ChemSpider 2D Image | geosmin | C12H22O

geosmin

  • Molecular FormulaC12H22O
  • Average mass182.303 Da
  • Monoisotopic mass182.167068 Da
  • ChemSpider ID27642
  • defined stereocentres - 3 of 3 defined stereocentres


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

(-)-geosmin
(4S,4aS,8aR)-4,8a-Diméthyloctahydro-4a(2H)-naphtalénol [French] [ACD/IUPAC Name]
(4S,4aS,8aR)-4,8a-Dimethyloctahydro-4a(2H)-naphthalenol [ACD/IUPAC Name]
(4S,4aS,8aR)-4,8a-Dimethyloctahydro-4a(2H)-naphthalinol [German] [ACD/IUPAC Name]
(4S,4aS,8aR)-4,8a-Dimethyloctahydronaphthalen-4a(2H)-ol
[4S-(4a,4aa,8ab)]-Octahydro-4,8a-dimethyl-4a(2H)-naphthalenol
1,10-trans-Dimethyl-trans-(9)-decalol
19700-21-1 [RN]
4a(2H)-Naphthalenol, octahydro-4,8a-dimethyl-, (4S,4aS,8aR)- [ACD/Index Name]
geosmin [Wiki]
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Validated by Experts, Validated by Users, Non-Validated, Removed by Users

nchembio.2007.29-comp1 [DBID]
  • Gas Chromatography
    • Retention Index (Normal Alkane):

      1430 (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: 5 K/min; Start T: 50 C; End T: 320 C; Start time: 5 min; CAS no: 19700211; Active phase: BPX5; Carrier gas: Helium; Phase thickness: 0.25 um; Data type: Normal alkane RI; Authors: Dickschat, J.S.; Bode, H.B.; Wenzel, S.C.; Muller, R.; Schulz, S., Biosinthesis and Identification of Volatiles Released by the Myxobacterium Stigmatella aurantiaca, ChemBioChem, 6, 2005, 2023-2033.) NIST Spectra nist ri
      1431.2 (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: 8 K/min; Start T: 10 C; End T: 250 C; Start time: 1 min; CAS no: 19700211; Active phase: HP-5; Carrier gas: He; Phase thickness: 1 um; Data type: Normal alkane RI; Authors: Zierler, B.; Siegmund, B.; Pfannhauser, W., Determination of off-flavour compounds in apple juice caused by microorganisms using headspace solid phase microextraction-gas chromatography-mass spectrometry, Anal. Chim. Acta., 520, 2004, 3-11.) NIST Spectra nist ri
      1417 (Program type: Ramp; Column cl... (show more) ass: Semi-standard non-polar; Column diameter: 0.32 mm; Column length: 30 m; Column type: Capillary; Heat rate: 5 K/min; Start T: 40 C; End T: 195 C; End time: 40 min; Start time: 5 min; CAS no: 19700211; Active phase: DB-5MS; Carrier gas: He; Phase thickness: 0.25 um; Data type: Normal alkane RI; Authors: Suriyaphan, O.; Drake, M.; Chen, X.Q.; Cadwallader, K.R., Characteristic aroma components of British farmhouse cheddar cheese, J. Agric. Food Chem., 49, 2001, 1382-1387.) NIST Spectra nist ri
      1444 (Program type: Ramp; Column cl... (show more) ass: Semi-standard non-polar; Column type: Capillary; Heat rate: 6 K/min; Start T: 35 C; End T: 200 C; Start time: 2 min; CAS no: 19700211; Active phase: HP-5; Data type: Normal alkane RI; Authors: Larsen, T.O.; Frisvad, J.C., Characterization of volatile metabolites from 47 Penicillium taxa, Mycol. Res., 99(10), 1995, 1153-1166.) NIST Spectra nist ri
      1423 (Program type: Ramp; Column cl... (show more) ass: Semi-standard non-polar; Column diameter: 0.3 mm; Column length: 50 m; Column type: Capillary; Heat rate: 16 K/min; Start T: 80 C; End T: 250 C; CAS no: 19700211; Active phase: HP-5; Carrier gas: H2; Data type: Normal alkane RI; Authors: Spadone, J.-C.; Takeoka, G.; Liardon, R., Analytical Investigation of Rio Off-Flavor in Green Coffee, J. Agric. Food Chem., 38(1), 1990, 226-233.) NIST Spectra nist ri
      1861 (Program type: Ramp; Column cl... (show more) ass: Standard polar; Column diameter: 0.25 mm; Column length: 60 m; Column type: Capillary; Heat rate: 6 K/min; Start T: 50 C; End T: 230 C; End time: 15 min; Start time: 2 min; CAS no: 19700211; Active phase: CP-Wax; Carrier gas: Helium; Phase thickness: 0.25 um; Data type: Normal alkane RI; Authors: Mo, X.; Fan, W.; Xu, Y., Changes in volatile compounds of Chinese rice wine wheat qu during fermentation and storage, J. of the Institute of Brewing, 115(4), 2009, 300-307.) NIST Spectra nist ri
      1858 (Program type: Complex; Column... (show more) class: Standard polar; Column diameter: 0.32 mm; Column length: 30 m; Column type: Capillary; Description: 40 0C ^ 2 0C/min -> 12 0C/min -> 105 0C ^ 6 0C/min -> 220 0C (20 min); CAS no: 19700211; Active phase: DB-Wax; Carrier gas: Hydrogen; Phase thickness: 0.50 um; Data type: Normal alkane RI; Authors: Prat, C.; Trias, R.; Cullere, L.; Escudero, A.; Antico, E.; BAneras, L., Off-odor compounds produced in cork by isolated bacteria and fungi: a gas chromatography - mass spectrometry and gas chromatography - olfactometry study, J. Agric. Food Chem., 57(16), 2009, 7473-7479.) NIST Spectra nist ri
      1869 (Program type: Ramp; Column cl... (show more) ass: Standard polar; Column diameter: 0.22 mm; Column length: 50 m; Column type: Capillary; Heat rate: 3 K/min; Start T: 45 C; End T: 230 C; End time: 15 min; Start time: 1 min; CAS no: 19700211; Active phase: BP-20; Carrier gas: H2; Phase thickness: 0.25 um; Data type: Normal alkane RI; Authors: La Guerche S.; Dauphin B.; Pons M.; Blancard D.; Darriet P., Characterization of some mushroom and earthy off-odors microbially induced by the development of rot on grapes, J. Agric. Food Chem., 54, 2006, 9193-9200.) NIST Spectra nist ri
      1810 (Program type: Ramp; Column cl... (show more) ass: Standard polar; Column diameter: 0.32 mm; Column length: 30 m; Column type: Capillary; Heat rate: 3 K/min; Start T: 40 C; End T: 210 C; End time: 25 min; Start time: 1 min; CAS no: 19700211; Active phase: DB-Wax; Carrier gas: He; Phase thickness: 0.5 um; Data type: Normal alkane RI; Authors: Pollak, F.C.; Berger, R.G., Geosmin and Related Volatiles in Bioreactor-Cultured Streptomyces citreus CBS 109.60, Appl. Environ. Microbiol., 62(4), 1996, 1295-1299.) NIST Spectra nist ri
    • Retention Index (Linear):

