N-Butylbenzenesulfonamide
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| Category | Antibiotics |
| Catalog number | BBF-00594 |
| CAS | 3622-84-2 |
| Molecular Weight | 213.30 |
| Molecular Formula | C10H15NO2S |
| Purity | > 98.0 % (N) |
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Description
N-Butylbenzenesulphonamide N is an antifungal antibiotic produced by Pseudomonas sp. AB2. It has anti-phytopathogenic fungus activity. The ED50 for Pythiurn ultimum, Phytophthora capsici, Rhizoctonia solani and Botrytis cinerea are respectively (㎍/mL) ) 73, 41, 33 and 101.
Specification
| Synonyms | Benzenesulfonamide, N-butyl-; N-n-Butylbenzenesulfonamide; N-Butylbenzenesulphonamide |
| IUPAC Name | N-butylbenzenesulfonamide |
| Canonical SMILES | CCCCNS(=O)(=O)C1=CC=CC=C1 |
| InChI | InChI=1S/C10H15NO2S/c1-2-3-9-11-14(12,13)10-7-5-4-6-8-10/h4-8,11H,2-3,9H2,1H3 |
| InChI Key | IPRJXAGUEGOFGG-UHFFFAOYSA-N |
| Source | N-Butylbenzenesulfonamide, a plasticizer used commercially in the polymerization of polyamide compounds. |
Properties
| Appearance | Oil |
| Application | Used in the polymers and textile processing industries; Used as a plasticizer, smelting agent for moulding, and softener; Used mainly as a plasticizer. |
| Antibiotic Activity Spectrum | fungi |
| Boiling Point | 314 ℃ |
| Melting Point | 314 ℃ (lit.) |
| Flash Point | 118 °C |
| Density | 1.15 g/mL at 25 ℃ (lit.) |
| LogP | 3.23670 |
Toxicity
| Carcinogenicity | No indication of carcinogenicity to humans (not listed by IARC). |
Reference Reading
1. Toxicokinetics of the plasticizer, N-butylbenzenesulfonamide, in plasma and brain following oral exposure in rodents: Route, species, and sex comparison
Suramya Waidyanatha, Seth Gibbs, Natalie South, Jeremy P Smith, Esra Mutlu, Brian Burback, Yu Cao, Cynthia V Rider Toxicol Rep. 2020 May 26;7:711-722. doi: 10.1016/j.toxrep.2020.05.005. eCollection 2020.
N-Butylbenzenesulfonamide (NBBS) is a widely used plasticizer and hence there is potential for human exposure via oral routes. This work investigates the toxicokinetic behavior of NBBS in rodents following a single gavage (20, 60, and 200 mg/kg body weight) or multi-day feed administration (500, 1000, and 2000 ppm). In male and female rats following gavage administration, maximum plasma NBBS concentration, Cmax, was reached at ≤0.539 h. Cmax increased proportionally to the dose. Area under the curve (AUC) increased more than proportionally to the dose and was 4- to 5-fold higher in females than in males. In mice, plasma Cmax was reached at ≤0.136 h and increased proportionally to the dose in female mice and more than proportionally to the dose in males. AUC increased more than proportionally to the dose with no apparent sex difference. Elimination of NBBS in plasma was faster in mice (half-life (h); mice ≤0.432, rat ≤3.55). Oral bioavailability was higher in female rats (≥60%) than males (23-52%) with apparent saturation of clearance at ~200 mg/kg body weight in females. In mice, bioavailability (5-14%) was lower with no apparent sex difference. NBBS was detected in brains of rats and mice but with low brain:plasma ratios (rats, ≤5; mice, ≤1) suggesting low potential to cross the blood brain barrier. Systemic exposure in male rats and mice following a single gavage administration was ≥48-fold higher than multi-day feed exposure. These data demonstrate potential species, sex, dose- and route-related difference in toxicokinetics of NBBS in rodents.
2. Disposition and metabolism of N-butylbenzenesulfonamide in Sprague Dawley rats and B6C3F1/N mice and in vitro in hepatocytes from rats, mice, and humans
Suramya Waidyanatha, Sherry R Black, Purvi R Patel, Cynthia V Rider, Scott L Watson, Rodney W Snyder, Timothy R Fennell Toxicol Lett. 2020 Feb 1;319:225-236. doi: 10.1016/j.toxlet.2019.11.015. Epub 2019 Nov 21.
N-Butylbenzenesulfonamide (NBBS) is a plasticizer detected in the environment suggesting potential human exposure. These studies investigated the in vitro hepatic clearance and disposition of [14C]NBBS in rodents following a single gavage (2, 20 or 200 mg/kg) or intravenous (IV) administration (20 mg/kg). NBBS was cleared slower in hepatocytes from humans compared to rodents. [14C]NBBS was well-absorbed in male rats following gavage administration and excreted extensively in urine (70-76 %) and feces (11-15 %) 72 h following administration. Following a 20 mg/kg gavage dose in male rats, 25 % of the dose was excreted in bile by 24 h suggesting that observed fecal excretion was due to biliary excretion. The radioactivity was distributed to tissues with 14 % and 8 % of the administered dose remaining in tissues at 24 and 72 h, respectively. There was no apparent dose-dependent effect in disposition in male rats. Disposition patterns were similar in female rats (urine, 83 %; feces, 14 %) and male (urine, 69 %; feces, 11 %) and female (urine, 72 %; feces, 9 %) mice following gavage administration of 20 mg/kg. The disposition following IV administration was similar to that of gavage. Urinary radiochemical profiles were similar between doses, routes, species, and sexes. Among numerous metabolites identified, oxidative metabolites of NBBS predominated.
