Isethionic acid

Isethionic acid

Isethionic acid
Names
IUPAC name 2-hydroxyethanesulfonic acid
Identifiers
CAS Number	107-36-8
ChEBI	CHEBI:1157
ChemSpider	7578
Jmol interactive 3D	Image
KEGG	C05123
PubChem	7866
InChI InChI=1S/C2H6O4S/c3-1-2-7(4,5)6/h3H,1-2H2,(H,4,5,6) Key: SUMDYPCJJOFFON-UHFFFAOYSA-N InChI=1/C2H6O4S/c3-1-2-7(4,5)6/h3H,1-2H2,(H,4,5,6) Key: SUMDYPCJJOFFON-UHFFFAOYAO
SMILES O=S(=O)(O)CCO
Properties
Chemical formula	C2H6O4S
Molar mass	126.13 g/mol
Density	1.63 g/cm^3
Melting point	191 to 194 °C (376 to 381 °F; 464 to 467 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

Isethionic acid is an organosulfur compound containing a alkylsulfonic acid located beta to a hydroxy group. Its discovery is generally attributed to Heinrich Gustav Magnus, who prepared it by the action of solid sulphur trioxide on ethanol in 1833.^[1] It is a white water-soluble solid used in the manufacture of certain surfactants and in the industrial production of taurine.

Synthesis

Its original synthesis, by the reaction of sulphur trioxide on ethanol,^[1] has largely been surpassed. Modern synthetic methods include the reaction of ethylene oxide with aqueous sodium bisulfite:

It may be produced by the hydrolysis of carbyl sulfate, which is obtained by the sulfonation of ethylene.

Reactions

Isethionic acid is used as a starting material in the industrial production of taurine.

Dehydration of isethionic acid gives vinylsulfonic acid.^[2]

Derivatives

Fatty acid esters of isethionic acid (such as sodium lauroyl isethionate and sodium cocoyl isethionate) are used as biodegradable anionic surfactants.^[3] These materials are much milder to skin that other sulphate based surfactants (i.e. sodium lauryl sulfate)^[4] making them popular for use in make-up, shampoos and ‘Dove type’ soap bars.

Isethionic acid is also used as a counter ion in certain pharmaceutical formulations, including the antimicrobials hexamidine and pentamidine.^[5]

Biological importance

Studies made on dog heart slices suggested that heart tissue may be capable of converting taurine to isethionic acid, further experiments demonstrated that this tissue may synthetize taurine from cystine.^[6]

References

1. Magnus, G. (1833). "Ueber die Weinschwefelsäure, ihren Einfluss auf die Aetherbildung, und über zwei neue Säuren ähnlicher Zusammensetzung". Annalen der Physik und Chemie 103 (2): 367–388. doi:10.1002/andp.18331030213. ISSN 0003-3804.
2. Kosswig, Kurt (2000). "Sulfonic Acids, Aliphatic". Ullmann's Encyclopedia of Industrial Chemistry (Wiley-VCH). doi:10.1002/14356007.a25_503. ISBN 3-527-30673-0.
3. Petter, P. J. (1984). "Fatty acid sulphoalkyl amides and esters as cosmetic surfactants". International Journal of Cosmetic Science 6 (5): 249–260. doi:10.1111/j.1467-2494.1984.tb00382.x. ISSN 0142-5463.
4. Tupker, R. A.; Bunte, E. E.; Fidler, V.; Wlechers, J. W.; Coenraads, P. J. (1999). "Irritancy ranking of anionic detergents using one-time occlusive, repeated occlusive and repeated open tests". Contact Dermatitis 40 (6): 316–322. doi:10.1111/j.1600-0536.1999.tb06082.x. ISSN 0105-1873.
5. Wicho, H, ed. (2009). Austria-Codex Stoffliste (in German) (42 ed.). Vienna: Österreichischer Apothekerverlag.
6. W.O Read and J.D.Welty (1961). "Synthesis of Taurine and Isethionic Acid by Dog Heart Slices". The Journal of Biological Chemistry 237: 1521–1522.