ChemSpider 2D Image | Homovanillic acid | C9H10O4

Homovanillic acid

  • Molecular FormulaC9H10O4
  • Average mass182.173 Da
  • Monoisotopic mass182.057907 Da
  • ChemSpider ID1675

More details:



Featured data source



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

(4-Hydroxy-3-methoxyphenyl)acetic acid [ACD/IUPAC Name]
(4-Hydroxy-3-methoxyphenyl)essigsäure [German] [ACD/IUPAC Name]
2-(4-hydroxy-3-methoxyphenyl)ethanoic acid
206-176-7 [EINECS]
306-08-1 [RN]
3-methoxy-4-hydroxyphenylacetic acid
3-methoxy-4-hydroxy-phenylacetic acid
4-Hydroxy-3-methoxy-a-toluic Acid
Acide (4-hydroxy-3-méthoxyphényl)acétique [French] [ACD/IUPAC Name]
Benzeneacetic acid, 4-hydroxy-3-methoxy- [ACD/Index Name]
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Validated by Experts, Validated by Users, Non-Validated, Removed by Users

CHEBI:545959 [DBID]
bmse000132 [DBID]
C05582 [DBID]
C06045 [DBID]
CCRIS 4693 [DBID]
e2 [DBID]
EU-0100632 [DBID]
H1252_SIGMA [DBID]
Lopac-H-1252 [DBID]
MFCD00004350 [DBID]
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  • Experimental Physico-chemical Properties
  • Predicted Physico-chemical Properties
  • Miscellaneous
    • Appearance:

      Light-yellow Liquid Novochemy [NC-46537]
    • Safety:

      20/21/22 Novochemy [NC-46537]
      20/21/36/37/39 Novochemy [NC-46537]
      26-37 Alfa Aesar A12441
      26-37-60 Alfa Aesar A12441
      36/37/38 Alfa Aesar A12441
      GHS07; GHS09 Novochemy [NC-46537]
      H315-H319-H335 Alfa Aesar A12441
      H332; H403 Novochemy [NC-46537]
      IRRITANT Matrix Scientific 001455
      Irritant SynQuest 2729-1-Y3, 66561
      P102; P210; P262; P270; P302+P352; P308+P313 Novochemy [NC-46537]
      P261-P280-P305+P351+P338-P304+P340-P405-P501a Alfa Aesar A12441
      Warning Alfa Aesar A12441
      Warning Novochemy [NC-46537]
      WARNING: Irritates lungs, eyes, skin Alfa Aesar A12441
      Xn Novochemy [NC-46537]
    • Chemical Class:

      A monocarboxylic acid that is the 3-<element>O</element>-methyl ether of (3,4-dihydroxyphenyl)acetic acid. It is a catecholamine metabolite. ChEBI CHEBI:545959
    • Bio Activity:

      Fluorescent Imaging Tocris Bioscience 2875
      Fluorescent Probes Tocris Bioscience 2875
      Fluorimetric reagent Tocris Bioscience 2875
      Fluorimetric reagent and major catecholamine metabolite. Used for fluorimetric determination of oxidative enzymes including glucose oxidase. Tocris Bioscience 2875
  • Gas Chromatography
    • Retention Index (Kovats):

      1659 (estimated with error: 89) NIST Spectra mainlib_230828, replib_7659, replib_248367
    • Retention Index (Normal Alkane):

      1603 (Program type: Ramp; Column cl... (show more) ass: Standard non-polar; Column diameter: 0.2 mm; Column length: 50 m; Column type: Capillary; Heat rate: 2 K/min; Start T: 60 C; End T: 250 C; End time: 120 min; CAS no: 306081; Active phase: HP-1; Carrier gas: He; Phase thickness: 0.5 um; Data type: Normal alkane RI; Authors: Castel, C.; Fernandez, X.; Lizzani-Cuvelier, L.; Perichet, C.; Lavoine, S., Characterization of the Chemical Composition of a Byproduct from Siam Benzoin Gum, J. Agric. Food Chem., 54, 2006, 8848-8854.) NIST Spectra nist ri
      1685 (Program type: Ramp; Column cl... (show more) ass: Semi-standard non-polar; Column diameter: 0.53 mm; Column length: 30 m; Column type: Capillary; Heat rate: 5 K/min; Start T: 100 C; End T: 250 C; CAS no: 306081; Active phase: SPB-5; Carrier gas: He; Data type: Normal alkane RI; Authors: Kilic, A.; Kollmannsberger, H.; Nitz, S., Glycosidically bound volatiles and flavor precursors in Laurus nobilis L., J. Agric. Food Chem., 53, 2005, 2231-2235.) NIST Spectra nist ri
      1657 (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: 60 C; End T: 300 C; CAS no: 306081; Active phase: DB5-30W; Carrier gas: He; Phase thickness: 0.25 um; Data type: Normal alkane RI; Authors: Schwab, W.; Schreier, P., Simultaneous enzyme catalysis extraction: A versatile technique for the study of flavor precursors, J. Agric. Food Chem., 36(6), 1988, 1238-1242.) NIST Spectra nist ri
      3099 (Program type: Complex; Column... (show more) class: Standard polar; Column diameter: 0.25 mm; Column length: 60 m; Column type: Capillary; Description: 40 0C (3 min) ^ 10 0C/min -> 90 0C ^ 2 0C/min -> 230 0C (37 min); CAS no: 306081; Active phase: DB-Wax; Carrier gas: Helium; Phase thickness: 0.50 um; Data type: Normal alkane RI; Authors: Loscos, N.; Hernandez-Orte, P.; Cacho, J.; Ferreira, V., Fate of grape flavor precursors during storage on yeast lees, J. Agric. Food Chem., 57(12), 2009, 5468-5479., Program type: Complex; Column... (show more) class: Standard polar; Column diameter: 0.25 mm; Column length: 60 m; Column type: Capillary; Description: 40C(3min) =>10C/min =>90C =>2C/min =>230C (37min); CAS no: 306081; Active phase: DB-Wax Etr; Carrier gas: He; Phase thickness: 0.5 um; Data type: Normal alkane RI; Authors: Loskos, N.; Hernandez-Orte, P.; Cacho, J.; Ferreira, V., Release and formation of varietal aroma compounds during alcoholic fermentation from nonfloral grape odorless flavor precursors fractions, J. Agric. Food Chem., 55, 2007, 6674-6684.) NIST Spectra nist ri
    • Retention Index (Linear):

