ISETHIONIC ACID

CAS Number: 107-36-8  
Chemical formula: C2H6O4S
Molar mass: 126.13 g/mol
Preferred IUPAC name: 2-Hydroxyethane-1-sulfonic acid

Isethionic acid is an organosulfur compound containing an alkylsulfonic acid located beta to a hydroxy group. 
Isethionic acids discovery is generally attributed to Heinrich Gustav Magnus, who prepared it by the action of solid sulfur trioxide on ethanol in 1833.
Isethionic acid is a white water-soluble solid used in the manufacture of certain surfactants and in the industrial production of taurine. 
Isethionic acid is most commonly available in the form of its sodium salt (sodium isethionate).

Isethionic acid is a major metabolite in F. cylindrus. 
Isethionic acid is a organosulfur compound containing a short chain alkane sulfonate linked to a hydroxyl group. 
Isethionic acid is a water-soluble liquid used in the manufacture of mild, biodegradable, and high-foaming anionic surfactants.

Applications of Isethionic acid:
Isethionic acid sodium salt is an amphoteric detergent used in detergent bar soaps. 
Isethionic acid makes a dense lather in addition to the lather made by the soap. 

Isethionic acid is mild on the skin, and non-drying. 
Isethionic acid works equally well in soft or hard water. 
Isethionic acid is also an anti-static agent in shampoos.

Synthesis of Isethionic acid:
Isethionic acids original synthesis, by the reaction of sulfur trioxide on ethanol, has largely been surpassed. 
Isethionic acid may be produced by the hydrolysis of carbyl sulfate, which is obtained by the sulfonation of ethylene.

Reactions of Isethionic acid:
Isethionic acid is used as a starting material in the industrial production of taurine.
Dehydration of isethionic acid gives vinylsulfonic acid.

Derivatives of Isethionic acid:
Fatty acid esters of isethionic acid (such as sodium lauroyl isethionate and sodium cocoyl isethionate) are used as biodegradable anionic surfactants.
These materials are much milder to skin that other sulfate based surfactants (i.e. sodium lauryl sulfate) 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.

Biological importance of Isethionic acid:
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.

Preferred IUPAC name:
2-Hydroxyethane-1-sulfonic acid

Isethionic acid (2-hydroxyethane sulfonic acid) and floridoside (2-O-alpha-D-galactopyranosylglycerol) were extracted from the red alga, Grateloupia turuturu, and tested for anti-settlement activity against cyprid larvae of the tropical barnacle, Balanus amphitrite and for their toxicity to nauplius larvae. 
Isethionic acid was active for anti-settlement but had the disadvantage of being toxic to nauplius larvae. 
Floridoside was a potent inhibitor of cyprid settlement at non-toxic concentrations to nauplii (0.01 mg ml(-1)).

CAS Number: 107-36-8  
CHEBI: 1157 
ChemSpider: 7578  
ECHA InfoCard: 100.003.169  
KEGG: C05123 
PubChem CID: 7866
UNII: 97J3QN9884 
CompTox Dashboard (EPA): DTXSID1041427

Isethionic acid (2-Hydroxyethanesulfonic acid) is an organosulfur compound. 
Isethionic acid is widely distributed in animal species and in a few red algal species. 
Isethionic acid can be used as an anionic detergent and has anti-settlement activity against Balanus amphitrite.

Isethionic acid is an organosulfur compound containing a short chain alkane sulfonate linked to a hydroxyl group. 
Isethionic acid is a water-soluble liquid used in the manufacture of mild, biodegradable, and high-foaming anionic surfactants. 
These surfactants provide gentle cleansing and a soft skin feel. 
Isethionic acid forms a colourless, syrupy, and strongly acidic liquid that can form detergents with oleic acid. 
Isethionic acid is frequently used in the industrial production of taurine. 
Mammals are also able to endogenously synthesize Isethionic acid via taurine through a possible enzymatic deamination process. 
Isethionic acid can be found in both human plasma and urine. 
Higher plasma levels of Isethionic acid have been shown to be protective against type 2 diabetes.

Chemical formula: C2H6O4S
Molar mass: 126.13 g/mol
Density: 1.63 g/cm3
Acidity (pKa): 1.39 (predicted)

Description of Isethionic acid:    
Isethionic acid (C2H6O4S) is a short chain alkane sulfonate containing hydroxy group, is a water soluble liquid used in the manufacture of mild, biodegradable and high foaming anionic surfactants which provides gentle cleansing and soft skin feel.
Isethionic acid is a colorless, syrupy, strongly acidic liquid that can form detergents with oleic acid. 
The Pseudomonas aeruginosa ssuEADCB gene cluster is required for the utilization of alkanesulfonates (such as isethionic acid) as sulfur sources, and is expressed under conditions of sulfate or cysteine starvation.

