ChemSpider 2D Image | (2R,5S)-2-Isopropenyl-5-methylcyclohexanone | C10H16O

(2R,5S)-2-Isopropenyl-5-methylcyclohexanone

  • Molecular FormulaC10H16O
  • Average mass152.233 Da
  • Monoisotopic mass152.120117 Da
  • ChemSpider ID4937564

  • defined stereocentres - 2 of 2 defined stereocentres

More details:

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

(2R,5S)-2-Isopropenyl-5-methylcyclohexanon [German] [ACD/IUPAC Name]
(2R,5S)-2-Isopropenyl-5-methylcyclohexanone [ACD/IUPAC Name]
(2R,5S)-2-Isopropényl-5-méthylcyclohexanone [French] [ACD/IUPAC Name]
(2R,5S)-5-Methyl-2-(1-methylethenyl)cyclohexanone
29606-79-9 [RN]
57129-09-6 [RN]
Cyclohexanone, 5-methyl-2-(1-methylethenyl)-, (2R,5S)- [ACD/Index Name]
(2R,5S)-2-isopropenyl-5-methyl-1-cyclohexanone
(2R,5S)-2-isopropenyl-5-methyl-cyclohexan-1-one
(2R,5S)-5-methyl-2-prop-1-en-2-ylcyclohexan-1-one
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Validated by Experts, Validated by Users, Non-Validated, Removed by Users

681XD66YSR [DBID]
ERN62726IX [DBID]
UNII:681XD66YSR [DBID]
UNII:ERN62726IX [DBID]
UNII-ERN62726IX [DBID]
  • Gas Chromatography

    • Retention Index (Kovats):

      1157 (Program type: Ramp; Column cl... (show more) ass: Standard non-polar; Column diameter: 0.25 mm; Column length: 25 m; Column type: Capillary; Heat rate: 5 K/min; Start T: 50 C; End T: 200 C; CAS no: 29606799; Active phase: OV-101; Carrier gas: N2; Phase thickness: 0.25 um; Data type: Kovats RI; Authors: von Poser, G.L.; Menut, C.; Toffoli, M.E.; Verin, P.; Sobral, M.; Bessiere, J.-M.; Lamaty, G.; Henriques, A.T., Essential oil composition and allelopathic effect of the Brazilian Lamiaceae Hesperozygis ringens (Benth.) Epling and Hesperozygis rhododon Epling, J. Agric. Food Chem., 44, 1996, 1829-1832.) NIST Spectra nist ri
      1188 (Program type: Complex; Column... (show more) class: Semi-standard non-polar; Column diameter: 0.25 mm; Column length: 60 m; Column type: Capillary; Description: 60 C (1 min) ^ 4 K/min -> 200 C ^ 10 K/min -> 280 C; CAS no: 29606799; Active phase: AT-5; Carrier gas: He; Phase thickness: 0.25 um; Data type: Kovats RI; Authors: Rojas, L.B.; Usubillaga, A., Composition of the essential oil fo Satureja brownei (SW.) Briq. from Venezuela, Flavour Fragr. J., 15, 2000, 21-22.) NIST Spectra nist ri

    • Retention Index (Normal Alkane):

