ChemSpider 2D Image | 4-[3-(3,5-ditert-butylphenyl)-3-oxoprop-1-enyl]benzoic acid | C24H28O3

4-[3-(3,5-ditert-butylphenyl)-3-oxoprop-1-enyl]benzoic acid

  • Molecular FormulaC24H28O3
  • Average mass364.477 Da
  • Monoisotopic mass364.203857 Da
  • ChemSpider ID4834579

  • Double-bond stereo - Double-bond stereo

More details:

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

110368-33-7 [RN]
4-[(1E)-3-(3,5-Di-tert-butylphenyl)-3-oxoprop-1-en-1-yl]benzoic acid
4-[3-(3,5-ditert-butylphenyl)-3-oxoprop-1-enyl]benzoic acid
4-{(1E)-3-[3,5-Bis(2-methyl-2-propanyl)phenyl]-3-oxo-1-propen-1-yl}benzoesäure [German] [ACD/IUPAC Name]
4-{(1E)-3-[3,5-Bis(2-methyl-2-propanyl)phenyl]-3-oxo-1-propen-1-yl}benzoic acid [ACD/IUPAC Name]
Acide 4-{(1E)-3-[3,5-bis(2-méthyl-2-propanyl)phényl]-3-oxo-1-propén-1-yl}benzoïque [French] [ACD/IUPAC Name]
Benzoic acid, 4-[(1E)-3-[3,5-bis(1,1-dimethylethyl)phenyl]-3-oxo-1-propen-1-yl]- [ACD/Index Name]
(E)-4-(3-(3,5-Bis(1,1-dimethylethyl)phenyl)-3-oxo-1-propenyl)benzoic acid
(E)-4-[3-(3,5-di-tert-butylphenyl)-3-oxo-1-propenyl]benzoic acid
[110368-33-7] [RN]
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Validated by Experts, Validated by Users, Non-Validated, Removed by Users

Ch 55 [DBID]
AIDS130646 [DBID]
AIDS-130646 [DBID]
CH-55 [DBID]
NSC608002 [DBID]
  • Experimental Physico-chemical Properties
  • Miscellaneous

    • Bio Activity:

      Highly potent synthetic retinoid that has high affinity for RAR-? and RAR-? receptors and low affinity for cellular retinoic acid binding protein (CRABP). Inhibits rabbit tracheal epithelial cell diff erentiation by inhibiting transglutaminase and increasing cholesterol sulfate (EC50 values are 0.02 and 0.03 nM respectively). Induces differentiation of embryonic carcinoma F9 and melanoma S91 cells (EC50 values are 0.26 and 0.5 nM respectively) and inhibits the induction of ornithine decarboxylase activity in 3T6 fibroblasts (EC50 = 1 nM). Tocris Bioscience 2020
      Highly potent synthetic retinoid that has high affinity for RAR-? and RAR-? receptors and low affinity for cellular retinoic acid binding protein (CRABP). Inhibits rabbit tracheal epithelial cell differentiation by inhibiting transglutaminase and increasing cholesterol sulfate (EC50 values are 0.02 and 0.03 nM respectively). Induces differentiation of embryonic carcinoma F9 and melanoma S91 cells (EC50 values are 0.26 and 0.5 nM respectively) and inhibits the induction of ornithine decarboxylase activity in 3T6 fibroblasts (EC50 = 1 nM). Tocris Bioscience 2020
      Highly potent synthetic retinoid that has high affinity for RAR-alpha and RAR-beta receptors and low affinity for cellular retinoic acid binding protein (CRABP). Inhibits rabbit tracheal epithelial cell differentiation by inhibiting transglutaminase and increasing cholesterol sulfate (EC50 values are 0.02 and 0.03 nM respectively). Induces differentiation of embryonic carcinoma F9 and melanoma S91 cells (EC50 values are 0.26 and 0.5 nM respectively) and inhibits the induction of ornithine decarboxylase activity in 3T6 fibroblasts (EC50 = 1 nM). Tocris Bioscience 2020
      Nuclear Receptors Tocris Bioscience 2020
      Potent RAR agonist Tocris Bioscience 2020
      Retinoic Acid Receptors Tocris Bioscience 2020

Predicted data is generated using the ACD/Labs Percepta Platform - PhysChem Module, version: 14.00

