Sodium tetradecyl sulfate

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

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.^[1]

Sodium tetradecyl sulfate

Clinical data
Other names	7-Ethyl-2-methyl-4-hendecanol sulfate sodium salt
AHFS/Drugs.com	Consumer Drug Information
Routes of administration	Intravenous injection
ATC code	C05BB04 (WHO)
Legal status
Legal status	In general: ℞ (Prescription only)
Identifiers
IUPAC name Sodium 7-ethyl-2-methyl-4-undecanyl sulfate
CAS Number	139-88-8 N
PubChem CID	14492
ChemSpider	8440 N
UNII	Q1SUG5KBD6
ChEMBL	ChEMBL1200354 N
CompTox Dashboard (EPA)	DTXSID3041530
ECHA InfoCard	100.004.892
Chemical and physical data
Formula	C14H29NaO4S
Molar mass	316.43 g·mol−1
3D model (JSmol)	Interactive image
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 drugs Sotradecol and Fibrovein. 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]