ChemSpider 2D Image | (+)-lariciresinol | C20H24O6


  • Molecular FormulaC20H24O6
  • Average mass360.401 Da
  • Monoisotopic mass360.157288 Da
  • ChemSpider ID294521
  • defined stereocentres - 3 of 3 defined stereocentres

More details:

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

27003-73-2 [RN]
3-Furanmethanol, tetrahydro-2-(4-hydroxy-3-methoxyphenyl)-4-[(4-hydroxy-3-methoxyphenyl)methyl]-, (2S,3R,4R)- [ACD/Index Name]
4-[(2S,3R,4R)-4-(4-Hydroxy-3-methoxybenzyl)-3-(hydroxymethyl)tetrahydro-2-furanyl]-2-methoxyphenol [ACD/IUPAC Name]
4-[(2S,3R,4R)-4-(4-Hydroxy-3-methoxybenzyl)-3-(hydroxymethyl)tetrahydro-2-furanyl]-2-methoxyphenol [German] [ACD/IUPAC Name]
4-[(2S,3R,4R)-4-(4-Hydroxy-3-méthoxybenzyl)-3-(hydroxyméthyl)tétrahydro-2-furanyl]-2-méthoxyphénol [French] [ACD/IUPAC Name]
lariciresinol [Wiki]

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

4560057 [DBID]
27003-73-2; 83327-19-9 [DBID]
C10646 [DBID]
NSC329247 [DBID]
  • Miscellaneous
    • Chemical Class:

      A lignan that is tetrahydrofuran substituted at positions 2, 3 and 4 by 4-hydroxy-3-methoxyphenyl, hydroxymethyl and 4-hydroxy-3-methoxybenzyl groups respectively (the 2<stereo>S</stereo>,3<stereo>R</ stereo>,4<stereo>R</stereo>-diastereomer). ChEBI CHEBI:67246
      A lignan that is tetrahydrofuran substituted at positions 2, 3 and 4 by 4-hydroxy-3-methoxyphenyl, hydroxymethyl and 4-hydroxy-3-methoxybenzyl groups respectively (the 2S,3R,4R-diastereomer). ChEBI, CHEBI:67246
      Lignans Phenol-Explorer 596
    • Compound Source:

