ChemSpider 2D Image | Dimethyl fumarate | C6H8O4

Dimethyl fumarate

  • Molecular FormulaC6H8O4
  • Average mass144.125 Da
  • Monoisotopic mass144.042252 Da
  • ChemSpider ID553171
  • Double-bond stereo - Double-bond stereo


More details:



Featured data source



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

(2E)-2-Butènedioate de diméthyle [French] [ACD/IUPAC Name]
(E)-2-Butenedioic acid dimethyl ester
(E)-But-2-enedioic acid dimethyl ester
(E)-Dimethyl fumarate
210-849-0 [EINECS]
2-Butenedioic acid (2E)-, 1,4-dimethyl ester
2-Butenedioic acid (2E)-, dimethyl ester
2-Butenedioic acid, dimethyl ester [ACD/Index Name]
2-Butenedioic acid, dimethyl ester, (2E)- [ACD/Index Name]
624-49-7 [RN]
More...

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

AZL O 211089 [DBID]
242926_ALDRICH [DBID]
47967_FLUKA [DBID]
AI3-07872 [DBID]
AIDS208583 [DBID]
AIDS-208583 [DBID]
BRN 0774590 [DBID]
D03846 [DBID]
NSC 167432 [DBID]
NSC 25942 [DBID]
More...
  • Experimental Physico-chemical Properties
  • Predicted Physico-chemical Properties
  • Miscellaneous
    • Appearance:

      fine white crystalline powder Oxford University Chemical Safety Data (No longer updated) More details
    • Stability:

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 Oxford University Chemical Safety Data (No longer updated) More details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

      ORL-RAT LD50 2240 mg kg-1, SKN-RBT LD50 1250 mg kg-1 Oxford University Chemical Safety Data (No longer updated) More details
    • Safety:

      21-36/37/38-43 Alfa Aesar A10402
      26-36/37-60 Alfa Aesar A10402
      H312-H315-H319-H317-H335 Alfa Aesar A10402
      Harmful/Irritant/Moisture Sensitive/Store under Argon SynQuest 2323-1-16
      N07XX09 Wikidata Q418123
      P261-P280-P305+P351+P338-P304+P340-P405-P501a Alfa Aesar A10402
      Safety glasses. Oxford University Chemical Safety Data (No longer updated) More details
      Warning Alfa Aesar A10402
      WARNING: Harmful through skin absorbtion or ingestion. Alfa Aesar A10402
    • Target Organs:

      NF-??B inhibitor TargetMol T0492
    • Chemical Class:

      An enoate ester resulting from the formal condensation of both carboxy groups of fumaric acid with methanol. Used for treatment of adults with relapsing forms of multiple sclerosis. ChEBI CHEBI:76004
    • Bio Activity:

      Antioxidants Tocris Bioscience 4512
      Dimethyl fumarate(DMF) is a nuclear factor (erythroid-derived)-like 2 (Nrf2) pathway activator; induces upregulation of antioxidant gene expression. MedChem Express http://www.medchemexpress.com/dexpramipexole-dihydrochloride.html, HY-17363
      Dimethyl fumarate(DMF) is a nuclear factor (erythroid-derived)-like 2 (Nrf2) pathway activator; induces upregulation of antioxidant gene expression. ;IC50 value:;Target: Nrf2Dimethyl fumarate displays cytoprotective effects in human spinal cord astrocytes, oligodendrocyte precursor cells and hippocampal neurons following hydrogen peroxide challenge. Dimethyl fumarate exerts neuroprotective effects in vivo in experimental autoimmune encephalomyelitis. MedChem Express HY-17363
      Immunology/Inflammation TargetMol T0492
      Keap1-Nrf2 MedChem Express HY-17363
      KEAP1-Nrf2 TargetMol T0492
      NF-kB MedChem Express HY-17363
      NF-kB; MedChem Express HY-17363
      Nrf2 pathway activator; neuroprotective Tocris Bioscience 4512
      Nuclear factor (erythroid-derived)-like 2 (Nrf2) pathway activator; induces upregulation of antioxidant gene expression. Displays cytoprotective effects in human spinal cord astrocytes, oligodendrocyt e precursor cells and hippocampal neurons following hydrogen peroxide challenge. Exerts neuroprotective effects in vivo in experimental autoimmune encephalomyelitis. Primary metabolite (MMF, Cat. No. 4511) available. Tocris Bioscience 4512
      Nuclear factor (erythroid-derived)-like 2 (Nrf2) pathway activator; induces upregulation of antioxidant gene expression. Displays cytoprotective effects in human spinal cord astrocytes, oligodendrocyte precursor cells and hippocampal neurons following hydrogen peroxide challenge. Exerts neuroprotective effects in vivo in experimental autoimmune encephalomyelitis. Primary metabolite (MMF, Cat. No. 4511) available. Tocris Bioscience 4512
      Other Pharmacology Tocris Bioscience 4512
  • Gas Chromatography

