(1R,3R,4S,5R)-1,3,4-Trihydroxy-5-{[(2E)-3-(4-hydroxyphenyl)-2-propenoyl]oxy}cyclohexanecarboxylic acid

Molecular FormulaC₁₆H₁₈O₈
Average mass338.309 Da
Monoisotopic mass338.100159 Da
ChemSpider ID8121397

- Double-bond stereo
- 4 of 4 defined stereocentres

More details:

Names and Synonyms
Database ID(s)

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

(1R,3R,4S,5R)-1,3,4-Trihydroxy-5-{[(2E)-3-(4-hydroxyphenyl)-2-propenoyl]oxy}cyclohexancarbonsäure [German] [ACD/IUPAC Name]

(1R,3R,4S,5R)-1,3,4-Trihydroxy-5-{[(2E)-3-(4-hydroxyphenyl)-2-propenoyl]oxy}cyclohexanecarboxylic acid [ACD/IUPAC Name]

87099-71-6 [RN]

Acide (1R,3R,4S,5R)-1,3,4-trihydroxy-5-{[(2E)-3-(4-hydroxyphényl)-2-propenoyl]oxy}cyclohexanecarboxylique [French] [ACD/IUPAC Name]

Cyclohexanecarboxylic acid, 1,3,4-trihydroxy-5-[[(2E)-3-(4-hydroxyphenyl)-1-oxo-2-propen-1-yl]oxy]-, (1R,3R,4S,5R)- [ACD/Index Name]

(1R,3R,4S,5R)-1,3,4-TRIHYDROXY-5-[(E)-3-(4-HYDROXYPHENYL)PROP-2-ENOYL]OXY-CYCLOHEXANE-1-CARBOXYLIC ACID

(1R,3R,4S,5R)-1,3,4-trihydroxy-5-{[(2E)-3-(4-hydroxyphenyl)prop-2-enoyl]oxy}cyclohexane-1-carboxylic acid

1,4,5-Trihydroxy-3-[[3-(4-hydroxyphenyl)-1-oxo-2-propenyl]oxy]cyclohexanecarboxylic acid, 9CI

3-O-p-Coumaroylquinic acid

3-p-coumaroylquinic acid

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

1AF7V9VW0S [DBID]

UNII:1AF7V9VW0S [DBID]

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

Experimental Physico-chemical Properties
- Experimental Melting Point:
  
  247-248 °C FooDB FDB000866
- Experimental Optical Rotation:
  
  20 FooDB FDB000866

Miscellaneous

Chemical Class:

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

Density:	1.6±0.1 g/cm³
Boiling Point:	613.2±55.0 °C at 760 mmHg
Vapour Pressure:	0.0±1.9 mmHg at 25°C
Enthalpy of Vaporization:	95.7±3.0 kJ/mol
Flash Point:	227.0±25.0 °C
Index of Refraction:	1.662
Molar Refractivity:	80.5±0.4 cm³
#H bond acceptors:	8
#H bond donors:	5
#Freely Rotating Bonds:	5
#Rule of 5 Violations:	1

ACD/LogP:	0.10
ACD/LogD (pH 5.5):	-2.35
ACD/BCF (pH 5.5):	1.00
ACD/KOC (pH 5.5):	1.00
ACD/LogD (pH 7.4):	-3.79
ACD/BCF (pH 7.4):	1.00
ACD/KOC (pH 7.4):	1.00
Polar Surface Area:	145 Å²
Polarizability:	31.9±0.5 10^-24cm³
Surface Tension:	88.0±5.0 dyne/cm
Molar Volume:	217.7±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) =  -0.53

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  540.59  (Adapted Stein & Brown method)
    Melting Pt (deg C):  231.56  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  5.23E-015  (Modified Grain method)
    Subcooled liquid VP: 8.72E-013 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):  1.965e+005
       log Kow used: -0.53 (estimated)
       no-melting pt equation used

 Water Sol Estimate from Fragments:
    Wat Sol (v1.01 est) =  1e+006 mg/L

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

 Henrys Law Constant (25 deg C) [HENRYWIN v3.10]:
   Bond Method :   1.21E-018  atm-m3/mole
   Group Method:   Incomplete
 Henrys LC [VP/WSol estimate using EPI values]:  1.185E-020 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  -0.53  (KowWin est)
  Log Kaw used:  -16.306  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  15.776
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :   1.0827
   Biowin2 (Non-Linear Model)     :   0.9872
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   3.1205  (weeks       )
   Biowin4 (Primary Survey Model) :   4.1193  (days        )
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :   0.8067
   Biowin6 (MITI Non-Linear Model):   0.4645
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model):  0.5563
 Ready Biodegradability Prediction:   YES

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

 Sorption to aerosols (25 Dec C)[AEROWIN v1.00]:
  Vapor pressure (liquid/subcooled):  1.16E-010 Pa (8.72E-013 mm Hg)
  Log Koa (Koawin est  ): 15.776
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  2.58E+004 
       Octanol/air (Koa) model:  1.47E+003 
   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 =  86.1251 E-12 cm3/molecule-sec [Cis-isomer]
      OVERALL OH Rate Constant =  88.7851 E-12 cm3/molecule-sec [Trans-isomer]
      Half-Life =    1.490 Hrs (12-hr day; 1.5E6 OH/cm3) [Cis-isomer]
      Half-Life =    1.446 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    :  10
      Log Koc:  1.000 

 Aqueous Base/Acid-Catalyzed Hydrolysis (25 deg C) [HYDROWIN v1.67]:
  Total Kb for pH > 8 at 25 deg C :  2.826E-003  L/mol-sec
  Kb Half-Life at pH 8:       7.773  years  
  Kb Half-Life at pH 7:      77.731  years  

 Bioaccumulation Estimates from Log Kow (BCFWIN v2.17):
   Log BCF from regression-based method = 0.500 (BCF = 3.162)
       log Kow used: -0.53 (estimated)

 Volatilization from Water:
    Henry LC:  1.21E-018 atm-m3/mole  (estimated by Bond SAR Method)
    Half-Life from Model River:   8.9E+014  hours   (3.708E+013 days)
    Half-Life from Model Lake : 9.709E+015  hours   (4.045E+014 days)

 Removal In Wastewater Treatment:
    Total removal:               1.85  percent
    Total biodegradation:        0.09  percent
    Total sludge adsorption:     1.76  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       4.44e-005       2.68         1000       
   Water     38.8            360          1000       
   Soil      61.1            720          1000       
   Sediment  0.0712          3.24e+003    0          
     Persistence Time: 580 hr

Click to predict properties on the Chemicalize site

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(1R,3R,4S,5R)-1,3,4-Trihydroxy-5-{[(2E)-3-(4-hydroxyphenyl)-2-propenoyl]oxy}cyclohexanecarboxylic acid

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Experimental Optical Rotation:

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