Sodium tetradecyl sulfate

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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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]

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]

References

^ ^a ^b Holmberg, Krister (2019). "Surfactants". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. pp. 1–56. doi:10.1002/14356007.a25_747.pub2. ISBN 9783527306732. S2CID 242339510.
^ 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. S2CID 21358174.
^ 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.
^ Fibro-Vein history and details

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[Ull-1] Holmberg, Krister (2019). "Surfactants". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. pp. 1–56. doi:10.1002/14356007.a25_747.pub2. ISBN 9783527306732. S2CID 242339510.

[Jenkinson_2017-2] 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. S2CID 21358174.

[Burling_2019-3] 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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