(2E)-1-{2,4-Dihydroxy-3-[(2S)-2-hydroxy-3-methyl-3-buten-1-yl]-6-methoxyphenyl}-3-(4-hydroxyphenyl)-2-propen-1-one

Molecular FormulaC₂₁H₂₂O₆
Average mass370.396 Da
Monoisotopic mass370.141632 Da
ChemSpider ID552946

- Double-bond stereo
- 1 of 1 defined stereocentres

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Names and Synonyms

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

(2E)-1-{2,4-Dihydroxy-3-[(2S)-2-hydroxy-3-methyl-3-buten-1-yl]-6-methoxyphenyl}-3-(4-hydroxyphenyl)-2-propen-1-on [German] [ACD/IUPAC Name]

(2E)-1-{2,4-Dihydroxy-3-[(2S)-2-hydroxy-3-methyl-3-buten-1-yl]-6-methoxyphenyl}-3-(4-hydroxyphenyl)-2-propen-1-one [ACD/IUPAC Name]

(2E)-1-{2,4-Dihydroxy-3-[(2S)-2-hydroxy-3-méthyl-3-butén-1-yl]-6-méthoxyphényl}-3-(4-hydroxyphényl)-2-propén-1-one [French] [ACD/IUPAC Name]

2-Propen-1-one, 1-[2,4-dihydroxy-3-[(2S)-2-hydroxy-3-methyl-3-buten-1-yl]-6-methoxyphenyl]-3-(4-hydroxyphenyl)-, (2E)- [ACD/Index Name]

(2E)-1-[2,4-Dihydroxy-3-(2-hydroxy-3-methylbut-3-en-1-yl)-6-methoxyphenyl]-3-(4-hydroxyphenyl)prop-2-en-1-one

1-[2,4-Dihydroxy-3-(2-hydroxy-3-methyl-but-3-enyl)-6-methoxy-phenyl]-3-(4-hydroxy-phenyl)-propenone

2-propen-1-one, 1-[2,4-dihydroxy-3-(2-hydroxy-3-methyl-3-butenyl)-6-methoxyphenyl]-3-(4-hydroxyphenyl)-, (2E)-

Xanthohumol D

Predicted - ACD/Labs
Predicted - EPISuite
Predicted - ChemAxon

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

Density:	1.3±0.1 g/cm³
Boiling Point:	624.2±55.0 °C at 760 mmHg
Vapour Pressure:	0.0±1.9 mmHg at 25°C
Enthalpy of Vaporization:	97.2±3.0 kJ/mol
Flash Point:	220.9±25.0 °C
Index of Refraction:	1.652
Molar Refractivity:	103.9±0.3 cm³
#H bond acceptors:	6
#H bond donors:	4
#Freely Rotating Bonds:	7
#Rule of 5 Violations:	0

ACD/LogP:	3.54
ACD/LogD (pH 5.5):	3.57
ACD/BCF (pH 5.5):	301.60
ACD/KOC (pH 5.5):	2053.32
ACD/LogD (pH 7.4):	3.01
ACD/BCF (pH 7.4):	82.90
ACD/KOC (pH 7.4):	564.41
Polar Surface Area:	107 Å²
Polarizability:	41.2±0.5 10^-24cm³
Surface Tension:	59.1±3.0 dyne/cm
Molar Volume:	284.2±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) =  3.97

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  546.55  (Adapted Stein & Brown method)
    Melting Pt (deg C):  234.34  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  3.82E-014  (Modified Grain method)
    Subcooled liquid VP: 6.89E-012 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):  23.41
       log Kow used: 3.97 (estimated)
       no-melting pt equation used

 Water Sol Estimate from Fragments:
    Wat Sol (v1.01 est) =  763.44 mg/L

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

 Henrys Law Constant (25 deg C) [HENRYWIN v3.10]:
   Bond Method :   2.14E-021  atm-m3/mole
   Group Method:   Incomplete
 Henrys LC [VP/WSol estimate using EPI values]:  7.953E-016 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  3.97  (KowWin est)
  Log Kaw used:  -19.058  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  23.028
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :   1.2708
   Biowin2 (Non-Linear Model)     :   0.9814
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   2.5543  (weeks-months)
   Biowin4 (Primary Survey Model) :   3.5482  (days-weeks  )
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :   0.2373
   Biowin6 (MITI Non-Linear Model):   0.0469
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model): -0.2209
 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):  9.19E-010 Pa (6.89E-012 mm Hg)
  Log Koa (Koawin est  ): 23.028
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  3.27E+003 
       Octanol/air (Koa) model:  2.62E+010 
   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 = 282.1661 E-12 cm3/molecule-sec [Cis-isomer]
      OVERALL OH Rate Constant = 284.8261 E-12 cm3/molecule-sec [Trans-isomer]
      Half-Life =   27.293 Min (12-hr day; 1.5E6 OH/cm3) [Cis-isomer]
      Half-Life =   27.038 Min (12-hr day; 1.5E6 OH/cm3) [Trans-isomer]
   Ozone Reaction:
      OVERALL Ozone Rate Constant =     2.250000 E-17 cm3/molecule-sec [Cis-]
      OVERALL Ozone Rate Constant =     3.300000 E-17 cm3/molecule-sec [Trans-]
      Half-Life =   733.439 Min (at 7E11 mol/cm3) [Cis-isomer]
      Half-Life =   500.072 Min (at 7E11 mol/cm3) [Trans-isomer]
   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    :  9705
      Log Koc:  3.987 

 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 = 0.865 (BCF = 7.334)
       log Kow used: 3.97 (estimated)

 Volatilization from Water:
    Henry LC:  2.14E-021 atm-m3/mole  (estimated by Bond SAR Method)
    Half-Life from Model River: 5.266E+017  hours   (2.194E+016 days)
    Half-Life from Model Lake : 5.744E+018  hours   (2.393E+017 days)

 Removal In Wastewater Treatment:
    Total removal:              28.71  percent
    Total biodegradation:        0.31  percent
    Total sludge adsorption:    28.40  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       3.1e-009        0.847        1000       
   Water     11              900          1000       
   Soil      86.6            1.8e+003     1000       
   Sediment  2.41            8.1e+003     0          
     Persistence Time: 1.89e+003 hr

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(2E)-1-{2,4-Dihydroxy-3-[(2S)-2-hydroxy-3-methyl-3-buten-1-yl]-6-methoxyphenyl}-3-(4-hydroxyphenyl)-2-propen-1-one

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