ChemSpider 2D Image | Beta-Hydroxybutyric acid | C4H8O3

β-Hydroxybutyric acid

  • Molecular FormulaC4H8O3
  • Average mass104.104 Da
  • Monoisotopic mass104.047340 Da
  • ChemSpider ID428

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

β-Hydroxybutyric acid [Wiki]
(±)-3-Hydroxybutanoic acid
(±)3-hydroxybutyric acid
206-099-9 [EINECS]
300-85-6 [RN]
3-Hydroxybutanoic acid [ACD/IUPAC Name]
3-HYDROXYBUTANOIC ACID, (R)-
3-HYDROXYBUTANOIC ACID, (S)-
3-Hydroxybutansäure [German] [ACD/IUPAC Name]
3-Hydroxybutyric acid
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Validated by Experts, Validated by Users, Non-Validated, Removed by Users

TZP1275679 [DBID]
UNII:TZP1275679 [DBID]
148ULJ1DF4 [DBID]
166898_ALDRICH [DBID]
363502_ALDRICH [DBID]
AI3-21675 [DBID]
bmse000161 [DBID]
CHEBI:20067 [DBID]
CPD-335 [DBID]
LMFA01050005 [DBID]
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  • References
  • Experimental Physico-chemical Properties
  • Miscellaneous
    • Safety:

      26-37 Alfa Aesar 43354, H30426
      36/37/38 Alfa Aesar 43354, H30426
      H315-H319-H335 Alfa Aesar 43354, H30426
      P261-P280-P305+P351+P338-P304+P340-P405-P501a Alfa Aesar 43354
      P280g-P305+P351+P338 Alfa Aesar H30426
      Warning Alfa Aesar 43354, H30426
      WARNING: Irritates lungs, eyes, skin Alfa Aesar 43354, H30426
    • Chemical Class:

      A straight-chain 3-hydroxy monocarboxylic acid comprising a butyric acid core with a single hydroxy substituent in the 3- position; a ketone body whose levels are raised during ketosis, used as an ene rgy source by the brain during fasting in humans. Also used to synthesise biodegradable plastics. ChEBI CHEBI:20067, https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:20067
    • Bio Activity:

      Biochemicals & small molecules/Antagonists & inhibitors Hello Bio [HB4640]
      Endogenous HDAC1, HDAC3 and HDAC4 inhibitor Hello Bio [HB4640]
      Enzymes/Deacetylase/Histone deacetylase (HDAC)/Non-selective Hello Bio [HB4640]
      HDAC1, HDAC3 and HDAC4 inhibitor. Key metabolite of the ketolytic pathway generating acetyl-CoA. Stereoselective product of D-3-hydroxybutyrate dehydreogenase. Clinically and physiologically significant stereoisomer. Energy carrier from adipocytes to peripheral tissues during fasting or exercise. Ligand of free fatty acid receptor 3 (FFAR3; GPR41) and hydroxycarboxylic acid receptor 2 (HCAR2; GPR109B). NLRP3 inflammasome inhibitor. Prevents K+-efflux and reduces ASC oligomerization and speck formation. Hello Bio [HB4640]
  • Gas Chromatography
    • Retention Index (Kovats):

      938 (estimated with error: 89) NIST Spectra mainlib_332868, replib_1309
    • Retention Index (Linear):

      976.6 (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: 300856; 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: 1.2±0.1 g/cm3
Boiling Point: 269.2±0.0 °C at 760 mmHg
Vapour Pressure: 0.0±1.2 mmHg at 25°C
Enthalpy of Vaporization: 58.9±6.0 kJ/mol
Flash Point: 121.0±19.1 °C
Index of Refraction: 1.455
Molar Refractivity: 23.6±0.3 cm3
#H bond acceptors: 3
#H bond donors: 2
#Freely Rotating Bonds: 2
#Rule of 5 Violations: 0
ACD/LogP: -1.14
ACD/LogD (pH 5.5): -2.00
ACD/BCF (pH 5.5): 1.00
ACD/KOC (pH 5.5): 1.00
ACD/LogD (pH 7.4): -3.78
ACD/BCF (pH 7.4): 1.00
ACD/KOC (pH 7.4): 1.00
Polar Surface Area: 58 Å2
Polarizability: 9.4±0.5 10-24cm3
Surface Tension: 46.4±3.0 dyne/cm
Molar Volume: 87.1±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) =  -0.47

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  223.46  (Adapted Stein & Brown method)
    Melting Pt (deg C):  33.91  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  0.00972  (Modified Grain method)
    MP  (exp database):  49 deg C
    Subcooled liquid VP: 0.0161 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: -0.47 (estimated)
       no-melting pt equation used

 Water Sol Estimate from Fragments:
    Wat Sol (v1.01 est) =  1e+006 mg/L

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

 Henrys Law Constant (25 deg C) [HENRYWIN v3.10]:
   Bond Method :   3.53E-011  atm-m3/mole
   Group Method:   1.12E-011  atm-m3/mole
 Henrys LC [VP/WSol estimate using EPI values]:  1.332E-009 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  -0.47  (KowWin est)
  Log Kaw used:  -8.841  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  8.371
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :   0.9294
   Biowin2 (Non-Linear Model)     :   0.9641
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   3.4937  (days-weeks  )
   Biowin4 (Primary Survey Model) :   4.2126  (days        )
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :   0.7439
   Biowin6 (MITI Non-Linear Model):   0.8816
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model):  0.9362
 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):  2.15 Pa (0.0161 mm Hg)
  Log Koa (Koawin est  ): 8.371
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  1.4E-006 
       Octanol/air (Koa) model:  5.77E-005 
   Fraction sorbed to airborne particulates (phi):
       Junge-Pankow model     :  5.05E-005 
       Mackay model           :  0.000112 
       Octanol/air (Koa) model:  0.00459 

 Atmospheric Oxidation (25 deg C) [AopWin v1.92]:
   Hydroxyl Radicals Reaction:
      OVERALL OH Rate Constant =  10.0406 E-12 cm3/molecule-sec
      Half-Life =     1.065 Days (12-hr day; 1.5E6 OH/cm3)
      Half-Life =    12.783 Hrs
   Ozone Reaction:
      No Ozone Reaction Estimation
   Fraction sorbed to airborne particulates (phi): 8.11E-005 (Junge,Mackay)
    Note: the sorbed fraction may be resistant to atmospheric oxidation

 Soil Adsorption Coefficient (PCKOCWIN v1.66):
      Koc    :  1
      Log Koc:  0.000 

 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: -0.47 (estimated)

 Volatilization from Water:
    Henry LC:  1.12E-011 atm-m3/mole  (estimated by Group SAR Method)
    Half-Life from Model River: 5.334E+007  hours   (2.222E+006 days)
    Half-Life from Model Lake : 5.819E+008  hours   (2.424E+007 days)

 Removal In Wastewater Treatment:
    Total removal:               1.85  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       0.000394        25.6         1000       
   Water     34.3            208          1000       
   Soil      65.6            416          1000       
   Sediment  0.0596          1.87e+003    0          
     Persistence Time: 388 hr




                    

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