- 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
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Isethionic acid
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Names |
IUPAC name
2-hydroxyethanesulfonic acid
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Identifiers |
CAS Number
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3D model (JSmol)
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ChEBI |
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ChemSpider |
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ECHA InfoCard |
100.003.169 |
KEGG |
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InChI
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InChI=1S/C2H6O4S/c3-1-2-7(4,5)6/h3H,1-2H2,(H,4,5,6) Y
Key: SUMDYPCJJOFFON-UHFFFAOYSA-N Y
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InChI=1/C2H6O4S/c3-1-2-7(4,5)6/h3H,1-2H2,(H,4,5,6)
Key: SUMDYPCJJOFFON-UHFFFAOYAO
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Properties |
Chemical formula
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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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Y verify (what is YN ?) |
Infobox references |
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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).
Contents
- 1 Synthesis
- 2 Reactions
- 3 Biological importance
- 4 See also
- 5 References
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]
See also
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.
UpToDate Contents
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English Journal
- [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
- PMID 27558689
- 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.
- BACKGROUND: Leishmania (Viannia) guyanensis is believed to be the principal cause of cutaneous leishmaniasis (CL) in Suriname. This disease is treated with pentamidine isethionate (PI), but treatment failure has increasingly been reported.AIM: To evaluate PI for its clinical efficacy, to compare par
- PMID 26648589
- Early Deep Anterior Lamellar Keratoplasty (DALK) for Acanthamoeba Keratitis Poorly Responsive to Medical Treatment.
- 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
- In Vitro Antiproliferative Effects of Several Diaryl Derivatives on Leishmania spp
- Alves Luciana Vignolio,Do Canto-Cavalheiro Marilene Marcuzzo,Cysne-Finkelstein Lea [他],LEON Leonor
- Biological & pharmaceutical bulletin 26(4), 453-456, 2003-04-01
- … amazonensis and using Pentamidine Isethionate as reference drug. …
- NAID 110003608453
- 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)
Related Links
- [Sodium Isethionate] [1562-00-1] | 価格や在庫、物性値などの詳細情報ページです。 ... ・川口の在庫は即日,つくばの在庫は2〜3日以内の出荷となります。・詳細につきましては,お手数ですが営業部までお問い合わせください。
- forum Join the Word of the Day Mailing List For webmasters TheFreeDictionary Google Bing? Word / Article Starts with Ends with Text ... isethionate /is·eth·i·o·nate/ (i″sĕ-thi´ah-nāt) USAN contraction for 2-hydroxyethanesulfonate. ...
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★リンクテーブル★
[★]
- 英
- isethionic acid、isethionate
- 関
- イセチオン酸塩
[★]
- 英
- isethionate
- 関
- イセチオン酸
[★]
- 関
- isethionate
[★]
ペンタミジン。イセチオン酸ペンタミジン