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Details

Stereochemistry ACHIRAL
Molecular Formula C6H6O3S
Molecular Weight 158.175
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of BENZENESULFONIC ACID

SMILES

OS(=O)(=O)C1=CC=CC=C1

InChI

InChIKey=SRSXLGNVWSONIS-UHFFFAOYSA-N
InChI=1S/C6H6O3S/c7-10(8,9)6-4-2-1-3-5-6/h1-5H,(H,7,8,9)

HIDE SMILES / InChI

Molecular Formula C6H6O3S
Molecular Weight 158.175
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

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
Impact of linear alkyl benzene sulphonate (LAS) on phosphatase activity in testis of the teleostean fish, Heteropneustes fossilis (Bloch).
2001 Oct
Comparative study of the acute toxicity of anionic surfactans alkyl benzene sulphonate (ABS) and sodium dodecyl sulphate (SDS) on gilthead, Sparus aurata L., eggs.
2001 Oct
Stability study and determination of benzene- and naphthalenesulfonates following an on-line solid-phase extraction method using the new programmable field extraction system.
2002 Apr
Role of CA(2+)-activated K+ channels in the regulation of basilar arterial tone in spontaneously hypertensive rats.
2002 Jul
Integration of aquatic fate and ecological responses to linear alkyl benzene sulfonate (LAS) in model stream ecosystems.
2002 Jun
Anti-inflammatory action of sulfoaryl 3,3-disubstituted triazenes in rat experimental edema models.
2003 Oct
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
Fate of linear alkylbenzene sulfonate (LAS) in activated sludge plants.
2004 Feb
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
New extraction method for the analysis of linear alkylbenzene sulfonates in marine organisms. Pressurized liquid extraction versus Soxhlet extraction.
2004 Oct 15
Nonpeptide alpha V beta 3 antagonists. Part 9: Improved pharmacokinetic profile through the use of an aliphatic, des-amide backbone.
2004 Sep 6
Mucosal colonisation with Lactobacillus casei mitigates barrier injury induced by exposure to trinitronbenzene sulphonic acid.
2005 Jul
Structure-activity considerations and in vitro approaches to assess the genotoxicity of 19 methane-, benzene- and toluenesulfonic acid esters.
2005 Mar 7
Raman spectroscopic study of hydrogen bonding in benzenesulfonic acid/acrylonitrile solutions.
2005 Oct
Permeation flux of organic molecules through silica-surfactant nanochannels in a porous alumina membrane.
2006 Dec
Formation of drug-arylsulfonate complexes inside liposomes: a novel approach to improve drug retention.
2006 Jan 10
The suramin analog 4,4',4'',4'''-(carbonylbis(imino-5,1,3-benzenetriylbis (carbonylimino)))tetra-kis-benzenesulfonic acid (NF110) potently blocks P2X3 receptors: subtype selectivity is determined by location of sulfonic acid groups.
2006 Jun
Inorganic asymmetric synthesis: asymmetric synthesis of a two-bladed propeller, octahedral metal complex.
2006 Oct 16
A scalable machine-learning approach to recognize chemical names within large text databases.
2006 Sep 6
Study of biodegradation products from azo dyes in fungal degradation by capillary electrophoresis/electrospray mass spectrometry.
2007 Aug 3
Donor-bound glycosylation for various glycosyl acceptors: bidirectional solid-phase semisynthesis of vancomycin and its derivatives.
2007 Jan 8
Histopathological changes in testis of the freshwater fish, Heteropneustes fossilis (Bloch) exposed to linear alkyl benzene sulphonate (LAS).
2007 Jul
R2(2)(8) motifs in Aminopyrimidine sulfonate/carboxylate interactions: crystal structures of pyrimethaminium benzenesulfonate monohydrate (2:2:1) and 2-amino-4,6-dimethylpyrimidinium sulfosalicylate dihydrate (4:2:2).
