ChemSpider 2D Image | alpha-Cyano-4-hydroxycinnamic acid | C10H7NO3

α-Cyano-4-hydroxycinnamic acid

  • Molecular FormulaC10H7NO3
  • Average mass189.167 Da
  • Monoisotopic mass189.042587 Da
  • ChemSpider ID4485953
  • Double-bond stereo - Double-bond stereo


More details:






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

(2E)-2-Cyan-3-(4-hydroxyphenyl)acrylsäure [German] [ACD/IUPAC Name]
(2E)-2-Cyano-3-(4-hydroxyphenyl)acrylic acid [ACD/IUPAC Name]
(2E)-2-cyano-3-(4-hydroxyphenyl)prop-2-enoic acid
2-Propenoic acid, 2-cyano-3-(4-hydroxyphenyl)-, (2E)- [ACD/Index Name]
Acide (2E)-2-cyano-3-(4-hydroxyphényl)acrylique [French] [ACD/IUPAC Name]
α-cyano-4-hydroxycinnamic acid
α-Cyano-4-hydroxycinnamic acid [Wiki]
28166-41-8 [RN]
(2E)-2-Cyano-3-(4-hydroxyphenyl)-2-propenoic acid
(E)-2-cyano-3-(4-hydroxyphenyl)acrylic acid
More...

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

145505_ALDRICH [DBID]
476870_ALDRICH [DBID]
70990_FLUKA [DBID]
C2020_SIGMA [DBID]
C8982_SIGMA [DBID]
CCRIS 4693 [DBID]
MFCD00004204 [DBID]
  • Experimental Physico-chemical Properties
  • Miscellaneous
    • Chemical Class:

      A monohydroxycinnamic acid that is 4-hydroxycinnamic acid in which the hydrogen <locant>alpha</locant>- to the carboxy group is replaced by a cyano group. It is used as a matrix in matrix-assisted las er desorption/ionization (MALDI) mass spectrometry for the analysis of peptides and oligonucleotides. ChEBI CHEBI:64340
    • Therapeutical Effect:

      inhibitor of mitochondrial pyruvate transport Microsource [01502096]
    • Drug Status:

      experimental Microsource [01502096]
    • Compound Source:

      synthetic Microsource [01502096]
    • Bio Activity:

      Ion Pumps/Transporters Tocris Bioscience 5029
      MCT inhibitor; decreases glycoloysis Tocris Bioscience 5029
      Monocarboxylate Transporters Tocris Bioscience 5029
      Monocarboxylic acid transport (MCT) inhibitor. Exhibits antitumoral and antiangiogenic activity in gliomas in vivo; decreases glycolytic metabolism, migration, and invasion in U251 cells. Enhances the effect of antitumor agent temozolomide (Cat No. 2706). Blocks lactate efflux from glioma cells and sensitizes cells to irradiation. Tocris Bioscience 5029
      Monocarboxylic acid transport (MCT) inhibitor. Exhibits antitumoral and antiangiogenic activity in gliomas in vivo; decreases glycolytic metabolism, migration, and invasion in U251 cells. Enhances the effect of DNA-methylating antitumor agent temozolomide (Cat No. 2706). Tocris Bioscience 5029
      Monocarboxylic acid transport (MCT) inhibitor. Exhibits antitumoral and antiangiogenic activity in gliomas in vivo; decreases glycolytic metabolism, migration, and invasion in U251 cells. Enhances the effect of DNA-methylating antitumor agent temozolomide (Cat No. 2706). Tocris Bioscience 5029
      Transporters Tocris Bioscience 5029
  • Gas Chromatography

