ChemSpider 2D Image | Tretinoin | C20H28O2

Tretinoin

  • Molecular FormulaC20H28O2
  • Average mass300.435 Da
  • Monoisotopic mass300.208923 Da
  • ChemSpider ID392618

  • Double-bond stereo - Double-bond stereo

More details:

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

(2E,4E,6E,8E)-3,7-Dimethyl-9-(2,6,6-trimethylcyclohex-1-en-1-yl)nona-2,4,6,8-tetraensäure [German]
15-Apo-b-caroten-15-oic acid
2057223 [Beilstein]
206-129-0 [EINECS]
302-79-4 [RN]
5688UTC01R
Acid A Vit
acide (2E,4E,6E,8E)-3,7-diméthyl-9-(2,6,6-triméthylcyclohex-1-én-1-yl)nona-2,4,6,8-tétraénoïque [French]
all trans-Retinoic acid
All-Trans Retinoic Acid
More...

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

2875 [DBID]
CHEBI:15367 [DBID]
DRG 0147 [DBID]
MFCD00001551 [DBID]
AGN 100335 [DBID]
AGN 192013 [DBID]
AIDS000179 [DBID]
AIDS-000179 [DBID]
ALRT 1057 [DBID]
Bio1_000106 [DBID]
More...
  • Experimental Physico-chemical Properties

    • Experimental Melting Point:

      180 °C TCI R0064
      180-182 °C Alfa Aesar
      189-190 °C OU Chemical Safety Data (No longer updated) More details
      189 °C LKT Labs [R1777] , [R1779] , [R1780]
      174 °C LKT Labs [R1777] , [R1779] , [R1780]
      180 °C LKT Labs [R1777] , [R1779] , [R1780]
      181 °C Jean-Claude Bradley Open Melting Point Dataset 8396
      180-182 °C (Literature, Literature) Alfa Aesar 44540
      180-181 °C Sigma-Aldrich USP-1674004
      180-181 °C Oakwood 317904

    • Experimental Solubility:

      DMSO 100 mg/ml MedChem Express HY-14649
      Soluble in DMSO and ethanol. LKT Labs [R1777] , [R1779] , [R1780]
      Soluble in DMSO. Slightly soluble in polyethylene glycol, octanol or ethanol. Practically insoluble in water, mineral oil or glycerin. LKT Labs [R1777] , [R1779] , [R1780]
      Soluble to 25 mM in DMSO and to 10 mM in ethanol Tocris Bioscience 0695, 695
      Soluble to 25 mM in DMSO and to 50 mM in ethanol Tocris Bioscience 0695
      Sparingly soluble in water. LKT Labs [R1777] , [R1779] , [R1780]
  • Predicted Physico-chemical Properties
  • Miscellaneous

    • Appearance:

      yellow to orange crystalline powder OU Chemical Safety Data (No longer updated) More details

    • Stability:

      Stable, but probably air and light sensitive. Combustible. Incompatiblewith strong oxidizing agents. OU Chemical Safety Data (No longer updated) More details

    • Safety:

      22-63 Alfa Aesar 44540
      36/37 Alfa Aesar 44540
      61-36/37/38-20/21/22 LKT Labs [R1777] , [R1779] , [R1780]
      CAUTION: May irritate eyes, skin, and respiratory tract Alfa Aesar 44540
      D10AD01 Wikidata Q29417
      H302 H315 H361d LKT Labs [R1777] , [R1779] , [R1780]
      H315 H319 H335 H360 LKT Labs [R1777] , [R1779] , [R1780]
      H360D H315 H319 H335 LKT Labs [R1777] , [R1779] , [R1780]
      H361-H302 Alfa Aesar 44540
      IRRITANT Matrix Scientific 076198
      L01XX14 Wikidata Q29417
      Minimize exposure. OU Chemical Safety Data (No longer updated) More details
      None LKT Labs [R1777] , [R1779] , [R1780]
      P281-P264-P301+P312-P308+P313-P405-P501a Alfa Aesar 44540
      R22;R38;R63 LKT Labs [R1777] , [R1779] , [R1780]
      R36/37/38;R61 LKT Labs [R1777] , [R1779] , [R1780]
      Repr., Xn, Xi LKT Labs [R1777] , [R1779] , [R1780]
      T LKT Labs [R1777] , [R1779] , [R1780]
      Warning Alfa Aesar 44540
      WARNING: Irritates skin and eyes, harmful if swallowed Alfa Aesar 44540
      Xi, Repr. LKT Labs [R1777] , [R1779] , [R1780]
      Xn Abblis Chemicals AB1009361

    • Target Organs:

      RXR/RAR agonist TargetMol T1051

    • Chemical Class:

      A retinoic acid in which all four exocyclic double bonds have <stereo>E</stereo>- (<stereo>trans</stereo>-) geometry. ChEBI CHEBI:15367
      A retinoic acid in which all four exocyclic double bonds have E- (trans-) geometry. ChEBI https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:15367

    • Compound Source:

      semisynthetic Microsource [01502016]

    • Bio Activity:

      All-trans retinoic acid (ATRA; Vitamin A acid) has been widely investigated for treatments of many cancers including prostate cancer.; IC50 Value:; Target: RAR; in vitro: ATRA was able to induce the growth arrest and to increase HOXB13 expression in AR?prostate cancer cells. MedChem Express HY-14649
      Endogenous agonist for retinoic acid receptors (IC50 = 14 nM for RAR?, RAR? and RAR? receptors). Also promotes differentiation of mouse embryonic stem cells (ESCs) into adipocytes, neurons and glia in vitro. Proposed ligand of ROR? (Kd = 280 nM). Tocris Bioscience 695
      Endogenous agonist for retinoic acid receptors (IC50 = 14 nM for RAR?, RAR? and RAR? receptors). Also promotes differentiation of mouse embryonic stem cells (ESCs) into adipocytes, neurons and glia in vitro. Proposed ligand of ROR? (Kd = 280 nM). Tocris Bioscience 0695
      Endogenous agonist for retinoic acid receptors (IC50 = 14 nM for RARalpha, RARbeta and RARgamma receptors). Also promotes differentiation of mouse embryonic stem cells (ESCs) into adipocytes, neurons and glia in vitro. Proposed ligand of RORbeta (Kd = 280 nM). Activates autophagy. Tocris Bioscience 695
      Endogenous retinoic acid receptor agonist Tocris Bioscience 0695, 695
      Metabolism TargetMol T1051
      Nuclear Receptors Tocris Bioscience 695
      Others MedChem Express HY-14649
      Retinoic Acid Receptors Tocris Bioscience 695
      RXR, RAR TargetMol T1051
  • Gas Chromatography

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

Density: 1.0±0.1 g/cm3
Boiling Point: 462.8±14.0 °C at 760 mmHg
Vapour Pressure: 0.0±2.5 mmHg at 25°C
Enthalpy of Vaporization: 79.3±6.0 kJ/mol
Flash Point: 350.6±11.0 °C
Index of Refraction: 1.556
Molar Refractivity: 95.5±0.3 cm3
#H bond acceptors: 2
#H bond donors: 1
#Freely Rotating Bonds: 5
#Rule of 5 Violations: 1
ACD/LogP: 6.83
ACD/LogD (pH 5.5): 5.06
ACD/BCF (pH 5.5): 2580.25
ACD/KOC (pH 5.5): 5560.61
ACD/LogD (pH 7.4): 3.26
ACD/BCF (pH 7.4): 41.02
ACD/KOC (pH 7.4): 88.40
Polar Surface Area: 37 Å2
Polarizability: 37.9±0.5 10-24cm3
Surface Tension: 39.1±3.0 dyne/cm
Molar Volume: 297.2±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) =  7.85
    Log Kow (Exper. database match) =  6.30
       Exper. Ref:  Hansch,C et al. (1995)

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  411.79  (Adapted Stein & Brown method)
    Melting Pt (deg C):  147.95  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  1.02E-007  (Modified Grain method)
    MP  (exp database):  181 deg C
    Subcooled liquid VP: 4.29E-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):  0.1263
       log Kow used: 6.30 (expkow database)
       no-melting pt equation used

 Water Sol Estimate from Fragments:
    Wat Sol (v1.01 est) =  0.23409 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 :   9.50E-006  atm-m3/mole
   Group Method:   Incomplete
 Henrys LC [VP/WSol estimate using EPI values]:  3.193E-007 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  6.30  (exp database)
  Log Kaw used:  -3.411  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  9.711
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :   0.4933
   Biowin2 (Non-Linear Model)     :   0.0880
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   2.6877  (weeks-months)
   Biowin4 (Primary Survey Model) :   3.6464  (days-weeks  )
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :   0.1655
   Biowin6 (MITI Non-Linear Model):   0.0257
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model): -0.5104
 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):  0.000572 Pa (4.29E-006 mm Hg)
  Log Koa (Koawin est  ): 9.711
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  0.00524 
       Octanol/air (Koa) model:  0.00126 
   Fraction sorbed to airborne particulates (phi):
       Junge-Pankow model     :  0.159 
       Mackay model           :  0.296 
       Octanol/air (Koa) model:  0.0917 

 Atmospheric Oxidation (25 deg C) [AopWin v1.92]:
   Hydroxyl Radicals Reaction:
      OVERALL OH Rate Constant = 292.5375 E-12 cm3/molecule-sec
      Half-Life =     0.037 Days (12-hr day; 1.5E6 OH/cm3)
      Half-Life =    26.325 Min
   Ozone Reaction:
      OVERALL Ozone Rate Constant =    24.180000 E-17 cm3/molecule-sec
      Half-Life =     0.047 Days (at 7E11 mol/cm3)
      Half-Life =      1.137 Hrs
   Fraction sorbed to airborne particulates (phi): 0.227 (Junge,Mackay)
    Note: the sorbed fraction may be resistant to atmospheric oxidation

 Soil Adsorption Coefficient (PCKOCWIN v1.66):
      Koc    :  9987
      Log Koc:  3.999 

 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 = 1.750 (BCF = 56.23)
       log Kow used: 6.30 (expkow database)

 Volatilization from Water:
    Henry LC:  9.5E-006 atm-m3/mole  (estimated by Bond SAR Method)
    Half-Life from Model River:      108.6  hours   (4.525 days)
    Half-Life from Model Lake :       1330  hours   (55.42 days)

 Removal In Wastewater Treatment:
    Total removal:              93.09  percent
    Total biodegradation:        0.77  percent
    Total sludge adsorption:    92.31  percent
    Total to Air:                0.01  percent
      (using 10000 hr Bio P,A,S)

 Level III Fugacity Model:
           Mass Amount    Half-Life    Emissions
            (percent)        (hr)       (kg/hr)
   Air       0.0088          0.495        1000       
   Water     3.08            900          1000       
   Soil      32.3            1.8e+003     1000       
   Sediment  64.6            8.1e+003     0          
     Persistence Time: 2.7e+003 hr

Click to predict properties on the Chemicalize site


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