ChemSpider 2D Image | Arachidonic acid | C20H32O2

Arachidonic acid

  • Molecular FormulaC20H32O2
  • Average mass304.467 Da
  • Monoisotopic mass304.240234 Da
  • ChemSpider ID392692
  • Double-bond stereo - Double-bond stereo


More details:



Featured data source



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

(5Z,8Z,11Z,14Z)-5,8,11,14-Eicosatetraenoic acid
(5Z,8Z,11Z,14Z)-5,8,11,14-Icosatetraenoic acid [ACD/IUPAC Name]
(5Z,8Z,11Z,14Z)-5,8,11,14-Icosatetraensäure [German] [ACD/IUPAC Name]
(5Z,8Z,11Z,14Z)-Icosa-5,8,11,14-tetraenoic acid
(all-Z)-5,8,11,14-Eicosatetraenoic acid
5,8,11,14-all-cis-Eicosatetraenoic acid
5,8,11,14-Eicosatetraenoic acid, (5Z,8Z,11Z,14Z)- [ACD/Index Name]
5,8,11,14-Eicosatetraenoic acid, (all-Z)-
506-32-1 [RN]
AA
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Validated by Experts, Validated by Users, Non-Validated, Removed by Users

CHEBI:15843 [DBID]
10931_FLUKA [DBID]
A3555_SIGMA [DBID]
A3925_SIGMA [DBID]
A9673_SIGMA [DBID]
AI3-09613 [DBID]
AIDS045704 [DBID]
AIDS-045704 [DBID]
C00219 [DBID]
CCRIS 6312 [DBID]
More...
  • Experimental Physico-chemical Properties
  • Miscellaneous
    • Appearance:

      colorless to light yellow Indofine [20-2024]
    • Safety:

      IRRITANT Matrix Scientific 098965
    • Therapeutical Effect:

      prostaglandin & leucotriene precursor, stimulates NO biosynthesis Microsource [01504138]
    • Drug Status:

      experimental Microsource [01504138]
    • Compound Source:

      widespread in animal tissue Microsource [01504138]
    • Bio Activity:

      Cell Biology Tocris Bioscience 2756
      Cell Metabolism Tocris Bioscience 2756
      Endogenous free fatty acid (in water-soluble emulsion) Tocris Bioscience 2756
      Endogenous free fatty acid released from phospholipids by phospholipase A2, in water-soluble emulsion (for details see TocrisolveTM 100, Cat. No. 1684). Important cellular signaling mediator and precu rsor of eicosanoids. Metabolized by lipoxygenases, cyclooxygenases and cytochrome P450 monooxygenases. Tocris Bioscience 2756
      Endogenous free fatty acid released from phospholipids by phospholipase A2, in water-soluble emulsion (for details see TocrisolveTM 100, Cat. No. 1684). Important cellular signaling mediator and precursor of eicosanoids. Metabolized by lipoxygenases, cyclooxygenases and cytochrome P450 monooxygenases. Tocris Bioscience 2756
      Lipid Metabolism Tocris Bioscience 2756
  • Gas Chromatography
    • Retention Index (Kovats):

      2398 (estimated with error: 51) NIST Spectra mainlib_333229, replib_232969, replib_379308
    • Retention Index (Linear):

      2324.3 (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: 506321; 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: 407.5±0.0 °C at 760 mmHg
Vapour Pressure: 0.0±2.0 mmHg at 25°C
Enthalpy of Vaporization: 72.3±6.0 kJ/mol
Flash Point: 336.3±18.0 °C
Index of Refraction: 1.501
Molar Refractivity: 96.5±0.3 cm3
#H bond acceptors: 2
#H bond donors: 1
#Freely Rotating Bonds: 14
#Rule of 5 Violations: 1
ACD/LogP: 6.91
ACD/LogD (pH 5.5): 5.70
ACD/BCF (pH 5.5): 8067.66
ACD/KOC (pH 5.5): 12745.00
ACD/LogD (pH 7.4): 3.90
ACD/BCF (pH 7.4): 128.76
ACD/KOC (pH 7.4): 203.41
Polar Surface Area: 37 Å2
Polarizability: 38.3±0.5 10-24cm3
Surface Tension: 35.2±3.0 dyne/cm
Molar Volume: 327.8±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) =  8.07
    Log Kow (Exper. database match) =  6.98
       Exper. Ref:  Sangster (1993)

