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.[1]

Compare sodium dodecyl sulfate and sodium laureth sulfate, which are also anionic surfactants in common use.

Sodium tetradecyl sulfate
Clinical data
Other names7-Ethyl-2-methyl-4-hendecanol sulfate sodium salt
AHFS/Drugs.comConsumer Drug Information
Routes of
administration		Intravenous injection
ATC code
Legal status
Legal status
  • In general: ℞ (Prescription only)
Identifiers
IUPAC name
  • Sodium 7-ethyl-2-methyl-4-undecanyl sulfate
CAS Number
PubChem CID
ChemSpider
UNII
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.004.892
Chemical and physical data
FormulaC14H29NaO4S
Molar mass316.43 g·mol−1
3D model (JSmol)
SMILES
  • CCCCC(CC)CCC(CC(C)C)OS(=O)(=O)[O-].[Na+]
InChI
  • InChI=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 N
  • Key:FVEFRICMTUKAML-UHFFFAOYSA-M N
 NY (what is this?)  (verify)

Applications

Medicine

It the active component of the sclerosant drug Sotradecol. It is commonly used in the treatment of varicose and spider veins of the leg, during the procedure of sclerotherapy.[2] 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.[3] 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%.[4]

Synthesis

Tetradecyl alcohol is treated with sulfur trioxide followed by neutralization of the resulting pyrosulfuric acid with sodium hydroxide.[1]

References
  1. Holmberg, Krister (2019). "Surfactants". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. pp. 1–56. doi:10.1002/14356007.a25_747.pub2.
  2. Jenkinson HA, Wilmas KM, Silapunt S (November 2017). "Sodium Tetradecyl Sulfate: A Review of Clinical Uses". Dermatologic Surgery. 43 (11): 1313–1320. doi:10.1097/DSS.0000000000001143. PMID 28430735.
  3. Burling F (2019). "Comparison of tetradecyl sulfate versus polidocanol injections for stabilisation of joints that regularly dislocate in an Ehlers-Danlos population". BMJ Open Sport & Exercise Medicine. 5 (1): e000481. doi:10.1136/bmjsem-2018-000481. PMC 6350757. PMID 30792884.
  4. Fibro-Vein history and details


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