ChemSpider 2D Image | Citraconic acid | C5H6O4

Citraconic acid

  • Molecular FormulaC5H6O4
  • Average mass130.099 Da
  • Monoisotopic mass130.026611 Da
  • ChemSpider ID553689
  • Double-bond stereo - Double-bond stereo


More details:



Featured data source



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

(2Z)-2-Methyl-2-butendisäure [German] [ACD/IUPAC Name]
(2Z)-2-Methyl-2-butenedioic acid [ACD/IUPAC Name]
(2Z)-2-methylbut-2-enedioic acid
0RQ6CXO9KD
207-858-7 [EINECS]
2-Butenedioic acid, 2-methyl-, (2Z)- [ACD/Index Name]
498-23-7 [RN]
Acide (2Z)-2-méthyl-2-butènedioïque [French] [ACD/IUPAC Name]
Citraconate
Citraconic acid [Wiki]
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Validated by Experts, Validated by Users, Non-Validated, Removed by Users

27420_FLUKA [DBID]
bmse000199 [DBID]
BRN 1722679 [DBID]
BRN 1722680 [DBID]
C01732 [DBID]
C02226 [DBID]
C82604_ALDRICH [DBID]
CHEBI:17626 [DBID]
NSC 32949 [DBID]
NSC 65438 [DBID]
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  • Experimental Physico-chemical Properties
  • Miscellaneous
  • Gas Chromatography
    • Retention Index (Kovats):

      1216 (estimated with error: 51) NIST Spectra mainlib_230419, replib_2931
    • Retention Index (Normal Alkane):

      1222 (Program type: Complex; Column... (show more) class: Standard non-polar; Column diameter: 0.25 mm; Column length: 60 m; Column type: Capillary; Description: 50 0C (5 min) ^ 3 0C/min -> 120 0C ^ 5 0C/min -> 250 0C (3 min) ^ 15 0C/min -> 300 0C (20 min); CAS no: 498237; Active phase: DB-1; Carrier gas: Helium; Phase thickness: 0.25 um; Data type: Normal alkane RI; Authors: Delort, E.; Jaquier, A., Novel terpenyl esters from Australian finger lime (Citrus australasica) peel extract, Flav. Fragr. J., 24, 2009, 123-132.) NIST Spectra nist ri

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

Density: 1.4±0.1 g/cm3
Boiling Point: 336.6±25.0 °C at 760 mmHg
Vapour Pressure: 0.0±1.6 mmHg at 25°C
Enthalpy of Vaporization: 63.7±6.0 kJ/mol
Flash Point: 171.5±19.7 °C
Index of Refraction: 1.514
Molar Refractivity: 28.2±0.3 cm3
#H bond acceptors: 4
#H bond donors: 2
#Freely Rotating Bonds: 2
#Rule of 5 Violations: 0
ACD/LogP: 0.54
ACD/LogD (pH 5.5): -2.47
ACD/BCF (pH 5.5): 1.00
ACD/KOC (pH 5.5): 1.00
ACD/LogD (pH 7.4): -4.28
ACD/BCF (pH 7.4): 1.00
ACD/KOC (pH 7.4): 1.00
Polar Surface Area: 75 Å2
Polarizability: 11.2±0.5 10-24cm3
Surface Tension: 57.4±3.0 dyne/cm
Molar Volume: 93.7±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) =  0.60

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  296.33  (Adapted Stein & Brown method)
    Melting Pt (deg C):  88.30  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  2.99E-005  (Modified Grain method)
    MP  (exp database):  204.5 deg C
    Subcooled liquid VP: 0.00237 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):  6.99e+004
       log Kow used: 0.60 (estimated)
       no-melting pt equation used
     Water Sol (Exper. database match) =  7.83e+005 mg/L (25 deg C)
        Exper. Ref:  YALKOWSKY,SH & DANNENFELSER,RM (1992)
     Water Sol (Exper. database match) =  2.63e+004 mg/L (18 deg C)
        Exper. Ref:  YALKOWSKY,SH & DANNENFELSER,RM (1992)

 Water Sol Estimate from Fragments:
    Wat Sol (v1.01 est) =  1.747e+005 mg/L
    Wat Sol (Exper. database match) =  783000.00
       Exper. Ref:  YALKOWSKY,SH & DANNENFELSER,RM (1992)
    Wat Sol (Exper. database match) =  26300.00
       Exper. Ref:  YALKOWSKY,SH & DANNENFELSER,RM (1992)

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

 Henrys Law Constant (25 deg C) [HENRYWIN v3.10]:
   Bond Method :   2.12E-012  atm-m3/mole
   Group Method:   5.35E-013  atm-m3/mole
 Henrys LC [VP/WSol estimate using EPI values]:  7.322E-011 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  0.60  (KowWin est)
  Log Kaw used:  -10.062  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  10.662
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :   0.8310
   Biowin2 (Non-Linear Model)     :   0.9204
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   3.6409  (days-weeks  )
   Biowin4 (Primary Survey Model) :   4.4312  (hours-days  )
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :   0.6940
   Biowin6 (MITI Non-Linear Model):   0.7478
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model):  1.0565
 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):  0.316 Pa (0.00237 mm Hg)
  Log Koa (Koawin est  ): 10.662
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  9.49E-006 
       Octanol/air (Koa) model:  0.0113 
   Fraction sorbed to airborne particulates (phi):
       Junge-Pankow model     :  0.000343 
       Mackay model           :  0.000759 
       Octanol/air (Koa) model:  0.474 

 Atmospheric Oxidation (25 deg C) [AopWin v1.92]:
   Hydroxyl Radicals Reaction:
      OVERALL OH Rate Constant =  11.8212 E-12 cm3/molecule-sec
      Half-Life =     0.905 Days (12-hr day; 1.5E6 OH/cm3)
      Half-Life =    10.858 Hrs
   Ozone Reaction:
      OVERALL Ozone Rate Constant =     1.137500 E-17 cm3/molecule-sec
      Half-Life =     1.007 Days (at 7E11 mol/cm3)
      Half-Life =     24.179 Hrs
   Fraction sorbed to airborne particulates (phi): 0.000551 (Junge,Mackay)
    Note: the sorbed fraction may be resistant to atmospheric oxidation

 Soil Adsorption Coefficient (PCKOCWIN v1.66):
      Koc    :  10.44
      Log Koc:  1.019 

 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: 0.60 (estimated)

 Volatilization from Water:
    Henry LC:  5.35E-013 atm-m3/mole  (estimated by Group SAR Method)
    Half-Life from Model River: 1.248E+009  hours   (5.201E+007 days)
    Half-Life from Model Lake : 1.362E+010  hours   (5.674E+008 days)

 Removal In Wastewater Treatment:
    Total removal:               1.86  percent
    Total biodegradation:        0.09  percent
    Total sludge adsorption:     1.77  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       1.87e-005       11.4         1000       
   Water     32.9            208          1000       
   Soil      67              416          1000       
   Sediment  0.059           1.87e+003    0          
     Persistence Time: 393 hr




                    

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