ChemSpider 2D Image | Lapachol | C15H14O3

Lapachol

  • Molecular FormulaC15H14O3
  • Average mass242.270 Da
  • Monoisotopic mass242.094299 Da
  • ChemSpider ID10770962

More details:

Featured data source
The Merck Index Online

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

1,4-Naphthalenedione, 2-hydroxy-3- (3-methyl-2-butenyl)-
1,4-Naphthalenedione, 2-hydroxy-3-(3-methyl-2-buten-1-yl)- [ACD/Index Name]
1,4-Naphthoquinone, 2-hydroxy-3- (3-methyl-2-butenyl)-
201-563-7 [EINECS]
2-Hydroxy-3-(3-methyl-2-buten-1-yl)-1,4-naphthochinon [German] [ACD/IUPAC Name]
2-Hydroxy-3-(3-methyl-2-buten-1-yl)-1,4-naphthochinone
2-Hydroxy-3-(3-methyl-2-buten-1-yl)-1,4-naphthoquinone [ACD/IUPAC Name]
2-Hydroxy-3-(3-méthyl-2-butén-1-yl)-1,4-naphtoquinone [French] [ACD/IUPAC Name]
2-Hydroxy-3-(3-méthyl-2-butèn-1-yl)-1,4-naphtoquinone
2-Hydroxy-3-(3-methyl-2-butenyl)-1,4-naphthoquinone
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Validated by Experts, Validated by Users, Non-Validated, Removed by Users

142905_ALDRICH [DBID]
75490 [DBID]
C.I. 75490 [DBID]
C10366 [DBID]
NSC 11905 [DBID]
NSC 629756 [DBID]
  • Experimental Physico-chemical Properties

    • Experimental Melting Point:

      141-143 °C (Literature) Indofine [020481]
      139.5 °C Jean-Claude Bradley Open Melting Point Dataset 26377
      141-143 °C (Literature) Indofine [020481] , [020481]
      139.5 °C Parchem – fine & specialty chemicals 132373
      141-143 °C Sigma-Aldrich ALDRICH-142905
  • Miscellaneous

    • Chemical Class:

      A hydroxy-1,4-naphthoquinone that is 1,4-naphthoquinone substituted by hydroxy and 3-methylbut-2-en-1-yl groups at positions 2 and 3, respectively. It is a natural compound that exhibits antibacterial and anticancer properties, first isolated in 1882 from the bark of Tabebuia avellanedae. ChEBI CHEBI:6377
  • Gas Chromatography

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

Density: 1.2±0.1 g/cm3
Boiling Point: 390.1±42.0 °C at 760 mmHg
Vapour Pressure: 0.0±0.9 mmHg at 25°C
Enthalpy of Vaporization: 67.5±3.0 kJ/mol
Flash Point: 203.9±24.4 °C
Index of Refraction: 1.606
Molar Refractivity: 67.6±0.3 cm3
#H bond acceptors: 3
#H bond donors: 1
#Freely Rotating Bonds: 2
#Rule of 5 Violations: 0
ACD/LogP: 4.08
ACD/LogD (pH 5.5): 1.79
ACD/BCF (pH 5.5): 8.76
ACD/KOC (pH 5.5): 99.38
ACD/LogD (pH 7.4): 0.02
ACD/BCF (pH 7.4): 1.00
ACD/KOC (pH 7.4): 1.68
Polar Surface Area: 54 Å2
Polarizability: 26.8±0.5 10-24cm3
Surface Tension: 51.2±3.0 dyne/cm
Molar Volume: 196.0±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) =  3.13

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  414.71  (Adapted Stein & Brown method)
    Melting Pt (deg C):  158.19  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  4.78E-009  (Modified Grain method)
    MP  (exp database):  139.5 deg C
    Subcooled liquid VP: 6.83E-008 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):  55.6
       log Kow used: 3.13 (estimated)
       no-melting pt equation used

 Water Sol Estimate from Fragments:
    Wat Sol (v1.01 est) =  5.8201 mg/L

 ECOSAR Class Program (ECOSAR v0.99h):
    Class(es) found:
       Quinone/Hydroquinone
       Vinyl/Allyl Alcohols

 Henrys Law Constant (25 deg C) [HENRYWIN v3.10]:
   Bond Method :   1.23E-008  atm-m3/mole
   Group Method:   Incomplete
 Henrys LC [VP/WSol estimate using EPI values]:  2.741E-011 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  3.13  (KowWin est)
  Log Kaw used:  -6.299  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  9.429
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :   0.8046
   Biowin2 (Non-Linear Model)     :   0.4453
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   2.7788  (weeks       )
   Biowin4 (Primary Survey Model) :   3.5832  (days-weeks  )
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :   0.4773
   Biowin6 (MITI Non-Linear Model):   0.3057
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model): -0.4033
 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):  9.11E-006 Pa (6.83E-008 mm Hg)
  Log Koa (Koawin est  ): 9.429
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  0.329 
       Octanol/air (Koa) model:  0.000659 
   Fraction sorbed to airborne particulates (phi):
       Junge-Pankow model     :  0.922 
       Mackay model           :  0.963 
       Octanol/air (Koa) model:  0.0501 

 Atmospheric Oxidation (25 deg C) [AopWin v1.92]:
   Hydroxyl Radicals Reaction:
      OVERALL OH Rate Constant = 102.4702 E-12 cm3/molecule-sec
      Half-Life =     0.104 Days (12-hr day; 1.5E6 OH/cm3)
      Half-Life =     1.253 Hrs
   Ozone Reaction:
      OVERALL Ozone Rate Constant =    44.137501 E-17 cm3/molecule-sec
      Half-Life =     0.026 Days (at 7E11 mol/cm3)
      Half-Life =     37.389 Min
   Fraction sorbed to airborne particulates (phi): 0.943 (Junge,Mackay)
    Note: the sorbed fraction may be resistant to atmospheric oxidation

 Soil Adsorption Coefficient (PCKOCWIN v1.66):
      Koc    :  13.77
      Log Koc:  1.139 

 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 = 0.869 (BCF = 7.391)
       log Kow used: 3.13 (estimated)

 Volatilization from Water:
    Henry LC:  1.23E-008 atm-m3/mole  (estimated by Bond SAR Method)
    Half-Life from Model River: 7.409E+004  hours   (3087 days)
    Half-Life from Model Lake : 8.084E+005  hours   (3.368E+004 days)

 Removal In Wastewater Treatment:
    Total removal:               6.96  percent
    Total biodegradation:        0.13  percent
    Total sludge adsorption:     6.83  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       0.0492          0.499        1000       
   Water     24.8            360          1000       
   Soil      74.6            720          1000       
   Sediment  0.531           3.24e+003    0          
     Persistence Time: 469 hr

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