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Details

Stereochemistry ACHIRAL
Molecular Formula 2C6H6O3S.3H2O
Molecular Weight 370.396
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of BENZENESULFONIC ACID SESQUIHYDRATE

SMILES

O.O.O.OS(=O)(=O)C1=CC=CC=C1.OS(=O)(=O)C2=CC=CC=C2

InChI

InChIKey=HYSWQRQDKRNNIU-UHFFFAOYSA-N
InChI=1S/2C6H6O3S.3H2O/c2*7-10(8,9)6-4-2-1-3-5-6;;;/h2*1-5H,(H,7,8,9);3*1H2

HIDE SMILES / InChI

Description
Curator's Comment: description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/26529301 | https://www.ncbi.nlm.nih.gov/pubmed/28391947 | https://www.ncbi.nlm.nih.gov/pubmed/926196

Benzenesulfonic acid (conjugate base benzenesulfonate) is the simplest aromatic sulfonic acid, that is soluble in water and ethanol, slightly soluble in benzene and insoluble in nonpolar solvents like diethyl ether. Benzenesulfonic acid was first obtained, together with diphenyl sulfone, by E. MITSCHERLICH in 1834 by heating benzene with fuming sulfuric acid. The industrially important reaction of benzenesulfonic acid with alkali hydroxide to form phenol (alkali fusion) was developed by A. WURTZ and A. KEKUL_e in 1867 and by P. O. DEGENER in 1878. Until the early 1960s benzenesulfonic acid was used chiefly in the manufacture of phenol. Benzenesulfonic acid has the characteristic reactions of a strong aromatic sulfonic acid. Acid hydrolysis at 175 C splits it into benzene and sulfuric acid. Additional sulfonation with fuming sulfuric acid gives 1,3-benzenedisulfonic acid, which reacts further to 1,3,5-benzenetrisulfonic acid, and also diphenyl sulfone disulfonic acid. Benzenesulfonic acid is used as an acid catalyst. The sodium salt is used to standardize dyes. A variety of pharmaceutical drugs are prepared as benzenesulfonate salts and are known as besilates (INN) or besylates (USAN).

