ChemSpider 2D Image | Crotamiton | C13H17NO

Crotamiton

  • Molecular FormulaC13H17NO
  • Average mass203.280 Da
  • Monoisotopic mass203.131012 Da
  • ChemSpider ID2780

More details:






Validated by Experts, Validated by Users, Non-Validated, Removed by Users

Crotamiton [BAN] [INN] [JAN] [Wiki]
(2E)-N-Ethyl-N-(2-methylphenyl)-2-butenamid [German] [ACD/IUPAC Name]
(2E)-N-Ethyl-N-(2-methylphenyl)-2-butenamide [ACD/IUPAC Name]
(2E)-N-Éthyl-N-(2-méthylphényl)-2-buténamide [French] [ACD/IUPAC Name]
2-Butenamide, N-ethyl-N-(2-methylphenyl)-, (2E)- [ACD/Index Name]
483-63-6 [RN]
Crotaglin
Crotalgin
Crotamitex
Crotamitone
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Validated by Experts, Validated by Users, Non-Validated, Removed by Users

KBio3_001942 [DBID]
KBioGR_001728 [DBID]
MFCD00011698 [DBID]
NCIOpen2_004405 [DBID]
NSC78382 [DBID]
Prestwick0_000951 [DBID]
Prestwick1_000951 [DBID]
SPBio_001660 [DBID]
SPBio_003091 [DBID]
Spectrum2_001700 [DBID]
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  • Miscellaneous
    • Chemical Class:

      The amide resulting from the formal condensation of crotonic acid with <element>N</element>-ethyl-2-methylaniline. A colourless or pale yellow oily liquid, it is used in the treatment of pruritus (itc hing) by producing a counter-irritation: as it evaporates from the skin, it produces a cooling effect that diverts attention away from the itching. It has also been used as an acaricide in the treatme nt of scabies, though more effective drugs are usually preferred. ChEBI CHEBI:31439

Predicted data is generated using the ACD/Labs Percepta Platform - PhysChem Module

Density: 1.0±0.1 g/cm3
Boiling Point: 282.7±19.0 °C at 760 mmHg
Vapour Pressure: 0.0±0.6 mmHg at 25°C
Enthalpy of Vaporization: 52.2±3.0 kJ/mol
Flash Point: 115.5±12.7 °C
Index of Refraction: 1.552
Molar Refractivity: 64.0±0.3 cm3
#H bond acceptors: 2
#H bond donors: 0
#Freely Rotating Bonds: 3
#Rule of 5 Violations: 0
ACD/LogP: 3.10
ACD/LogD (pH 5.5): 2.35
ACD/BCF (pH 5.5): 36.25
ACD/KOC (pH 5.5): 454.77
ACD/LogD (pH 7.4): 2.35
ACD/BCF (pH 7.4): 36.26
ACD/KOC (pH 7.4): 454.79
Polar Surface Area: 20 Å2
Polarizability: 25.4±0.5 10-24cm3
Surface Tension: 38.2±3.0 dyne/cm
Molar Volume: 200.5±3.0 cm3

Predicted data is generated using the US Environmental Protection Agency’s EPISuite™

                        
 Log Octanol-Water Partition Coef (SRC):
    Log Kow (KOWWIN v1.67 estimate) =  2.73

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  325.88  (Adapted Stein & Brown method)
    Melting Pt (deg C):  93.97  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  0.000489  (Modified Grain method)
    MP  (exp database):  < 25 deg C
    BP  (exp database):  154 @ 13 mm Hg deg C

 Water Solubility Estimate from Log Kow (WSKOW v1.41):
    Water Solubility at 25 deg C (mg/L):  195.3
       log Kow used: 2.73 (estimated)
       no-melting pt equation used