      1155 (Program type: Complex; Column... (show more) class: Standard non-polar; Column diameter: 0.25 mm; Column length: 50 m; Column type: Capillary; Description: 70C(3min) =>4C/min =>120C =>8C/min =>250C(5min); CAS no: 29606799; Active phase: SPB-1; Phase thickness: 0.25 um; Data type: Normal alkane RI; Authors: Diaz-Maroto, M.C.; Castillo, N.; Castro-Vazquez, L.; Gonzalez-Vinas, M.A.; Perez-Coello, M.S., Volatile composition and olfactory profile of pennyroyal (Mentha pulegium L.) plants, Flavour Fragr. J., 22, 2007, 114-118., Program type: Ramp; Column cl... (show more) ass: Semi-standard non-polar; Column diameter: 0.25 mm; Column length: 30 m; Column type: Capillary; Heat rate: 3 K/min; Start T: 70 C; End T: 250 C; End time: 2 min; Start time: 3 min; CAS no: 29606799; Active phase: DB-5; Carrier gas: He; Phase thickness: 0.25 um; Data type: Normal alkane RI; Authors: Phatak, S.V.; Heble, M.R., Organogenesis and terpenoid synthesis in Mentha arvensis, Fitoterapia, 73, 2002, 32-39.) NIST Spectra nist ri
      1152 (Program type: Ramp; Column cl... (show more) ass: Standard non-polar; Column diameter: 0.25 mm; Column length: 25 m; Column type: Capillary; Heat rate: 3 K/min; Start T: 40 C; End T: 220 C; End time: 5 min; Start time: 5 min; CAS no: 29606799; Active phase: OV-1; Carrier gas: H2; Phase thickness: 0.25 um; Data type: Normal alkane RI; Authors: Oberhofer, B.; Nikiforov, A.; Buchbauer, G.; Jirovetz, L.; Bicchi, C., Investigation of the alteration of the composition of various essential oils used in aroma lamp applications, Flavour Fragr. J., 14, 1999, 293-299.) NIST Spectra nist ri
      1175 (Program type: Complex; Column... (show more) class: Semi-standard non-polar; Column diameter: 0.25 mm; Column length: 30 m; Column type: Capillary; Description: 40 0C (5 min) ^ 2 0C/min -> 250 0C (15 min) ^ 10 0C/min -> 270 0C; CAS no: 29606799; Active phase: HP-5 MS; Carrier gas: Helium; Phase thickness: 0.25 um; Data type: Normal alkane RI; Authors: Formisano, C.; Rigano, D.; Napolitano, F.; Senatore, F.; Arnold, N.A.; Piozzi, F.; Rosselli, S., Volatile constituents of Calamintha ariganifolia Boiss. growing wild in Lebanon, Natural Product Communications, 2(12), 2007, 1253-1256., Program type: Ramp; Column cl... (show more) ass: Semi-standard non-polar; Column type: Capillary; CAS no: 29606799; Active phase: DB-5; Data type: Normal alkane RI; Authors: Vilaseca, A.; Guy, I.; Charles, B.; Guinaudeau, H.; de Arias, A.R.; Fournet, A., Chemical composition and insecticidal activity of Hedeoma mandoniana essential oils, J. Essent. Oil Res., 16, 2004, 380-383.) NIST Spectra nist ri
      1160 (Program type: Ramp; Column cl... (show more) ass: Semi-standard non-polar; Column diameter: 0.25 mm; Column length: 30 m; Column type: Capillary; Heat rate: 5 K/min; Start T: 50 C; End T: 230 C; End time: 10 min; Start time: 2 min; CAS no: 29606799; Active phase: HP-5MS; Carrier gas: He; Phase thickness: 0.25 um; Data type: Normal alkane RI; Authors: Li, R.; Jiang, Z.-T., Chemical composition of the essential oil of Cuminum cyminum L. from China, Flavour Fragr. J., 19, 2004, 311-313.) NIST Spectra nist ri