Approval Year

Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
PubMed

PubMed

TitleDatePubMed
Morpho-histochemical changes in the liver and intestine of young giltheads (fish-nursery), Sparus aurata, L., induced by acute action of the anionic tensioactive alkylbenzene sulphonate.
2001
Antibody-based methods for surfactant screening.
2001 Oct
Role of CA(2+)-activated K+ channels in the regulation of basilar arterial tone in spontaneously hypertensive rats.
2002 Jul
Anti-inflammatory action of sulfoaryl 3,3-disubstituted triazenes in rat experimental edema models.
2003 Oct
Factors contributing to the incompatibility between simplified-step adhesives and chemically-cured or dual-cured composites. Part III. Effect of acidic resin monomers.
2003 Winter
Stereocontrol in organic synthesis using silicon-containing compounds. Studies directed towards the synthesis of ebelactone A.
2004 Apr 7
An in vitro evaluation of human dermal exposure to benzene sulfonate, m-benzene disulfonate and p-phenol sulfonate.
2004 Aug
Preparation of natural alpha-tocopherol from non-alpha-tocopherols.
2004 Dec
New trends in sample preparation: on-line microextraction in packed syringe (MEPS) for LC and GC applications Part III: Determination and validation of local anaesthetics in human plasma samples using a cation-exchange sorbent, and MEPS-LC-MS-MS.
2004 Dec 25
Fate of linear alkylbenzene sulfonate (LAS) in activated sludge plants.
2004 Feb
Preparation, properties, reactions, and adenosine receptor affinities of sulfophenylxanthine nitrophenyl esters: toward the development of sulfonic acid prodrugs with peroral bioavailability.
2004 Feb 12
Dermal irritation assessment of three benzene sulfonate compounds.
2004 Jan-Feb
Raman spectroscopy of benzenesulfonic and 4-toluenesulfonic acids dissolved in dimethylsulfoxide.
2004 Jun
2,4-Bis(octadecanoylamino)benzenesulfonic acid sodium salt as a novel scavenger receptor inhibitor with low molecular weight.
2004 Jun 7
Differentiation and quantification of linear alkyl benzenesulfonate isomers by liquid chromatography-ion-trap mass spectrometry.
2004 Mar 26
Gene expression changes in peripheral blood-derived dendritic cells following exposure to a contact allergen.
2004 May 2
Simultaneous extraction and fate of linear alkylbenzene sulfonates, coconut diethanol amides, nonylphenol ethoxylates and their degradation products in wastewater treatment plants, receiving coastal waters and sediments in the Catalonian area (NE Spain).
2004 Oct 15
New extraction method for the analysis of linear alkylbenzene sulfonates in marine organisms. Pressurized liquid extraction versus Soxhlet extraction.
2004 Oct 15
Silver(I) arylsulfonates: a systematic study of "softer" hybrid inorganic-organic solids.
2004 Oct 18
Nonpeptide alpha V beta 3 antagonists. Part 9: Improved pharmacokinetic profile through the use of an aliphatic, des-amide backbone.
2004 Sep 6
Hydrogen-shift isomerism: mass spectrometry of isomeric benzenesulfonate and 2-, 3- and 4-dehydrobenzenesulfonic acid anions in the gas phase.
2005 Aug
Dihydroxy-2,5 benzenesulphonate (dobesilate) elicits growth arrest and apoptosis in glioma cells.
2005 Dec
Photoreaction of aromatic compounds at alpha-FeOOH/H2O interface in the presence of H2O2: evidence for organic-goethite surface complex formation.
2005 Jan
Linear alkyl benzene sulphonate (LAS) degradation by immobilized Pseudomonas aeruginosa under low intensity ultrasound.
2005 Jan 15
Mucosal colonisation with Lactobacillus casei mitigates barrier injury induced by exposure to trinitronbenzene sulphonic acid.
2005 Jul
Anaerobic digestion of linear alkyl benzene sulfonates: biodegradation kinetics and metabolite analysis.
2005 Sep
Inhibition of (Na(+)/K(+))-ATPase by Cibacron Blue 3G-A and its analogues.
2006 Dec
Permeation flux of organic molecules through silica-surfactant nanochannels in a porous alumina membrane.
2006 Dec
Hierarchical ionic self-assembly of rod-comb block copolypeptide-surfactant complexes.
2006 Dec
Synthesis of the enediol isofurans, endogenous oxidation products of arachidonic acid.
2006 Feb 3
Enrichment of N-terminal sulfonated peptides by a water-soluble fullerene derivative and its applications to highly efficient proteomics.
2006 Jan 18
Low level determination of p-toluenesulfonate and benzenesulfonate esters in drug substance by high performance liquid chromatography/mass spectrometry.
2006 Jun 30
Inorganic asymmetric synthesis: asymmetric synthesis of a two-bladed propeller, octahedral metal complex.
2006 Oct 16
Study of biodegradation products from azo dyes in fungal degradation by capillary electrophoresis/electrospray mass spectrometry.
2007 Aug 3
Silica-supported sodium sulfonate with ionic liquid: a neutral catalyst system for Michael reactions of indoles in water.
2007 Jan 18
Peripheral infusion of rat bone marrow derived endothelial progenitor cells leads to homing in acute lung injury.
2007 Jul 9
[Effects and mechanisms of inorganic anions in water on degradation of LAS by UV/H2 O2 combination process].
2007 Nov
In vitro effect of agriculture pollutants and their joint action on Pseudokirchneriella subcapitata acid phosphatase.
2007 Oct
Selection and evaluation of adsorbents for the removal of anionic surfactants from laundry rinsing water.
2007 Oct
The reactor design and comparison of Fenton, electro-Fenton and photoelectro-Fenton processes for mineralization of benzene sulfonic acid (BSA).
2008 Aug 15
J-aggregates of diprotonated tetrakis(4-sulfonatophenyl)porphyrin induced by ionic liquid 1-butyl-3-methylimidazolium tetrafluoroborate.
2008 Jul 10
Evidence of PPII-like helical conformation and glass transition in a self-assembled solid-state polypeptide-surfactant complex: poly(L-histidine)/docylbenzenesulfonic acid.
2008 May
Reduction of 2,3,5-triphenyl-2H-tetrazolium chloride in the presence of polyelectrolytes containing 4-styrenesulfonate moieties.
2008 May 1
Stacking of 2,3,5-triphenyl-2H-tetrazolium chloride onto polyelectrolytes containing 4-styrenesulfonate groups.
2008 Sep 11
Ultrasonic nebulization in aqueous solutions and the role of interfacial adsorption dynamics in surfactant enrichment.
2008 Sep 16
Controllable one-step synthesis of spirocycles, polycycles, and di- and tetrahydronaphthalenes from aryl-substituted propargylic alcohols.
2008 Sep 5
Patents

