ChemSpider 2D Image | (R)-(+)-verbenone | C10H14O

(R)-(+)-verbenone

  • Molecular FormulaC10H14O
  • Average mass150.218 Da
  • Monoisotopic mass150.104462 Da
  • ChemSpider ID59147

  • defined stereocentres - 2 of 2 defined stereocentres

More details:

Featured data source
The Merck Index Online

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

(R)-(+)-verbenone
(+)-Verbenone
(1R,5R)-(+)-2-Pinen-4-one
(1R,5R)-(+)-pin-2-en-4-one
(1R,5R)-2-pinen-4-one
(1R,5R)-4,6,6-Trimethylbicyclo[3.1.1]hept-3-en-2-on [German] [ACD/IUPAC Name]
(1R,5R)-4,6,6-Trimethylbicyclo[3.1.1]hept-3-en-2-one [ACD/IUPAC Name]
(1R,5R)-4,6,6-Triméthylbicyclo[3.1.1]hept-3-én-2-one [French] [ACD/IUPAC Name]
18309-32-5 [RN]
242-195-7 [EINECS]
More...

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

AI3-23127 [DBID]
EPA Pesticide Chemical Code 128986 [DBID]
ZINC00967600 [DBID]
  • Miscellaneous

    • Chemical Class:

      A 4,6,6-trimethylbicyclo[3.1.1]hept-3-en-2-one in which both chiral centres have <stereo>R</stereo> configuration. It is a component of Spanish verbena oil, from <ital>Verbena triphylla</ital>. ChEBI CHEBI:9955
      A 4,6,6-trimethylbicyclo[3.1.1]hept-3-en-2-one in which both chiral centres have R configuration. It is a component of Spanish verbena oil, from Verbena triphylla. ChEBI https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:9955, CHEBI:9955
  • Gas Chromatography

    • Retention Index (Normal Alkane):

      1170 (Program type: Complex; Column... (show more) class: Standard non-polar; Column diameter: 0.25 mm; Column length: 30 m; Column type: Capillary; Description: 45C=>3C/min =>175C =>15C/min=> 300C (15min); CAS no: 18309325; Active phase: DB-1; Carrier gas: He; Phase thickness: 0.25 um; Data type: Normal alkane RI; Authors: Touafek, O.; Nacer, A.; Kabouce, A.; Kabouche, Z.; Bruneau, C., Chemical composition of the essential oil of Rosmarinus officinalis cultivated in the Algerian sahara, Chem. Nat. Compd. (Engl. Transl.), 40(1), 2004, 28-29, In original 25-26.) NIST Spectra nist ri
      1228 (Program type: Ramp; Column cl... (show more) ass: Semi-standard non-polar; Column diameter: 0.25 mm; Column length: 60 m; Column type: Capillary; Heat rate: 6 K/min; Start T: 40 C; End T: 260 C; End time: 1 min; Start time: 7 min; CAS no: 18309325; Active phase: ZP-5; Carrier gas: He; Phase thickness: 0.25 um; Data type: Normal alkane RI; Authors: Fussel, U.; Dotterl, S.; Jurgens, A.; Aas, G., Inter- and intraspecific variation in floral scent in the genus Salix and its implication for pollination, J. Chem. Ecol., 33, 2007, 749-765.) NIST Spectra nist ri

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

Density: 1.0±0.1 g/cm3
Boiling Point: 227.5±0.0 °C at 760 mmHg
Vapour Pressure: 0.1±0.4 mmHg at 25°C
Enthalpy of Vaporization: 46.4±3.0 kJ/mol
Flash Point: 86.9±8.9 °C
Index of Refraction: 1.494
Molar Refractivity: 44.1±0.3 cm3
#H bond acceptors: 1
#H bond donors: 0
#Freely Rotating Bonds: 0
#Rule of 5 Violations: 0
ACD/LogP: 1.97
ACD/LogD (pH 5.5): 2.37
ACD/BCF (pH 5.5): 37.42
ACD/KOC (pH 5.5): 465.15
ACD/LogD (pH 7.4): 2.37
ACD/BCF (pH 7.4): 37.42
ACD/KOC (pH 7.4): 465.15
Polar Surface Area: 17 Å2
Polarizability: 17.5±0.5 10-24cm3
Surface Tension: 29.5±3.0 dyne/cm
Molar Volume: 151.4±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) =  3.21
    Log Kow (Exper. database match) =  2.23
       Exper. Ref:  Griffin,S et al. (1999)