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  419.55  (Adapted Stein & Brown method)
    Melting Pt (deg C):  148.30  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  2.77E-006  (Modified Grain method)
    MP  (exp database):  -49.5 deg C
    BP  (exp database):  170 @ 0.15 mm Hg deg C

 Water Solubility Estimate from Log Kow (WSKOW v1.41):
    Water Solubility at 25 deg C (mg/L):  0.03141
       log Kow used: 6.98 (expkow database)
       no-melting pt equation used

 Water Sol Estimate from Fragments:
    Wat Sol (v1.01 est) =  0.020196 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 :   5.38E-005  atm-m3/mole
   Group Method:   7.05E-007  atm-m3/mole
 Henrys LC [VP/WSol estimate using EPI values]:  3.533E-005 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  6.98  (exp database)
  Log Kaw used:  -2.658  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  9.638
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :   0.7837
   Biowin2 (Non-Linear Model)     :   0.7635
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   3.1893  (weeks       )
   Biowin4 (Primary Survey Model) :   4.0631  (days        )
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :   0.5316
   Biowin6 (MITI Non-Linear Model):   0.3573
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model):  0.2973
 Ready Biodegradability Prediction:   YES

Hydrocarbon Biodegradation (BioHCwin v1.01):
    Structure incompatible with current estimation method!

 Sorption to aerosols (25 Dec C)[AEROWIN v1.00]:
  Vapor pressure (liquid/subcooled):  0.000369 Pa (2.77E-006 mm Hg)
  Log Koa (Koawin est  ): 9.638
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  0.00812 
       Octanol/air (Koa) model:  0.00107 
   Fraction sorbed to airborne particulates (phi):
       Junge-Pankow model     :  0.227 
       Mackay model           :  0.394 
       Octanol/air (Koa) model:  0.0786 

 Atmospheric Oxidation (25 deg C) [AopWin v1.92]:
   Hydroxyl Radicals Reaction:
      OVERALL OH Rate Constant = 237.6365 E-12 cm3/molecule-sec [Cis-isomer]
      OVERALL OH Rate Constant = 268.0365 E-12 cm3/molecule-sec [Trans-isomer]
      Half-Life =    0.540 Hrs (12-hr day; 1.5E6 OH/cm3) [Cis-isomer]
      Half-Life =   28.732 Min (12-hr day; 1.5E6 OH/cm3) [Trans-isomer]
   Ozone Reaction:
      OVERALL Ozone Rate Constant =    52.000000 E-17 cm3/molecule-sec [Cis-]
      OVERALL Ozone Rate Constant =    80.000000 E-17 cm3/molecule-sec [Trans-]
      Half-Life =     0.529 Hrs (at 7E11 mol/cm3) [Cis-isomer]
      Half-Life =     0.344 Hrs (at 7E11 mol/cm3) [Trans-isomer]
   Reaction With Nitrate Radicals May Be Important!
   Fraction sorbed to airborne particulates (phi): 0.31 (Junge,Mackay)
    Note: the sorbed fraction may be resistant to atmospheric oxidation

 Soil Adsorption Coefficient (PCKOCWIN v1.66):
      Koc    :  3.97E+004
      Log Koc:  4.599 

 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 = 1.750 (BCF = 56.23)
       log Kow used: 6.98 (expkow database)

 Volatilization from Water:
    Henry LC:  7.05E-007 atm-m3/mole  (estimated by Group SAR Method)
    Half-Life from Model River:       1451  hours   (60.45 days)
    Half-Life from Model Lake : 1.597E+004  hours   (665.6 days)

 Removal In Wastewater Treatment:
    Total removal:              93.84  percent
    Total biodegradation:        0.78  percent
    Total sludge adsorption:    93.06  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       0.0142          0.355        1000       
   Water     4.24            360          1000       
   Soil      29.1            720          1000       
   Sediment  66.6            3.24e+003    0          
     Persistence Time: 1.19e+003 hr




                    

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