ChemSpider 2D Image | (-)-Shikimic acid | C7H10O5

(-)-Shikimic acid

  • Molecular FormulaC7H10O5
  • Average mass174.151 Da
  • Monoisotopic mass174.052826 Da
  • ChemSpider ID8412

  • defined stereocentres - 3 of 3 defined stereocentres

More details:

Featured data source
The Merck Index Online

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(-)-Shikimic acid
(-)Shikimic acid
(3R,4S,5R)-(-)-3,4,5-Trihydroxy-1-cyclohexenecarboxylic acid
(3R,4S,5R)-3,4,5-Trihydroxy-1-cyclohexen-1-carbonsäure [German] [ACD/IUPAC Name]
(3R,4S,5R)-3,4,5-Trihydroxy-1-cyclohexene-1-carboxylic acid [ACD/IUPAC Name]
(3R,4S,5R)-3,4,5-trihydroxycyclohex-1-ene-1-carboxylic acid
[3R-(3a,4a,5b)]-3,4,5-Trihydroxy-1-cyclohexene-1-carboxylic Acid
138-59-0 [RN]
1-Cyclohexene-1-carboxylic acid, 3,4,5-trihydroxy-, (3R,4S,5R)- [ACD/Index Name]
205-334-2 [EINECS]
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Validated by Experts, Validated by Users, Non-Validated, Removed by Users

bmse000114 [DBID]
C00493 [DBID]
CCRIS 7681 [DBID]
CHEBI:16119 [DBID]
DivK1c_006584 [DBID]
HSDB 3537 [DBID]
KBio1_001528 [DBID]
KBio2_001712 [DBID]
KBio2_004280 [DBID]
KBio2_006848 [DBID]
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  • Experimental Physico-chemical Properties
  • Predicted Physico-chemical Properties
  • Miscellaneous

    • Safety:

      CAUTION: May irritate eyes, skin, and respiratory tract Alfa Aesar L04848

    • Chemical Class:

      A cyclohexenecarboxylic acid that is cyclohex-1-ene-1-carboxylic acid substituted by hydroxy groups at positions 3, 4 and 5 (the 3<stereo>R</stereo>,4<stereo>S</stereo>,5<stereo>R</stereo> stereoisome r). It is an intermediate metabolite in plants and microorganisms. ChEBI CHEBI:16119
      A cyclohexenecarboxylic acid that is cyclohex-1-ene-1-carboxylic acid substituted by hydroxy groups at positions 3, 4 and 5 (the 3R,4S,5R stereoisome; r). It is an intermediate metabolite in plants an d microorganisms. ChEBI https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:16119
      A cyclohexenecarboxylic acid that is cyclohex-1-ene-1-carboxylic acid substituted by hydroxy groups at positions 3, 4 and 5 (the 3R,4S,5R stereoisomer). It is an intermediate metabolite in plants and microorganisms. ChEBI CHEBI:16119

Predicted data is generated using the ACD/Labs Percepta Platform - PhysChem Module, version: 14.00

Density: 1.7±0.1 g/cm3
Boiling Point: 400.5±45.0 °C at 760 mmHg
Vapour Pressure: 0.0±2.1 mmHg at 25°C
Enthalpy of Vaporization: 75.3±6.0 kJ/mol
Flash Point: 210.1±25.2 °C
Index of Refraction: 1.680
Molar Refractivity: 38.1±0.3 cm3
#H bond acceptors: 5
#H bond donors: 4
#Freely Rotating Bonds: 1
#Rule of 5 Violations: 0
ACD/LogP: -0.92
ACD/LogD (pH 5.5): -2.43
ACD/BCF (pH 5.5): 1.00
ACD/KOC (pH 5.5): 1.00
ACD/LogD (pH 7.4): -4.23
ACD/BCF (pH 7.4): 1.00
ACD/KOC (pH 7.4): 1.00
Polar Surface Area: 98 Å2
Polarizability: 15.1±0.5 10-24cm3
Surface Tension: 116.6±3.0 dyne/cm
Molar Volume: 100.9±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) =  -1.34

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  372.48  (Adapted Stein & Brown method)
    Melting Pt (deg C):  133.21  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  5E-009  (Modified Grain method)
    MP  (exp database):  186 deg C
    Subcooled liquid VP: 2.41E-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):  1e+006
       log Kow used: -1.34 (estimated)
       no-melting pt equation used
     Water Sol (Exper. database match) =  1.5e+005 mg/L (21 deg C)
        Exper. Ref:  YALKOWSKY,SH & DANNENFELSER,RM (1992)

 Water Sol Estimate from Fragments:
    Wat Sol (v1.01 est) =  1e+006 mg/L
    Wat Sol (Exper. database match) =  150000.00
       Exper. Ref:  YALKOWSKY,SH & DANNENFELSER,RM (1992)

 ECOSAR Class Program (ECOSAR v0.99h):
    Class(es) found:
       Vinyl/Allyl Alcohols-acid

 Henrys Law Constant (25 deg C) [HENRYWIN v3.10]:
   Bond Method :   2.69E-014  atm-m3/mole
   Group Method:   Incomplete
 Henrys LC [VP/WSol estimate using EPI values]:  1.146E-015 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  -1.34  (KowWin est)
  Log Kaw used:  -11.959  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  10.619
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :   1.2135
   Biowin2 (Non-Linear Model)     :   0.9894
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   3.6588  (days-weeks  )
   Biowin4 (Primary Survey Model) :   4.3704  (hours-days  )
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :   0.9219
   Biowin6 (MITI Non-Linear Model):   0.8208
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model):  1.3460
 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):  3.21E-005 Pa (2.41E-007 mm Hg)
  Log Koa (Koawin est  ): 10.619
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  0.0934 
       Octanol/air (Koa) model:  0.0102 
   Fraction sorbed to airborne particulates (phi):
       Junge-Pankow model     :  0.771 
       Mackay model           :  0.882 
       Octanol/air (Koa) model:  0.45 

 Atmospheric Oxidation (25 deg C) [AopWin v1.92]:
   Hydroxyl Radicals Reaction:
      OVERALL OH Rate Constant =  61.4007 E-12 cm3/molecule-sec
      Half-Life =     0.174 Days (12-hr day; 1.5E6 OH/cm3)
      Half-Life =     2.090 Hrs
   Ozone Reaction:
      OVERALL Ozone Rate Constant =     7.393750 E-17 cm3/molecule-sec
      Half-Life =     0.155 Days (at 7E11 mol/cm3)
      Half-Life =      3.720 Hrs
   Fraction sorbed to airborne particulates (phi): 0.827 (Junge,Mackay)
    Note: the sorbed fraction may be resistant to atmospheric oxidation

 Soil Adsorption Coefficient (PCKOCWIN v1.66):
      Koc    :  10
      Log Koc:  1.000 

 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 = 0.500 (BCF = 3.162)
       log Kow used: -1.34 (estimated)

 Volatilization from Water:
    Henry LC:  2.69E-014 atm-m3/mole  (estimated by Bond SAR Method)
    Half-Life from Model River: 2.872E+010  hours   (1.197E+009 days)
    Half-Life from Model Lake : 3.133E+011  hours   (1.306E+010 days)

 Removal In Wastewater Treatment:
    Total removal:               1.85  percent
    Total biodegradation:        0.09  percent
    Total sludge adsorption:     1.75  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       1.55e-005       1.97         1000       
   Water     34.4            208          1000       
   Soil      65.5            416          1000       
   Sediment  0.0596          1.87e+003    0          
     Persistence Time: 387 hr

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