      1423 (Program type: Ramp; Column cl... (show more) ass: Standard non-polar; Column type: Capillary; CAS no: 19700211; Active phase: PONA; Data type: Linear RI; Authors: Cantergiani, E.; Brevard, H.; Krebs, Y.; Feria-Morales, A.; Amado, R.; Yeretzian, C., Characterisation of the aroma of green Mexican coffee and identification of mouldy/earthy defect, Eur. Food Res. Technol., 212, 2001, 648-657.) NIST Spectra nist ri
      1439 (Program type: Complex; Column... (show more) class: Semi-standard non-polar; Column diameter: 0.32 mm; Column length: 30 m; Column type: Capillary; Description: 50C=> 5C/min =>200C =>8C/min =>260C(5min); CAS no: 19700211; Active phase: DB-5MS; Carrier gas: He; Phase thickness: 0.5 um; Data type: Linear RI; Authors: Selli, S.; Rannou, C.; Prost, C.; Robin, J.; Serot, T., Characterization of Aroma-Active Compounds in Rainbow Trout (Oncorhynchus mykiss) Eliciting an Off-Odor, J. Agric. Food Chem., 54, 2006, 9496-9502.) NIST Spectra nist ri
      1430 (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: 5 K/min; Start T: 50 C; End T: 300 C; Start time: 5 min; CAS no: 19700211; Active phase: BPX-5; Carrier gas: He; Phase thickness: 0.25 um; Data type: Linear RI; Authors: Dickschat, J.S.; Wenzel, S.C.; Bode, H.B.; Muller, R.; Schulz, S., Biosynthesis of Volatiles by the Myxobacterium Myxococcus xanthus, ChemBioChem, 5, 2004, 778-787.) NIST Spectra nist ri
      1821 (Program type: Ramp; Column cl... (show more) ass: Standard polar; Column diameter: 0.25 mm; Column length: 30 m; Column type: Capillary; Heat rate: 4 K/min; Start T: 50 C; End T: 260 C; End time: 5 min; CAS no: 19700211; Active phase: DB-Wax; Carrier gas: He; Phase thickness: 0.5 um; Data type: Linear RI; Authors: Selli, S.; Rannou, C.; Prost, C.; Robin, J.; Serot, T., Characterization of Aroma-Active Compounds in Rainbow Trout (Oncorhynchus mykiss) Eliciting an Off-Odor, J. Agric. Food Chem., 54, 2006, 9496-9502.) NIST Spectra nist ri
      1808 (Program type: Complex; Column... (show more) class: Standard polar; Column diameter: 0.25 mm; Column length: 30 m; Column type: Capillary; Description: 20C(30s) =>fast=>60C =>4C/min => 220C (20min); CAS no: 19700211; Active phase: DB-Wax; Phase thickness: 0.25 um; Data type: Linear RI; Authors: Cantergiani, E.; Brevard, H.; Krebs, Y.; Feria-Morales, A.; Amado, R.; Yeretzian, C., Characterisation of the aroma of green Mexican coffee and identification of mouldy/earthy defect, Eur. Food Res. Technol., 212, 2001, 648-657.) NIST Spectra nist ri
      1823 (Program type: Complex; Column... (show more) class: Standard polar; Column diameter: 0.25 mm; Column length: 30 m; Column type: Capillary; Description: 20C(30s) =>fast=>60C =>4C/min => 220C (20min); CAS no: 19700211; Active phase: DB-Wax; Phase thickness: 0.25 um; Data type: Linear RI; Authors: Cantergiani, E.; Brevard, H.; Krebs, Y.; Feria-Morales, A.; Amado, R.; Yeretzian, C., Characterisation of the aroma of green Mexican coffee and identification of mouldy/earthy defect, Eur. Food Res. Technol., 212, 2001, 648-657.) NIST Spectra nist ri

