ChemSpider 2D Image | 5-[(1S)-1,2-Dihydroxyethyl]-3,4-dihydroxy-2(5H)-furanone | C6H8O6

5-[(1S)-1,2-Dihydroxyethyl]-3,4-dihydroxy-2(5H)-furanone

  • Molecular FormulaC6H8O6
  • Average mass176.124 Da
  • Monoisotopic mass176.032089 Da
  • ChemSpider ID17206850
  • defined stereocentres - 1 of 2 defined stereocentres


More details:






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

5-[(1S)-1,2-Dihydroxyethyl]-3,4-dihydroxy-2(5H)-furanon [German] [ACD/IUPAC Name]
5-[(1S)-1,2-Dihydroxyethyl]-3,4-dihydroxy-2(5H)-furanone [ACD/IUPAC Name]
5-[(1S)-1,2-Dihydroxyéthyl]-3,4-dihydroxy-2(5H)-furanone [French] [ACD/IUPAC Name]
5-[(1S)-1,2-Dihydroxyethyl]-3,4-dihydroxyfuran-2(5H)-one (non-preferred name)
Ascorbyl radical
Monodehydroascorbate radical
monodehydroascorbic acid
Semidehydroascorbate
Semidehydroascorbic acid

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

MFCD00064328 [DBID]
  • Miscellaneous
    • Compound Source:

