Sodium Dodecyl Sulfate
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Sodium dodecyl sulfate (SDS) or sodium lauryl sulfate (SLS), sometimes written sodium laurilsulfate, is an
organic compound Some chemical authorities define an organic compound as a chemical compound that contains a carbon–hydrogen or carbon–carbon bond; others consider an organic compound to be any chemical compound that contains carbon. For example, carbon-co ...
with the
formula In science, a formula is a concise way of expressing information symbolically, as in a mathematical formula or a ''chemical formula''. The informal use of the term ''formula'' in science refers to the general construct of a relationship betwe ...
and structure . 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 conven ...
ic
surfactant Surfactants are chemical compounds that decrease the surface tension or interfacial tension between two liquids, a liquid and a gas, or a liquid and a solid. The word ''surfactant'' is a Blend word, blend of "surface-active agent", coined in ...
used in many cleaning and hygiene products. This compound is the sodium
salt In common usage, salt is a mineral composed primarily of sodium chloride (NaCl). When used in food, especially in granulated form, it is more formally called table salt. In the form of a natural crystalline mineral, salt is also known as r ...
of the 12-carbon
organosulfate In organosulfur chemistry, organosulfates are a class of organic compounds sharing a common functional group with the structure . The core is a sulfate group and the R group is any organic residue. All organosulfates are formally esters deri ...
. 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 Hydrophobe, hydrophobic; their odor is usually fain ...
tail combined with a polar " headgroup" give the compound
amphiphilic In chemistry, an amphiphile (), or amphipath, is a chemical compound possessing both hydrophilic (''water-loving'', polar) and lipophilic (''fat-loving'', nonpolar) properties. Such a compound is called amphiphilic or amphipathic. Amphiphilic c ...
properties that make it useful as a
detergent A detergent is a surfactant or a mixture of surfactants with Cleanliness, cleansing properties when in Concentration, dilute Solution (chemistry), solutions. There are a large variety of detergents. A common family is the alkylbenzene sulfonate ...
. SDS is also component of mixtures produced from inexpensive
coconut The coconut tree (''Cocos nucifera'') is a member of the palm tree family (biology), family (Arecaceae) and the only living species of the genus ''Cocos''. The term "coconut" (or the archaic "cocoanut") can refer to the whole coconut palm, ...
and
palm oil Palm oil is an edible vegetable oil derived from the mesocarp (reddish pulp) of the fruit of oil palms. The oil is used in food manufacturing, in beauty products, and as biofuel. Palm oil accounted for about 36% of global oils produced from o ...
s. 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 chemistry, 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) in water at 25 °C is 8.2 mM, and the
aggregation number In colloidal chemistry, 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 ...
at this concentration is usually considered to be about 62. The
micelle A micelle () or micella () ( 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 colloidal system). ...
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 Surfactants are chemical compounds that decrease the surface tension or interfacial tension between two liquids, a liquid and a gas, or a liquid and a solid. The word ''surfactant'' is a Blend word, blend of "surface-active agent", coined in ...
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 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 Generally recognized as safe (GRAS) is a United States Food and Drug Administration (FDA) designation that a chemical or substance added to food is considered safe by experts under the conditions of its intended use. An ingredient with a GRAS d ...
(GRAS) ingredient for food use according to the USFDA (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 t ...
or
DNA extraction The first isolation of deoxyribonucleic acid (DNA) was done in 1869 by Friedrich Miescher. DNA extraction is the process of isolating DNA from the cells of an organism isolated from a sample, typically a biological sample such as blood, saliva, ...
, inhibiting the activity of nucleases, enzymes that can degrade DNA, protecting the integrity of the isolated genetic material, and for denaturing proteins in preparation for
electrophoresis Electrophoresis is the motion of charged dispersed particles or dissolved charged molecules relative to a fluid under the influence of a spatially uniform electric field. As a rule, these are zwitterions with a positive or negative net ch ...
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 Leland Stanford Junior University, commonly referred to as Stanford University, is a Private university, private research university in Stanford, California, United States. It was founded in 1885 by railroad magnate Leland Stanford (the eighth ...
, 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 residue (biochemistry), residues. Proteins perform a vast array of functions within organisms, including Enzyme catalysis, catalysing metab ...
s,
nucleic acid Nucleic acids are large biomolecules that are crucial in all cells and viruses. They are composed of nucleotides, which are the monomer components: a pentose, 5-carbon sugar, a phosphate group and a nitrogenous base. The two main classes of nuclei ...
s, 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 In physics, scattering is 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 particles and radia ...
with minimal protein loss, rendering the tissue quasi-transparent. Along with sodium dodecylbenzene sulfonate 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-tetr ...
, aqueous solutions of SDS are popular for dispersing or suspending nanotubes, such as
carbon nanotube A carbon nanotube (CNT) is a tube made of carbon with a diameter in the nanometre range ( nanoscale). They are one of the allotropes of carbon. Two broad classes of carbon nanotubes are recognized: * ''Single-walled carbon nanotubes'' (''S ...
s.