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

Density: 1.4±0.1 g/cm3
Boiling Point: 398.1±32.0 °C at 760 mmHg
Vapour Pressure: 0.0±1.0 mmHg at 25°C
Enthalpy of Vaporization: 68.4±3.0 kJ/mol
Flash Point: 194.5±25.1 °C
Index of Refraction: 1.674
Molar Refractivity: 50.0±0.3 cm3
#H bond acceptors: 4
#H bond donors: 2
#Freely Rotating Bonds: 3
#Rule of 5 Violations: 0
ACD/LogP: 1.53
ACD/LogD (pH 5.5): -2.21
ACD/BCF (pH 5.5): 1.00
ACD/KOC (pH 5.5): 1.00
ACD/LogD (pH 7.4): -2.26
ACD/BCF (pH 7.4): 1.00
ACD/KOC (pH 7.4): 1.00
Polar Surface Area: 81 Å2
Polarizability: 19.8±0.5 10-24cm3
Surface Tension: 74.6±3.0 dyne/cm
Molar Volume: 133.2±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) =  1.79

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  385.55  (Adapted Stein & Brown method)
    Melting Pt (deg C):  143.97  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  2.62E-007  (Modified Grain method)
    Subcooled liquid VP: 4.2E-006 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):  7549
       log Kow used: 1.79 (estimated)
       no-melting pt equation used

 Water Sol Estimate from Fragments:
    Wat Sol (v1.01 est) =  2.0058e+005 mg/L

 ECOSAR Class Program (ECOSAR v0.99h):
    Class(es) found:
       Allylic/Vinyl Nitriles-acid
       Phenols-acid

 Henrys Law Constant (25 deg C) [HENRYWIN v3.10]:
   Bond Method :   3.00E-015  atm-m3/mole
   Group Method:   Incomplete
 Henrys LC [VP/WSol estimate using EPI values]:  8.639E-012 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  1.79  (KowWin est)
  Log Kaw used:  -12.911  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  14.701
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :   1.1530
   Biowin2 (Non-Linear Model)     :   0.9985
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   3.1197  (weeks       )
   Biowin4 (Primary Survey Model) :   3.9349  (days        )
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :   0.5055
   Biowin6 (MITI Non-Linear Model):   0.3614
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model):  0.6483
 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):  0.00056 Pa (4.2E-006 mm Hg)
  Log Koa (Koawin est  ): 14.701
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  0.00536 
       Octanol/air (Koa) model:  123 
   Fraction sorbed to airborne particulates (phi):
       Junge-Pankow model     :  0.162 
       Mackay model           :  0.3 
       Octanol/air (Koa) model:  1 

 Atmospheric Oxidation (25 deg C) [AopWin v1.92]:
   Hydroxyl Radicals Reaction:
      OVERALL OH Rate Constant =  36.8593 E-12 cm3/molecule-sec
      Half-Life =     0.290 Days (12-hr day; 1.5E6 OH/cm3)
      Half-Life =     3.482 Hrs
   Ozone Reaction:
      OVERALL Ozone Rate Constant =     0.105000 E-17 cm3/molecule-sec
      Half-Life =    10.914 Days (at 7E11 mol/cm3)
   Reaction With Nitrate Radicals May Be Important!
   Fraction sorbed to airborne particulates (phi): 0.231 (Junge,Mackay)
    Note: the sorbed fraction may be resistant to atmospheric oxidation

 Soil Adsorption Coefficient (PCKOCWIN v1.66):
      Koc    :  47.36
      Log Koc:  1.675 

 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 = 0.500 (BCF = 3.162)
       log Kow used: 1.79 (estimated)

 Volatilization from Water:
    Henry LC:  3E-015 atm-m3/mole  (estimated by Bond SAR Method)
    Half-Life from Model River: 2.684E+011  hours   (1.118E+010 days)
    Half-Life from Model Lake : 2.928E+012  hours   (1.22E+011 days)

 Removal In Wastewater Treatment:
    Total removal:               2.09  percent
    Total biodegradation:        0.09  percent
    Total sludge adsorption:     2.00  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       7.34e-008       6.78         1000       
   Water     25.3            360          1000       
   Soil      74.6            720          1000       
   Sediment  0.0731          3.24e+003    0          
     Persistence Time: 686 hr




                    

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