ChemSpider 2D Image | Petasin | C20H28O3

Petasin

  • Molecular FormulaC20H28O3
  • Average mass316.435 Da
  • Monoisotopic mass316.203857 Da
  • ChemSpider ID4444859

  • Double-bond stereo - Double-bond stereo

    defined stereocentres - 4 of 4 defined stereocentres

More details:

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

(+)-Petasin
(1R,2R,7S,8aR)-1,8a-dimethyl-7-(1-methylethenyl)-6-oxo-1,2,3,4,6,7,8,8a-octahydronaphthalen-2-yl (2Z)-2-methylbut-2-enoate
(1R,2R,7S,8aR)-7-Isopropenyl-1,8a-dimethyl-6-oxo-1,2,3,4,6,7,8,8a-octahydro-2-naphthalenyl (2Z)-2-methyl-2-butenoate [ACD/IUPAC Name]
(1R,2R,7S,8aR)-7-Isopropenyl-1,8a-dimethyl-6-oxo-1,2,3,4,6,7,8,8a-octahydro-2-naphthalinyl-(2Z)-2-methyl-2-butenoat [German] [ACD/IUPAC Name]
(2Z)-2-Méthyl-2-buténoate de (1R,2R,7S,8aR)-7-isopropényl-1,8a-diméthyl-6-oxo-1,2,3,4,6,7,8,8a-octahydro-2-naphtalényle [French] [ACD/IUPAC Name]
26577-85-5 [RN]
2-Butenoic acid, 2-methyl-, (1R,2R,7S,8aR)-1,2,3,4,6,7,8,8a-octahydro-1,8a-dimethyl-7-(1-methylethenyl)-6-oxo-2-naphthalenyl ester, (2Z)- [ACD/Index Name]
9Z0Q32J0QC
O-Angeloylsencathenone
Petasin [Wiki]
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Validated by Experts, Validated by Users, Non-Validated, Removed by Users

C09706 [DBID]
  • Miscellaneous

    • Chemical Class:

      An enoate ester obtained by formal condensation of the carboxy group of angelic acid with the hydroxy group of (1<stereo>R</stereo>,2<stereo>R</stereo>,7<stereo>S</stereo>,8a<stereo>R</stereo>)-1,8a-d imethyl-6-oxo-7-(prop-1-en-2-yl)-1,2,3,4,6,7,8,8a-octahydronaphthalen-2-ol. ChEBI CHEBI:8030
      An enoate ester obtained by formal condensation of the carboxy group of angelic acid with the hydroxy group of (1R,2R,7S,8aR)-1,8a-d; imethyl-6-oxo-7-(prop-1-en-2-yl)-1,2,3,4,6,7,8,8a-octahydronaphtha len-2-ol. ChEBI https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:8030
      An enoate ester obtained by formal condensation of the carboxy group of angelic acid with the hydroxy group of (1R,2R,7S,8aR)-1,8a-dimethyl-6-oxo-7-(prop-1-en-2-yl)-1,2,3,4,6,7,8,8a-octahydronaphthale n-2-ol. ChEBI CHEBI:8030

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

Density: 1.0±0.1 g/cm3
Boiling Point: 421.1±45.0 °C at 760 mmHg
Vapour Pressure: 0.0±1.0 mmHg at 25°C
Enthalpy of Vaporization: 67.5±3.0 kJ/mol
Flash Point: 181.6±28.8 °C
Index of Refraction: 1.514
Molar Refractivity: 91.4±0.4 cm3
#H bond acceptors: 3
#H bond donors: 0
#Freely Rotating Bonds: 4
#Rule of 5 Violations: 0
ACD/LogP: 4.79
ACD/LogD (pH 5.5): 4.84
ACD/BCF (pH 5.5): 2784.02
ACD/KOC (pH 5.5): 10169.31
ACD/LogD (pH 7.4): 4.84
ACD/BCF (pH 7.4): 2784.02
ACD/KOC (pH 7.4): 10169.31
Polar Surface Area: 43 Å2
Polarizability: 36.2±0.5 10-24cm3
Surface Tension: 36.4±5.0 dyne/cm
Molar Volume: 303.7±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) =  5.66

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  385.58  (Adapted Stein & Brown method)
    Melting Pt (deg C):  130.41  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  1.64E-006  (Modified Grain method)
    Subcooled liquid VP: 1.86E-005 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):  0.143
       log Kow used: 5.66 (estimated)
       no-melting pt equation used

 Water Sol Estimate from Fragments:
    Wat Sol (v1.01 est) =  0.23547 mg/L

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

 Henrys Law Constant (25 deg C) [HENRYWIN v3.10]:
   Bond Method :   4.33E-007  atm-m3/mole
   Group Method:   Incomplete
 Henrys LC [VP/WSol estimate using EPI values]:  4.775E-006 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  5.66  (KowWin est)
  Log Kaw used:  -4.752  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  10.412
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :   0.5940
   Biowin2 (Non-Linear Model)     :   0.6031
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   2.4055  (weeks-months)
   Biowin4 (Primary Survey Model) :   3.4445  (days-weeks  )
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :   0.4231
   Biowin6 (MITI Non-Linear Model):   0.0833
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model): -0.6518
 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):  0.00248 Pa (1.86E-005 mm Hg)
  Log Koa (Koawin est  ): 10.412
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  0.00121 
       Octanol/air (Koa) model:  0.00634 
   Fraction sorbed to airborne particulates (phi):
       Junge-Pankow model     :  0.0419 
       Mackay model           :  0.0882 
       Octanol/air (Koa) model:  0.336 

 Atmospheric Oxidation (25 deg C) [AopWin v1.92]:
   Hydroxyl Radicals Reaction:
      OVERALL OH Rate Constant = 177.2305 E-12 cm3/molecule-sec
      Half-Life =     0.060 Days (12-hr day; 1.5E6 OH/cm3)
      Half-Life =     0.724 Hrs
   Ozone Reaction:
      OVERALL Ozone Rate Constant =     9.731250 E-17 cm3/molecule-sec
      Half-Life =     0.118 Days (at 7E11 mol/cm3)
      Half-Life =      2.826 Hrs
   Fraction sorbed to airborne particulates (phi): 0.065 (Junge,Mackay)
    Note: the sorbed fraction may be resistant to atmospheric oxidation

 Soil Adsorption Coefficient (PCKOCWIN v1.66):
      Koc    :  5714
      Log Koc:  3.757 

 Aqueous Base/Acid-Catalyzed Hydrolysis (25 deg C) [HYDROWIN v1.67]:
  Total Kb for pH > 8 at 25 deg C :  2.063E-004  L/mol-sec
  Kb Half-Life at pH 8:     106.461  years  
  Kb Half-Life at pH 7:    1064.613  years  

 Bioaccumulation Estimates from Log Kow (BCFWIN v2.17):
   Log BCF from regression-based method = 3.662 (BCF = 4588)
       log Kow used: 5.66 (estimated)

 Volatilization from Water:
    Henry LC:  4.33E-007 atm-m3/mole  (estimated by Bond SAR Method)
    Half-Life from Model River:       2407  hours   (100.3 days)
    Half-Life from Model Lake : 2.641E+004  hours   (1100 days)

 Removal In Wastewater Treatment:
    Total removal:              89.99  percent
    Total biodegradation:        0.76  percent
    Total sludge adsorption:    89.24  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       0.0218          0.958        1000       
   Water     6.03            900          1000       
   Soil      42.2            1.8e+003     1000       
   Sediment  51.7            8.1e+003     0          
     Persistence Time: 2.07e+003 hr

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