      Aegilops tauschii PlantCyc CPD-8907
      Amaranthus hypochondriacus PlantCyc CPD-8907
      Amborella trichopoda PlantCyc CPD-8907
      Anacardium occidentale PlantCyc CPD-8907
      Ananas comosus PlantCyc CPD-8907
      Aquilegia coerulea PlantCyc CPD-8907
      Arabidopsis halleri PlantCyc CPD-8907
      Arabidopsis lyrata PlantCyc CPD-8907
      Arabidopsis thaliana col PlantCyc CPD-8907
      Asparagus officinalis PlantCyc CPD-8907
      Beta vulgaris subsp. vulgaris PlantCyc CPD-8907
      Boechera stricta PlantCyc CPD-8907
      Brachypodium distachyon PlantCyc CPD-8907
      Brassica napus PlantCyc CPD-8907
      Brassica oleracea var. capitata PlantCyc CPD-8907
      Brassica oleracea var. oleracea PlantCyc CPD-8907
      Brassica rapa FPsc PlantCyc CPD-8907
      Brassica rapa subsp. pekinensis PlantCyc CPD-8907
      Calotropis gigantea PlantCyc CPD-8907
      Camptotheca acuminata PlantCyc CPD-8907
      Cannabis sativa PlantCyc CPD-8907
      Capsella grandiflora PlantCyc CPD-8907
      Capsella rubella PlantCyc CPD-8907
      Capsicum annuum PlantCyc CPD-8907
      Carica papaya PlantCyc CPD-8907
      Catharanthus roseus PlantCyc CPD-8907
      Chenopodium quinoa PlantCyc CPD-8907
      Cicer arietinum PlantCyc CPD-8907
      Citrus clementina PlantCyc CPD-8907
      Citrus sinensis PlantCyc CPD-8907
      Coccomyxa subellipsoidea C-169 PlantCyc CPD-8907
      Corchorus capsularis PlantCyc CPD-8907
      Cucumis sativus PlantCyc CPD-8907
      Daucus carota subsp. sativus PlantCyc CPD-8907
      Dianthus caryophyllus PlantCyc CPD-8907
      Dioscorea rotundata PlantCyc CPD-8907
      Eucalyptus grandis PlantCyc CPD-8907
      Eutrema salsugineum PlantCyc CPD-8907
      Fragaria vesca subsp. vesca PlantCyc CPD-8907
      Glycine max PlantCyc CPD-8907
      Gossypium raimondii PlantCyc CPD-8907
      Helianthus annuus PlantCyc CPD-8907
      Hordeum vulgare subsp. vulgare PlantCyc CPD-8907
      Humulus lupulus var. lupulus PlantCyc CPD-8907
      Isolated from a plant Susan Richardson [Structure found in ChemSpider, confirmed from ACD/Dictionary, ChEBI and ChEMBL]
      Kalanchoe fedtschenkoi PlantCyc CPD-8907
      Kalanchoe laxiflora PlantCyc CPD-8907
      Leersia perrieri PlantCyc CPD-8907
      Linum usitatissimum PlantCyc CPD-8907
      Lotus japonicus PlantCyc CPD-8907
      Malus domestica PlantCyc CPD-8907
      Manihot esculenta PlantCyc CPD-8907
      matairesinol biosynthesis PlantCyc CPD-8907
      Medicago truncatula PlantCyc CPD-8907
      Mimulus guttatus PlantCyc CPD-8907
      Miscanthus sinensis PlantCyc CPD-8907
      Musa acuminata PlantCyc CPD-8907
      Nicotiana tabacum PlantCyc CPD-8907
      Olea europaea var. sylvestris PlantCyc CPD-8907
      Oropetium thomaeum PlantCyc CPD-8907
      Oryza brachyantha PlantCyc CPD-8907
      Oryza glaberrima PlantCyc CPD-8907
      Oryza punctata PlantCyc CPD-8907
      Oryza rufipogon PlantCyc CPD-8907
      Oryza sativa Japonica Group PlantCyc CPD-8907
      Panicum hallii PlantCyc CPD-8907
      Panicum virgatum PlantCyc CPD-8907
      Petunia axillaris PlantCyc CPD-8907
      Phaseolus vulgaris PlantCyc CPD-8907
      Populus trichocarpa PlantCyc CPD-8907
      Prunus persica PlantCyc CPD-8907
      Ricinus communis PlantCyc CPD-8907
      Rosa chinensis PlantCyc CPD-8907
      Rosa multiflora PlantCyc CPD-8907
      Salvia miltiorrhiza PlantCyc CPD-8907
      Selaginella moellendorffii PlantCyc CPD-8907
      Setaria italica PlantCyc CPD-8907
      Setaria viridis PlantCyc CPD-8907
      Solanum lycopersicum PlantCyc CPD-8907
      Solanum melongena PlantCyc CPD-8907
      Solanum pennellii PlantCyc CPD-8907
      Solanum tuberosum PlantCyc CPD-8907
      Sorghum bicolor PlantCyc CPD-8907
      Spinacia oleracea PlantCyc CPD-8907
      Spirodela polyrhiza PlantCyc CPD-8907
      Styrax camporum (Styracaceae) Susan Richardson [Structure found in ChemSpider, confirmed from ACD/Dictionary, ChEBI and ChEMBL]
      Thellungiella parvula PlantCyc CPD-8907
      Theobroma cacao PlantCyc CPD-8907
      Trifolium pratense PlantCyc CPD-8907
      Triticum aestivum PlantCyc CPD-8907
      Triticum urartu PlantCyc CPD-8907
      Vitis vinifera PlantCyc CPD-8907
      Zea mays subsp. mays PlantCyc CPD-8907
    • Bio Activity:

      (+)-lariciresinol + NADP+ <- (+)-pinoresinol + NADPH + H+ PlantCyc CPD-8907
      (+)-lariciresinol + NADPH + H+ -> (-)-secoisolariciresinol + NADP+ PlantCyc CPD-8907
      (+)-pinoresinol + NADPH + H+ -> (+)-lariciresinol + NADP+ PlantCyc CPD-8907

Predicted data is generated using the ACD/Labs Percepta Platform - PhysChem Module, version: 14.00