 Water Sol Estimate from Fragments:
    Wat Sol (v1.01 est) =  420.38 mg/L

 ECOSAR Class Program (ECOSAR v0.99h):
    Class(es) found:
       Acrylamides

 Henrys Law Constant (25 deg C) [HENRYWIN v3.10]:
   Bond Method :   1.53E-007  atm-m3/mole
   Group Method:   Incomplete
 Henrys LC [VP/WSol estimate using EPI values]:  6.697E-007 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  2.73  (KowWin est)
  Log Kaw used:  -5.204  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  7.934
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :   0.9156
   Biowin2 (Non-Linear Model)     :   0.9674
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   2.6209  (weeks-months)
   Biowin4 (Primary Survey Model) :   3.6913  (days-weeks  )
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :   0.3709
   Biowin6 (MITI Non-Linear Model):   0.2416
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model): -0.7655
 Ready Biodegradability Prediction:   NO

Hydrocarbon Biodegradation (BioHCwin v1.01):
    Structure incompatible with current estimation method!

 Sorption to aerosols (25 Dec C)[AEROWIN v1.00]:
  Vapor pressure (liquid/subcooled):  0.0652 Pa (0.000489 mm Hg)
  Log Koa (Koawin est  ): 7.934
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  4.6E-005 
       Octanol/air (Koa) model:  2.11E-005 
   Fraction sorbed to airborne particulates (phi):
       Junge-Pankow model     :  0.00166 
       Mackay model           :  0.00367 
       Octanol/air (Koa) model:  0.00168 

 Atmospheric Oxidation (25 deg C) [AopWin v1.92]:
   Hydroxyl Radicals Reaction:
      OVERALL OH Rate Constant =  39.2296 E-12 cm3/molecule-sec [Cis-isomer]
      OVERALL OH Rate Constant =  41.8896 E-12 cm3/molecule-sec [Trans-isomer]
      Half-Life =    3.272 Hrs (12-hr day; 1.5E6 OH/cm3) [Cis-isomer]
      Half-Life =    3.064 Hrs (12-hr day; 1.5E6 OH/cm3) [Trans-isomer]
   Ozone Reaction:
      OVERALL Ozone Rate Constant =     0.568750 E-17 cm3/molecule-sec [Cis-]
      OVERALL Ozone Rate Constant =     1.137500 E-17 cm3/molecule-sec [Trans-]
      Half-Life =     2.015 Days (at 7E11 mol/cm3) [Cis-isomer]
      Half-Life =     1.007 Days (at 7E11 mol/cm3) [Trans-isomer]
   Fraction sorbed to airborne particulates (phi): 0.00266 (Junge,Mackay)
    Note: the sorbed fraction may be resistant to atmospheric oxidation

 Soil Adsorption Coefficient (PCKOCWIN v1.66):
      Koc    :  550.1
      Log Koc:  2.740 

 Aqueous Base/Acid-Catalyzed Hydrolysis (25 deg C) [HYDROWIN v1.67]:
    Rate constants can NOT be estimated for this structure!

 Bioaccumulation Estimates from Log Kow (BCFWIN v2.17):
   Log BCF from regression-based method = 1.404 (BCF = 25.34)
       log Kow used: 2.73 (estimated)

 Volatilization from Water:
    Henry LC:  1.53E-007 atm-m3/mole  (estimated by Bond SAR Method)
    Half-Life from Model River:       5458  hours   (227.4 days)
    Half-Life from Model Lake : 5.966E+004  hours   (2486 days)

 Removal In Wastewater Treatment:
    Total removal:               3.96  percent
    Total biodegradation:        0.11  percent
    Total sludge adsorption:     3.84  percent
    Total to Air:                0.01  percent
      (using 10000 hr Bio P,A,S)

 Level III Fugacity Model:
           Mass Amount    Half-Life    Emissions
            (percent)        (hr)       (kg/hr)
   Air       0.216           5.76         1000       
   Water     20              900          1000       
   Soil      79.6            1.8e+003     1000       
   Sediment  0.255           8.1e+003     0          
     Persistence Time: 1.06e+003 hr




                    

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