ChemSpider 2D Image | trans-caffeic acid | C9H8O4

trans-caffeic acid

  • Molecular FormulaC9H8O4
  • Average mass180.157 Da
  • Monoisotopic mass180.042252 Da
  • ChemSpider ID600426
  • Double-bond stereo - Double-bond stereo


More details:



Featured data source



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

trans-caffeic acid
(2E)-3-(3,4-Dihydroxyphenyl)acrylic acid [ACD/IUPAC Name]
(2E)-3-(3,4-Dihydroxyphenyl)acrylsäure [German] [ACD/IUPAC Name]
2-propenoic acid, 3-(3,4-dihydroxyphenyl)-
2-Propenoic acid, 3-(3,4-dihydroxyphenyl)-, (2E)- [ACD/Index Name]
331-39-5 [RN]
Acide (2E)-3-(3,4-dihydroxyphényl)acrylique [French] [ACD/IUPAC Name]
Caffeic acid [Wiki]
(2E)-3-(3,4-Dihydroxyphenyl)-2-propenoic acid
(2E)-3-(3,4-dihydroxyphenyl)prop-2-enoic acid
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Validated by Experts, Validated by Users, Non-Validated, Removed by Users

60018_FLUKA [DBID]
60020_FLUKA [DBID]
AI3-63211 [DBID]
AIDS002287 [DBID]
AIDS-002287 [DBID]
AIDS026339 [DBID]
AIDS-026339 [DBID]
AR-360/40806927 [DBID]
C01197 [DBID]
C0625_SIGMA [DBID]
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  • Experimental Physico-chemical Properties
  • Predicted Physico-chemical Properties
  • Miscellaneous
    • Appearance:

      light yellow crystalline powder Oxford University Chemical Safety Data (No longer updated) More details
      yellow to tan Indofine [C-001N]
    • Stability:

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 Oxford University Chemical Safety Data (No longer updated) More details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

      26-36/37 Alfa Aesar A15950
      26-36/37-60 Alfa Aesar A15950
      36/37/38-40 Alfa Aesar A15950
      Carc., Xi LKT Labs [C0121]
      Carcinogenic/Harmful/Irritant SynQuest 2929-1-05
      GHS07; GHS08 Biosynth C-1500
      H315 H319 H335 H351 LKT Labs [C0121]
      H315; H319; H335; H341 Biosynth C-1500
      H351-H315-H319-H335 Alfa Aesar A15950
      P261; P280; P281; P312; P302+P352; P304+P340; P305+P351+P338 Biosynth C-1500
      P261-P280-P281-P305+P351+P338-P405-P501a Alfa Aesar A15950
      R36/37/38;R40 LKT Labs [C0121]
      Safety glasses, gloves, good ventilation. Oxford University Chemical Safety Data (No longer updated) More details
      Warning Alfa Aesar A15950
      Warning Biosynth C-1500
      WARNING: Irreversible damage risk, protect skin/eyes/lungs. Alfa Aesar A15950
      Xn Abblis Chemicals AB1002167
    • Chemical Class:

      aromatic Microsource [01503987]
    • Drug Status:

      undetermined activity Microsource [01503987]
    • Compound Source:

      Isolated from a plant Susan Richardson [Structure found on ChemSpider, confirmed from Natural Product Updates, ChEBI and ChEMBL]
      Pterogyne nitens (Fabaceae), Citrus sp. (Rutaceae), Tocoyena formosa (Rubiaceae), Alibertia macrophylla (Rubiaceae) Susan Richardson [Structure found on ChemSpider, confirmed from Natural Product Updates, ChEBI and ChEMBL]
      widespread in plants Microsource [01503987]
      Widespread in plants, free and as glycosides. Found by Bate-Smith in 66% of investigated dicotyledonous and 50% of investigated monocotyledonous plant spp. Zerenex Molecular [ZBioX-0241]
    • Bio Activity:

      Antineoplastic agent; Zerenex Molecular [ZBioX-0241]
  • Gas Chromatography
    • Retention Index (Kovats):

      1798 (estimated with error: 89) NIST Spectra mainlib_25442, replib_26654
    • Retention Index (Normal Alkane):

