ChemSpider 2D Image | Caffeic acid phenethyl ester | C17H16O4

Caffeic acid phenethyl ester

  • Molecular FormulaC17H16O4
  • Average mass284.306 Da
  • Monoisotopic mass284.104858 Da
  • ChemSpider ID4445100

  • Double-bond stereo - Double-bond stereo

More details:

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

(2E)-3-(3,4-Dihydroxyphényl)acrylate de 2-phényléthyle [French] [ACD/IUPAC Name]
(E)-Caffeic acid phenethyl ester
100981-80-4 [RN]
104594-70-9 [RN]
115610-29-2 [RN]
2-Phenyethyl caffeate
2-Phenylethyl (2E)-3-(3,4-dihydroxyphenyl)acrylate [ACD/IUPAC Name]
2-phenylethyl (2E)-3-(3,4-dihydroxyphenyl)prop-2-enoate
2-Phenylethyl caffeate
2-Phenylethyl caffeoate
More...

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

104594-70-9 100981-80-4 [DBID]
104594-70-9; 115610-29-2 [DBID]
AIDS028600 [DBID]
AIDS-028600 [DBID]
Bio2_000280 [DBID]
Bio2_000760 [DBID]
C10484 [DBID]
C8221_SIGMA [DBID]
EU-0100269 [DBID]
KBio2_000280 [DBID]
More...
  • Experimental Physico-chemical Properties
  • Miscellaneous

    • Chemical Class:

      An alkyl caffeate ester in which 2-phenylethyl is the alkyl component. ChEBI https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:8062, CHEBI:8062

    • Compound Source:

      Alibertia macrophylla (Rubiaceae) Susan Richardson [Structure found in DOI: 10.1016/0031-9422(91)85077-D]
      Isolated from a plant Susan Richardson [Structure found in DOI: 10.1016/0031-9422(91)85077-D]

    • Bio Activity:

      Antioxidant, antimitogenic, anticarcinogenic, anti-inflammatory and antiviral. Specifically inhibits NF-?B activation and inhibits the growth of transformed cells. Also suppresses lipid peroxidation a nd inhibits ornithine decarboxylase, protein tyrosine kinase and lipoxygenase activities. Tocris Bioscience 2743
      Antioxidant, antimitogenic, anticarcinogenic, anti-inflammatory and antiviral. Specifically inhibits NF-?B activation and inhibits the growth of transformed cells. Also suppresses lipid peroxidation and inhibits ornithine decarboxylase, protein tyrosine kinase and lipoxygenase activities. Tocris Bioscience 2743
      Antioxidant, antimitogenic, anticarcinogenic, anti-inflammatory and antiviral. Specifically inhibits NF-kappaB activation and inhibits the growth of transformed cells. Also suppresses lipid peroxidation and inhibits ornithine decarboxylase, protein tyrosine kinase and lipoxygenase activities. Tocris Bioscience 2743
      Cell Biology Tocris Bioscience 2743
      Cytokine and NF-kB Signaling Tocris Bioscience 2743
      NF-kB/IkB Tocris Bioscience 2743
      Signal Transduction Tocris Bioscience 2743
      Specific inhibitor of NF-?B activation Tocris Bioscience 2743
      Specific inhibitor of NF-kappaB activation Tocris Bioscience 2743

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

Density: 1.3±0.1 g/cm3
Boiling Point: 498.6±45.0 °C at 760 mmHg
Vapour Pressure: 0.0±1.3 mmHg at 25°C
Enthalpy of Vaporization: 79.6±3.0 kJ/mol
Flash Point: 185.1±22.2 °C
Index of Refraction: 1.646
Molar Refractivity: 81.4±0.3 cm3
#H bond acceptors: 4
#H bond donors: 2
#Freely Rotating Bonds: 6
#Rule of 5 Violations: 0
ACD/LogP: 3.38
ACD/LogD (pH 5.5): 3.05
ACD/BCF (pH 5.5): 121.56
ACD/KOC (pH 5.5): 1081.13
ACD/LogD (pH 7.4): 3.04
ACD/BCF (pH 7.4): 119.36
ACD/KOC (pH 7.4): 1061.54
Polar Surface Area: 67 Å2
Polarizability: 32.3±0.5 10-24cm3
Surface Tension: 57.0±3.0 dyne/cm
Molar Volume: 224.5±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) =  3.60

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  428.09  (Adapted Stein & Brown method)
    Melting Pt (deg C):  173.38  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  2.04E-009  (Modified Grain method)
    Subcooled liquid VP: 7.02E-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):  48.91
       log Kow used: 3.60 (estimated)
       no-melting pt equation used

 Water Sol Estimate from Fragments:
    Wat Sol (v1.01 est) =  178.86 mg/L

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

 Henrys Law Constant (25 deg C) [HENRYWIN v3.10]:
   Bond Method :   4.80E-015  atm-m3/mole
   Group Method:   3.46E-016  atm-m3/mole
 Henrys LC [VP/WSol estimate using EPI values]:  1.560E-011 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  3.60  (KowWin est)
  Log Kaw used:  -12.707  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  16.307
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :   1.2008
   Biowin2 (Non-Linear Model)     :   0.9993
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   2.7710  (weeks       )
   Biowin4 (Primary Survey Model) :   3.6822  (days-weeks  )
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :   0.4103
   Biowin6 (MITI Non-Linear Model):   0.2817
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model):  0.3813
 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):  9.36E-006 Pa (7.02E-008 mm Hg)
  Log Koa (Koawin est  ): 16.307
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  0.321 
       Octanol/air (Koa) model:  4.98E+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 =  49.4225 E-12 cm3/molecule-sec [Cis-isomer]
      OVERALL OH Rate Constant =  52.0825 E-12 cm3/molecule-sec [Trans-isomer]
      Half-Life =    2.597 Hrs (12-hr day; 1.5E6 OH/cm3) [Cis-isomer]
      Half-Life =    2.464 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]
   Reaction With Nitrate Radicals May Be Important!
   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    :  5.132E+004
      Log Koc:  4.710 

 Aqueous Base/Acid-Catalyzed Hydrolysis (25 deg C) [HYDROWIN v1.67]:
  Total Kb for pH > 8 at 25 deg C :  1.397E-002  L/mol-sec
  Kb Half-Life at pH 8:       1.572  years  
  Kb Half-Life at pH 7:      15.721  years  

 Bioaccumulation Estimates from Log Kow (BCFWIN v2.17):
   Log BCF from regression-based method = 2.069 (BCF = 117.1)
       log Kow used: 3.60 (estimated)

 Volatilization from Water:
    Henry LC:  3.46E-016 atm-m3/mole  (estimated by Group SAR Method)
    Half-Life from Model River: 2.853E+012  hours   (1.189E+011 days)
    Half-Life from Model Lake : 3.113E+013  hours   (1.297E+012 days)

 Removal In Wastewater Treatment:
    Total removal:              15.51  percent
    Total biodegradation:        0.20  percent
    Total sludge adsorption:    15.31  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       9.62e-008       4.33         1000       
   Water     16              360          1000       
   Soil      83.1            720          1000       
   Sediment  0.874           3.24e+003    0          
     Persistence Time: 787 hr

Click to predict properties on the Chemicalize site


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