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ChemSpider 2D Image | Docosahexaenoic acid | C22H32O2

Docosahexaenoic acid

  • Molecular FormulaC22H32O2
  • Average mass328.488 Da
  • Monoisotopic mass328.240234 Da
  • ChemSpider ID393183
  • Double-bond stereo - Double-bond stereo


More details:



Featured data source



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

Docosahexaenoic acid [Wiki]
(4Z,7Z,10Z,13Z,16Z,19Z)-4,7,10,13,16,19-Docosahexaenoic acid [ACD/IUPAC Name]
(4Z,7Z,10Z,13Z,16Z,19Z)-4,7,10,13,16,19-Docosahexaensäure [German] [ACD/IUPAC Name]
(4Z,7Z,10Z,13Z,16Z,19Z)-Docosa-4,7,10,13,16,19-hexaenoic acid
(4Z,7Z,10Z,13Z,16Z,19Z)-Docosahexaenoic acid
(all-Z)- 4,7,10,13,16,19-Docosahexaenoic Acid
(all-Z)-4,7,10,13,16,19-Docosahexaenoic acid
4,7,10,13,16,19-Docosahexaenoic acid, (4Z,7Z,10Z,13Z,16Z,19Z)- [ACD/Index Name]
4,7,10,13,16,19-Docosahexaenoic acid, (4Z,7Z,10Z,13Z,16Z,19Z)- (9CI)
More...

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

62160_FLUKA [DBID]
62170_FLUKA [DBID]
BSPBio_001376 [DBID]
C06427 [DBID]
C06429 [DBID]
CCRIS 7670 [DBID]
CHEBI:27432 [DBID]
CHEBI:28125 [DBID]
CMC_7371 [DBID]
D2534_SIGMA [DBID]
More...
  • Experimental Physico-chemical Properties
  • Miscellaneous
    • Chemical Class:

      A docosahexaenoic acid having six <stereo>cis</stereo>-double bonds at positions 4, 7, 10, 13, 16 and 19. ChEBI CHEBI:28125
      A docosahexaenoic acid having six cis-double bonds at positions 4, 7, 10, 13, 16 and 19. ChEBI https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:28125
    • Bio Activity:

      Endogenous omega-3 fatty acid. Acts as a selective retinoid X receptor (RXR) agonist that displays no activity at RAR, thyroid hormone receptor or the vitamin D receptor (VDR). Activates all three RXR isoforms. Also shown to inhibit A?1-42 fibrillation and toxicity in vitro. Tocris Bioscience 3687
      Endogenous omega-3 fatty acid. Acts as a selective retinoid X receptor (RXR) agonist that displays no activity at RAR, thyroid hormone receptor or the vitamin D receptor (VDR). Activates all three RXR isoforms. Also shown to inhibit Abeta1-42 fibrillation and toxicity in vitro. Tocris Bioscience 3687
      Endogenous omega-3 fatty acid. Acts as a selective retinoid X receptor (RXR) agonist that displays no activity at RAR, thyroid hormone receptor or the vitamin D receptor (VDR). Activates all three RXR isoforms. Also shown to inhibit A?1-42 fibrillation and toxicity in vitro. Tocris Bioscience 3687
      Nuclear Receptors Tocris Bioscience 3687
      Retinoid X Receptor Tocris Bioscience 3687
      RXR agonist Tocris Bioscience 3687
  • Gas Chromatography
    • Retention Index (Kovats):

      2612 (estimated with error: 51) NIST Spectra mainlib_333235
    • Retention Index (Normal Alkane):

      2501.9 (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: 130 C; End T: 250 C; CAS no: 6217545; Active phase: DB-5; Carrier gas: He; Data type: Normal alkane RI; Authors: Jalali-Heravi, M.; Vosough, M., Characterization and determination of fatty acids in fish oil using gas chromatography-mass spectrometry coupled with chemometric resolution techniques, J. Chromatogr. A, 1024, 2004, 165-176.) NIST Spectra nist ri
    • Retention Index (Linear):

      2520.9 (Program type: Complex; Column... (show more) class: Semi-standard non-polar; Column diameter: 0.25 mm; Column length: 30 m; Column type: Capillary; Description: Multi-step temperature program; T(initial)=60C; T(final)=270C; CAS no: 6217545; Active phase: VF-5MS; Carrier gas: He; Phase thickness: 0.25 um; Data type: Linear RI; Authors: Tret'yakov, K.V., Retention Data. NIST Mass Spectrometry Data Center., 2007.) NIST Spectra nist ri