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

Density: 1.0±0.1 g/cm3
Boiling Point: 270.0±0.0 °C at 760 mmHg
Vapour Pressure: 0.0±1.2 mmHg at 25°C
Enthalpy of Vaporization: 59.0±6.0 kJ/mol
Flash Point: 104.2±10.9 °C
Index of Refraction: 1.506
Molar Refractivity: 55.0±0.3 cm3
#H bond acceptors: 1
#H bond donors: 1
#Freely Rotating Bonds: 0
#Rule of 5 Violations: 0
ACD/LogP: 3.85
ACD/LogD (pH 5.5): 3.13
ACD/BCF (pH 5.5): 141.30
ACD/KOC (pH 5.5): 1204.17
ACD/LogD (pH 7.4): 3.13
ACD/BCF (pH 7.4): 141.30
ACD/KOC (pH 7.4): 1204.17
Polar Surface Area: 20 Å2
Polarizability: 21.8±0.5 10-24cm3
Surface Tension: 38.5±3.0 dyne/cm
Molar Volume: 184.9±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) =  3.57

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  248.80  (Adapted Stein & Brown method)
    Melting Pt (deg C):  47.08  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  0.00057  (Modified Grain method)
    BP  (exp database):  270 deg C
    Subcooled liquid VP: 0.000907 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):  156.7
       log Kow used: 3.57 (estimated)
       no-melting pt equation used

 Water Sol Estimate from Fragments:
    Wat Sol (v1.01 est) =  294.88 mg/L

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

 Henrys Law Constant (25 deg C) [HENRYWIN v3.10]:
   Bond Method :   1.18E-005  atm-m3/mole
   Group Method:   3.15E-006  atm-m3/mole
 Henrys LC [VP/WSol estimate using EPI values]:  8.726E-007 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  3.57  (KowWin est)
  Log Kaw used:  -3.317  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  6.887
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :   0.2929
   Biowin2 (Non-Linear Model)     :   0.0462
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   2.3721  (weeks-months)
   Biowin4 (Primary Survey Model) :   3.2778  (days-weeks  )
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :   0.4564
   Biowin6 (MITI Non-Linear Model):   0.4075
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model): -0.7922
 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):  0.121 Pa (0.000907 mm Hg)
  Log Koa (Koawin est  ): 6.887
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  2.48E-005 
       Octanol/air (Koa) model:  1.89E-006 
   Fraction sorbed to airborne particulates (phi):
       Junge-Pankow model     :  0.000895 
       Mackay model           :  0.00198 
       Octanol/air (Koa) model:  0.000151 

 Atmospheric Oxidation (25 deg C) [AopWin v1.92]:
   Hydroxyl Radicals Reaction:
      OVERALL OH Rate Constant =  22.3859 E-12 cm3/molecule-sec
      Half-Life =     0.478 Days (12-hr day; 1.5E6 OH/cm3)
      Half-Life =     5.734 Hrs
   Ozone Reaction:
      No Ozone Reaction Estimation
   Fraction sorbed to airborne particulates (phi): 0.00144 (Junge,Mackay)
    Note: the sorbed fraction may be resistant to atmospheric oxidation

 Soil Adsorption Coefficient (PCKOCWIN v1.66):
      Koc    :  218.6
      Log Koc:  2.340 

 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 = 2.045 (BCF = 110.9)
       log Kow used: 3.57 (estimated)

 Volatilization from Water:
    Henry LC:  3.15E-006 atm-m3/mole  (estimated by Group SAR Method)
    Half-Life from Model River:      252.3  hours   (10.51 days)
    Half-Life from Model Lake :       2866  hours   (119.4 days)

 Removal In Wastewater Treatment:
    Total removal:              14.87  percent
    Total biodegradation:        0.20  percent
    Total sludge adsorption:    14.52  percent
    Total to Air:                0.15  percent
      (using 10000 hr Bio P,A,S)

 Level III Fugacity Model:
           Mass Amount    Half-Life    Emissions
            (percent)        (hr)       (kg/hr)
   Air       0.445           11.5         1000       
   Water     17.7            900          1000       
   Soil      80.3            1.8e+003     1000       
   Sediment  1.51            8.1e+003     0          
     Persistence Time: 1.07e+003 hr




                    

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