ChemSpider 2D Image | Orlandin | C22H18O8


  • Molecular FormulaC22H18O8
  • Average mass410.374 Da
  • Monoisotopic mass410.100159 Da
  • ChemSpider ID4588423

More details:

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

[8,8'-Bi-2H-1-benzopyran]-2,2'-dione, 7,7'-dihydroxy-4,4'-dimethoxy-5,5'-dimethyl- [ACD/Index Name]
7,7'-Dihydroxy-4,4'-dimethoxy-5,5'-dimethyl-2H,2'H-8,8'-bichromen-2,2'-dion [German] [ACD/IUPAC Name]
7,7'-Dihydroxy-4,4'-dimethoxy-5,5'-dimethyl-2H,2'H-8,8'-bichromene-2,2'-dione [ACD/IUPAC Name]
7,7'-Dihydroxy-4,4'-diméthoxy-5,5'-diméthyl-2H,2'H-8,8'-bichromène-2,2'-dione [French] [ACD/IUPAC Name]
(8,8'-Bi-2H-1-Benzopyran)-2,2'-dione, 7,7'-dihydroxy-4,4'-dimethoxy-5,5'-dimethyl-
69975-77-5 [RN]
  • Miscellaneous
    • Chemical Class:

      A member of the class of 8,8'-bicoumarins that is kotanin in which the methoxy groups at the 7 and 7' positions are replaced by hydroxy groups. A fungal metabolite, its isolation from <ital>Aspergillu s niger</ital> was first reported in 1979. ChEBI CHEBI:64473
      A member of the class of 8,8'-bicoumarins that is kotanin in which the methoxy groups at the 7 and 7' positions are replaced by hydroxy groups. A fungal metabolite, its isolation from Aspergillu; s ni ger was first reported in 1979. ChEBI

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

Density: 1.5±0.1 g/cm3
Boiling Point: 729.9±60.0 °C at 760 mmHg
Vapour Pressure: 0.0±2.5 mmHg at 25°C
Enthalpy of Vaporization: 110.3±3.0 kJ/mol
Flash Point: 260.7±26.4 °C
Index of Refraction: 1.686
Molar Refractivity: 103.3±0.4 cm3
#H bond acceptors: 8
#H bond donors: 2
#Freely Rotating Bonds: 3
#Rule of 5 Violations: 0
ACD/LogP: 3.43
ACD/LogD (pH 5.5): 3.12
ACD/BCF (pH 5.5): 135.35
ACD/KOC (pH 5.5): 1141.77
ACD/LogD (pH 7.4): 2.06
ACD/BCF (pH 7.4): 11.87
ACD/KOC (pH 7.4): 100.15
Polar Surface Area: 112 Å2
Polarizability: 40.9±0.5 10-24cm3
Surface Tension: 74.8±5.0 dyne/cm
Molar Volume: 271.4±5.0 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) =  0.54

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  642.86  (Adapted Stein & Brown method)
    Melting Pt (deg C):  279.33  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  9.97E-018  (Modified Grain method)
    Subcooled liquid VP: 6.43E-015 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):  3460
       log Kow used: 0.54 (estimated)
       no-melting pt equation used

 Water Sol Estimate from Fragments:
    Wat Sol (v1.01 est) =  1795.4 mg/L

 ECOSAR Class Program (ECOSAR v0.99h):
    Class(es) found:
       Vinyl/Allyl Ethers

 Henrys Law Constant (25 deg C) [HENRYWIN v3.10]:
   Bond Method :   6.39E-018  atm-m3/mole
   Group Method:   Incomplete
 Henrys LC [VP/WSol estimate using EPI values]:  1.556E-021 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  0.54  (KowWin est)
  Log Kaw used:  -15.583  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  16.123
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :   0.5350
   Biowin2 (Non-Linear Model)     :   0.7474
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   2.6969  (weeks-months)
   Biowin4 (Primary Survey Model) :   3.7947  (days        )
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :   0.4765
   Biowin6 (MITI Non-Linear Model):   0.0704
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model): -0.0477
 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):  8.57E-013 Pa (6.43E-015 mm Hg)
  Log Koa (Koawin est  ): 16.123
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  3.5E+006 
       Octanol/air (Koa) model:  3.26E+003 
   Fraction sorbed to airborne particulates (phi):
       Junge-Pankow model     :  1 
       Mackay model           :  1 
       Octanol/air (Koa) model:  1 

 Atmospheric Oxidation (25 deg C) [AopWin v1.92]:
   Hydroxyl Radicals Reaction:
      OVERALL OH Rate Constant = 406.6121 E-12 cm3/molecule-sec
      Half-Life =     0.026 Days (12-hr day; 1.5E6 OH/cm3)
      Half-Life =    18.940 Min
   Ozone Reaction:
      OVERALL Ozone Rate Constant =   772.710022 E-17 cm3/molecule-sec
      Half-Life =     0.001 Days (at 7E11 mol/cm3)
      Half-Life =      2.136 Min
   Reaction With Nitrate Radicals May Be Important!
   Fraction sorbed to airborne particulates (phi): 1 (Junge,Mackay)
    Note: the sorbed fraction may be resistant to atmospheric oxidation

 Soil Adsorption Coefficient (PCKOCWIN v1.66):
      Koc    :  11.38
      Log Koc:  1.056 

 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: 0.54 (estimated)

 Volatilization from Water:
    Henry LC:  6.39E-018 atm-m3/mole  (estimated by Bond SAR Method)
    Half-Life from Model River: 1.856E+014  hours   (7.734E+012 days)
    Half-Life from Model Lake : 2.025E+015  hours   (8.437E+013 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       0.00239         0.0337       1000       
   Water     50.7            900          1000       
   Soil      49.2            1.8e+003     1000       
   Sediment  0.101           8.1e+003     0          
     Persistence Time: 633 hr


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