ChemSpider 2D Image | (E)-Diethylstilbestrol | C18H20O2

(E)-Diethylstilbestrol

  • Molecular FormulaC18H20O2
  • Average mass268.350 Da
  • Monoisotopic mass268.146332 Da
  • ChemSpider ID395306
  • Double-bond stereo - Double-bond stereo


More details:



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(E)-Diethylstilbestrol
(E)-3,4-Bis(p-hydroxyphenyl)-3-hexene
(E)-a,a'-Diethyl-4,4'-stilbenediol
200-278-5 [EINECS]
388
4,4'-(3E)-hex-3-ene-3,4-diyldiphenol
4,4'-[(1E)-1,2-Diethyl-1,2-ethenediyl]bisphenol
4,4'-[(3E)-3-Hexen-3,4-diyl]diphenol [German] [ACD/IUPAC Name]
4,4'-[(3E)-3-Hexene-3,4-diyl]diphenol [ACD/IUPAC Name]
4,4'-[(3E)-3-Hexène-3,4-diyl]diphénol [French] [ACD/IUPAC Name]
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Validated by Experts, Validated by Users, Non-Validated, Removed by Users

218944_ALDRICH [DBID]
46207_RIEDEL [DBID]
AI3-17297 [DBID]
BRN 2056095 [DBID]
C07620 [DBID]
CCRIS 240 [DBID]
CHEBI:4531 [DBID]
D00577 [DBID]
D4628_SIGMA [DBID]
DivK1c_000519 [DBID]
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  • Experimental Physico-chemical Properties
  • Predicted Physico-chemical Properties
  • Miscellaneous
    • Appearance:

      white crystalline powder Oxford University Chemical Safety Data (No longer updated) More details
    • Stability:

      Stable. Incompatible with strong bases, strong oxidizing agents, acid chlorides,acid anhydrides. Oxford University Chemical Safety Data (No longer updated) More details
    • Toxicity:

      ORL-RAT LD50 > 3000 mg kg-1, IPR-RAT LD50 34 mg kg-1, IVN-MUS LD50 3000 mg kg-1 Oxford University Chemical Safety Data (No longer updated) More details
    • Safety:

      45-61-36/37/38-51/53 LKT Labs [D3218]
      Danger Biosynth Q-200984
      G03CB02 Wikidata Q423989
      G03CC05 Wikidata Q423989
      GHS07; GHS08; GHS09 Biosynth Q-200984
      H315 H319 H335 H350 H360 H410 LKT Labs [D3218]
      H315; H319; H335; H350; H360; H410 Biosynth Q-200984
      IRRITANT Matrix Scientific 054654
      L02AA01 Wikidata Q423989
      Minimize exposure. Oxford University Chemical Safety Data (No longer updated) More details
      P201; P261; P273; P305+P351+P338; P308+P313; P501 Biosynth Q-200984
      T, N LKT Labs [D3218]
      T,N Abblis Chemicals AB1009528
      UN 3077 9/PG 3 LKT Labs [D3218]
    • Target Organs:

      Estrogen/Progestogen Receptor agonist TargetMol T1216
    • Compound Source:

      synthetic Microsource [01500244]
    • Bio Activity:

      Diethylstilbestrol, a synthetic nonsteroidal estrogen used in the treatment of menopausal and postmenopausal disorders. MedChem Express
      Diethylstilbestrol, a synthetic nonsteroidal estrogen used in the treatment of menopausal and postmenopausal disorders.; Target: Estrogen Receptor/ERR; Diethylstilbestrol (DES), a synthetic estrogen that was used in pregnancy, is a prototype endocrine-disrupting chemical. MedChem Express HY-14598
      Diethylstilbestrol, a synthetic nonsteroidal estrogen used in the treatment of menopausal and postmenopausal disorders.;Target: Estrogen Receptor/ERRDiethylstilbestrol (DES), a synthetic estrogen that was used in pregnancy, is a prototype endocrine-disrupting chemical. Although prenatal exposure to DES is known to increase risks of vaginal/cervical adenocarcinoma and adverse reproductive outcomes in women, and urogenital anomalies in men, data on nonreproductive medical conditions are lacking. Comparing persons exposed prenatally to DES with those who were not exposed, the hazard ratios were 1.21 (95% confidence interval = 0.96-1.54) for diabetes, 1.27 (1.00-1.62) for all cardiovascular disease, 1.18 (0.88-1.59) for coronary artery disease, 1.28 (0.88-1.86) for myocardial infarction, 1.12 (1.02-1.22) for high cholesterol, 1.14 (1.02-1.28) for hypertension, 1.24 (0.99-1.54) for osteoporosis, and 1.30 (0.95-1.79) for fractures. The associations did not differ by dose and timing of DE MedChem Express HY-14598
      Endocrinology/ Hormones TargetMol T1216
      Estrogen receptor TargetMol T1216
      Estrogen Receptor/ERR MedChem Express HY-14598
      Non-steroidal estrogen; Zerenex Molecular [ZBioX-0699]
      Others MedChem Express HY-14598
  • Gas Chromatography
    • Retention Index (Kovats):

      2367 (estimated with error: 70) NIST Spectra mainlib_234131, replib_75977, replib_290788
    • Retention Index (Normal Alkane):