      1633 (Program type: Complex; Column... (show more) class: Semi-standard non-polar; Column diameter: 0.25 mm; Column length: 30 m; Column type: Capillary; Description: 40C (5min) => 2C/min => 200C => 5C/min => 250C (15min); CAS no: 306081; Active phase: DB-5MS; Carrier gas: H2/N2; Phase thickness: 0.25 um; Data type: Linear RI; Authors: Boulanger, R.; Crouzet, J., Free and bound flavour components of Amazonian fruits: 3-glycosidically bound components of cupuacu, Food Chem., 70, 2000, 463-470.) NIST Spectra nist ri

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

Density: 1.3±0.1 g/cm3
Boiling Point: 368.7±27.0 °C at 760 mmHg
Vapour Pressure: 0.0±0.9 mmHg at 25°C
Enthalpy of Vaporization: 64.9±3.0 kJ/mol
Flash Point: 151.9±17.2 °C
Index of Refraction: 1.573
Molar Refractivity: 45.9±0.3 cm3
#H bond acceptors: 4
#H bond donors: 2
#Freely Rotating Bonds: 3
#Rule of 5 Violations: 0
ACD/LogP: 0.47
ACD/LogD (pH 5.5): -0.40
ACD/BCF (pH 5.5): 1.00
ACD/KOC (pH 5.5): 4.17
ACD/LogD (pH 7.4): -2.19
ACD/BCF (pH 7.4): 1.00
ACD/KOC (pH 7.4): 1.00
Polar Surface Area: 67 Å2
Polarizability: 18.2±0.5 10-24cm3
Surface Tension: 53.8±3.0 dyne/cm
Molar Volume: 139.3±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) =  0.77
    Log Kow (Exper. database match) =  0.33
       Exper. Ref:  LaHann,TR et al. (1989)

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  338.85  (Adapted Stein & Brown method)
    Melting Pt (deg C):  117.66  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  4.3E-006  (Modified Grain method)
    MP  (exp database):  143.5 deg C
    Subcooled liquid VP: 6.8E-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):  6.973e+004
       log Kow used: 0.33 (expkow database)
       no-melting pt equation used

 Water Sol Estimate from Fragments:
    Wat Sol (v1.01 est) =  1.1495e+005 mg/L

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

 Henrys Law Constant (25 deg C) [HENRYWIN v3.10]:
   Bond Method :   2.72E-013  atm-m3/mole
   Group Method:   Incomplete
 Henrys LC [VP/WSol estimate using EPI values]:  1.478E-011 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  0.33  (exp database)
  Log Kaw used:  -10.954  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  11.284
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :   1.0359
   Biowin2 (Non-Linear Model)     :   0.9918
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   3.0846  (weeks       )
   Biowin4 (Primary Survey Model) :   4.0187  (days        )
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :   0.5802
   Biowin6 (MITI Non-Linear Model):   0.6148
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model):  0.7939
 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):  0.00907 Pa (6.8E-005 mm Hg)
  Log Koa (Koawin est  ): 11.284
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  0.000331 
       Octanol/air (Koa) model:  0.0472 
   Fraction sorbed to airborne particulates (phi):
       Junge-Pankow model     :  0.0118 
       Mackay model           :  0.0258 
       Octanol/air (Koa) model:  0.791 

 Atmospheric Oxidation (25 deg C) [AopWin v1.92]:
   Hydroxyl Radicals Reaction:
      OVERALL OH Rate Constant =  31.9218 E-12 cm3/molecule-sec
      Half-Life =     0.335 Days (12-hr day; 1.5E6 OH/cm3)
      Half-Life =     4.021 Hrs
   Ozone Reaction:
      No Ozone Reaction Estimation
   Reaction With Nitrate Radicals May Be Important!
   Fraction sorbed to airborne particulates (phi): 0.0188 (Junge,Mackay)
    Note: the sorbed fraction may be resistant to atmospheric oxidation

 Soil Adsorption Coefficient (PCKOCWIN v1.66):
      Koc    :  30.81
      Log Koc:  1.489 

 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: 0.33 (expkow database)

 Volatilization from Water:
    Henry LC:  2.72E-013 atm-m3/mole  (estimated by Bond SAR Method)
    Half-Life from Model River: 2.905E+009  hours   (1.211E+008 days)
    Half-Life from Model Lake : 3.169E+010  hours   (1.321E+009 days)

 Removal In Wastewater Treatment:
    Total removal:               1.86  percent
    Total biodegradation:        0.09  percent
    Total sludge adsorption:     1.76  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       6.49e-006       8.04         1000       
   Water     37.9            360          1000       
   Soil      62              720          1000       
   Sediment  0.0707          3.24e+003    0          
     Persistence Time: 586 hr




                    

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