      2 L-ascorbate + hydrogen peroxide + H+ -> L-ascorbate + L-dehydro-ascorbate + 2 H2O PlantCyc CPD-318
      Aegilops tauschii PlantCyc CPD-318
      Amaranthus hypochondriacus PlantCyc CPD-318
      Amborella trichopoda PlantCyc CPD-318
      Anacardium occidentale PlantCyc CPD-318
      Ananas comosus PlantCyc CPD-318
      Aquilegia coerulea PlantCyc CPD-318
      Arabidopsis halleri PlantCyc CPD-318
      Arabidopsis lyrata PlantCyc CPD-318
      Arabidopsis thaliana col PlantCyc CPD-318
      ascorbate glutathione cycle PlantCyc CPD-318
      ascorbate recycling (cytosolic) PlantCyc CPD-318
      Asparagus officinalis PlantCyc CPD-318
      Beta vulgaris subsp. vulgaris PlantCyc CPD-318
      Boechera stricta PlantCyc CPD-318
      Brachypodium distachyon PlantCyc CPD-318
      Brassica napus PlantCyc CPD-318
      Brassica oleracea var. capitata PlantCyc CPD-318
      Brassica oleracea var. oleracea PlantCyc CPD-318
      Brassica rapa FPsc PlantCyc CPD-318
      Brassica rapa subsp. pekinensis PlantCyc CPD-318
      Calotropis gigantea PlantCyc CPD-318
      Camptotheca acuminata PlantCyc CPD-318
      Cannabis sativa PlantCyc CPD-318
      Capsella grandiflora PlantCyc CPD-318
      Capsella rubella PlantCyc CPD-318
      Capsicum annuum PlantCyc CPD-318
      Carica papaya PlantCyc CPD-318
      Catharanthus roseus PlantCyc CPD-318
      Chenopodium quinoa PlantCyc CPD-318
      Chlamydomonas reinhardtii PlantCyc CPD-318
      Chromochloris zofingiensis PlantCyc CPD-318
      Cicer arietinum PlantCyc CPD-318
      Citrus clementina PlantCyc CPD-318
      Citrus sinensis PlantCyc CPD-318
      Coccomyxa subellipsoidea C-169 PlantCyc CPD-318
      Corchorus capsularis PlantCyc CPD-318
      Cucumis sativus PlantCyc CPD-318
      Daucus carota subsp. sativus PlantCyc CPD-318
      Dianthus caryophyllus PlantCyc CPD-318
      Dioscorea rotundata PlantCyc CPD-318
      Eucalyptus grandis PlantCyc CPD-318
      Eutrema salsugineum PlantCyc CPD-318
      Fragaria vesca subsp. vesca PlantCyc CPD-318
      Glycine max PlantCyc CPD-318
      Gossypium raimondii PlantCyc CPD-318
      Helianthus annuus PlantCyc CPD-318
      Hordeum vulgare subsp. vulgare PlantCyc CPD-318
      Humulus lupulus var. lupulus PlantCyc CPD-318
      Kalanchoe fedtschenkoi PlantCyc CPD-318
      Kalanchoe laxiflora PlantCyc CPD-318
      L-ascorbate[in] + Fe3+[out] -> monodehydroascorbate radical[in] + Fe2+[out] PlantCyc CPD-318
      Leersia perrieri PlantCyc CPD-318
      Linum usitatissimum PlantCyc CPD-318
      Lotus japonicus PlantCyc CPD-318
      Malus domestica PlantCyc CPD-318
      Manihot esculenta PlantCyc CPD-318
      Marchantia polymorpha PlantCyc CPD-318
      Medicago truncatula PlantCyc CPD-318
      Micromonas commoda RCC299 PlantCyc CPD-318
      Micromonas pusilla CCMP1545 PlantCyc CPD-318
      Mimulus guttatus PlantCyc CPD-318
      Miscanthus sinensis PlantCyc CPD-318
      Musa acuminata PlantCyc CPD-318
      Nicotiana tabacum PlantCyc CPD-318
      Olea europaea var. sylvestris PlantCyc CPD-318
      Oropetium thomaeum PlantCyc CPD-318
      Oryza brachyantha PlantCyc CPD-318
      Oryza glaberrima PlantCyc CPD-318
      Oryza punctata PlantCyc CPD-318
      Oryza rufipogon PlantCyc CPD-318
      Oryza sativa Japonica Group PlantCyc CPD-318
      Ostreococcus lucimarinus PlantCyc CPD-318
      Panicum hallii PlantCyc CPD-318
      Panicum virgatum PlantCyc CPD-318
      Petunia axillaris PlantCyc CPD-318
      Phaseolus vulgaris PlantCyc CPD-318
      Physcomitrella patens PlantCyc CPD-318
      Populus trichocarpa PlantCyc CPD-318
      Prunus persica PlantCyc CPD-318
      Ricinus communis PlantCyc CPD-318
      Rosa chinensis PlantCyc CPD-318
      Rosa multiflora PlantCyc CPD-318
      Salvia miltiorrhiza PlantCyc CPD-318
      Selaginella moellendorffii PlantCyc CPD-318
      Setaria italica PlantCyc CPD-318
      Setaria viridis PlantCyc CPD-318
      Solanum lycopersicum PlantCyc CPD-318
      Solanum melongena PlantCyc CPD-318
      Solanum pennellii PlantCyc CPD-318
      Solanum tuberosum PlantCyc CPD-318
      Sorghum bicolor PlantCyc CPD-318
      Sphagnum fallax PlantCyc CPD-318
      Spinacia oleracea PlantCyc CPD-318
      Spirodela polyrhiza PlantCyc CPD-318
      Thellungiella parvula PlantCyc CPD-318
      Theobroma cacao PlantCyc CPD-318
      Trifolium pratense PlantCyc CPD-318
      Triticum aestivum PlantCyc CPD-318
      Triticum urartu PlantCyc CPD-318
      Vitis vinifera PlantCyc CPD-318
      Volvox carteri PlantCyc CPD-318
      Zea mays subsp. mays PlantCyc CPD-318
      Zostera marina PlantCyc CPD-318
    • Bio Activity:

      2 L-ascorbate + an oxidized electron acceptor + 2 H+ -> 2 monodehydroascorbate radical + a reduced electron acceptor PlantCyc CPD-318
      2 L-ascorbate + hydrogen peroxide + 2 H+ -> 2 monodehydroascorbate radical + 2 H2O PlantCyc CPD-318
      2 monodehydroascorbate radical -> L-ascorbate + L-dehydro-ascorbate + H+ PlantCyc CPD-318
      2 monodehydroascorbate radical + NADH -> 2 L-ascorbate + NAD+ + H+ PlantCyc CPD-318
      2 monodehydroascorbate radical + NADPH + H+ -> 2 L-ascorbate + NADP+ + 2 H+ PlantCyc CPD-318
      monodehydroascorbate radical[in] + e-[membrane] -> L-ascorbate[in] PlantCyc CPD-318