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

Density: 1.1±0.1 g/cm3
Boiling Point: 193.0±0.0 °C at 760 mmHg
Vapour Pressure: 0.5±0.3 mmHg at 25°C
Enthalpy of Vaporization: 42.9±3.0 kJ/mol
Flash Point: 91.1±0.0 °C
Index of Refraction: 1.435
Molar Refractivity: 33.5±0.3 cm3
#H bond acceptors: 4
#H bond donors: 0
#Freely Rotating Bonds: 4
#Rule of 5 Violations: 0
ACD/LogP: 0.62
ACD/LogD (pH 5.5): 0.50
ACD/BCF (pH 5.5): 1.41
ACD/KOC (pH 5.5): 44.51
ACD/LogD (pH 7.4): 0.50
ACD/BCF (pH 7.4): 1.41
ACD/KOC (pH 7.4): 44.51
Polar Surface Area: 53 Å2
Polarizability: 13.3±0.5 10-24cm3
Surface Tension: 33.2±3.0 dyne/cm
Molar Volume: 128.2±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) =  1.21
    Log Kow (Exper. database match) =  0.22
       Exper. Ref:  Hansch,C et al. (1995)
    Log Kow (Exper. database match) =  0.74
       Exper. Ref:  Hansch,C et al. (1995)

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  150.99  (Adapted Stein & Brown method)
    Melting Pt (deg C):  -95.85  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  0.0797  (Modified Grain method)
    MP  (exp database):  103.5 deg C
    BP  (exp database):  193 deg C
    VP  (exp database):  3.00E-01 mm Hg at 25 deg C
    Subcooled liquid VP: 1.79 mm Hg (25 deg C, exp database VP )

 Water Solubility Estimate from Log Kow (WSKOW v1.41):
    Water Solubility at 25 deg C (mg/L):  1.877e+004
       log Kow used: 0.74 (expkow database)
       no-melting pt equation used
     Water Sol (Exper. database match) =  8e+004 mg/L (25 deg C)
        Exper. Ref:  RIDDICK,JA ET AL. (1986)

 Water Sol Estimate from Fragments:
    Wat Sol (v1.01 est) =  1.5407e+005 mg/L
    Wat Sol (Exper. database match) =  80000.00
       Exper. Ref:  RIDDICK,JA ET AL. (1986)

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

 Henrys Law Constant (25 deg C) [HENRYWIN v3.10]:
   Bond Method :   1.39E-007  atm-m3/mole
   Group Method:   1.34E-008  atm-m3/mole
   Exper Database: 7.11E-07  atm-m3/mole
 Henrys LC [VP/WSol estimate using EPI values]:  8.053E-007 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  0.74  (exp database)
  Log Kaw used:  -4.537  (exp database)
      Log Koa (KOAWIN v1.10 estimate):  5.277
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :   1.0273
   Biowin2 (Non-Linear Model)     :   0.9999
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   3.1611  (weeks       )
   Biowin4 (Primary Survey Model) :   4.0977  (days        )
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :   0.9840
   Biowin6 (MITI Non-Linear Model):   0.9662
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model):  0.8736
 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):  239 Pa (1.79 mm Hg)
  Log Koa (Koawin est  ): 5.277
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  1.26E-008 
       Octanol/air (Koa) model:  4.65E-008 
   Fraction sorbed to airborne particulates (phi):
       Junge-Pankow model     :  4.54E-007 
       Mackay model           :  1.01E-006 
       Octanol/air (Koa) model:  3.72E-006 

 Atmospheric Oxidation (25 deg C) [AopWin v1.92]:
   Hydroxyl Radicals Reaction:
      OVERALL OH Rate Constant =   7.3442 E-12 cm3/molecule-sec [Cis-isomer]
      OVERALL OH Rate Constant =   8.2752 E-12 cm3/molecule-sec [Trans-isomer]
      Half-Life =    1.456 Days (12-hr day; 1.5E6 OH/cm3) [Cis-isomer]
      Half-Life =    1.293 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): 7.3E-007 (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 :  6.718E-001  L/mol-sec
  Kb Half-Life at pH 8:      11.941  days   
  Kb Half-Life at pH 7:     119.413  days   

 Bioaccumulation Estimates from Log Kow (BCFWIN v2.17):
   Log BCF from regression-based method = 0.500 (BCF = 3.162)
       log Kow used: 0.74 (expkow database)

 Volatilization from Water:
    Henry LC:  7.11E-007 atm-m3/mole  (Henry experimental database)
    Half-Life from Model River:      989.8  hours   (41.24 days)
    Half-Life from Model Lake :  1.09E+004  hours   (454.1 days)

 Removal In Wastewater Treatment:
    Total removal:               1.91  percent
    Total biodegradation:        0.09  percent
    Total sludge adsorption:     1.78  percent
    Total to Air:                0.04  percent
      (using 10000 hr Bio P,A,S)

 Level III Fugacity Model:
           Mass Amount    Half-Life    Emissions
            (percent)        (hr)       (kg/hr)
   Air       2.64            31.4         1000       
   Water     43.7            360          1000       
   Soil      53.6            720          1000       
   Sediment  0.084           3.24e+003    0          
     Persistence Time: 379 hr




                    

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