Molecular Weight: 126.13     
XLogP3-AA: -1.6     
Hydrogen Bond Donor Count: 2     
Hydrogen Bond Acceptor Count: 4     
Rotatable Bond Count: 2     
Exact Mass: 125.99867984 
Monoisotopic Mass: 125.99867984 
Topological Polar Surface Area: 83 Ų 
Heavy Atom Count: 7     
Complexity: 117     
Isotope Atom Count: 0     
Defined Atom Stereocenter Count: 0     
Undefined Atom Stereocenter Count: 0     
Defined Bond Stereocenter Count: 0     
Undefined Bond Stereocenter Count: 0     
Covalently-Bonded Unit Count: 1     
Compound Is Canonicalized: Yes     

Chemical Name: 2-Hydroxyethanesulphonic acid
Synonyms:    Isethionic acid; Ethanolsulfonic acid; Hydroxyethylsulfonic acid;
SMILES: OCCS(=O)(O)=O
Formula: C2H6O4S
M.Wt:    126.13

Formula: C2H6O4S
Net Charge: 0
Average Mass: 126.13200
Monoisotopic Mass: 125.99868
InChI: InChI=1S/C2H6O4S/c3-1-2-7(4,5)6/h3H,1-2H2,(H,4,5,6)
InChIKey: SUMDYPCJJOFFON-UHFFFAOYSA-N
SMILES: OCCS(O)(=O)=O

Substituents:    
-Alkanesulfonic acid
-Sulfonyl
-Organosulfonic acid
-Organic oxygen compound
-Organic oxide
-Hydrocarbon derivative
-Primary alcohol
-Organosulfur compound
-Organooxygen compound
-Alcohol
-Aliphatic acyclic compound

ISETHIONIC ACID
107-36-8
2-Hydroxyethanesulfonic acid
2-Hydroxyethanesulphonic acid
Ethanesulfonic acid, 2-hydroxy-
Ethanolsulfonic acid
Hydroxyethylsulfonic acid
2-Hydroxyethane-1-sulfonic acid
Caswell No. 502
(2-Hydroxyethyl)sulfonic acid
2-Hydroxyethanesulfonate
Kyselina isethionova
USAF DO-14
Kyselina isethionova [Czech]
2-hydroxyethylsulfonic acid
EPA Pesticide Chemical Code 047701
BRN 1751214
Kyselina 2-hydroxyethansulfonova [Czech]
UNII-97J3QN9884
AI3-19644
Potassium isethionate
97J3QN9884
2-hydroxyethane-1-sulfonate
MFCD00242599
NSC1898
Sodium beta-hydroxyethanesulfonate
21561-88-6
2-Hydroxyethanesulfonic acid(80% in water)
EINECS 203-484-3
NSC 60516
C2H6O4S
Ethanolsulfonate
Kyselina 2-hydroxyethansulfonova
8X3
Hydroxyethylsulfonate
2-Hydroxyethanesulphonate
(2-Hydroxyethyl)sulfonate
SCHEMBL827
WLN: WSQ2Q
bmse000242
bmse000819
Isethionic Acid, Free Base
2-oxidanylethanesulfonic acid
4-04-00-00084 (Beilstein Handbook Reference)
beta-hydroxyethanesulfonic acid
CHEBI:1157
DTXSID1041427
HY-Y0095
NSC60516
ZINC3875755
5066AH
AC-538
NSC-60516
AKOS006228878
ACN-053378
CS-W019640
MCULE-8075949368
AS-44331
FT-0627313
Isethionic acid pound 80% in water pound(c)
C05123
11039-EP2269610A2
11039-EP2269988A2
11039-EP2270008A1
11039-EP2275401A1
11039-EP2275413A1
11039-EP2277848A1
11039-EP2281563A1
11039-EP2287156A1
11039-EP2289510A1
11039-EP2289890A1
11039-EP2292617A1
11039-EP2301940A1
11039-EP2305646A1
11039-EP2311807A1
11039-EP2311842A2
11039-EP2316457A1
11039-EP2316458A1
11039-EP2316459A1
11039-EP2316825A1
11039-EP2316826A1
11039-EP2316827A1
11039-EP2316828A1
27244-EP2292234A1
27244-EP2292611A1
27244-EP2314575A1
107I368
A801683
Q339734
W-108750
2-HYDROXYETHANESULPHONIC ACID (80% IN WATER)
(2-Hydroxyethyl)sulfonic acid
107-36-8 [RN]
203-484-3 [EINECS]
2-Hydroxyethane-1-sulfonic acid
2-Hydroxyethanesulfonic acid [ACD/IUPAC Name]
2-Hydroxyethanesulphonic acid
2-Hydroxyethansulfonsäure [German] [ACD/IUPAC Name]
2-hydroxyethylsulfonic acid
Acide 2-hydroxyéthanesulfonique [French] [ACD/IUPAC Name]
Ethanesulfonic acid, 2-hydroxy- [ACD/Index Name]
Isethionic acid [Wiki]
WSQ2Q [WLN]
[107-36-8]
1-Cbz-2-ethylpiperidin-4-one
1N7
2-Hydroxyethanesulfonic acid, 80% in water
2-Hydroxyethanesulphonic acid (80% in water)
4-04-00-00084 (Beilstein Handbook Reference) [Beilstein]
4-04-00-04261 [Beilstein]
benzyl 2-ethyl-4-oxopiperidine-1-carboxylate
CHAPSO
EINECS 203-484-3
Ethanolsulfonic acid
Hydroxyethanesulfonic acid
hydroxyethanesulfonic acid (hes)
Hydroxyethylsulfonate
Hydroxyethylsulfonic acid
Jsp000660
Kyselina 2-hydroxyethansulfonova [Czech]
Kyselina 2-hydroxyethansulfonova [Czech]
Kyselina isethionova [Czech]
Kyselina isethionova
Kyselina isethionova [Czech]
MFCD00242599
sulfoacetic acid [ACD/IUPAC Name]
WLN: WSQ2Q
β-hydroxyethanesulfonic acid

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