Patents

Sample Use Guides

Rat LD50 (oral) 890 mg/kg. Wild bird LD50 (oral) 75 mg/kg
Route of Administration: Oral
Biodegradation had been quantified in aqueous medium and P. fluorescens in agitated flasks experiments without sand matrix. The concentration of the MCs were determined every day (t=6 d for phenol, salicylic acid, and benzenesulfonic acid). Batch experiments were conducted in wide-neck bottles (Vinner = 250 ml) with defined moisture contents. The moisture content (θ) is the ratio between the volume of water and the total volume of the sample. To prevent unwanted strains from being included, the empty bottles were sterilized for t=20 min (T=121 °C) and the experimentswere done on a sterile bench. The sterilized bottles were filled with 40 g of sterilized sand (t = 20 min, T = 121 °C) each. The substrate solution was prepared by adding c0 (MC) = 0.5 mmol/l and nutrient solution to V = 1 l of deionized water. Each MC was investigated individually. In addition, the calculated volume of P. fluorescens solution was added. Five different moisture contents were used (θ = 5, 10, 24, 37 and 42%) by adding Vsubstrate = 1.3 to 12 ml (c0 (MC) = 0.5 mmol/l), inorganic medium and P. fluorescens (OD600=0.1, 7 × 107 cells/ml). The bottles were closed with a rubber stopper to prevent ambient air from entering and they were shaken slightly in the dark obtain a fairly homogeneous substrate distribution. The temperature was kept at T = 22 ±1 °C. The oxygen concentration was measured by sensor spots fixed to the inner glass surface of the bottles. After defined time periods (t=6 d or 60 d), 50 ml of deionized water (Millipore) were added with a dispenser and allwas shaken for t=1 min. The supernatantwas filtered (pore size 0.4 μm, polycarbonate) and prepared for analysis. Each bottle was “sacrificed” and each supernatant was analyzed once. For example, a triplicate experiment with five differentmoisture contents and a maximum reaction time of three days with daily control needed 45 bottles (3 × 5 × 3).
Name Type Language
BENZENESULFONIC ACID SESQUIHYDRATE
MI  
Common Name English
BENZENESULFONIC ACID, HYDRATE (2:3)
Common Name English
BENZENESULFONIC ACID, SESQUIHYDRATE
Common Name English
BENZENESULFONIC ACID 1.5 HYDRATE
Common Name English
BENZENESULFONIC ACID SESQUIHYDRATE [MI]
Common Name English
Code System Code Type Description
CAS
5928-72-3
Created by admin on Sat Dec 16 03:24:19 GMT 2023 , Edited by admin on Sat Dec 16 03:24:19 GMT 2023
PRIMARY
FDA UNII
425795DP0Y
Created by admin on Sat Dec 16 03:24:19 GMT 2023 , Edited by admin on Sat Dec 16 03:24:19 GMT 2023
PRIMARY
MERCK INDEX
m2341
Created by admin on Sat Dec 16 03:24:19 GMT 2023 , Edited by admin on Sat Dec 16 03:24:19 GMT 2023
PRIMARY Merck Index
PUBCHEM
57358281
Created by admin on Sat Dec 16 03:24:19 GMT 2023 , Edited by admin on Sat Dec 16 03:24:19 GMT 2023
PRIMARY
EPA CompTox
DTXSID40974711
Created by admin on Sat Dec 16 03:24:19 GMT 2023 , Edited by admin on Sat Dec 16 03:24:19 GMT 2023
PRIMARY