      1199 (Program type: Ramp; Column cl... (show more) ass: Semi-standard non-polar; Column diameter: 0.22 mm; Column length: 25 m; Column type: Capillary; Heat rate: 3 K/min; Start T: 60 C; End T: 250 C; End time: 10 min; Start time: 5 min; CAS no: 29606799; Active phase: BPX-5; Carrier gas: He; Phase thickness: 1 um; Data type: Normal alkane RI; Authors: Vilaseca, A.; Guy, I.; Charles, B.; Guinaudeau, H.; de Arias, A.R.; Fournet, A., Chemical composition and insecticidal activity of Hedeoma mandoniana essential oils, J. Essent. Oil Res., 16, 2004, 380-383.) NIST Spectra nist ri
      1582 (Program type: Ramp; Column cl... (show more) ass: Standard polar; Column diameter: 0.25 mm; Column length: 30 m; Column type: Capillary; Description: 40 0C (5 min) ^ 2 0C/min -> 250 0C; Heat rate: 2 K/min; Start T: 40 C; End T: 250 C; Start time: 5 min; CAS no: 29606799; Active phase: HP-Innowax; Carrier gas: Helium; Phase thickness: 0.25 um; Data type: Normal alkane RI; Authors: Formisano, C.; Rigano, D.; Napolitano, F.; Senatore, F.; Arnold, N.A.; Piozzi, F.; Rosselli, S., Volatile constituents of Calamintha ariganifolia Boiss. growing wild in Lebanon, Natural Product Communications, 2(12), 2007, 1253-1256.) NIST Spectra nist ri
      1597 (Program type: Complex; Column... (show more) class: Standard polar; Column diameter: 0.25 mm; Column length: 60 m; Column type: Capillary; Description: 60C(10min) =>4C/min =>220C(10min) =>1C/min=>240C; CAS no: 29606799; Active phase: Innowax FSC; Carrier gas: He; Phase thickness: 0.25 um; Data type: Normal alkane RI; Authors: Baser, K.H.C.; Ozek, T.; Kirimer, N.; Deliorman, D.; Ergun, F., Composition of the essential oils of Galium aparine L. and Galium odoratum (L.) Scop. from Turkey, J. Essent. Oil Res., 16, 2004, 305-307., Program type: Ramp; Column cl... (show more) ass: Standard polar; Column diameter: 0.25 mm; Column length: 60 m; Column type: Capillary; Heat rate: 4 K/min; Start T: 60 C; End T: 240 C; End time: 10 min; Start time: 10 min; CAS no: 29606799; Active phase: HP-Innowax FSC; Carrier gas: He; Data type: Normal alkane RI; Authors: Baser, K.H.C.; Kirimer, N.; Duman, H., Composition of the essential oil of Micromeria dolichodontha P. H. Davis, Flavour Fragr. J., 12, 1997, 289-291., Program type: Ramp; Column cl... (show more) ass: Standard polar; Column diameter: 0.25 mm; Column length: 60 m; Column type: Capillary; Start T: 60 C; End T: 220 C; Start time: 10 min; CAS no: 29606799; Active phase: HP-Innowax; Carrier gas: He; Phase thickness: 0.25 um; Data type: Normal alkane RI; Authors: Kaya, A.; Baser, K.H.C.; Tumen, G.; Koca, F., The essential oil of Acinos suaveolens (Sm.) G. Don fil. Acinos arvensis (Lam.) Dandy and Acinos rotundifolius Pers. growing wild in Turkey, Flavour Fragr. J., 14, 1999, 60-64.) NIST Spectra nist ri
      1598 (Program type: Complex; Column... (show more) class: Standard polar; Column diameter: 0.25 mm; Column length: 60 m; Column type: Capillary; Description: 60 0C (10 min) ^ 4 K/min -> 220 0C (10 min) ^ 1 K/min -> 240 0C; CAS no: 29606799; Active phase: HP-Innowax; Carrier gas: He; Phase thickness: 0.25 um; Data type: Normal alkane RI; Authors: Baser, K.H.C.; Demirci, B.; Kirimer, N.; Satil, F.; Tumen, G., The essential oils of Thymus migricus and T. fedtschenkoi var. handelii from Turkey, Flavour Fragr. J., 17, 2002, 41-45.) NIST Spectra nist ri

