ChemSpider 2D Image | Rotenone | C23H22O6

Rotenone

  • Molecular FormulaC23H22O6
  • Average mass394.417 Da
  • Monoisotopic mass394.141632 Da
  • ChemSpider ID6500
  • defined stereocentres - 3 of 3 defined stereocentres


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Rotenone [Wiki]
(2R,6aS,12aS)-2-Isopropenyl-8,9-dimethoxy-1,2,12,12a-tetrahydrochromeno[3,4-b]furo[2,3-h]chromen-6(6aH)-on [German] [ACD/IUPAC Name]
(2R,6aS,12aS)-2-Isopropenyl-8,9-dimethoxy-1,2,12,12a-tetrahydrochromeno[3,4-b]furo[2,3-h]chromen-6(6aH)-one [ACD/IUPAC Name]
(2R,6aS,12aS)-2-Isopropényl-8,9-diméthoxy-1,2,12,12a-tétrahydrochroméno[3,4-b]furo[2,3-h]chromén-6(6aH)-one [French] [ACD/IUPAC Name]
(2R,6aS,12aS)-8,9-dimethoxy-2-(1-methylethenyl)-1,2,12,12a-tetrahydrochromeno[3,4-b]furo[2,3-h]chromen-6(6aH)-one
(2R,6aS,12aS)-8,9-Diméthoxy-2-(1-propèn-2-yl)-1,2,12,12a-tétrahydrochroméno[3,4-b]furo[2,3-h]chromén-6(6aH)-one
(2R,6aS,12aS)-8,9-Dimethoxy-2-(prop-1-en-2-yl)-1,2,12,12a-tetrahydrochromeno[3,4-b]furo[2,3-h]chromen-6(6aH)-on
(2R,6aS,12aS)-8,9-Dimethoxy-2-(prop-1-en-2-yl)-1,2,12,12a-tetrahydrochromeno[3,4-b]furo[2,3-h]chromen-6(6aH)-one
[1]Benzopyrano[3,4-b]furo[2,3-h][1]benzopyran-6(6aH)-one, 1,2,12,12a-tetrahydro-8,9-dimethoxy-2-(1-methylethenyl)-, (2R,6aS,12aS)-
[2R-(2a,6aa,12aa)]-1,2,12,12a-Tetrahydro-8,9-dimethoxy-2-(1-methylethenyl)-[1]benzopyrano[3,4-b]furo[2,3-h][1]benzopyran-6(6aH)-one
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Validated by Experts, Validated by Users, Non-Validated, Removed by Users

45656_RIEDEL [DBID]
AI3-00133 [DBID]
AIDS002703 [DBID]
AIDS-002703 [DBID]
C07593 [DBID]
Caswell No. 725 [DBID]
CCRIS 895 [DBID]
CHEBI:28201 [DBID]
DivK1c_000947 [DBID]
ENT 133 [DBID]
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  • Experimental Physico-chemical Properties
  • Predicted Physico-chemical Properties
  • Miscellaneous
    • Appearance:

      Colorless to red, odorless, crystalline solid. [insecticide] NIOSH DJ2800000
      white or off-white powder Oxford University Chemical Safety Data (No longer updated) More details
    • Stability:

      Stable, but light and air sensitive. Combustible. Incompatible with oxidizing agents, especially in thepresence of alkalies. Oxford University Chemical Safety Data (No longer updated) More details
    • Toxicity:

      ORL-RAT LD50 60 mg kg-1, IPR-MUS LD50 2.6 mg kg-1, IPR-RAT LD50 5 mg kg-1 Oxford University Chemical Safety Data (No longer updated) More details
    • Safety:

      Danger Biosynth W-104134
      GHS06; GHS09 Biosynth W-104134
      H301; H315; H319; H335; H410 Biosynth W-104134
      IRRITANT Matrix Scientific 099429
      P261; P273; P301+P310; P305+P351+P338; P501 Biosynth W-104134
      Safety glasses, adequate ventilation. Keep off the skin. Oxford University Chemical Safety Data (No longer updated) More details
    • First-Aid:

      Eye: Irrigate immediately Skin: Soap wash promptly Breathing: Respiratory support Swallow: Medical attention immediately NIOSH DJ2800000
    • Exposure Routes:

      inhalation, ingestion, skin and/or eye contact NIOSH DJ2800000
    • Symptoms:

      Irritation eyes, skin, respiratory system; numb mucous membrane; nausea, vomiting, abdominal pain; muscle tremor, incoordination, clonic convulsions, stupor NIOSH DJ2800000
    • Target Organs:

      Eyes, skin, respiratory system, central nervous system NIOSH DJ2800000
    • Incompatibility:

      Strong oxidizers, alkalis NIOSH DJ2800000
    • Personal Protection:

      Skin: Prevent skin contact Eyes: Prevent eye contact Wash skin: When contaminated Remove: When wet or contaminated Change: Daily NIOSH DJ2800000
    • Exposure Limits:

      NIOSH REL : TWA 5 mg/m 3 OSHA PEL : TWA 5 mg/m 3 NIOSH DJ2800000
    • Chemical Class:

      rotenoid Microsource [00200013]
    • Drug Status:

      agricultural use Microsource [00200013]
    • Compound Source:

      Constit. of the root of Derris elliptica . Widely distrib. in the Leguminosae (Papilionoideae) e.g. in many other Derris spp. Lonchocarpus spp. Millettia spp., Tephrosia spp. Zerenex Molecular [ZBioX-0281]
    • Bio Activity:

      Antineoplastic agent; Zerenex Molecular [ZBioX-0281]

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

Density: 1.3±0.1 g/cm3
Boiling Point: 559.8±50.0 °C at 760 mmHg
Vapour Pressure: 0.0±1.5 mmHg at 25°C
Enthalpy of Vaporization: 84.2±3.0 kJ/mol
Flash Point: 244.6±30.2 °C
Index of Refraction: 1.591
Molar Refractivity: 104.9±0.3 cm3
#H bond acceptors: 6
#H bond donors: 0
#Freely Rotating Bonds: 3
#Rule of 5 Violations: 0
ACD/LogP: 4.65
ACD/LogD (pH 5.5): 4.24
ACD/BCF (pH 5.5): 984.74
ACD/KOC (pH 5.5): 4833.02
ACD/LogD (pH 7.4): 4.24
ACD/BCF (pH 7.4): 984.74
ACD/KOC (pH 7.4): 4833.02
Polar Surface Area: 63 Å2
Polarizability: 41.6±0.5 10-24cm3
Surface Tension: 45.3±3.0 dyne/cm
Molar Volume: 310.3±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) =  2.54

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  495.80  (Adapted Stein & Brown method)
    Melting Pt (deg C):  210.64  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  3.74E-010  (Modified Grain method)
    Subcooled liquid VP: 3.51E-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):  22.38
       log Kow used: 2.54 (estimated)
       no-melting pt equation used

 Water Sol Estimate from Fragments:
    Wat Sol (v1.01 est) =  1.0591 mg/L

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

 Henrys Law Constant (25 deg C) [HENRYWIN v3.10]:
   Bond Method :   8.31E-013  atm-m3/mole
   Group Method:   Incomplete
 Henrys LC [VP/WSol estimate using EPI values]:  8.673E-012 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  2.54  (KowWin est)
  Log Kaw used:  -10.469  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  13.009
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :   0.3223
   Biowin2 (Non-Linear Model)     :   0.0703
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   2.0385  (months      )
   Biowin4 (Primary Survey Model) :   3.3998  (days-weeks  )
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :   0.3421
   Biowin6 (MITI Non-Linear Model):   0.0328
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model): -0.5024
 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):  4.68E-006 Pa (3.51E-008 mm Hg)
  Log Koa (Koawin est  ): 13.009
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  0.641 
       Octanol/air (Koa) model:  2.51 
   Fraction sorbed to airborne particulates (phi):
       Junge-Pankow model     :  0.959 
       Mackay model           :  0.981 
       Octanol/air (Koa) model:  0.995 

 Atmospheric Oxidation (25 deg C) [AopWin v1.92]:
   Hydroxyl Radicals Reaction:
      OVERALL OH Rate Constant = 651.9133 E-12 cm3/molecule-sec
      Half-Life =     0.016 Days (12-hr day; 1.5E6 OH/cm3)
      Half-Life =    11.813 Min
   Ozone Reaction:
      OVERALL Ozone Rate Constant =    10.937500 E-17 cm3/molecule-sec
      Half-Life =     0.105 Days (at 7E11 mol/cm3)
      Half-Life =      2.515 Hrs
   Fraction sorbed to airborne particulates (phi): 0.97 (Junge,Mackay)
    Note: the sorbed fraction may be resistant to atmospheric oxidation

 Soil Adsorption Coefficient (PCKOCWIN v1.66):
      Koc    :  622.3
      Log Koc:  2.794 

 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 = 1.257 (BCF = 18.08)
       log Kow used: 2.54 (estimated)

 Volatilization from Water:
    Henry LC:  8.31E-013 atm-m3/mole  (estimated by Bond SAR Method)
    Half-Life from Model River: 1.399E+009  hours   (5.83E+007 days)
    Half-Life from Model Lake : 1.526E+010  hours   (6.36E+008 days)

 Removal In Wastewater Treatment:
    Total removal:               3.21  percent
    Total biodegradation:        0.10  percent
    Total sludge adsorption:     3.11  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       0.000168        0.341        1000       
   Water     14.3            1.44e+003    1000       
   Soil      85.6            2.88e+003    1000       
   Sediment  0.132           1.3e+004     0          
     Persistence Time: 2.37e+003 hr




                    

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