Sodium tetradecyl sulfate (STS), also known by its

INCI The International Nomenclature of Cosmetic Ingredients (INCI) are the unique identifiers for cosmetic ingredients such as waxes, oils, pigments, and other chemicals that are assigned in accordance with rules established by the Personal Care Pro ...

name, sodium myristyl sulfate, is a common

anionic 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 convent ...

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 ...

. The compound consists of the sodium salt of 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). ...

-forming

sulfate ester 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 Organyl group, organic residue. All organosulfates are formally ...

of tetradecanol. It is a white, water-soluble solid of low toxicity with many practical uses.

Applications

Medicine

It the active component of the sclerosant drugs Sotradecol and Fibrovein. It is commonly used in the treatment of varicose and spider veins of the leg, during the procedure of

sclerotherapy Sclerotherapy (the word reflects the Greek ''skleros'', meaning ''hard'') is a procedure used to treat blood vessel malformations ( vascular malformations) and also malformations of the lymphatic system. A medication is injected into the vessels ...

. Being 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 ...

, its action is on the

lipid Lipids are a broad group of organic compounds which include fats, waxes, sterols, fat-soluble vitamins (such as vitamins A, D, E and K), monoglycerides, diglycerides, phospholipids, and others. The functions of lipids include storing ...

molecules in the cells of the vein wall, causing inflammatory destruction of the internal lining of the vein and thrombus formation eventually leading to sclerosis of the vein. It is used in concentrations ranging from 0.1% to 3% for this purpose. It is occasionally used for the treatment of stabilisation of joints that regularly dislocate, particularly in patients with Ehlers-Danlos syndrome. In the UK, Ireland, Italy, Australia, New Zealand and South Africa, it is sold under the trade-name Fibro-Vein in concentrations of 0.2%, 0.5%, 1.0%, and 3%.Fibro-Vein history and details
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Synthesis

Tetradecyl alcohol is treated with

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 ...

followed by neutralization of the resulting pyrosulfuric acid with sodium hydroxide.

References

Organic sodium salts Sulfate esters Anionic surfactants {{cardiovascular-drug-stub