      1478 (Program type: Complex; Column... (show more) class: Standard non-polar; Column diameter: 0.25 mm; Column length: 30 m; Column type: Capillary; Description: 60C =>4C/min=>200C (5min) => 10C/min =>280C (20min); CAS no: 331395; Active phase: DB-1; Carrier gas: He; Phase thickness: 0.25 um; Data type: Normal alkane RI; Authors: Variyar, P.S.; Ahmad, R.; Bhat, R.; Niyas, Z.; Sharma, A., Flavoring components of raw monsooned Arabica coffee and their changes during radiation processing, J. Agric. Food Chem., 51, 2003, 7945-7950.) NIST Spectra nist ri

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

Density: 1.5±0.1 g/cm3
Boiling Point: 416.8±35.0 °C at 760 mmHg
Vapour Pressure: 0.0±1.0 mmHg at 25°C
Enthalpy of Vaporization: 70.7±3.0 kJ/mol
Flash Point: 220.0±22.4 °C
Index of Refraction: 1.707
Molar Refractivity: 47.5±0.3 cm3
#H bond acceptors: 4
#H bond donors: 3
#Freely Rotating Bonds: 2
#Rule of 5 Violations: 0
ACD/LogP: 1.42
ACD/LogD (pH 5.5): 0.04
ACD/BCF (pH 5.5): 1.00
ACD/KOC (pH 5.5): 6.27
ACD/LogD (pH 7.4): -1.74
ACD/BCF (pH 7.4): 1.00
ACD/KOC (pH 7.4): 1.00
Polar Surface Area: 78 Å2
Polarizability: 18.8±0.5 10-24cm3
Surface Tension: 77.8±3.0 dyne/cm
Molar Volume: 121.9±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) =  1.11
    Log Kow (Exper. database match) =  1.15
       Exper. Ref:  Sangster (1993)

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  365.39  (Adapted Stein & Brown method)
    Melting Pt (deg C):  144.43  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  2.94E-008  (Modified Grain method)
    MP  (exp database):  225 dec deg C
    Subcooled liquid VP: 4.09E-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):  5.407e+004
       log Kow used: 1.15 (expkow database)
       no-melting pt equation used

 Water Sol Estimate from Fragments:
    Wat Sol (v1.01 est) =  1.7241e+005 mg/L

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

 Henrys Law Constant (25 deg C) [HENRYWIN v3.10]:
   Bond Method :   1.40E-016  atm-m3/mole
   Group Method:   3.08E-017  atm-m3/mole
 Henrys LC [VP/WSol estimate using EPI values]:  1.289E-013 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  1.15  (exp database)
  Log Kaw used:  -14.242  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  15.392
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :   0.9661
   Biowin2 (Non-Linear Model)     :   0.9484
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   3.2784  (days-weeks  )
   Biowin4 (Primary Survey Model) :   4.0528  (days        )
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :   0.5228
   Biowin6 (MITI Non-Linear Model):   0.4634
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model):  0.7510
 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):  0.000545 Pa (4.09E-006 mm Hg)
  Log Koa (Koawin est  ): 15.392
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  0.0055 
       Octanol/air (Koa) model:  605 
   Fraction sorbed to airborne particulates (phi):
       Junge-Pankow model     :  0.166 
       Mackay model           :  0.306 
       Octanol/air (Koa) model:  1 

 Atmospheric Oxidation (25 deg C) [AopWin v1.92]:
   Hydroxyl Radicals Reaction:
      OVERALL OH Rate Constant =  42.1105 E-12 cm3/molecule-sec [Cis-isomer]
      OVERALL OH Rate Constant =  44.7705 E-12 cm3/molecule-sec [Trans-isomer]
      Half-Life =    3.048 Hrs (12-hr day; 1.5E6 OH/cm3) [Cis-isomer]
      Half-Life =    2.867 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): 0.236 (Junge,Mackay)
    Note: the sorbed fraction may be resistant to atmospheric oxidation

 Soil Adsorption Coefficient (PCKOCWIN v1.66):
      Koc    :  129.3
      Log Koc:  2.112 

 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: 1.15 (expkow database)

 Volatilization from Water:
    Henry LC:  3.08E-017 atm-m3/mole  (estimated by Group SAR Method)
    Half-Life from Model River: 2.551E+013  hours   (1.063E+012 days)
    Half-Life from Model Lake : 2.783E+014  hours   (1.16E+013 days)

 Removal In Wastewater Treatment:
    Total removal:               1.90  percent
    Total biodegradation:        0.09  percent
    Total sludge adsorption:     1.81  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       3.13e-009       4.94         1000       
   Water     30.1            208          1000       
   Soil      69.9            416          1000       
   Sediment  0.0586          1.87e+003    0          
     Persistence Time: 406 hr




                    

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