Inherent Properties, Identifiers and References
ChemSpider ID: 3350
Empirical Formula: C7H6O4
Molecular Weight: 154.1201
Nominal Mass: 154 Da
Average Mass: 154.1201 Da
Monoisotopic Mass: 154.026609 Da
Quick Links: Permalink Similar Isomers
Systematic Name: 2,5-dihydroxybenzoic acid
SMILES: O=C(O)c1cc(O)ccc1O
InChI: InChI=1/C7H6O4/c8-4-1-2-6(9)5(3-4)7(10)11/h1-3,8-9H,(H,10,11)
InChIKey: WXTMDXOMEHJXQO-UHFFFAOYAO
(Details...) Original Reference(s)
Gentisic acid is an aromatic carboxylic acid used as a sample matrix in Matrix-assisted laser desorption/ionization Mass spectrometry. As a hydroquinone, it is readily oxidised and is used as an antioxidant excipient in some pharmaceutical preparations. de:Gentisinsäure Category:Benzoic acids Category:Hydroxy acids Category:Benzenediols Read more... or Edit at Wikipedia...
Data SourceExternal ID(s)
UsefulChemUC0232
Disclaimer (Details...) Supplemental Information

User Data

  • experimental physchem properties
    • Melting Point: 204 - 207 C
  • miscellaneous
    • Appearance: white to beige powder
    • Stability: Stable. Combustible. Incompatible with strong acids,strong oxidizing agents, acid chlorides, acid anhydrides.
    • Toxicity: ORL-MUS LD50 4500 mg kg-1
    • Safety: Safety glasses.
    • Source: widely distributed in higher plants and Penicillium spp
    • Drug Status: experimental
    • Chemical Class: aromatic
(Details...) Names and Synonyms

Validated by Experts, Validated by Users, Non-Validated, Removed by Users, Redirected by Users, Redirect Approved by Experts

3,6-Dihyd​roxybenzo​ic Acid

4-10-00-0​1441

5-hydroxy​-Salicyli​c acid

Benzoic a​cid, 2,5-​dihydroxy-

Carboxyhy​droquinone

2,5-Dioxy​benzoate

3,6-Dihyd​roxybenzo​ate

5-hydroxy​-Salicyla​te

5-Hydroxy​salicylate

Gentisina​te

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(Details...) Database ID(s)

Validated by Experts, Validated by Users, Non-Validated, Removed by Users, Redirected by Users, Redirect Approved by Experts

149357_AL​DRICH

39319_FLU​KA

AI3-60431

AIDS002955

AIDS-0029​55

AIDS027706

AIDS-0277​06

BRN 22091​19

C00628

CHEBI:171​89

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(Details...) Predicted Properties
LogP: ACD/LogP: 1.56
ALOGPS: 1.23 		# of Rule of 5 Violations: 0
ACD/LogD (pH 5.5): -1.46 ACD/LogD (pH 7.4): -1.59
ACD/BCF (pH 5.5): 1 ACD/BCF (pH 7.4): 1
ACD/KOC (pH 5.5): 1 ACD/KOC (pH 7.4): 1
#H bond acceptors: 4 #H bond donors: 3
#Freely Rotating Bonds: 3 Polar Surface Area: 44.76 Å2
Index of Refraction: 1.67 Molar Refractivity: 36.94 cm3
Molar Volume: 98.8 cm3 Polarizability: 14.64 10-24cm3
Surface Tension: 84.2 dyne/cm Density: 1.559 g/cm3
Flash Point: 214 °C Enthalpy of Vaporization: 69.45 kJ/mol
Boiling Point: 406.9 °C at 760 mmHg Vapour Pressure: 2.38E-07 mmHg at 25°C
(Details...) EPI Summary 
            
 Log Octanol-Water Partition Coef (SRC):
    Log Kow (KOWWIN v1.67 estimate) =  1.76
    Log Kow (Exper. database match) =  1.74
       Exper. Ref:  Sangster (1994)

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  338.41  (Adapted Stein & Brown method)
    Melting Pt (deg C):  128.34  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  3.27E-007  (Modified Grain method)
    MP  (exp database):  199.5 deg C
    Subcooled liquid VP: 2.26E-005 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):  9034
       log Kow used: 1.74 (expkow database)
       no-melting pt equation used

 Water Sol Estimate from Fragments:
    Wat Sol (v1.01 est) =  2381.5 mg/L

 ECOSAR Class Program (ECOSAR v0.99h):
    Class(es) found:
       Phenols-acid
       Salicylic Acid-acid
       Quinone/Hydroquinone-acid

 Henrys Law Constant (25 deg C) [HENRYWIN v3.10]:
   Bond Method :   1.48E-012  atm-m3/mole
   Group Method:   6.89E-016  atm-m3/mole
 Henrys LC [VP/WSol estimate using EPI values]:  7.340E-012 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  1.74  (exp database)
  Log Kaw used:  -10.218  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  11.958
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :   1.0827
   Biowin2 (Non-Linear Model)     :   0.9937
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   3.0592  (weeks       )
   Biowin4 (Primary Survey Model) :   3.7125  (days-weeks  )
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :   0.7837
   Biowin6 (MITI Non-Linear Model):   0.8651
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model):  0.9768
 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):  0.00301 Pa (2.26E-005 mm Hg)
  Log Koa (Koawin est  ): 11.958
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  0.000996 
       Octanol/air (Koa) model:  0.223 
   Fraction sorbed to airborne particulates (phi):
       Junge-Pankow model     :  0.0347 
       Mackay model           :  0.0738 
       Octanol/air (Koa) model:  0.947 

 Atmospheric Oxidation (25 deg C) [AopWin v1.92]:
   Hydroxyl Radicals Reaction:
      OVERALL OH Rate Constant =   9.2953 E-12 cm3/molecule-sec
      Half-Life =     1.151 Days (12-hr day; 1.5E6 OH/cm3)
      Half-Life =    13.808 Hrs
   Ozone Reaction:
      No Ozone Reaction Estimation
   Reaction With Nitrate Radicals May Be Important!
   Fraction sorbed to airborne particulates (phi): 0.0542 (Junge,Mackay)
    Note: the sorbed fraction may be resistant to atmospheric oxidation

 Soil Adsorption Coefficient (PCKOCWIN v1.66):
      Koc    :  38.81
      Log Koc:  1.589 

 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: 1.74 (expkow database)

 Volatilization from Water:
    Henry LC:  1.48E-012 atm-m3/mole  (estimated by Bond SAR Method)
    Half-Life from Model River: 4.911E+008  hours   (2.046E+007 days)
    Half-Life from Model Lake : 5.358E+009  hours   (2.232E+008 days)

 Removal In Wastewater Treatment:
    Total removal:               2.07  percent
    Total biodegradation:        0.09  percent
    Total sludge adsorption:     1.97  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       3.75e-005       27.6         1000       
   Water     26              360          1000       
   Soil      74              720          1000       
   Sediment  0.072           3.24e+003    0          
     Persistence Time: 680 hr