イセチオン酸、イセチオン酸塩

関: isethionic acid

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出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2017/09/06 17:53:26」(JST)

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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. It is most commonly available in the form of its sodium salt (sodium isethionate).

Synthesis

Its original synthesis, by the reaction of sulfur trioxide on ethanol,^[1] has largely been surpassed. It may be produced by the hydrolysis of carbyl sulfate, which is obtained by the sulfonation of ethylene.

However the most common route is the reaction of ethylene oxide with aqueous sodium bisulfite, which produces the sodium salt (sodium isethionate):

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

^ ^a ^b 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. ISSN 0003-3804. doi:10.1002/andp.18331030213.
^ Kosswig, Kurt (2000). "Sulfonic Acids, Aliphatic". Ullmann's Encyclopedia of Industrial Chemistry. Wiley-VCH. ISBN 3-527-30673-0. doi:10.1002/14356007.a25_503.
^ Petter, P. J. (1984). "Fatty acid sulphoalkyl amides and esters as cosmetic surfactants". International Journal of Cosmetic Science. 6 (5): 249–260. ISSN 0142-5463. doi:10.1111/j.1467-2494.1984.tb00382.x.
^ 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. ISSN 0105-1873. doi:10.1111/j.1600-0536.1999.tb06082.x.
^ Wicho, H, ed. (2009). Austria-Codex Stoffliste (in German) (42 ed.). Vienna: Österreichischer Apothekerverlag.
^ 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.

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[Good outcome in Acanthamoeba keratitis].

Reichart-Peter S1, Manousaridis K2, Dirschmid H3, Mennel S2.
Der Ophthalmologe : Zeitschrift der Deutschen Ophthalmologischen Gesellschaft.Ophthalmologe.2016 Aug 24. [Epub ahead of print]
A 31-year-old woman presented with mild keratitis of her left eye. The use of daily disposable contact lenses, regularly rinsed with tap water, and the development of perineural corneal infiltrates resulted in the clinical suspicion of infection with Acanthamoeba. Corneal epithelial scraping probe f
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Monitoring the response of patients with cutaneous leishmaniasis to treatment with pentamidine isethionate by quantitative real-time PCR, and identification of Leishmania parasites not responding to therapy.

Mans DR1, Kent AD1, Hu RV2, Lai A Fat EJ3, Schoone GJ4, Adams ER4, Rood EJ4, Alba S4, Sabajo LO2, Lai A Fat RF3, de Vries HJ5,6,7, Schallig HD4.
Clinical and experimental dermatology.Clin Exp Dermatol.2016 Aug;41(6):610-5. doi: 10.1111/ced.12786. Epub 2015 Dec 9.
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Sarnicola E1, Sarnicola C, Sabatino F, Tosi GM, Perri P, Sarnicola V.
Cornea.Cornea.2016 Jan;35(1):1-5. doi: 10.1097/ICO.0000000000000681.
PURPOSE: To evaluate the success (eradication of infection) or failure (recurrence of infection in the cornea or sclera, or endophthalmitis) of early therapeutic deep anterior lamellar keratoplasty (DALK) for active Acanthamoeba keratitis (AK) poorly responsive to medical treatment.METHODS: Retrospe
PMID 26562819

Japanese Journal

Effect of Polyvinylpyrrolidone and Sodium Lauroyl Isethionate on Kaolinite Suspension in an Aqueous Phase

Kwan Chang-Chin,Chu Wen-Hweu,Shimabayashi Saburo
Chemical & pharmaceutical bulletin 54(8), 1082-1087, 2006-08-01
… Suspension of concentrated kaolinite (20g/30ml-medium) in the presence of polyvinylpyrrolidone (PVP) and sodium lauroyl isethionate (SLI) was allowed to evaluate its degree of dispersion based on their rheological studies. …
NAID 110004847222

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… amazonensis and using Pentamidine Isethionate as reference drug. …
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洗浄剤用植物原料の開発と応用 (特集/皮膚の洗浄と洗浄剤を検証する)

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フレグランスジャーナル 29(9), 71-76, 2001-09
NAID 40004479806

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リンク元	「イセチオン酸」「イセチオン酸塩」「isethionic acid」
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「イセチオン酸」

Isethionic acid
	; Isethionic acid
Names
	IUPAC name 2-hydroxyethanesulfonic acid
Identifiers
CAS Number	107-36-8 ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:1157 ;
ChemSpider	7578 ;
ECHA InfoCard	100.003.169
KEGG	C05123 ;
PubChem CID	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/cm3
	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

　　[★]

英: isethionic acid、isethionate
関: イセチオン酸塩

「イセチオン酸塩」

　　[★]

英: isethionate
関: イセチオン酸

「isethionic acid」

　　[★]

イセチオン酸

関: isethionate

「pentamidine isethionate」

　　[★] ペンタミジン。イセチオン酸ペンタミジン

[Magnus1833-1] 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. ISSN 0003-3804. doi:10.1002/andp.18331030213.

[2] Kosswig, Kurt (2000). "Sulfonic Acids, Aliphatic". Ullmann's Encyclopedia of Industrial Chemistry. Wiley-VCH. ISBN 3-527-30673-0. doi:10.1002/14356007.a25_503.

[Petter1984-3] Petter, P. J. (1984). "Fatty acid sulphoalkyl amides and esters as cosmetic surfactants". International Journal of Cosmetic Science. 6 (5): 249–260. ISSN 0142-5463. doi:10.1111/j.1467-2494.1984.tb00382.x.

[TupkerBunte1999-4] 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. ISSN 0105-1873. doi:10.1111/j.1600-0536.1999.tb06082.x.

[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.

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isethionate