InChI=1/C4H6O6/c5-1(3(7)8)2(6)4(9)10/h1-2,5-6H,(H,7,8)(H,9,10)

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Inherent Properties, Identifiers and References

ChemSpider ID:	852
Empirical Formula:	C₄H₆O₆
Molecular Weight:	150.0868
Nominal Mass:	150 Da
Average Mass:	150.0868 Da
Monoisotopic Mass:	150.016438 Da

Systematic Name:

2,3-dihydroxybutanedioic acid

SMILES:

O=C(O)C(O)C(O)C(=O)O Copy

InChI:

InChI=1/C4H6O6/c5-1(3(7)8)2(6)4(9)10/h1-2,5-6H,(H,7,8)(H,9,10) Copy

InChIKey:

FEWJPZIEWOKRBE-UHFFFAOYAZ

Std. InChI:

InChI=1S/C4H6O6/c5-1(3(7)8)2(6)4(9)10/h1-2,5-6H,(H,7,8)(H,9,10) Copy

Std. InChIKey:

FEWJPZIEWOKRBE-UHFFFAOYSA-N

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Identifiers

Names and Synonyms
Database ID(s)

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

2,3-dihydroxy-succinic acid

212-425-0 [EINECS/ELINCS]

815-82-7 [RN]

acide tartarique

butanedioic acid, 2,3-dihydroxy-

Butanedioic acid, 2,3-dihydroxy-, (R*,S*)-

Tartaric acid

Tartarsäure

(+)-(R,R)-tartaric acid

(+)-L-tartaric acid

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

AI3-06298

AIDS017708

AIDS-017708

bmse000167

C00552

C00898

CHEBI:15674

FEMA No. 3044

LS-3163

MFCD07368295

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Predicted Properties

Pred. Prop. (ACD/Labs)
Pred. Prop. (EPISuite)
NMRShiftDB
Exptl. Prop.

ACD/LogP:	-1.43	# of Rule of 5 Violations:	0
ACD/LogD (pH 5.5):	-5.86	ACD/LogD (pH 7.4):	-6.18
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:	6	#H bond donors:	4
#Freely Rotating Bonds:	5	Polar Surface Area:	71.06 Å²
Index of Refraction:	1.585	Molar Refractivity:	26.69 cm³
Molar Volume:	79.5 cm³	Polarizability:	10.58 10^-24cm³
Surface Tension:	119.4 dyne/cm	Density:	1.886 g/cm³
Flash Point:	209.4 °C	Enthalpy of Vaporization:	75.13 kJ/mol
Boiling Point:	399.3 °C at 760 mmHg	Vapour Pressure:	4.93E-08 mmHg at 25°C

                    
 Log Octanol-Water Partition Coef (SRC):
    Log Kow (KOWWIN v1.67 estimate) =  -1.00

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  355.84  (Adapted Stein & Brown method)
    Melting Pt (deg C):  130.20  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  9.68E-008  (Modified Grain method)
    MP  (exp database):  147 deg C
    Subcooled liquid VP: 1.68E-006 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: -1.00 (estimated)
       no-melting pt equation used
     Water Sol (Exper. database match) =  5.82e+005 mg/L (20 deg C)
        Exper. Ref:  YALKOWSKY,SH & DANNENFELSER,RM (1992)
     Water Sol (Exper. database match) =  2.15e+005 mg/L (25 deg C)
        Exper. Ref:  YALKOWSKY,SH & DANNENFELSER,RM (1992)
     Water Sol (Exper. database match) =  1e+006 mg/L (25 deg C)
        Exper. Ref:  YALKOWSKY,SH & DANNENFELSER,RM (1992)
     Water Sol (Exper. database match) =  5.6e+005 mg/L (20 deg C)
        Exper. Ref:  YALKOWSKY,SH & DANNENFELSER,RM (1992)
     Water Sol (Exper. database match) =  2.46e+005 mg/L (25 deg C)
        Exper. Ref:  BEILSTEIN