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

Density: 0.9±0.1 g/cm3
Boiling Point: 446.7±24.0 °C at 760 mmHg
Vapour Pressure: 0.0±2.3 mmHg at 25°C
Enthalpy of Vaporization: 77.3±6.0 kJ/mol
Flash Point: 343.4±18.0 °C
Index of Refraction: 1.521
Molar Refractivity: 105.9±0.3 cm3
#H bond acceptors: 2
#H bond donors: 1
#Freely Rotating Bonds: 14
#Rule of 5 Violations: 1
ACD/LogP: 6.78
ACD/LogD (pH 5.5): 5.20
ACD/BCF (pH 5.5): 3070.59
ACD/KOC (pH 5.5): 5789.98
ACD/LogD (pH 7.4): 3.39
ACD/BCF (pH 7.4): 48.25
ACD/KOC (pH 7.4): 90.98
Polar Surface Area: 37 Å2
Polarizability: 42.0±0.5 10-24cm3
Surface Tension: 36.0±3.0 dyne/cm
Molar Volume: 348.0±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) =  8.62

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  449.90  (Adapted Stein & Brown method)
    Melting Pt (deg C):  164.24  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  1.83E-008  (Modified Grain method)
    Subcooled liquid VP: 4.94E-007 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):  0.0009028
       log Kow used: 8.62 (estimated)
       no-melting pt equation used

 Water Sol Estimate from Fragments:
    Wat Sol (v1.01 est) =  0.0089926 mg/L

 ECOSAR Class Program (ECOSAR v0.99h):
    Class(es) found:
       Surfactants-anionic-acid

 Henrys Law Constant (25 deg C) [HENRYWIN v3.10]:
   Bond Method :   7.33E-005  atm-m3/mole
   Group Method:   9.74E-008  atm-m3/mole
 Henrys LC [VP/WSol estimate using EPI values]:  8.762E-006 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  8.62  (KowWin est)
  Log Kaw used:  -2.523  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  11.143
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :   0.7723
   Biowin2 (Non-Linear Model)     :   0.6965
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   3.1362  (weeks       )
   Biowin4 (Primary Survey Model) :   4.0284  (days        )
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :   0.3860
   Biowin6 (MITI Non-Linear Model):   0.1165
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model): -0.0488
 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):  6.59E-005 Pa (4.94E-007 mm Hg)
  Log Koa (Koawin est  ): 11.143
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  0.0455 
       Octanol/air (Koa) model:  0.0341 
   Fraction sorbed to airborne particulates (phi):
       Junge-Pankow model     :  0.622 
       Mackay model           :  0.785 
       Octanol/air (Koa) model:  0.732 

 Atmospheric Oxidation (25 deg C) [AopWin v1.92]:
   Hydroxyl Radicals Reaction:
      OVERALL OH Rate Constant = 346.7017 E-12 cm3/molecule-sec [Cis-isomer]
      OVERALL OH Rate Constant = 392.3017 E-12 cm3/molecule-sec [Trans-isomer]
      Half-Life =   22.212 Min (12-hr day; 1.5E6 OH/cm3) [Cis-isomer]
      Half-Life =   19.631 Min (12-hr day; 1.5E6 OH/cm3) [Trans-isomer]
   Ozone Reaction:
      OVERALL Ozone Rate Constant =    78.000000 E-17 cm3/molecule-sec [Cis-]
      OVERALL Ozone Rate Constant =   120.000000 E-17 cm3/molecule-sec [Trans-]
      Half-Life =    21.157 Min (at 7E11 mol/cm3) [Cis-isomer]
      Half-Life =    13.752 Min (at 7E11 mol/cm3) [Trans-isomer]
   Reaction With Nitrate Radicals May Be Important!
   Fraction sorbed to airborne particulates (phi): 0.703 (Junge,Mackay)
    Note: the sorbed fraction may be resistant to atmospheric oxidation

 Soil Adsorption Coefficient (PCKOCWIN v1.66):
      Koc    :  1.351E+005
      Log Koc:  5.131 

 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 = 1.000 (BCF = 10)
       log Kow used: 8.62 (estimated)

 Volatilization from Water:
    Henry LC:  9.74E-008 atm-m3/mole  (estimated by Group SAR Method)
    Half-Life from Model River:  1.09E+004  hours   (454 days)
    Half-Life from Model Lake :  1.19E+005  hours   (4959 days)

 Removal In Wastewater Treatment:
    Total removal:              94.03  percent
    Total biodegradation:        0.78  percent
    Total sludge adsorption:    93.25  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       0.00914         0.239        1000       
   Water     3.75            360          1000       
   Soil      28.2            720          1000       
   Sediment  68.1            3.24e+003    0          
     Persistence Time: 1.24e+003 hr




                    

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