    • Retention Index (Linear):

      1159 (Program type: Ramp; Column cl... (show more) ass: Standard non-polar; Column diameter: 0.22 mm; Column length: 50 m; Column type: Capillary; Heat rate: 2 K/min; Start T: 60 C; End T: 220 C; End time: 20 min; CAS no: 29606799; Active phase: BP-1; Carrier gas: He; Phase thickness: 0.25 um; Data type: Linear RI; Authors: Castilho, P.; Liu, K.; Rodrigues, A.I.; Feio, S.; Tomi, F.; Casanova, J., Composition and antimicrobial activity of the essential oil of Clinopodium ascendens (Jordan) Sampaio from Madeira, Flavour Fragr. J., 22, 2007, 139-144.) NIST Spectra nist ri
      1177 (Program type: Ramp; Column cl... (show more) ass: Semi-standard non-polar; Column diameter: 0.25 mm; Column length: 30 m; Column type: Capillary; Heat rate: 5 K/min; Start T: 40 C; End T: 250 C; End time: 10 min; Start time: 1 min; CAS no: 29606799; Active phase: HP-5; Carrier gas: He; Phase thickness: 0.25 um; Data type: Linear RI; Authors: Benzo, M.; Gilardoni, G.; Gandini, C.; Caccialanza, G.; Finzi, P.V.; Vidari, G.; Abdo, S.; Layedra, P., Determination of the threshold odor concentration of main odorants in essential oils using gas chromatography-olfactometry incremental dilution technique, J. Chromatogr. A, 1150, 2007, 131-135.) NIST Spectra nist ri
      1192 (Program type: Complex; Column... (show more) class: Semi-standard non-polar; Column diameter: 0.25 mm; Column length: 30 m; Column type: Capillary; Description: 35C(5min) =>3C/min =>210C =>40C/min =>240C (4min); CAS no: 29606799; Active phase: BPX-5; Phase thickness: 0.25 um; Data type: Linear RI; Authors: Cardeal, Z.L.; da Silva, M.D.R.G.; Marriott, P.J., Comprehensive two-dimensional gas chromatography/mass spectrometric analysis of pepper volatiles, Rapid Commun. Mass Spectrom., 20, 2006, 2823-2836.) NIST Spectra nist ri
      1167 (Program type: Complex; Column... (show more) class: Semi-standard non-polar; Column diameter: 0.32 mm; Column length: 30 m; Column type: Capillary; Description: 60C(8min) => 3C/min =>180C => 20C/min =>250C(10min); CAS no: 29606799; Active phase: SE-52; Carrier gas: H2; Phase thickness: 0.42 um; Data type: Linear RI; Authors: Lorenzo, D.; Paz, D.; Dellacassa, E.; Davies, P.; Vila, R.; Canigueral, S., Essential oils of Mentha pulegium and Mentha rotundifolia from Uruguay, Braz. Arch. Biol. Technol., 45(4), 2002, 519-524.) NIST Spectra nist ri
      1592 (Program type: Ramp; Column cl... (show more) ass: Standard polar; Column diameter: 0.22 mm; Column length: 50 m; Column type: Capillary; Heat rate: 2 K/min; Start T: 60 C; End T: 220 C; End time: 20 min; CAS no: 29606799; Active phase: BP-20; Carrier gas: He; Phase thickness: 0.25 um; Data type: Linear RI; Authors: Castilho, P.; Liu, K.; Rodrigues, A.I.; Feio, S.; Tomi, F.; Casanova, J., Composition and antimicrobial activity of the essential oil of Clinopodium ascendens (Jordan) Sampaio from Madeira, Flavour Fragr. J., 22, 2007, 139-144.) NIST Spectra nist ri

