ChemSpider 2D Image | Thymoquinone | C10H12O2

Thymoquinone

  • Molecular FormulaC10H12O2
  • Average mass164.201 Da
  • Monoisotopic mass164.083725 Da
  • ChemSpider ID9861

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

2,5-Cyclohexadiene-1,4-dione, 2-methyl-5- (1-methylethyl)-
2,5-Cyclohexadiene-1,4-dione, 2-methyl-5-(1-methylethyl)- [ACD/Index Name]
2-Isopropyl-5-methyl-1,4-benzochinon [German] [ACD/IUPAC Name]
2-Isopropyl-5-methyl-1,4-benzoquinone [ACD/IUPAC Name]
2-Isopropyl-5-méthyl-1,4-benzoquinone [French] [ACD/IUPAC Name]
2-isopropyl-5-methylbenzo-1,4-quinone
2-methyl-5-(propan-2-yl)cyclohexa-2,5-diene-1,4-dione
2-Methyl-5-iso-propylbenzoquinone
2-methyl-5-propan-2-ylcyclohexa-2,5-diene-1,4-dione
4-07-00-02100 [Beilstein]
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Validated by Experts, Validated by Users, Non-Validated, Removed by Users

274666_ALDRICH [DBID]
AI3-17758 [DBID]
BRN 1939047 [DBID]
CCRIS 7152 [DBID]
DivK1c_006553 [DBID]
KBio1_001497 [DBID]
KBio2_001717 [DBID]
KBio2_004285 [DBID]
KBio2_006853 [DBID]
KBio3_002349 [DBID]
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  • Spectroscopy
  • Experimental Physico-chemical Properties
  • Predicted Physico-chemical Properties
  • Miscellaneous
  • Gas Chromatography
    • Retention Index (Kovats):

      1340 (estimated with error: 57) NIST Spectra mainlib_233824, replib_135732, replib_261744
      1260 (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: 2 K/min; Start T: 60 C; End T: 280 C; End time: 30 min; Start time: 8 min; CAS no: 490915; Active phase: HP-5MS; Carrier gas: He; Phase thickness: 0.25 um; Data type: Kovats RI; Authors: Hazzit, M.; Baaliouamer, A.; Faleiro, M.L.; Miguel, M.G., Composition of the Essential Oils of Thymus and Origanum Species from Algeria and Their Antioxidant and Antimicrobial Activities, J. Agric. Food Chem., 54, 2006, 6314-6321.) NIST Spectra nist ri
    • Retention Index (Normal Alkane):

