Sodium tetradecyl sulfate

Sodium tetradecyl sulfate (STS) is a commonly used synonym for 7-ethyl-2-methyl-4-undecanyl sulfate sodium salt[1] which is anionic surfactant that is 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. 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. [2] 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%.[3]

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
PubChem CID	14492
ChemSpider	8440
UNII	Q1SUG5KBD6
ChEMBL	ChEMBL1200354
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 Key:FVEFRICMTUKAML-UHFFFAOYSA-M
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Synthesis

It may be prepared by the aldol condensation of methyl isobutyl ketone and 2-ethylhexanal (which is itself formed by the aldol self-concensation of butyraldehyde), followed by sulfonation of the resulting alcohol.

References

1. "SOTRADECOL® (Sodium tetradecyl sulfate)" (PDF). Retrieved 29 August 2014.
3. Fibro-Vein history and details

4. Medical research paper Dr Fraser Burling.