3. Short-term perinatal toxicity study in sprague Dawley rats with the plasticizer and emerging contaminant N-Butylbenzenesulfonamide
Cynthia V Rider, Molly Vallant, Chad Blystone, Suramya Waidyanatha, Natalie L South, Guanhua Xie, Katie Turner Toxicol Lett. 2020 May 11;330:159-166. doi: 10.1016/j.toxlet.2020.05.005. Online ahead of print.
N-Butylbenzenesulfonamide (NBBS) is a plasticizer and emerging contaminant that has been detected in a wide array of environmental samples. There are very little toxicity data available with which to evaluate potential risk from exposure to NBBS or other structurally-related sulfonamide plasticizers. To address this knowledge gap, NBBS was selected by the National Toxicology Program for evaluation. The current short-term pre- and post-natal (perinatal) study aims to provide preliminary toxicity and gestational transfer data for NBBS. NBBS was administered via dosed feed at concentrations of 0, 625, 1250, 2500, 5000, and 10,000 ppm to time-mated Sprague Dawley (Hsd:Sprague Dawley SD®) rats from gestation day (GD) 6 through postnatal day (PND) 28. The high concentration of 10,000 ppm NBBS was overtly toxic to dams, and the group was removed on GD 17-18. Exposure to NBBS resulted in lower maternal weights during the gestational period in the 5000 and 10,000 ppm groups as compared to control weights. Dams also displayed lower weights in the lactational period, which resolved to control levels by PND 28. NBBS exposure did not affect pregnancy or littering parameters in F0 dams. However, pup survival was lower in the 5000 ppm group, and pup weights were dose-responsively lower than control pup weights with the difference expanding over the postnatal period. The lowest observed effect level (LOEL) based on significantly lower body weights was 5000 ppm NBBS for F0 dams and 2500 ppm NBBS for F1 pups. Preliminary data for NBBS levels indicated that the chemical was transferred from dams to offspring during the gestational period.
Spectrum
Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive
Experimental Conditions
Ionization Mode: Positive
Ionization Energy: 70 eV
Chromatography Type: Gas Chromatography Column (GC)
Instrument Type: Single quadrupole, spectrum predicted by CFM-ID(EI)
Mass Resolution: 0.0001 Da
Molecular Formula: C10H15NO2S
Molecular Weight (Monoisotopic Mass): 213.0823 Da
Molecular Weight (Avergae Mass): 213.297 Da
Ionization Energy: 70 eV
Chromatography Type: Gas Chromatography Column (GC)
Instrument Type: Single quadrupole, spectrum predicted by CFM-ID(EI)
Mass Resolution: 0.0001 Da
Molecular Formula: C10H15NO2S
Molecular Weight (Monoisotopic Mass): 213.0823 Da
Molecular Weight (Avergae Mass): 213.297 Da
LC-MS/MS Spectrum - LC-ESI-ITFT , positive
Experimental Conditions
Instrument Type: LC-ESI-ITFT
Ionization Mode: positive
Ionization Mode: positive
Predicted LC-MS/MS Spectrum - 10V, Positive
Experimental Conditions
Ionization Mode: Positive
Collision Energy: 10 eV
Instrument Type: QTOF (generic), spectrum predicted by CFM-ID
Mass Resolution: 0.0001 Da
Molecular Formula: C10H15NO2S
Molecular Weight (Monoisotopic Mass): 213.0823 Da
Molecular Weight (Avergae Mass): 213.297 Da
Collision Energy: 10 eV
Instrument Type: QTOF (generic), spectrum predicted by CFM-ID
Mass Resolution: 0.0001 Da
Molecular Formula: C10H15NO2S
Molecular Weight (Monoisotopic Mass): 213.0823 Da
Molecular Weight (Avergae Mass): 213.297 Da
Mass Spectrum (Electron Ionization)
1H NMR Spectrum
Experimental Conditions
Solvent: CDCl3
Instrument Type: JEOL
Nucleus: 1H
Frequency: 90 MHz
Chemical Shift Reference: TMS
Instrument Type: JEOL
Nucleus: 1H
Frequency: 90 MHz
Chemical Shift Reference: TMS
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Bio Calculators
* Our calculator is based on the following equation:
Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
It is commonly abbreviated as: C1V1 = C2V2
* Total Molecular Weight:
g/mol
Tip: Chemical formula is case sensitive. C22H30N4O √ c22h30n40 ╳