2007 Nov 13
Impact of surface derivatization of poly-L-lysine dendrimers with anionic arylsulfonate or succinate groups on intravenous pharmacokinetics and disposition.
2007 Nov-Dec
In vitro effect of agriculture pollutants and their joint action on Pseudokirchneriella subcapitata acid phosphatase.
2007 Oct
Simultaneous enantioseparation of antiparkinsonian medication Rotigotine and related chiral impurities by capillary zone electrophoresis using dual cyclodextrin system.
2008 Apr 14
Development and validation of RP-HPLC method for the determination of genotoxic alkyl benzenesulfonates in amlodipine besylate.
2008 Sep 10
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).
Substance Class Chemical
Created
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on Fri Dec 15 15:15:42 GMT 2023
Edited
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on Fri Dec 15 15:15:42 GMT 2023
Record UNII
685928Z18A
Record Status Validated (UNII)
Record Version
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Name Type Language
BENZENESULFONIC ACID
HSDB   II   MI  
Systematic Name English
BENZENSULFONIC ACID
Systematic Name English
BENZENESULFONIC ACID [HSDB]
Common Name English
BENZENESULFONATE
Common Name English
BENZENESULFONIC ACID [II]
Common Name English
BENZENESULFONIC ACID [MI]
Common Name English
Classification Tree Code System Code
EPA PESTICIDE CODE 224900
Created by admin on Fri Dec 15 15:15:42 GMT 2023 , Edited by admin on Fri Dec 15 15:15:42 GMT 2023
Code System Code Type Description
PUBCHEM
7371
Created by admin on Fri Dec 15 15:15:42 GMT 2023 , Edited by admin on Fri Dec 15 15:15:42 GMT 2023
PRIMARY
EPA CompTox
DTXSID9024568
Created by admin on Fri Dec 15 15:15:42 GMT 2023 , Edited by admin on Fri Dec 15 15:15:42 GMT 2023
PRIMARY
RXCUI
993243
Created by admin on Fri Dec 15 15:15:42 GMT 2023 , Edited by admin on Fri Dec 15 15:15:42 GMT 2023
PRIMARY RxNorm
WIKIPEDIA
BENZENESULFONIC ACID
Created by admin on Fri Dec 15 15:15:42 GMT 2023 , Edited by admin on Fri Dec 15 15:15:42 GMT 2023
PRIMARY
MESH
C032365
Created by admin on Fri Dec 15 15:15:42 GMT 2023 , Edited by admin on Fri Dec 15 15:15:42 GMT 2023
PRIMARY
MERCK INDEX
m2341
Created by admin on Fri Dec 15 15:15:42 GMT 2023 , Edited by admin on Fri Dec 15 15:15:42 GMT 2023
PRIMARY Merck Index
HSDB
2642
Created by admin on Fri Dec 15 15:15:42 GMT 2023 , Edited by admin on Fri Dec 15 15:15:42 GMT 2023
PRIMARY
EVMPD
SUB23114
Created by admin on Fri Dec 15 15:15:42 GMT 2023 , Edited by admin on Fri Dec 15 15:15:42 GMT 2023
PRIMARY
SMS_ID
100000088622
Created by admin on Fri Dec 15 15:15:42 GMT 2023 , Edited by admin on Fri Dec 15 15:15:42 GMT 2023
PRIMARY
NCI_THESAURUS
C80891
Created by admin on Fri Dec 15 15:15:42 GMT 2023 , Edited by admin on Fri Dec 15 15:15:42 GMT 2023
PRIMARY
CAS
98-11-3
Created by admin on Fri Dec 15 15:15:42 GMT 2023 , Edited by admin on Fri Dec 15 15:15:42 GMT 2023
PRIMARY
DAILYMED
685928Z18A
Created by admin on Fri Dec 15 15:15:42 GMT 2023 , Edited by admin on Fri Dec 15 15:15:42 GMT 2023
PRIMARY
NCI_THESAURUS
C45678
Created by admin on Fri Dec 15 15:15:42 GMT 2023 , Edited by admin on Fri Dec 15 15:15:42 GMT 2023
CONCEPT Industrial Aid
ECHA (EC/EINECS)
202-638-7
Created by admin on Fri Dec 15 15:15:42 GMT 2023 , Edited by admin on Fri Dec 15 15:15:42 GMT 2023
PRIMARY
RXCUI
1313278
Created by admin on Fri Dec 15 15:15:42 GMT 2023 , Edited by admin on Fri Dec 15 15:15:42 GMT 2023
ALTERNATIVE
FDA UNII
685928Z18A
Created by admin on Fri Dec 15 15:15:42 GMT 2023 , Edited by admin on Fri Dec 15 15:15:42 GMT 2023
PRIMARY
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