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street name for lysergic acid diethylamide (同)back breaker, battery-acid, dose, dot, Elvis, loony toons, Lucy in the sky with diamonds, pane, superman, window pane, Zen
any of various water-soluble compounds having a sour taste and capable of turning litmus red and reacting with a base to form a salt
having the characteristics of an acid; "an acid reaction"

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酸性の / 酸味のある,すっぱい(sour) / (言葉・態度などが)厳しい,しんらつな / 酸 / すっぱいもの / 《俗》=LSD

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出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2016/12/07 00:54:16」(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.

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

^ ^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. doi:10.1002/andp.18331030213. ISSN 0003-3804.
^ 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.
^ 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.
^ 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.
^ 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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3. 妊娠中の葉酸補充 folic acid supplementation in pregnancy
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English Journal

A mechanistic change results in 100 times faster CH functionalization for ethane versus methane by a homogeneous Pt catalyst.

Konnick MM1, Bischof SM, Yousufuddin M, Hashiguchi BG, Ess DH, Periana RA.
Journal of the American Chemical Society.J Am Chem Soc.2014 Jul 16;136(28):10085-94. doi: 10.1021/ja504368r. Epub 2014 Jun 30.
The selective, oxidative functionalization of ethane, a significant component of shale gas, to products such as ethylene or ethanol at low temperatures and pressures remains a significant challenge. Herein we report that ethane is efficiently and selectively functionalized to the ethanol ester of H2
PMID 24925375

Radiation metabolomics. 5. Identification of urinary biomarkers of ionizing radiation exposure in nonhuman primates by mass spectrometry-based metabolomics.

Johnson CH1, Patterson AD, Krausz KW, Kalinich JF, Tyburski JB, Kang DW, Luecke H, Gonzalez FJ, Blakely WF, Idle JR.
Radiation research.Radiat Res.2012 Oct;178(4):328-40. Epub 2012 Sep 6.
Mass spectrometry-based metabolomics has previously demonstrated utility for identifying biomarkers of ionizing radiation exposure in cellular, mouse and rat in vivo radiation models. To provide a valuable link from small laboratory rodents to humans, γ-radiation-induced urinary biomarkers were inv
PMID 22954391

Identification of isethionic acid and other small molecule metabolites of Fragilariopsis cylindrus with nuclear magnetic resonance.

Boroujerdi AF1, Lee PA, DiTullio GR, Janech MG, Vied SB, Bearden DW.
Analytical and bioanalytical chemistry.Anal Bioanal Chem.2012 Aug;404(3):777-84. doi: 10.1007/s00216-012-6169-2. Epub 2012 Jul 8.
Nuclear magnetic resonance (NMR) spectroscopy has been used to obtain metabolic profiles of the polar diatom Fragilariopsis cylindrus, leading to the identification of a novel metabolite in this organism. Initial results from an ongoing metabolomics study have led to the discovery of isethionic acid
PMID 22772138

Japanese Journal

Characterization of N-methyl-L-methionine sulfoxide and isethionic acid from the red alga Grateloupia doryphora

SIMON-COLIN Christelle,KERVAREC Nelly,PICHON Roger,BESSIERES Marie-anne,DESLANDES Eric
Phycological research 50(2), 125-128, 2002-06-01
NAID 10010848721

Isethionic acid from the marine red alga Ceramium flaccidum

BARROW K. D.
Phytochemistry 34, 1429-1430, 1993
NAID 30003910145

「isethionate」

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