Density: 1.1±0.1 g/cm3
Boiling Point: 509.5±50.0 °C at 760 mmHg
Vapour Pressure: 0.0±1.4 mmHg at 25°C
Enthalpy of Vaporization: 82.1±3.0 kJ/mol
Flash Point: 276.0±26.6 °C
Index of Refraction: 1.574
Molar Refractivity: 110.8±0.3 cm3
#H bond acceptors: 3
#H bond donors: 1
#Freely Rotating Bonds: 6
#Rule of 5 Violations: 1
ACD/LogP: 6.87
ACD/LogD (pH 5.5): 5.26
ACD/BCF (pH 5.5): 2675.75
ACD/KOC (pH 5.5): 3916.78
ACD/LogD (pH 7.4): 3.75
ACD/BCF (pH 7.4): 83.55
ACD/KOC (pH 7.4): 122.31
Polar Surface Area: 54 Å2
Polarizability: 43.9±0.5 10-24cm3
Surface Tension: 40.9±3.0 dyne/cm
Molar Volume: 335.7±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) =  7.36

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  483.77  (Adapted Stein & Brown method)
    Melting Pt (deg C):  205.02  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  8.76E-010  (Modified Grain method)
    Subcooled liquid VP: 7.05E-008 mm Hg (25 deg C, Mod-Grain method)

 Water Solubility Estimate from Log Kow (WSKOW v1.41):
    Water Solubility at 25 deg C (mg/L):  0.002634
       log Kow used: 7.36 (estimated)
       no-melting pt equation used

 Water Sol Estimate from Fragments:
    Wat Sol (v1.01 est) =  0.010133 mg/L

 ECOSAR Class Program (ECOSAR v0.99h):
    Class(es) found:
       Vinyl/Allyl Ketones-acid

 Henrys Law Constant (25 deg C) [HENRYWIN v3.10]:
   Bond Method :   3.11E-011  atm-m3/mole
   Group Method:   Incomplete
 Henrys LC [VP/WSol estimate using EPI values]:  1.595E-007 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  7.36  (KowWin est)
  Log Kaw used:  -8.896  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  16.256
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :   0.3899
   Biowin2 (Non-Linear Model)     :   0.0255
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   2.0348  (months      )
   Biowin4 (Primary Survey Model) :   3.0005  (weeks       )
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :   0.3301
   Biowin6 (MITI Non-Linear Model):   0.0519
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model): -1.2512
 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):  9.4E-006 Pa (7.05E-008 mm Hg)
  Log Koa (Koawin est  ): 16.256
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  0.319 
       Octanol/air (Koa) model:  4.43E+003 
   Fraction sorbed to airborne particulates (phi):
       Junge-Pankow model     :  0.92 
       Mackay model           :  0.962 
       Octanol/air (Koa) model:  1 

 Atmospheric Oxidation (25 deg C) [AopWin v1.92]:
   Hydroxyl Radicals Reaction:
      OVERALL OH Rate Constant =  25.9316 E-12 cm3/molecule-sec [Cis-isomer]
      OVERALL OH Rate Constant =  28.5916 E-12 cm3/molecule-sec [Trans-isomer]
      Half-Life =    4.950 Hrs (12-hr day; 1.5E6 OH/cm3) [Cis-isomer]
      Half-Life =    4.489 Hrs (12-hr day; 1.5E6 OH/cm3) [Trans-isomer]
   Ozone Reaction:
      OVERALL Ozone Rate Constant =     1.050000 E-17 cm3/molecule-sec [Cis-]
      OVERALL Ozone Rate Constant =     2.100000 E-17 cm3/molecule-sec [Trans-]
      Half-Life =     1.091 Days (at 7E11 mol/cm3) [Cis-isomer]
      Half-Life =    13.097 Hrs (at 7E11 mol/cm3) [Trans-isomer]
   Fraction sorbed to airborne particulates (phi): 0.941 (Junge,Mackay)
    Note: the sorbed fraction may be resistant to atmospheric oxidation

 Soil Adsorption Coefficient (PCKOCWIN v1.66):
      Koc    :  1.601E+004
      Log Koc:  4.205 

 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 = 1.000 (BCF = 10)
       log Kow used: 7.36 (estimated)

 Volatilization from Water:
    Henry LC:  3.11E-011 atm-m3/mole  (estimated by Bond SAR Method)
    Half-Life from Model River: 3.594E+007  hours   (1.498E+006 days)
    Half-Life from Model Lake : 3.921E+008  hours   (1.634E+007 days)

 Removal In Wastewater Treatment:
    Total removal:              93.95  percent
    Total biodegradation:        0.78  percent
    Total sludge adsorption:    93.17  percent
    Total to Air:                0.00  percent
      (using 10000 hr Bio P,A,S)

 Level III Fugacity Model:
           Mass Amount    Half-Life    Emissions
            (percent)        (hr)       (kg/hr)
   Air       0.00121         7.18         1000       
   Water     1.22            1.44e+003    1000       
   Soil      42.3            2.88e+003    1000       
   Sediment  56.5            1.3e+004     0          
     Persistence Time: 6.15e+003 hr

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