      2366 (Program type: Ramp; Column cl... (show more) ass: Standard non-polar; Column type: Other; CAS no: 56531; Active phase: Methyl Silicone; Data type: Normal alkane RI; Authors: Ardrey, R.E.; Moffat, A.C., Gas-liquid chromatographic retention indices of 1318 substances of toxicological interest on SE-30 or OV-1 stationary phase, J. Chromatogr., 220, 1981, 195-252.) NIST Spectra nist ri
      2298 (Program type: Ramp; Column cl... (show more) ass: Standard non-polar; Column type: Other; CAS no: 56531; Active phase: Methyl Silicone; Data type: Normal alkane RI; Authors: Ardrey, R.E.; Moffat, A.C., Gas-liquid chromatographic retention indices of 1318 substances of toxicological interest on SE-30 or OV-1 stationary phase, J. Chromatogr., 220, 1981, 195-252.) NIST Spectra nist ri

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

Density: 1.1±0.1 g/cm3
Boiling Point: 407.1±25.0 °C at 760 mmHg
Vapour Pressure: 0.0±1.0 mmHg at 25°C
Enthalpy of Vaporization: 68.5±3.0 kJ/mol
Flash Point: 186.9±17.8 °C
Index of Refraction: 1.603
Molar Refractivity: 83.2±0.3 cm3
#H bond acceptors: 2
#H bond donors: 2
#Freely Rotating Bonds: 4
#Rule of 5 Violations: 1
ACD/LogP: 5.93
ACD/LogD (pH 5.5): 4.79
ACD/BCF (pH 5.5): 2576.58
ACD/KOC (pH 5.5): 9620.96
ACD/LogD (pH 7.4): 4.79
ACD/BCF (pH 7.4): 2572.41
ACD/KOC (pH 7.4): 9605.39
Polar Surface Area: 40 Å2
Polarizability: 33.0±0.5 10-24cm3
Surface Tension: 46.3±3.0 dyne/cm
Molar Volume: 242.2±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) =  5.64
    Log Kow (Exper. database match) =  5.07
       Exper. Ref:  Hansch,C et al. (1995)

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  407.18  (Adapted Stein & Brown method)
    Melting Pt (deg C):  151.82  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  8.64E-009  (Modified Grain method)
    MP  (exp database):  170.5 deg C
    Subcooled liquid VP: 2.76E-007 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):  3.321
       log Kow used: 5.07 (expkow database)
       no-melting pt equation used
     Water Sol (Exper. database match) =  12 mg/L (25 deg C)
        Exper. Ref:  YALKOWSKY,SH & DANNENFELSER,RM (1992)

 Water Sol Estimate from Fragments:
    Wat Sol (v1.01 est) =  10.213 mg/L
    Wat Sol (Exper. database match) =  12.00
       Exper. Ref:  YALKOWSKY,SH & DANNENFELSER,RM (1992)

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

 Henrys Law Constant (25 deg C) [HENRYWIN v3.10]:
   Bond Method :   5.80E-012  atm-m3/mole
   Group Method:   Incomplete
 Henrys LC [VP/WSol estimate using EPI values]:  9.186E-010 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  5.07  (exp database)
  Log Kaw used:  -9.625  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  14.695
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :   0.8514
   Biowin2 (Non-Linear Model)     :   0.7340
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   2.7189  (weeks-months)
   Biowin4 (Primary Survey Model) :   3.5399  (days-weeks  )
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :   0.2076
   Biowin6 (MITI Non-Linear Model):   0.0843
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model):  0.1269
 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):  3.68E-005 Pa (2.76E-007 mm Hg)
  Log Koa (Koawin est  ): 14.695
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  0.0815 
       Octanol/air (Koa) model:  122 
   Fraction sorbed to airborne particulates (phi):
       Junge-Pankow model     :  0.746 
       Mackay model           :  0.867 
       Octanol/air (Koa) model:  1 

 Atmospheric Oxidation (25 deg C) [AopWin v1.92]:
   Hydroxyl Radicals Reaction:
      OVERALL OH Rate Constant = 175.1483 E-12 cm3/molecule-sec
      Half-Life =     0.061 Days (12-hr day; 1.5E6 OH/cm3)
      Half-Life =     0.733 Hrs
   Ozone Reaction:
      OVERALL Ozone Rate Constant =  1064.699951 E-17 cm3/molecule-sec
      Half-Life =     0.001 Days (at 7E11 mol/cm3)
      Half-Life =      1.550 Min
   Reaction With Nitrate Radicals May Be Important!
   Fraction sorbed to airborne particulates (phi): 0.807 (Junge,Mackay)
    Note: the sorbed fraction may be resistant to atmospheric oxidation

 Soil Adsorption Coefficient (PCKOCWIN v1.66):
      Koc    :  5.692E+005
      Log Koc:  5.755 

 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 = 3.204 (BCF = 1599)
       log Kow used: 5.07 (expkow database)

 Volatilization from Water:
    Henry LC:  5.8E-012 atm-m3/mole  (estimated by Bond SAR Method)
    Half-Life from Model River: 1.654E+008  hours   (6.89E+006 days)
    Half-Life from Model Lake : 1.804E+009  hours   (7.517E+007 days)

 Removal In Wastewater Treatment:
    Total removal:              79.80  percent
    Total biodegradation:        0.69  percent
    Total sludge adsorption:    79.11  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       0.000183        0.0254       1000       
   Water     8.52            900          1000       
   Soil      68.8            1.8e+003     1000       
   Sediment  22.7            8.1e+003     0          
     Persistence Time: 2.04e+003 hr




                    

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