, rendering the tissue quasi-transparent. Along with
sodium dodecylbenzene sulfonate Alkylbenzene sulfonates are a class of anionic surfactants, consisting of a hydrophilic sulfonate head-group and a hydrophobic alkylbenzene tail-group. Along with sodium laureth sulfate, they are one of the oldest and most widely used synthetic ...
and
Triton X-100 Triton X-100 (''n'') is a nonionic surfactant that has a hydrophilic polyethylene oxide chain (on average it has 9.5 ethylene oxide units) and an aromatic hydrocarbon lipophilic or hydrophobic group. The hydrocarbon group is a 4-( 1,1,3,3-tetramet ...
, aqueous solutions of SDS are popular for dispersing or suspending nanotubes, such as carbon nanotubes.


Other uses

SLS has been proposed as a potentially effective topical microbicide, for intravaginal use, to inhibit and possibly prevent infection by various enveloped and non-enveloped
virus A virus is a submicroscopic infectious agent that replicates only inside the living cells of an organism. Viruses infect all life forms, from animals and plants to microorganisms, including bacteria and archaea. Since Dmitri Ivanovsk ...
es such as the herpes simplex viruses,
HIV The human immunodeficiency viruses (HIV) are two species of ''Lentivirus'' (a subgroup of retrovirus) that infect humans. Over time, they cause acquired immunodeficiency syndrome (AIDS), a condition in which progressive failure of the immune ...
, and the
Semliki Forest virus The Semliki Forest virus is an alphavirus found in central, eastern, and southern Africa. It was first isolated from mosquitoes in the Semliki Forest, Uganda by the Uganda Virus Research Institute in 1942 and described by Smithburn and Haddow. ...
. Liquid membranes formed from SDS in water have been demonstrated to work as unusual particle separators. The device acts as a reverse filter, allowing large particles to pass while capturing smaller particles.


Production

SDS is synthesized by treating lauryl alcohol with sulfur trioxide, oleum, or chlorosulfuric acid to produce hydrogen lauryl sulfate. Lauryl alcohol can be used in pure form or as a mixtures of fatty alcohols. When produced from these sources, "SDS" products are a mixture of various sodium alkyl sulfates with SDS being the main component. For instance, SDS is a component, along with other chain-length amphiphiles, when produced from coconut oil, and is known as sodium coco sulfate (SCS). SDS is available commercially in powder, pellet, and other forms (each differing in rates of dissolution), as well as in aqueous solutions of varying concentrations.


Safety

SDS is not
carcinogen A carcinogen is any substance, radionuclide, or radiation that promotes carcinogenesis (the formation of cancer). This may be due to the ability to damage the genome or to the disruption of cellular metabolic processes. Several radioactive subs ...
ic in low concentrations according to some studies... Like all detergents, sodium lauryl sulfate removes oils from the
skin Skin is the layer of usually soft, flexible outer tissue covering the body of a vertebrate animal, with three main functions: protection, regulation, and sensation. Other animal coverings, such as the arthropod exoskeleton, have different de ...
, and can cause skin and eye irritation. It has been shown to irritate the skin of the face, with prolonged and constant exposure (more than an hour) in young adults. SDS may worsen skin problems in individuals with chronic skin hypersensitivity, with some people being affected more than others.


Oral concerns

SDS is a common ingredient in toothpastes due to its low cost, its lack of impact on taste, and its desirable action as a foaming agent.


VSCs

SDS may reduce the amount of
bad breath Bad breath, also known as halitosis, is a symptom in which a noticeably unpleasant breath odour is present. It can result in anxiety among those affected. It is also associated with depression and symptoms of obsessive compulsive disorder. Th ...
-causing volatile sulfur compounds (VSCs) in the mouth. A series of small crossover studies (25–34 patients) have supported the efficacy of SLS in the reduction of VSCs, and its related positive impact on breath malodor, although these studies have been generally noted to reflect technical challenges in the control of study design variables.


Dry mouth

Primary sources from the group of Irma Rantanen at University of Turku, Finland claim that SLS-containing pastes cause more dry mouth (
xerostomia Xerostomia, also known as dry mouth, is dryness in the mouth, which may be associated with a change in the composition of saliva, or reduced salivary flow, or have no identifiable cause. This symptom is very common and is often seen as a side eff ...
) than their proposed alternative. However, a 2011 Cochrane review of these studies, and of the more general area, concludes that there "is no strong evidence… that any topical therapy is effective for relieving the symptom of dry mouth."


Mouth ulceration

A safety concern has been raised on the basis of several studies regarding the effect of toothpaste SDS on
aphthous ulcers Aphthous stomatitis, or recurrent aphthous stomatitis (RAS), is a common condition characterized by the repeated formation of benign and non- contagious mouth ulcers (aphthae) in otherwise healthy individuals. The informal term ''canker sore'' ...
(more specifically, mouth ulcers or "canker sores"), commonly referred to as canker or white sores. According to the NHS, SLS is a cause for concern for mouth ulcers.Some of the published studies, from latest to earliest, are as follows. (i) A 2012 double-blind crossover study of 90-patients failed to find a significant difference in number of ulcers between groups using SLS-containing toothpaste, versus a group using an SLS-free toothpaste, but did suggest significant reduction in ulcer duration and improvement in patient pain scores, see , a study also cited in the Lippert (2013) book chapter. (ii) A 1999 double-blind crossover study of 47 patients failed to find any statistically significant difference in the number, episodes, and duration of such ulcers between these two groups, and of pain scores between them, see (iii) A 1997 study suggested a significantly higher number of ulcers after SLS toothpaste use, versus its control group, see , a study also cited in the Lippert (2013) book chapter. (iv) A 1996 follow-up 30-patient
double-blind In a blind or blinded experiment, information which may influence the participants of the experiment is withheld until after the experiment is complete. Good blinding can reduce or eliminate experimental biases that arise from a participants' expec ...
crossover study and a 1994 preliminary 10-patient
crossover study In medicine, a crossover study or crossover trial is a longitudinal study in which subjects receive a sequence of different treatments (or exposures). While crossover studies can be observational studies, many important crossover studies are con ...
by the same authors suggested significantly higher numbers of aphthous ulcers after using SLS-containing toothpaste, compared with an SLS-free toothpaste, see and
As Lippert notes, of 2013, "very few… marketed toothpastes contain a surfactant other than SLS DS" and leading manufacturers continue to formulate their produce with SDS.


See also

*
Sodium tetradecyl sulfate Sodium tetradecyl sulfate (STS) is a common anionic surfactant. The compound consists of the sodium salt of the micelle-forming sulfate ester of tetradecanol. It is a white, water-soluble solid of low toxicity with many practical uses. App ...
, another anionic surfactant in common use *
Mouth ulcer A mouth ulcer (aphtha) is an ulcer that occurs on the mucous membrane of the oral cavity. Mouth ulcers are very common, occurring in association with many diseases and by many different mechanisms, but usually there is no serious underlying ca ...


References


External links


Josh Clark, "Why does orange juice taste bad after you brush your teeth?"
* published on Aug 24, 2018
Science (journal) ''Science'', also widely referred to as ''Science Magazine'', is the peer-reviewed academic journal of the American Association for the Advancement of Science (AAAS) and one of the world's top academic journals. It was first published in 188 ...
{{Laxatives Organic sodium salts Cleaning product components Anionic surfactants Laxatives Excipients Reagents for biochemistry Sulfate esters