Density: 1.3±0.1 g/cm3
Boiling Point: 568.4±50.0 °C at 760 mmHg
Vapour Pressure: 0.0±1.6 mmHg at 25°C
Enthalpy of Vaporization: 89.7±3.0 kJ/mol
Flash Point: 297.6±30.1 °C
Index of Refraction: 1.595
Molar Refractivity: 97.0±0.3 cm3
#H bond acceptors: 6
#H bond donors: 3
#Freely Rotating Bonds: 6
#Rule of 5 Violations: 0
ACD/LogP: 1.64
ACD/LogD (pH 5.5): 1.93
ACD/BCF (pH 5.5): 17.37
ACD/KOC (pH 5.5): 268.60
ACD/LogD (pH 7.4): 1.93
ACD/BCF (pH 7.4): 17.28
ACD/KOC (pH 7.4): 267.25
Polar Surface Area: 88 Å2
Polarizability: 38.5±0.5 10-24cm3
Surface Tension: 53.8±3.0 dyne/cm
Molar Volume: 285.7±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) =  2.34

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  512.82  (Adapted Stein & Brown method)
    Melting Pt (deg C):  218.58  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  6.5E-013  (Modified Grain method)
    Subcooled liquid VP: 7.57E-011 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):  174.5
       log Kow used: 2.34 (estimated)
       no-melting pt equation used

 Water Sol Estimate from Fragments:
    Wat Sol (v1.01 est) =  1566.6 mg/L

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

 Henrys Law Constant (25 deg C) [HENRYWIN v3.10]:
   Bond Method :   1.34E-021  atm-m3/mole
   Group Method:   Incomplete
 Henrys LC [VP/WSol estimate using EPI values]:  1.766E-015 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  2.34  (KowWin est)
  Log Kaw used:  -19.261  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  21.601
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :   0.9374
   Biowin2 (Non-Linear Model)     :   0.9220
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   2.4757  (weeks-months)
   Biowin4 (Primary Survey Model) :   3.6126  (days-weeks  )
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :   0.4002
   Biowin6 (MITI Non-Linear Model):   0.1135
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model):  0.3935
 Ready Biodegradability Prediction:   NO

Hydrocarbon Biodegradation (BioHCwin v1.01):
    Structure incompatible with current estimation method!

 Sorption to aerosols (25 Dec C)[AEROWIN v1.00]:
  Vapor pressure (liquid/subcooled):  1.01E-008 Pa (7.57E-011 mm Hg)
  Log Koa (Koawin est  ): 21.601
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  297 
       Octanol/air (Koa) model:  9.79E+008 
   Fraction sorbed to airborne particulates (phi):
       Junge-Pankow model     :  1 
       Mackay model           :  1 
       Octanol/air (Koa) model:  1 

 Atmospheric Oxidation (25 deg C) [AopWin v1.92]:
   Hydroxyl Radicals Reaction:
      OVERALL OH Rate Constant = 101.8424 E-12 cm3/molecule-sec
      Half-Life =     0.105 Days (12-hr day; 1.5E6 OH/cm3)
      Half-Life =     1.260 Hrs
   Ozone Reaction:
      No Ozone Reaction Estimation
   Reaction With Nitrate Radicals May Be Important!
   Fraction sorbed to airborne particulates (phi): 1 (Junge,Mackay)
    Note: the sorbed fraction may be resistant to atmospheric oxidation

 Soil Adsorption Coefficient (PCKOCWIN v1.66):
      Koc    :  1719
      Log Koc:  3.235 

 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 = 0.451 (BCF = 2.824)
       log Kow used: 2.34 (estimated)

 Volatilization from Water:
    Henry LC:  1.34E-021 atm-m3/mole  (estimated by Bond SAR Method)
    Half-Life from Model River: 8.295E+017  hours   (3.456E+016 days)
    Half-Life from Model Lake : 9.049E+018  hours   (3.77E+017 days)

 Removal In Wastewater Treatment:
    Total removal:               2.71  percent
    Total biodegradation:        0.10  percent
    Total sludge adsorption:     2.62  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       1.95e-010       2.52         1000       
   Water     17.8            900          1000       
   Soil      82.1            1.8e+003     1000       
   Sediment  0.111           8.1e+003     0          
     Persistence Time: 1.58e+003 hr


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