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  215.05  (Adapted Stein & Brown method)
    Melting Pt (deg C):  28.88  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  0.136  (Mean VP of Antoine & Grain methods)
    MP  (exp database):  9.8 deg C
    BP  (exp database):  227.5 deg C

 Water Solubility Estimate from Log Kow (WSKOW v1.41):
    Water Solubility at 25 deg C (mg/L):  943.4
       log Kow used: 2.23 (expkow database)
       no-melting pt equation used

 Water Sol Estimate from Fragments:
    Wat Sol (v1.01 est) =  75.518 mg/L

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

 Henrys Law Constant (25 deg C) [HENRYWIN v3.10]:
   Bond Method :   3.87E-005  atm-m3/mole
   Group Method:   Incomplete
 Henrys LC [VP/WSol estimate using EPI values]:  2.849E-005 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  2.23  (exp database)
  Log Kaw used:  -2.801  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  5.031
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :   0.4989
   Biowin2 (Non-Linear Model)     :   0.2141
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   2.6326  (weeks-months)
   Biowin4 (Primary Survey Model) :   3.4553  (days-weeks  )
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :   0.5026
   Biowin6 (MITI Non-Linear Model):   0.3742
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model): -0.2434
 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):  17.2 Pa (0.129 mm Hg)
  Log Koa (Koawin est  ): 5.031
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  1.74E-007 
       Octanol/air (Koa) model:  2.64E-008 
   Fraction sorbed to airborne particulates (phi):
       Junge-Pankow model     :  6.3E-006 
       Mackay model           :  1.4E-005 
       Octanol/air (Koa) model:  2.11E-006 

 Atmospheric Oxidation (25 deg C) [AopWin v1.92]:
   Hydroxyl Radicals Reaction:
      OVERALL OH Rate Constant =  81.3732 E-12 cm3/molecule-sec
      Half-Life =     0.131 Days (12-hr day; 1.5E6 OH/cm3)
      Half-Life =     1.577 Hrs
   Ozone Reaction:
      OVERALL Ozone Rate Constant =     7.393750 E-17 cm3/molecule-sec
      Half-Life =     0.155 Days (at 7E11 mol/cm3)
      Half-Life =      3.720 Hrs
   Fraction sorbed to airborne particulates (phi): 1.01E-005 (Junge,Mackay)
    Note: the sorbed fraction may be resistant to atmospheric oxidation

 Soil Adsorption Coefficient (PCKOCWIN v1.66):
      Koc    :  112.5
      Log Koc:  2.051 

 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 = 1.017 (BCF = 10.4)
       log Kow used: 2.23 (expkow database)

 Volatilization from Water:
    Henry LC:  3.87E-005 atm-m3/mole  (estimated by Bond SAR Method)
    Half-Life from Model River:      19.79  hours
    Half-Life from Model Lake :      318.7  hours   (13.28 days)

 Removal In Wastewater Treatment:
    Total removal:               4.53  percent
    Total biodegradation:        0.10  percent
    Total sludge adsorption:     2.39  percent
    Total to Air:                2.04  percent
      (using 10000 hr Bio P,A,S)

 Level III Fugacity Model:
           Mass Amount    Half-Life    Emissions
            (percent)        (hr)       (kg/hr)
   Air       0.149           1.71         1000       
   Water     26              900          1000       
   Soil      73.7            1.8e+003     1000       
   Sediment  0.136           8.1e+003     0          
     Persistence Time: 733 hr

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