      1239 (Program type: Ramp; Column cl... (show more) ass: Standard non-polar; Column diameter: 0.25 mm; Column length: 50 m; Column type: Capillary; Heat rate: 4 K/min; Start T: 95 C; End T: 240 C; CAS no: 490915; Active phase: DB-1; Carrier gas: He; Phase thickness: 0.25 um; Data type: Normal alkane RI; Authors: Pala-Paul, J.; Brophy, J.J.; Perez-Alonso, M.J.; Usano, J.; Soria, S.C., Essential oil composition of the different parts of Eryngium corniculatum Lam. (Apiaceae) from Spain, J. Chromatogr. A, 1175, 2007, 289-293.) NIST Spectra nist ri
      1210 (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(10min); CAS no: 490915; Active phase: DB-1; Carrier gas: He; Phase thickness: 0.25 um; Data type: Normal alkane RI; Authors: Belhattab, R.; Larous, L.; Figueiredo, A.C.; Santos, P.A.G.; Barroso, J.G.; Pedro, L.G., Origanum glandulosum Desf. grown wild in Algeria: essential oil composition and glycosidic bound volatiles, Flavour Fragr. J., 20, 2005, 209-212.) NIST Spectra nist ri
      1226 (Program type: Ramp; Column cl... (show more) ass: Standard non-polar; Column diameter: 0.25 mm; Column length: 60 m; Column type: Capillary; Heat rate: 4 K/min; Start T: 40 C; End T: 220 C; CAS no: 490915; Active phase: DB-1; Carrier gas: He; Phase thickness: 0.25 um; Data type: Normal alkane RI; Authors: Rasooli, I.; Mirmostafa, S.A., Bacterial susceptibility to and chemical composition of essential oils from Thymus kotschyanus and Thymus persicus, J. Agric. Food Chem., 51, 2003, 2200-2205.) NIST Spectra nist ri
      1220 (Program type: Ramp; Column cl... (show more) ass: Standard non-polar; Column diameter: 0.2 mm; Column length: 25 m; Column type: Capillary; Heat rate: 3 K/min; Start T: 70 C; End T: 200 C; End time: 10 min; Start time: 2 min; CAS no: 490915; Active phase: HP-101; Carrier gas: He; Phase thickness: 0.2 um; Data type: Normal alkane RI; Authors: Milso, M.; Mastelic, J.; Radonic, A., Free and glycosidically bound volatile compounds from cypress cones (Cupressus Sempervirens L.), Croat. Chem. Acta, 71(1), 1998, 139-145.) NIST Spectra nist ri
      1228 (Program type: Ramp; Column cl... (show more) ass: Standard non-polar; Column length: 25 m; Column type: Capillary; CAS no: 490915; Active phase: CP Sil 5 CB; Carrier gas: N2; Data type: Normal alkane RI; Authors: Weyerstahl, P.; Marschall, H.; Seelmann, I.; Kaul, V.K., Constituents of the flower essential oil of Ageratina adenophora (Spreng.) K. et R. from India, Flavour Fragr. J., 12, 1997, 387-396.) NIST Spectra nist ri
      1246 (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: 2 K/min; Start T: 60 C; End T: 250 C; End time: 15 min; Start time: 8 min; CAS no: 490915; Active phase: HP-5MS; Carrier gas: He; Phase thickness: 0.25 um; Data type: Normal alkane RI; Authors: Ferhat, M.A.; Tigrine-Kordjani, N.; Chemat, S.; Meklati, B.Y.; Chemat, F., Rapid Extraction of Volatile Compounds Using a New Simultaneous Microwave Distillation: Solvent Extraction Device, Chromatographia, 65, 2007, 217-222.) NIST Spectra nist ri
      1253 (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: 45 C; End T: 210 C; CAS no: 490915; Active phase: RTX-5 MS; Carrier gas: He; Phase thickness: 0.25 um; Data type: Normal alkane RI; Authors: Hudaib, M.; Aburjai, T., Volatile components of Thymus vulgaris L. from wild-growing and cultivated plants in Jordan, Flavour Fragr. J., 22, 2007, 322-327.) NIST Spectra nist ri
      1250 (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: 50 C; End T: 250 C; End time: 10 min; CAS no: 490915; Active phase: DB-5; Carrier gas: He; Phase thickness: 0.25 um; Data type: Normal alkane RI; Authors: Havlik, J.; Kokoska, L.; Vasickova, S.; Valterova, I., Chemical composition of essential oil from the seeds of Nigella arvensis L. and assessment of its actimicrobial activity, Flavour Fragr. J., 21, 2006, 713-717.) NIST Spectra nist ri