 Water Sol Estimate from Fragments:
    Wat Sol (v1.01 est) =  1e+006 mg/L
    Wat Sol (Exper. database match) =  582000.00
       Exper. Ref:  YALKOWSKY,SH & DANNENFELSER,RM (1992)
    Wat Sol (Exper. database match) =  215000.00
       Exper. Ref:  YALKOWSKY,SH & DANNENFELSER,RM (1992)
    Wat Sol (Exper. database match) =  1000000.00
       Exper. Ref:  YALKOWSKY,SH & DANNENFELSER,RM (1992)
    Wat Sol (Exper. database match) =  560000.00
       Exper. Ref:  YALKOWSKY,SH & DANNENFELSER,RM (1992)
    Wat Sol (Exper. database match) =  246000.00
       Exper. Ref:  BEILSTEIN

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

 Henrys Law Constant (25 deg C) [HENRYWIN v3.10]:
   Bond Method :   1.32E-010  atm-m3/mole
   Group Method:   Incomplete
 Henrys LC [VP/WSol estimate using EPI values]:  1.912E-014 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  -1.00  (KowWin est)
  Log Kaw used:  -8.268  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  7.268
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :   1.1389
   Biowin2 (Non-Linear Model)     :   0.9879
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   3.9166  (days        )
   Biowin4 (Primary Survey Model) :   4.6612  (hours-days  )
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :   0.8489
   Biowin6 (MITI Non-Linear Model):   0.9064
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model):  1.1435
 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):  0.000224 Pa (1.68E-006 mm Hg)
  Log Koa (Koawin est  ): 7.268
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  0.0134 
       Octanol/air (Koa) model:  4.55E-006 
   Fraction sorbed to airborne particulates (phi):
       Junge-Pankow model     :  0.326 
       Mackay model           :  0.517 
       Octanol/air (Koa) model:  0.000364 

 Atmospheric Oxidation (25 deg C) [AopWin v1.92]:
   Hydroxyl Radicals Reaction:
      OVERALL OH Rate Constant =  13.8476 E-12 cm3/molecule-sec
      Half-Life =     0.772 Days (12-hr day; 1.5E6 OH/cm3)
      Half-Life =     9.269 Hrs
   Ozone Reaction:
      No Ozone Reaction Estimation
   Fraction sorbed to airborne particulates (phi): 0.422 (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: -1.00 (estimated)

 Volatilization from Water:
    Henry LC:  1.32E-010 atm-m3/mole  (estimated by Bond SAR Method)
    Half-Life from Model River: 5.434E+006  hours   (2.264E+005 days)
    Half-Life from Model Lake : 5.928E+007  hours   (2.47E+006 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       0.0269          18.5         1000       
   Water     26.8            55.9         1000       
   Soil      73.1            112          1000       
   Sediment  0.0344          503          0          
     Persistence Time: 123 hr

User Data

experimental physchem properties

Melting Point: 210-212 dec.

The melting point of a crystalline solid is the temperature range at which it changes state from solid to liquid. See also: Melting Point

Melting Point: 205 - 215 C

The melting point of a crystalline solid is the temperature range at which it changes state from solid to liquid. See also: Melting Point

Flash Point: 210 C

The flash point of a flammable liquid is the lowest temperature at which it can form an ignitable mixture in air. See also: Flash Point

miscellaneous

Appearance: colourless or translucent crystals, or a white, fine to granular crystaline powder which is odourless with an acid taste

Visual appearance of the given substance.

Appearance: white crystalline powder

Visual appearance of the given substance.

Stability: Stable. Incompatible with bases, oxidizing agents, reducing agents, silver.

Chemical stability occurs when a substance is in a (dynamic) chemical equilibrium with its environment. See also: Chemical Stability

Safety: WARNING: Irritates lungs, eyes, skin

See Chemical Safety

Safety: Safety glasses.

See Chemical Safety

Medical Subject Headings Classification

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