ChemSpider 2D Image | Dithranol | C14H10O3

Dithranol

  • Molecular FormulaC14H10O3
  • Average mass226.227 Da
  • Monoisotopic mass226.062988 Da
  • ChemSpider ID2117

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

1,8-Dihydroxy-9(10H)-anthracenon [German] [ACD/IUPAC Name]
1,8-Dihydroxy-9(10H)-anthracenone [ACD/IUPAC Name]
1,8-Dihydroxy-9(10H)-anthracénone [French] [ACD/IUPAC Name]
1,8-Dihydroxyanthracen-9(10H)-one
1143-38-0 [RN]
214-538-0 [EINECS]
83
9(10H)-Anthracenone, 1,8-dihydroxy- [ACD/Index Name]
Anthralin
dithranol [French] [INN]
More...

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

10608_FLUKA [DBID]
D2773_SIGMA [DBID]
MFCD00053409 [DBID]
  • Experimental Physico-chemical Properties
  • Miscellaneous
    • Appearance:

      Faint yellow to yellow powder Chemodex D0308
      Faint yellow to yellow powder. Chemodex D0308
    • Safety:

      GHS07 Biosynth W-108602
      H315; H319; H335 Biosynth W-108602
      P261; P305+P351+P338 Biosynth W-108602
      Warning Biosynth W-108602
    • Target Organs:

      Others TargetMol T1068
    • Chemical Class:

      An anthracene compound derived by the substitution of -OH groups for hydrogen at C-1 and C-8, and with an oxo group at C-9. ChEBI CHEBI:37510
    • Drug Status:

      approved BIONET-Key Organics KS-5183
    • Compound Source:

      synthetic Microsource [01500127]
    • Bio Activity:

      Dithranol is highly effective in the treatment of psoriasis. MedChem Express
      Dithranol is highly effective in the treatment of psoriasis.; Target: Others; Dithranol accumulates in mitochondria where it interferes with the supply of energy to the cell, probably by the oxidation of dithranol releasing free radicals. MedChem Express HY-B0738
      Dithranol is highly effective in the treatment of psoriasis.;Target: Dithranol accumulates in mitochondria where it interferes with the supply of energy to the cell, probably by the oxidation of dithranol releasing free radicals. This impedes DNA replication and so slows the excessive cell division that occurs in psoriatic plaques. In addition Dithranol may act by reducing the elevated levels of cGMP that occurs in psoriasis. MedChem Express HY-B0738
      Others MedChem Express HY-B0738
      Others TargetMol T1068
  • Gas Chromatography

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

Density: 1.4±0.1 g/cm3
Boiling Point: 464.1±45.0 °C at 760 mmHg
Vapour Pressure: 0.0±1.2 mmHg at 25°C
Enthalpy of Vaporization: 75.3±3.0 kJ/mol
Flash Point: 248.6±25.2 °C
Index of Refraction: 1.710
Molar Refractivity: 62.3±0.3 cm3
#H bond acceptors: 3
#H bond donors: 2
#Freely Rotating Bonds: 0
#Rule of 5 Violations: 0
ACD/LogP: 4.16
ACD/LogD (pH 5.5): 3.97
ACD/BCF (pH 5.5): 608.05
ACD/KOC (pH 5.5): 3401.35
ACD/LogD (pH 7.4): 3.48
ACD/BCF (pH 7.4): 197.38
ACD/KOC (pH 7.4): 1104.10
Polar Surface Area: 58 Å2
Polarizability: 24.7±0.5 10-24cm3
Surface Tension: 69.4±3.0 dyne/cm
Molar Volume: 159.4±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) =  4.40

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  400.52  (Adapted Stein & Brown method)
    Melting Pt (deg C):  166.13  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  1.06E-008  (Modified Grain method)
    MP  (exp database):  179 deg C
    Subcooled liquid VP: 4.25E-007 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):  1.635
       log Kow used: 4.40 (estimated)
       no-melting pt equation used

 Water Sol Estimate from Fragments:
    Wat Sol (v1.01 est) =  222.03 mg/L

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

 Henrys Law Constant (25 deg C) [HENRYWIN v3.10]:
   Bond Method :   1.35E-008  atm-m3/mole
   Group Method:   Incomplete
 Henrys LC [VP/WSol estimate using EPI values]:  1.930E-009 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  4.40  (KowWin est)
  Log Kaw used:  -6.258  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  10.658
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :   0.9330
   Biowin2 (Non-Linear Model)     :   0.8504
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   2.7147  (weeks-months)
   Biowin4 (Primary Survey Model) :   3.5100  (days-weeks  )
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :   0.2789
   Biowin6 (MITI Non-Linear Model):   0.1681
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model): -0.0887
 Ready Biodegradability Prediction:   NO

Hydrocarbon Biodegradation (BioHCwin v1.01):
    Structure incompatible with current estimation method!

 Sorption to aerosols (25 Dec C)[AEROWIN v1.00]:
  Vapor pressure (liquid/subcooled):  5.67E-005 Pa (4.25E-007 mm Hg)
  Log Koa (Koawin est  ): 10.658
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  0.0529 
       Octanol/air (Koa) model:  0.0112 
   Fraction sorbed to airborne particulates (phi):
       Junge-Pankow model     :  0.657 
       Mackay model           :  0.809 
       Octanol/air (Koa) model:  0.472 

 Atmospheric Oxidation (25 deg C) [AopWin v1.92]:
   Hydroxyl Radicals Reaction:
      OVERALL OH Rate Constant = 152.1976 E-12 cm3/molecule-sec
      Half-Life =     0.070 Days (12-hr day; 1.5E6 OH/cm3)
      Half-Life =     0.843 Hrs
   Ozone Reaction:
      No Ozone Reaction Estimation
   Reaction With Nitrate Radicals May Be Important!
   Fraction sorbed to airborne particulates (phi): 0.733 (Junge,Mackay)
    Note: the sorbed fraction may be resistant to atmospheric oxidation

 Soil Adsorption Coefficient (PCKOCWIN v1.66):
      Koc    :  5321
      Log Koc:  3.726 

 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 = 1.850 (BCF = 70.82)
       log Kow used: 4.40 (estimated)

 Volatilization from Water:
    Henry LC:  1.35E-008 atm-m3/mole  (estimated by Bond SAR Method)
    Half-Life from Model River: 6.523E+004  hours   (2718 days)
    Half-Life from Model Lake : 7.118E+005  hours   (2.966E+004 days)

 Removal In Wastewater Treatment:
    Total removal:              50.68  percent
    Total biodegradation:        0.48  percent
    Total sludge adsorption:    50.20  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       0.0543          1.69         1000       
   Water     14.6            900          1000       
   Soil      76.6            1.8e+003     1000       
   Sediment  8.73            8.1e+003     0          
     Persistence Time: 1.26e+003 hr




                    

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