      1276 (Program type: Complex; Column... (show more) class: Semi-standard non-polar; Column diameter: 0.25 mm; Column length: 30 m; Column type: Capillary; Description: 60C (4min) => 1C/min => 64C => 2.5C/min => 155C => 5C/min => 250C; CAS no: 490915; Active phase: HP-5; Carrier gas: He; Phase thickness: 0.25 um; Data type: Normal alkane RI; Authors: Jordan, M.J.; Martinez, R.M.; Cases, M.A.; Sotomayor. J.A., Watering level effect on Thymus hyemalis lange essential oil yield and composition, J. Agric. Food Chem., 51, 2003, 5420-5427., Program type: Complex; Column... (show more) class: Semi-standard non-polar; Column diameter: 0.25 mm; Column length: 30 m; Column type: Capillary; Description: 60C(4min) =>1C/min =>64C =>2.5C/min =>155C =>5C/min => 250C; CAS no: 490915; Active phase: HP-5; Carrier gas: He; Phase thickness: 0.25 um; Data type: Normal alkane RI; Authors: Jordan, M.J.; Martinez, R.M.; Goodner, K.L.; Baldwin, E.A.; Sotomayor, J.A., Seasonal variation of Thymus hyemalis Lange and Spanish Thymus vulgaris L. essential oils composition, Ind. Crops Prod., 24, 2006, 253-263., Program type: Complex; Column... (show more) class: Semi-standard non-polar; Column diameter: 0.25 mm; Column length: 30 m; Column type: Capillary; Description: 60C(4min)=>1C/min=>64C=>2.5C/min=>155C=>5C/min=>250C; CAS no: 490915; Active phase: HP-5; Carrier gas: He; Phase thickness: 0.25 um; Data type: Normal alkane RI; Authors: Sotomayor, J.A.; Martinez, R.M.; Garcia, A.J.; Jordan, M.J., Thymus zygis Subsp. Gracilis: watering level effect on phytomass production and essential oil quality, J. Agric. Food Chem., 52, 2004, 5418-5424.) NIST Spectra nist ri
      1258 (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: 300 C; End time: 5 min; Start time: 5 min; CAS no: 490915; Active phase: HP-5; Carrier gas: He; Phase thickness: 0.25 um; Data type: Normal alkane RI; Authors: Figueredo, G.; Cabassu, P.; Chalchat, J.-C.; Pasquier, B., Studies of Mediterranean oregano populations- V. Chemical composition of essential oils of oregano: Origanum syriacum L. var. bevanii (Holmes) Ietswaart, O. syriacum L. var. sinaicum (Boiss.) Ietswaart, and O. syriacum L. var. syriacum from Lebanon and Israel, Flavour Fragr. J., 20, 2005, 164-168.) NIST Spectra nist ri
      1248 (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: 4 K/min; Start T: 40 C; End T: 240 C; CAS no: 490915; Active phase: DB-5; Carrier gas: He; Data type: Normal alkane RI; Authors: Sefidkon, F.; Jamzad, Z., Chemical composition of the essential oil of three Iranian Satureja species (S. mutica, S. macrantha and S. intermedia), Food Chem., 91, 2005, 1-4.) NIST Spectra nist ri
      1252 (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: 60 C; End T: 230 C; End time: 20 min; CAS no: 490915; Active phase: DB-5; Carrier gas: He; Phase thickness: 0.25 um; Data type: Normal alkane RI; Authors: Skoula, M.; Grayer, R.J., Volatile oils of Coridothymus capitatus, Satureja thymbra, Satureja spinosa and Thymbra calostachya (Lamiaceae) from Crete, Flavour Fragr. J., 20, 2005, 573-576.) NIST Spectra nist ri
      1244 (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: 4 K/min; Start T: 60 C; End T: 275 C; CAS no: 490915; Active phase: HP-5MS; Carrier gas: He; Phase thickness: 0.25 um; Data type: Normal alkane RI; Authors: Hajhashemi V.; Ghannadi A.; Jafarabadi H., Black cumin seed essential oil, as a potent analgesic and antiinflammatory drug, Phytother. Res., 18, 2004, 195-199.) NIST Spectra nist ri
      1242 (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: 60 C; End T: 280 C; End time: 30 min; CAS no: 490915; Active phase: DB-5; Carrier gas: He; Phase thickness: 0.25 um; Data type: Normal alkane RI; Authors: Marongiu, B.; Porcedda, S.; Caredda, A.; de Gioannis, B.; Vargiu, L.; la Colla, P., Extraction of Juniperus oxycedrus ssp. Oxycedrus essential oil by supercritical carbon dioxide: influence of some process parameters and biological activity, Flavour Fragr. J., 18, 2003, 390-397.) NIST Spectra nist ri
      1245 (Program type: Ramp; Column cl... (show more) ass: Semi-standard non-polar; Column diameter: 0.32 mm; Column length: 60 m; Column type: Capillary; Heat rate: 3 K/min; Start T: 40 C; End T: 220 C; End time: 15 min; Start time: 5 min; CAS no: 490915; Active phase: SPB-5; Carrier gas: He; Data type: Normal alkane RI; Authors: Cornu, A.; Carnat, A.-P.; Martin, B.; Coulon, J.-B.; Lamaison, J.-L.; Berdague, J.-L., Solid-phase microextraction of volatile components from natural grassland plants, J. Agric. Food Chem., 49, 2001, 203-209.) NIST Spectra nist ri
    • Retention Index (Linear):

