ChemSpider 2D Image | Monomethyl fumarate | C5H6O4

Monomethyl fumarate

  • Molecular FormulaC5H6O4
  • Average mass130.099 Da
  • Monoisotopic mass130.026611 Da
  • ChemSpider ID4520322
  • Double-bond stereo - Double-bond stereo


More details:






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

(2E)-4-Methoxy-4-oxo-2-butenoic acid [ACD/IUPAC Name]
(2E)-4-Methoxy-4-oxo-2-butensäure [German] [ACD/IUPAC Name]
(2E)-4-Methoxy-4-oxobut-2-enoic acid
220-412-6 [EINECS]
2756-87-8 [RN]
2-Butenedioic acid, monomethyl ester [ACD/Index Name]
2-Butenedioic acid, monomethyl ester, (2E)- [ACD/Index Name]
2E-butenedioic acid, 1-methyl ester
Acide (2E)-4-méthoxy-4-oxo-2-buténoïque [French] [ACD/IUPAC Name]
Fumaric acid monomethyl ester
More...

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

45IUB1PX8R [DBID]
651419_ALDRICH [DBID]
CCRIS 4693 [DBID]
UNII:45IUB1PX8R [DBID]
UNII-45IUB1PX8R [DBID]
  • Experimental Physico-chemical Properties
  • Miscellaneous
    • Chemical Class:

      A dicarboxylic acid monoester resulting from the formal condensation of one of the carboxy groups of fumaric acid with methanol. Is is a metabolite of dimethyl fumarate and used for the the treatment of patients with relapsing multiple sclerosis (MS). It also induces the NFE2L2 (Nrf2) transcription factor by binding to KEAP1. ChEBI CHEBI:167450
    • Bio Activity:

      Activator of Nrf2 pathway; primary metabolite of DMF (Cat. No. 4512) Tocris Bioscience 4511
      Antioxidants Tocris Bioscience 4511
      Nuclear factor (erythroid-derived-2)-like 2 (Nrf2) pathway activator. Also exhibits agonist activity at GPR109A. Primary metabolite of DMF (Cat. No. 4512). Tocris Bioscience 4511
      Other Pharmacology Tocris Bioscience 4511
  • Gas Chromatography

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

Density: 1.3±0.1 g/cm3
Boiling Point: 250.0±23.0 °C at 760 mmHg
Vapour Pressure: 0.0±1.1 mmHg at 25°C
Enthalpy of Vaporization: 53.6±6.0 kJ/mol
Flash Point: 108.9±16.1 °C
Index of Refraction: 1.469
Molar Refractivity: 28.6±0.3 cm3
#H bond acceptors: 4
#H bond donors: 1
#Freely Rotating Bonds: 3
#Rule of 5 Violations: 0
ACD/LogP: -0.24
ACD/LogD (pH 5.5): -1.98
ACD/BCF (pH 5.5): 1.00
ACD/KOC (pH 5.5): 1.00
ACD/LogD (pH 7.4): -3.44
ACD/BCF (pH 7.4): 1.00
ACD/KOC (pH 7.4): 1.00
Polar Surface Area: 64 Å2
Polarizability: 11.3±0.5 10-24cm3
Surface Tension: 44.0±3.0 dyne/cm
Molar Volume: 102.8±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) =  0.93

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  237.23  (Adapted Stein & Brown method)
    Melting Pt (deg C):  40.17  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  0.0372  (Modified Grain method)
    Subcooled liquid VP: 0.0511 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):  3.685e+004
       log Kow used: 0.93 (estimated)
       no-melting pt equation used

 Water Sol Estimate from Fragments:
    Wat Sol (v1.01 est) =  2.2564e+005 mg/L

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

 Henrys Law Constant (25 deg C) [HENRYWIN v3.10]:
   Bond Method :   4.33E-010  atm-m3/mole
   Group Method:   3.38E-011  atm-m3/mole
 Henrys LC [VP/WSol estimate using EPI values]:  1.728E-007 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  0.93  (KowWin est)
  Log Kaw used:  -7.752  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  8.682
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :   0.9325
   Biowin2 (Non-Linear Model)     :   0.9972
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   3.4165  (days-weeks  )
   Biowin4 (Primary Survey Model) :   4.2746  (hours-days  )
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :   0.8628
   Biowin6 (MITI Non-Linear Model):   0.9189
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model):  0.9681
 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):  6.81 Pa (0.0511 mm Hg)
  Log Koa (Koawin est  ): 8.682
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  4.4E-007 
       Octanol/air (Koa) model:  0.000118 
   Fraction sorbed to airborne particulates (phi):
       Junge-Pankow model     :  1.59E-005 
       Mackay model           :  3.52E-005 
       Octanol/air (Koa) model:  0.00935 

 Atmospheric Oxidation (25 deg C) [AopWin v1.92]:
   Hydroxyl Radicals Reaction:
      OVERALL OH Rate Constant =   7.6466 E-12 cm3/molecule-sec [Cis-isomer]
      OVERALL OH Rate Constant =   8.5776 E-12 cm3/molecule-sec [Trans-isomer]
      Half-Life =    1.399 Days (12-hr day; 1.5E6 OH/cm3) [Cis-isomer]
      Half-Life =    1.247 Days (12-hr day; 1.5E6 OH/cm3) [Trans-isomer]
   Ozone Reaction:
      OVERALL Ozone Rate Constant =     0.087500 E-17 cm3/molecule-sec [Cis-]
      OVERALL Ozone Rate Constant =     0.175000 E-17 cm3/molecule-sec [Trans-]
      Half-Life =    13.097 Days (at 7E11 mol/cm3) [Cis-isomer]
      Half-Life =     6.549 Days (at 7E11 mol/cm3) [Trans-isomer]
   Fraction sorbed to airborne particulates (phi): 2.56E-005 (Junge,Mackay)
    Note: the sorbed fraction may be resistant to atmospheric oxidation

 Soil Adsorption Coefficient (PCKOCWIN v1.66):
      Koc    :  1
      Log Koc:  0.000 

 Aqueous Base/Acid-Catalyzed Hydrolysis (25 deg C) [HYDROWIN v1.67]:
  Total Kb for pH > 8 at 25 deg C :  2.256E-001  L/mol-sec
  Kb Half-Life at pH 8:      35.553  days   
  Kb Half-Life at pH 7:     355.535  days   

 Bioaccumulation Estimates from Log Kow (BCFWIN v2.17):
   Log BCF from regression-based method = 0.500 (BCF = 3.162)
       log Kow used: 0.93 (estimated)

 Volatilization from Water:
    Henry LC:  3.38E-011 atm-m3/mole  (estimated by Group SAR Method)
    Half-Life from Model River: 1.976E+007  hours   (8.232E+005 days)
    Half-Life from Model Lake : 2.155E+008  hours   (8.981E+006 days)

 Removal In Wastewater Treatment:
    Total removal:               1.88  percent
    Total biodegradation:        0.09  percent
    Total sludge adsorption:     1.79  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       0.00115         30.3         1000       
   Water     31.5            208          1000       
   Soil      68.4            416          1000       
   Sediment  0.0587          1.87e+003    0          
     Persistence Time: 399 hr




                    

Click to predict properties on the Chemicalize site






Advertisement