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 Cell (biology), cells of an organism. Viruses infect all life forms, from animals and plants to microorganisms, including bacteria and archaea. Viruses are ...
es such as the
herpes simplex virus Herpes simplex virus 1 and 2 (HSV-1 and HSV-2) are two members of the Herpesviridae#Human herpesvirus types, human ''Herpesviridae'' family, a set of viruses that produce Viral disease, viral infections in the majority of humans. Both HSV-1 a ...
es, HIV, and the
Semliki Forest virus 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. It ...
. 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

Dodecyl alcohol is sulfated using
sulfur trioxide Sulfur trioxide (alternative spelling sulphur trioxide) is the chemical compound with the formula SO3. It has been described as "unquestionably the most conomicallyimportant sulfur oxide". It is prepared on an industrial scale as a precursor to ...
. The reaction proceeds by initial formation of the pyrosulfate: : : Several million tons are produced annually. SDS can also be synthesized by treating lauryl alcohol with chlorosulfuric acid. The resulting half ester of sulfuric acid is then neutralized with alkali. 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 In chemistry, an amphiphile (), or amphipath, is a chemical compound possessing both hydrophilic (''water-loving'', polar) and lipophilic (''fat-loving'', nonpolar) properties. Such a compound is called amphiphilic or amphipathic. Amphiphili ...
, 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 agent that promotes the development of cancer. Carcinogens can include synthetic chemicals, naturally occurring substances, physical agents such as ionizing and non-ionizing radiation, and biologic agents such as viruse ...
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 ...
, 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 The University of Turku (, shortened ''UTU'') is a multidisciplinary public university with eight faculties located in the city of Turku in southwestern Finland. The university also has campuses in Rauma and Pori and research stations in Kevo ...
, Finland claim that SLS-containing pastes cause more dry mouth (
xerostomia Xerostomia, also known as dry mouth, is a subjective complaint of dryness in the mouth, which may be associated with a change in the composition of saliva, reduced salivary flow, or have no identifiable cause. This symptom is very common and is o ...
) 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 (more specifically,
mouth ulcer A mouth ulcer (aphtha), or sometimes called a canker sore or salt blister, 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 mechanis ...
s or "canker sores"), commonly referred to as canker or white sores. According to the NHS and Alessandro Villa of the Miami Cancer Institute, 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 c ...
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 Surfactants are chemical compounds that decrease the surface tension or interfacial tension between two liquids, a liquid and a gas, or a liquid and a solid. The word ''surfactant'' is a Blend word, blend of "surface-active agent", coined in ...
other than SLS DS" and leading manufacturers continue to formulate their produce with SDS. According to Allesandro Villa of the Miami Cancer Institute, one theory is that SLS disrupts the protective layer of mucus covering the mouth.


See also

* Sodium tetradecyl sulfate, another anionic surfactant in common use *
Mouth ulcer A mouth ulcer (aphtha), or sometimes called a canker sore or salt blister, 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 mechanis ...


References


External links


Josh Clark, "Why does orange juice taste bad after you brush your teeth?"
* published on Aug 24, 2018
Science (journal) ''Science'' is the peer review, 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 1880, is currently circulated weekly and h ...
{{Laxatives Organic sodium salts Cleaning product components Anionic surfactants Laxatives Excipients Reagents for biochemistry Sulfate esters Dodecyl compounds