      1216 (Program type: Ramp; Column cl... (show more) ass: Standard non-polar; Column diameter: 0.22 mm; Column length: 60 m; Column type: Capillary; Heat rate: 2 K/min; Start T: 60 C; End T: 230 C; End time: 30 min; CAS no: 490915; Active phase: RTX-1; Carrier gas: He; Phase thickness: 0.25 um; Data type: Linear RI; Authors: Bendahou, M.; Muselli, A.; Grignon-Dubois, M.; Benyoucef, M.; Desjobert, J.-M.; Bernardini, A.-F.; Costa, J., Antimicrobial activity and chemical composition of Origanum glandulosum Desf. essential oil and extract obtained by microwave extraction: Comparison with hydrodistillation, Food Chem., 106, 2008, 132-139.) NIST Spectra nist ri
      1251 (Program type: Ramp; Column cl... (show more) ass: Standard non-polar; Column diameter: 0.25 mm; Column length: 30 m; Column type: Capillary; Heat rate: 2 K/min; Start T: 40 C; End T: 270 C; End time: 20 min; Start time: 5 min; CAS no: 490915; Active phase: DB-1; Carrier gas: He; Phase thickness: 0.25 um; Data type: Linear RI; Authors: Senatore, F.; Lentini, F.; Venza, F.; Bruno, M.; Napolitano, F., Composition and antibacterial activity of the essential oil of Anisochilus carnosus (Linn. fil.) Benth., a Tamil plant acclimatized in Sicily, Flavour Fragr. J., 18, 2003, 202-204.) NIST Spectra nist ri
      1222 (Program type: Ramp; Column cl... (show more) ass: Standard non-polar; Column diameter: 0.2 mm; Column length: 25 m; Column type: Capillary; Heat rate: 3 K/min; Start T: 70 C; End T: 200 C; End time: 10 min; Start time: 2 min; CAS no: 490915; Active phase: HP-101; Carrier gas: He; Phase thickness: 0.2 um; Data type: Linear RI; Authors: Milos, M.; Radonic, A., Gas chromatography mass spectral analysis of free and glycosidically bound volatile compounds from Juniperus oxycedrus L. growing wild in Croatia, Food Chem., 68, 2000, 333-338.) NIST Spectra nist ri
      1252 (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: 2 K/min; Start T: 60 C; End T: 250 C; End time: 30 min; Start time: 8 min; CAS no: 490915; Active phase: HP-5MS; Carrier gas: He; Phase thickness: 0.25 um; Data type: Linear RI; Authors: Benkaci-Ali, F.; Baaliouamer, A.; Meklati, B.Y.; Chemat, F., Chemical composition of seed essential oils from Algerian Nigella sativa extracted by microwave and hydrodistillation, Flavour Fragr. J., 22, 2007, 148-153., 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: 2.5 K/min; Start T: 45 C; End T: 180 C; Start time: 10 min; CAS no: 490915; Active phase: RTX-5 MS; Carrier gas: He; Phase thickness: 0.25 um; Data type: Linear RI; Authors: Hudaib, M.; Speroni, E.; di Pietra, A.M.; Cavrini, V., GC/MS evaluation of thyme (Thymus vulgaris L.) oil composition and variations during the vegetative cycle, J. Pharm. Biomed. Anal., 29, 2002, 691-700.) NIST Spectra nist ri
      1249 (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: 50 C; End T: 280 C; Start time: 5 min; CAS no: 490915; Active phase: DB-5; Phase thickness: 0.25 um; Data type: Linear RI; Authors: Economakis, C.; Skaltsa, H.; Demetzos, C.; Sokovic, M.; Thanos, C.A., Effect of phosphorus concentration of the nutrient solution on the volatile constituents of leaves and bracts of Origanum dictamnus, J. Agric. Food Chem., 50, 2002, 6276-6280.) NIST Spectra nist ri

