sodium tetradecyl sulfate
{{Short description|Anionic surfactant in common use}}
{{Hatnote|Compare sodium dodecyl sulfate and sodium laureth sulfate, which are also anionic surfactants in common use.}}
{{Use dmy dates|date=January 2022}}
{{Drugbox
| Verifiedfields = changed
| Watchedfields = changed
| verifiedrevid = 459450489
| IUPAC_name = Sodium 7-ethyl-2-methyl-4-undecanyl sulfate
| image = Sodium 7-ethyl-2-methyl-4-undecanyl sulfate.svg
| tradename =
| Drugs.com = {{drugs.com|CDI|sodium_tetradecyl_sulfate}}
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| legal_UK =
| legal_US =
| legal_status = Prescription only
| routes_of_administration = Intravenous injection
| bioavailability =
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| CAS_number_Ref = {{cascite|changed|CAS}}
| CAS_number = 139-88-8
| ATC_prefix = C05
| ATC_suffix = BB04
| PubChem = 14492
| DrugBank_Ref = {{drugbankcite|correct|drugbank}}
| DrugBank =
| UNII_Ref = {{fdacite|changed|FDA}}
| UNII = Q1SUG5KBD6
| ChEMBL_Ref = {{ebicite|changed|EBI}}
| ChEMBL = 1200354
| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}}
| ChemSpiderID = 8440
| C=14 | H=29 | Na=1 | O=4 | S=1
| smiles = CCCCC(CC)CCC(CC(C)C)OS(=O)(=O)[O-].[Na+]
| StdInChI_Ref = {{stdinchicite|changed|chemspider}}
| StdInChI = 1S/C14H30O4S.Na/c1-5-7-8-13(6-2)9-10-14(11-12(3)4)18-19(15,16)17;/h12-14H,5-11H2,1-4H3,(H,15,16,17);/q;+1/p-1
| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}}
| StdInChIKey = FVEFRICMTUKAML-UHFFFAOYSA-M
| synonyms = 7-Ethyl-2-methyl-4-hendecanol sulfate sodium salt
}}
Sodium tetradecyl sulfate (STS), also known by its INCI name, sodium myristyl sulfate, 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.{{Ullmann |doi=10.1002/14356007.a25_747.pub2|title=Surfactants|year=2019|last1=Holmberg|first1=Krister|pages=1–56|isbn=9783527306732|s2cid=242339510}}
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.{{cite journal | vauthors = Jenkinson HA, Wilmas KM, Silapunt S | title = Sodium Tetradecyl Sulfate: A Review of Clinical Uses | journal = Dermatologic Surgery | volume = 43 | issue = 11 | pages = 1313–1320 | date = November 2017 | pmid = 28430735 | doi = 10.1097/DSS.0000000000001143 | s2cid = 21358174 }} Being a detergent, its action is on the lipid 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.{{cite journal | vauthors = Burling F | title = Comparison of tetradecyl sulfate versus polidocanol injections for stabilisation of joints that regularly dislocate in an Ehlers-Danlos population | journal = BMJ Open Sport & Exercise Medicine | volume = 5 | issue = 1 | pages = e000481 | date = 2019 | pmid = 30792884 | pmc = 6350757 | doi = 10.1136/bmjsem-2018-000481 }}
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%.[http://www.fibro-vein.co.uk Fibro-Vein history and details]
Synthesis
Tetradecyl alcohol is treated with sulfur trioxide followed by neutralization of the resulting pyrosulfuric acid with sodium hydroxide.
References
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