ChemSpider 2D Image | cafestol | C20H28O3

cafestol

  • Molecular FormulaC20H28O3
  • Average mass316.435 Da
  • Monoisotopic mass316.203857 Da
  • ChemSpider ID97155

  • defined stereocentres - 6 of 6 defined stereocentres

More details:

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

(1S,4S,12S,13R,16R,17R)-17-(Hydroxymethyl)-12-methyl-8-oxapentacyclo[14.2.1.01,13.04,12.05,9]nonadeca-5(9),6-dien-17-ol [ACD/IUPAC Name]
(1S,4S,12S,13R,16R,17R)-17-(Hydroxymethyl)-12-methyl-8-oxapentacyclo[14.2.1.01,13.04,12.05,9]nonadeca-5(9),6-dien-17-ol [German] [ACD/IUPAC Name]
(1S,4S,12S,13R,16R,17R)-17-(Hydroxyméthyl)-12-méthyl-8-oxapentacyclo[14.2.1.01,13.04,12.05,9]nonadéca-5(9),6-dién-17-ol [French] [ACD/IUPAC Name]
469-83-0 [RN]
AC465T6Q6W
cafestol [Wiki]
(-)-cafestol
(1S,4S,12S,13R,16R,17R)-17-(hydroxymethyl)-12-methyl-8-oxapentacyclo[14.2.1.0(1,13).0(4,12).0(5,9)]nonadeca-5(9),6-dien-17-ol
(3bS,5aS,7R,8R,10aR,10bS)-7-(hydroxymethyl)-10b-methyl-3b,4,5,6,7,8,9,10,10a,10b,11,12-dodecahydro-5a,8-methanocyclohepta[5,6]naphtho[2,1-b]furan-7-ol
3bS,4,5,6,7R,8R,9,10,10aR,10bS,11,12-dodecahydro-7-hydroxy-10b-methyl-5aS,8-methano-5aH-cyclohepta[5,6]naphtho[2,1-b]furan-7-methanol
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Validated by Experts, Validated by Users, Non-Validated, Removed by Users

C09066 [DBID]
CCRIS 1518 [DBID]
  • Miscellaneous

    • Chemical Class:

      An organic heteropentacyclic compound and furan diterpenoid with formula C<smallsub>20</smallsub>H<smallsub>28</smallsub>O<smallsub>3</smallsub> obtained from the unsaponifiable fraction of coffee oil (a lipid fraction obtained from coffee beans by organic solvent extraction). ChEBI CHEBI:3291
      An organic heteropentacyclic compound and furan diterpenoid with formula C20H28O3 obtained from the unsaponifiable fraction of coffee oil; (a lipid fraction obtained from coffee beans by organic solv ent extraction). ChEBI https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:3291

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

Density: 1.2±0.1 g/cm3
Boiling Point: 468.6±45.0 °C at 760 mmHg
Vapour Pressure: 0.0±1.2 mmHg at 25°C
Enthalpy of Vaporization: 77.0±3.0 kJ/mol
Flash Point: 237.2±28.7 °C
Index of Refraction: 1.604
Molar Refractivity: 88.2±0.4 cm3
#H bond acceptors: 3
#H bond donors: 2
#Freely Rotating Bonds: 1
#Rule of 5 Violations: 0
ACD/LogP: 4.03
ACD/LogD (pH 5.5): 3.91
ACD/BCF (pH 5.5): 551.87
ACD/KOC (pH 5.5): 3193.08
ACD/LogD (pH 7.4): 3.91
ACD/BCF (pH 7.4): 551.87
ACD/KOC (pH 7.4): 3193.08
Polar Surface Area: 54 Å2
Polarizability: 35.0±0.5 10-24cm3
Surface Tension: 54.5±5.0 dyne/cm
Molar Volume: 256.5±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) =  4.44

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  414.67  (Adapted Stein & Brown method)
    Melting Pt (deg C):  172.74  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  8.2E-010  (Modified Grain method)
    Subcooled liquid VP: 2.78E-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):  1.595
       log Kow used: 4.44 (estimated)
       no-melting pt equation used

 Water Sol Estimate from Fragments:
    Wat Sol (v1.01 est) =  5.5531 mg/L

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

 Henrys Law Constant (25 deg C) [HENRYWIN v3.10]:
   Bond Method :   1.75E-008  atm-m3/mole
   Group Method:   Incomplete
 Henrys LC [VP/WSol estimate using EPI values]:  2.141E-010 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  4.44  (KowWin est)
  Log Kaw used:  -6.145  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  10.585
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :   0.3132
   Biowin2 (Non-Linear Model)     :   0.0123
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   1.8738  (months      )
   Biowin4 (Primary Survey Model) :   2.9233  (weeks       )
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :   0.2985
   Biowin6 (MITI Non-Linear Model):   0.1011
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model): -1.2426
 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):  3.71E-006 Pa (2.78E-008 mm Hg)
  Log Koa (Koawin est  ): 10.585
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  0.809 
       Octanol/air (Koa) model:  0.00944 
   Fraction sorbed to airborne particulates (phi):
       Junge-Pankow model     :  0.967 
       Mackay model           :  0.985 
       Octanol/air (Koa) model:  0.43 

 Atmospheric Oxidation (25 deg C) [AopWin v1.92]:
   Hydroxyl Radicals Reaction:
      OVERALL OH Rate Constant = 155.5267 E-12 cm3/molecule-sec
      Half-Life =     0.069 Days (12-hr day; 1.5E6 OH/cm3)
      Half-Life =     0.825 Hrs
   Ozone Reaction:
      No Ozone Reaction Estimation
   Reaction With Nitrate Radicals May Be Important!
   Fraction sorbed to airborne particulates (phi): 0.976 (Junge,Mackay)
    Note: the sorbed fraction may be resistant to atmospheric oxidation

 Soil Adsorption Coefficient (PCKOCWIN v1.66):
      Koc    :  2740
      Log Koc:  3.438 

 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 = 2.067 (BCF = 116.7)
       log Kow used: 4.44 (estimated)

 Volatilization from Water:
    Henry LC:  1.75E-008 atm-m3/mole  (estimated by Bond SAR Method)
    Half-Life from Model River: 5.952E+004  hours   (2480 days)
    Half-Life from Model Lake : 6.494E+005  hours   (2.706E+004 days)

 Removal In Wastewater Treatment:
    Total removal:              52.84  percent
    Total biodegradation:        0.50  percent
    Total sludge adsorption:    52.34  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       0.0384          1.65         1000       
   Water     11.7            1.44e+003    1000       
   Soil      78.3            2.88e+003    1000       
   Sediment  10              1.3e+004     0          
     Persistence Time: 1.87e+003 hr

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