Predicted data is generated using the ACD/Labs Percepta Platform - PhysChem Module

Density: 1.1±0.1 g/cm3
Boiling Point: 232.0±15.0 °C at 760 mmHg
Vapour Pressure: 0.1±0.5 mmHg at 25°C
Enthalpy of Vaporization: 46.9±3.0 kJ/mol
Flash Point: 103.9±0.0 °C
Index of Refraction: 1.505
Molar Refractivity: 45.7±0.3 cm3
#H bond acceptors: 2
#H bond donors: 0
#Freely Rotating Bonds: 1
#Rule of 5 Violations: 0
ACD/LogP: 2.33
ACD/LogD (pH 5.5): 1.95
ACD/BCF (pH 5.5): 17.95
ACD/KOC (pH 5.5): 274.97
ACD/LogD (pH 7.4): 1.95
ACD/BCF (pH 7.4): 17.95
ACD/KOC (pH 7.4): 274.97
Polar Surface Area: 34 Å2
Polarizability: 18.1±0.5 10-24cm3
Surface Tension: 35.8±3.0 dyne/cm
Molar Volume: 154.1±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) =  2.25
    Log Kow (Exper. database match) =  2.20
       Exper. Ref:  Sangster (1993)

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  274.90  (Adapted Stein & Brown method)
    Melting Pt (deg C):  60.87  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  0.0673  (Modified Grain method)
    MP  (exp database):  45.5 deg C
    BP  (exp database):  232 deg C
    Subcooled liquid VP: 0.104 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):  865.3
       log Kow used: 2.20 (expkow database)
       no-melting pt equation used

 Water Sol Estimate from Fragments:
    Wat Sol (v1.01 est) =  542.69 mg/L

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

 Henrys Law Constant (25 deg C) [HENRYWIN v3.10]:
   Bond Method :   5.28E-009  atm-m3/mole
   Group Method:   Incomplete
 Henrys LC [VP/WSol estimate using EPI values]:  1.680E-005 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  2.20  (exp database)
  Log Kaw used:  -6.666  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  8.866
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :   0.6830
   Biowin2 (Non-Linear Model)     :   0.4430
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   2.7913  (weeks       )
   Biowin4 (Primary Survey Model) :   3.5664  (days-weeks  )
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :   0.4220
   Biowin6 (MITI Non-Linear Model):   0.3700
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model): -0.4993
 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):  13.9 Pa (0.104 mm Hg)
  Log Koa (Koawin est  ): 8.866
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  2.16E-007 
       Octanol/air (Koa) model:  0.00018 
   Fraction sorbed to airborne particulates (phi):
       Junge-Pankow model     :  7.81E-006 
       Mackay model           :  1.73E-005 
       Octanol/air (Koa) model:  0.0142 

 Atmospheric Oxidation (25 deg C) [AopWin v1.92]:
   Hydroxyl Radicals Reaction:
      OVERALL OH Rate Constant =  23.7011 E-12 cm3/molecule-sec
      Half-Life =     0.451 Days (12-hr day; 1.5E6 OH/cm3)
      Half-Life =     5.415 Hrs
   Ozone Reaction:
      OVERALL Ozone Rate Constant =     2.275000 E-17 cm3/molecule-sec
      Half-Life =     0.504 Days (at 7E11 mol/cm3)
      Half-Life =     12.090 Hrs
   Fraction sorbed to airborne particulates (phi): 1.26E-005 (Junge,Mackay)
    Note: the sorbed fraction may be resistant to atmospheric oxidation

 Soil Adsorption Coefficient (PCKOCWIN v1.66):
      Koc    :  11.56
      Log Koc:  1.063 

 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 = 0.994 (BCF = 9.863)
       log Kow used: 2.20 (expkow database)

 Volatilization from Water:
    Henry LC:  5.28E-009 atm-m3/mole  (estimated by Bond SAR Method)
    Half-Life from Model River: 1.421E+005  hours   (5921 days)
    Half-Life from Model Lake :  1.55E+006  hours   (6.459E+004 days)

 Removal In Wastewater Treatment:
    Total removal:               2.48  percent
    Total biodegradation:        0.10  percent
    Total sludge adsorption:     2.38  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       0.0841          5.71         1000       
   Water     22.1            360          1000       
   Soil      77.8            720          1000       
   Sediment  0.099           3.24e+003    0          
     Persistence Time: 665 hr




                    

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