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

Density: 0.9±0.1 g/cm3
Boiling Point: 216.4±29.0 °C at 760 mmHg
Vapour Pressure: 0.1±0.4 mmHg at 25°C
Enthalpy of Vaporization: 45.3±3.0 kJ/mol
Flash Point: 79.5±19.2 °C
Index of Refraction: 1.457
Molar Refractivity: 45.9±0.3 cm3
#H bond acceptors: 1
#H bond donors: 0
#Freely Rotating Bonds: 1
#Rule of 5 Violations: 0
ACD/LogP: 2.47
ACD/LogD (pH 5.5): 2.44
ACD/BCF (pH 5.5): 42.22
ACD/KOC (pH 5.5): 507.19
ACD/LogD (pH 7.4): 2.44
ACD/BCF (pH 7.4): 42.22
ACD/KOC (pH 7.4): 507.19
Polar Surface Area: 17 Å2
Polarizability: 18.2±0.5 10-24cm3
Surface Tension: 28.0±3.0 dyne/cm
Molar Volume: 168.5±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) =  2.86

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  217.88  (Adapted Stein & Brown method)
    Melting Pt (deg C):  -0.75  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  0.219  (Mean VP of Antoine & Grain methods)

 Water Solubility Estimate from Log Kow (WSKOW v1.41):
    Water Solubility at 25 deg C (mg/L):  266.2
       log Kow used: 2.86 (estimated)
       no-melting pt equation used

 Water Sol Estimate from Fragments:
    Wat Sol (v1.01 est) =  897.09 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 :   1.40E-004  atm-m3/mole
   Group Method:   Incomplete
 Henrys LC [VP/WSol estimate using EPI values]:  1.648E-004 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  2.86  (KowWin est)
  Log Kaw used:  -2.242  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  5.102
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :   0.6819
   Biowin2 (Non-Linear Model)     :   0.5972
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   2.8403  (weeks       )
   Biowin4 (Primary Survey Model) :   3.6059  (days-weeks  )
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :   0.4742
   Biowin6 (MITI Non-Linear Model):   0.3801
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model): -0.1431
 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):  27.2 Pa (0.204 mm Hg)
  Log Koa (Koawin est  ): 5.102
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  1.1E-007 
       Octanol/air (Koa) model:  3.1E-008 
   Fraction sorbed to airborne particulates (phi):
       Junge-Pankow model     :  3.98E-006 
       Mackay model           :  8.82E-006 
       Octanol/air (Koa) model:  2.48E-006 

 Atmospheric Oxidation (25 deg C) [AopWin v1.92]:
   Hydroxyl Radicals Reaction:
      OVERALL OH Rate Constant =  69.5542 E-12 cm3/molecule-sec
      Half-Life =     0.154 Days (12-hr day; 1.5E6 OH/cm3)
      Half-Life =     1.845 Hrs
   Ozone Reaction:
      OVERALL Ozone Rate Constant =     1.200000 E-17 cm3/molecule-sec
      Half-Life =     0.955 Days (at 7E11 mol/cm3)
      Half-Life =     22.920 Hrs
   Fraction sorbed to airborne particulates (phi): 6.4E-006 (Junge,Mackay)
    Note: the sorbed fraction may be resistant to atmospheric oxidation

 Soil Adsorption Coefficient (PCKOCWIN v1.66):
      Koc    :  123.7
      Log Koc:  2.092 

 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 = 1.505 (BCF = 31.96)
       log Kow used: 2.86 (estimated)

 Volatilization from Water:
    Henry LC:  0.00014 atm-m3/mole  (estimated by Bond SAR Method)
    Half-Life from Model River:      6.419  hours
    Half-Life from Model Lake :      173.5  hours   (7.229 days)

 Removal In Wastewater Treatment:
    Total removal:              10.82  percent
    Total biodegradation:        0.11  percent
    Total sludge adsorption:     4.37  percent
    Total to Air:                6.34  percent
      (using 10000 hr Bio P,A,S)

 Level III Fugacity Model:
           Mass Amount    Half-Life    Emissions
            (percent)        (hr)       (kg/hr)
   Air       0.481           3.18         1000       
   Water     22.3            360          1000       
   Soil      76.9            720          1000       
   Sediment  0.289           3.24e+003    0          
     Persistence Time: 402 hr

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