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

Density: 2.0±0.1 g/cm3
Boiling Point: 552.7±50.0 °C at 760 mmHg
Vapour Pressure: 0.0±3.4 mmHg at 25°C
Enthalpy of Vaporization: 95.8±6.0 kJ/mol
Flash Point: 238.2±23.6 °C
Index of Refraction: 1.711
Molar Refractivity: 35.3±0.3 cm3
#H bond acceptors: 6
#H bond donors: 4
#Freely Rotating Bonds: 2
#Rule of 5 Violations: 0
ACD/LogP: -2.41
ACD/LogD (pH 5.5): -3.33
ACD/BCF (pH 5.5): 1.00
ACD/KOC (pH 5.5): 1.00
ACD/LogD (pH 7.4): -4.99
ACD/BCF (pH 7.4): 1.00
ACD/KOC (pH 7.4): 1.00
Polar Surface Area: 107 Å2
Polarizability: 14.0±0.5 10-24cm3
Surface Tension: 140.6±3.0 dyne/cm
Molar Volume: 90.1±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) =  -1.88
    Log Kow (Exper. database match) =  -1.85
       Exper. Ref:  Avdeef,A (1997)

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  424.64  (Adapted Stein & Brown method)
    Melting Pt (deg C):  155.71  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  1.79E-010  (Modified Grain method)
    MP  (exp database):  168.5 deg C
    Subcooled liquid VP: 5.4E-009 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: -1.85 (expkow database)
       no-melting pt equation used
     Water Sol (Exper. database match) =  4e+005 mg/L (40 deg C)
        Exper. Ref:  MERCK INDEX (1996)
     Water Sol (Exper. database match) =  4e+005 mg/L (25 deg C)
        Exper. Ref:  MERCK INDEX (1996)

 Water Sol Estimate from Fragments:
    Wat Sol (v1.01 est) =  1e+006 mg/L
    Wat Sol (Exper. database match) =  400000.00
       Exper. Ref:  MERCK INDEX (1996)
    Wat Sol (Exper. database match) =  400000.00
       Exper. Ref:  MERCK INDEX (1996)

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

 Henrys Law Constant (25 deg C) [HENRYWIN v3.10]:
   Bond Method :   4.07E-008  atm-m3/mole
   Group Method:   Incomplete
 Henrys LC [VP/WSol estimate using EPI values]:  4.148E-017 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  -1.85  (exp database)
  Log Kaw used:  -5.779  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  3.929
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :   1.4728
   Biowin2 (Non-Linear Model)     :   0.9999
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   3.5900  (days-weeks  )
   Biowin4 (Primary Survey Model) :   4.3404  (hours-days  )
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :   1.1876
   Biowin6 (MITI Non-Linear Model):   0.9838
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model):  1.4386
 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):  7.2E-007 Pa (5.4E-009 mm Hg)
  Log Koa (Koawin est  ): 3.929
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  4.17 
       Octanol/air (Koa) model:  2.08E-009 
   Fraction sorbed to airborne particulates (phi):
       Junge-Pankow model     :  0.993 
       Mackay model           :  0.997 
       Octanol/air (Koa) model:  1.67E-007 

 Atmospheric Oxidation (25 deg C) [AopWin v1.92]:
   Hydroxyl Radicals Reaction:
      OVERALL OH Rate Constant =  55.7969 E-12 cm3/molecule-sec
      Half-Life =     0.192 Days (12-hr day; 1.5E6 OH/cm3)
      Half-Life =     2.300 Hrs
   Ozone Reaction:
      OVERALL Ozone Rate Constant =     1.137500 E-17 cm3/molecule-sec
      Half-Life =     1.007 Days (at 7E11 mol/cm3)
      Half-Life =     24.179 Hrs
   Fraction sorbed to airborne particulates (phi): 0.995 (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: -1.85 (expkow database)

 Volatilization from Water:
    Henry LC:  4.07E-008 atm-m3/mole  (estimated by Bond SAR Method)
    Half-Life from Model River: 1.909E+004  hours   (795.5 days)
    Half-Life from Model Lake : 2.084E+005  hours   (8683 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       0.618           3.87         1000       
   Water     41.8            208          1000       
   Soil      57.5            416          1000       
   Sediment  0.0723          1.87e+003    0          
     Persistence Time: 254 hr




                    

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