(2R,3R)-5,7-Dihydroxy-2-(3,4,5-trihydroxyphenyl)-3,4-dihydro-2H-chromen-3-yl (2E)-3-(4-hydroxyphenyl)acrylate

Molecular FormulaC₂₄H₂₀O₉
Average mass452.410 Da
Monoisotopic mass452.110718 Da
ChemSpider ID4976697

- Double-bond stereo
- 2 of 2 defined stereocentres

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Names and Synonyms
Database ID(s)

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

(2E)-3-(4-Hydroxyphényl)acrylate de (2R,3R)-5,7-dihydroxy-2-(3,4,5-trihydroxyphényl)-3,4-dihydro-2H-chromén-3-yle [French] [ACD/IUPAC Name]

(2R,3R)-5,7-Dihydroxy-2-(3,4,5-trihydroxyphenyl)-3,4-dihydro-2H-chromen-3-yl (2E)-3-(4-hydroxyphenyl)acrylate [ACD/IUPAC Name]

(2R,3R)-5,7-dihydroxy-2-(3,4,5-trihydroxyphenyl)-3,4-dihydro-2H-chromen-3-yl (2E)-3-(4-hydroxyphenyl)prop-2-enoate

(2R,3R)-5,7-Dihydroxy-2-(3,4,5-trihydroxyphenyl)-3,4-dihydro-2H-chromen-3-yl-(2E)-3-(4-hydroxyphenyl)acrylat [German] [ACD/IUPAC Name]

2-Propenoic acid, 3-(4-hydroxyphenyl)-, (2R,3R)-3,4-dihydro-5,7-dihydroxy-2-(3,4,5-trihydroxyphenyl)-2H-1-benzopyran-3-yl ester, (2E)- [ACD/Index Name]

(-)-Epigallocatechin 3-O-p-coumaroate

(-)-Epigallocatechin 3-p-coumaroate

(2R,3R)-5,7-dihydroxy-2-(3,4,5-trihydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-3-yl (2E)-3-(4-hydroxyphenyl)prop-2-enoate

(E)-3-(4-Hydroxy-phenyl)-acrylic acid (2R,3R)-5,7-dihydroxy-2-(3,4,5-trihydroxy-phenyl)-chroman-3-yl ester

3-O-p-Coumaroylepigallocatechin

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

AIDS051676 [DBID]

AIDS-051676 [DBID]

Experimental data
Predicted - ACD/Labs
Predicted - EPISuite
Predicted - ChemAxon

Experimental Physico-chemical Properties
- Experimental Optical Rotation:
  
  22 FooDB FDB017701

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

Density:	1.7±0.1 g/cm³
Boiling Point:	782.9±60.0 °C at 760 mmHg
Vapour Pressure:	0.0±2.8 mmHg at 25°C
Enthalpy of Vaporization:	117.9±3.0 kJ/mol
Flash Point:	273.6±26.4 °C
Index of Refraction:	1.779
Molar Refractivity:	114.5±0.4 cm³
#H bond acceptors:	9
#H bond donors:	6
#Freely Rotating Bonds:	5
#Rule of 5 Violations:	1

ACD/LogP:	2.18
ACD/LogD (pH 5.5):	2.39
ACD/BCF (pH 5.5):	38.44
ACD/KOC (pH 5.5):	474.12
ACD/LogD (pH 7.4):	2.37
ACD/BCF (pH 7.4):	36.48
ACD/KOC (pH 7.4):	449.97
Polar Surface Area:	157 Å²
Polarizability:	45.4±0.5 10^-24cm³
Surface Tension:	108.2±5.0 dyne/cm
Molar Volume:	273.2±5.0 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) =  3.63

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  677.59  (Adapted Stein & Brown method)
    Melting Pt (deg C):  295.56  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  2.47E-018  (Modified Grain method)
    Subcooled liquid VP: 2.55E-015 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):  4.381
       log Kow used: 3.63 (estimated)
       no-melting pt equation used

 Water Sol Estimate from Fragments:
    Wat Sol (v1.01 est) =  0.12551 mg/L

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

 Henrys Law Constant (25 deg C) [HENRYWIN v3.10]:
   Bond Method :   1.19E-033  atm-m3/mole
   Group Method:   Incomplete
 Henrys LC [VP/WSol estimate using EPI values]:  3.356E-019 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  3.63  (KowWin est)
  Log Kaw used:  -31.313  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  34.943
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :   1.5878
   Biowin2 (Non-Linear Model)     :   0.9999
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   2.5449  (weeks-months)
   Biowin4 (Primary Survey Model) :   3.6707  (days-weeks  )
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :   0.3156
   Biowin6 (MITI Non-Linear Model):   0.0568
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model):  0.7105
 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):  3.4E-013 Pa (2.55E-015 mm Hg)
  Log Koa (Koawin est  ): 34.943
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  8.82E+006 
       Octanol/air (Koa) model:  2.15E+022 
   Fraction sorbed to airborne particulates (phi):
       Junge-Pankow model     :  1 
       Mackay model           :  1 
       Octanol/air (Koa) model:  1 

 Atmospheric Oxidation (25 deg C) [AopWin v1.92]:
   Hydroxyl Radicals Reaction:
      OVERALL OH Rate Constant = 240.9807 E-12 cm3/molecule-sec [Cis-isomer]
      OVERALL OH Rate Constant = 243.6407 E-12 cm3/molecule-sec [Trans-isomer]
      Half-Life =    0.533 Hrs (12-hr day; 1.5E6 OH/cm3) [Cis-isomer]
      Half-Life =    0.527 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): 1 (Junge,Mackay)
    Note: the sorbed fraction may be resistant to atmospheric oxidation

 Soil Adsorption Coefficient (PCKOCWIN v1.66):
      Koc    :  1.054E+007
      Log Koc:  7.023 

 Aqueous Base/Acid-Catalyzed Hydrolysis (25 deg C) [HYDROWIN v1.67]:
  Total Kb for pH > 8 at 25 deg C :  2.630E-004  L/mol-sec
  Kb Half-Life at pH 8:      83.501  years  
  Kb Half-Life at pH 7:     835.011  years  

 Bioaccumulation Estimates from Log Kow (BCFWIN v2.17):
   Log BCF from regression-based method = 2.092 (BCF = 123.5)
       log Kow used: 3.63 (estimated)

 Volatilization from Water:
    Henry LC:  1.19E-033 atm-m3/mole  (estimated by Bond SAR Method)
    Half-Life from Model River: 1.046E+030  hours   (4.36E+028 days)
    Half-Life from Model Lake : 1.142E+031  hours   (4.757E+029 days)

 Removal In Wastewater Treatment:
    Total removal:              16.34  percent
    Total biodegradation:        0.21  percent
    Total sludge adsorption:    16.13  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       6.74e-018       1.02         1000       
   Water     11.4            900          1000       
   Soil      87.5            1.8e+003     1000       
   Sediment  1.13            8.1e+003     0          
     Persistence Time: 1.85e+003 hr

Click to predict properties on the Chemicalize site

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(2R,3R)-5,7-Dihydroxy-2-(3,4,5-trihydroxyphenyl)-3,4-dihydro-2H-chromen-3-yl (2E)-3-(4-hydroxyphenyl)acrylate

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