ChemSpider 2D Image | capsaicin | C18H27NO3

capsaicin

  • Molecular FormulaC18H27NO3
  • Average mass305.412 Da
  • Monoisotopic mass305.199097 Da
  • ChemSpider ID1265957
  • Double-bond stereo - Double-bond stereo


More details:



Featured data source



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

(1Z,6E)-N-(4-Hydroxy-3-methoxybenzyl)-8-methyl-6-nonenimidic acid [ACD/IUPAC Name]
(1Z,6E)-N-(4-Hydroxy-3-methoxybenzyl)-8-methyl-6-nonenimidsäure [German] [ACD/IUPAC Name]
(6E)-N-(4-Hydroxy-3-methoxybenzyl)-8-methyl-6-nonenamid [German] [ACD/IUPAC Name]
(6E)-N-(4-Hydroxy-3-methoxybenzyl)-8-methyl-6-nonenamide [ACD/IUPAC Name]
(6E)-N-(4-Hydroxy-3-méthoxybenzyl)-8-méthyl-6-nonénamide [French] [ACD/IUPAC Name]
(6E)-N-(4-Hydroxy-3-methoxybenzyl)-8-methylnon-6-enamid [German]
(6E)-N-(4-Hydroxy-3-methoxybenzyl)-8-methylnon-6-enamide
(E)-8-Methyl-N-vanillyl-6-nonenamide
(E)-Capsaicin
(E)-N-((4-Hydroxy-3-methoxyphenyl)methyl)-8-methyl-6-nonenamide
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Validated by Experts, Validated by Users, Non-Validated, Removed by Users

12084_FLUKA [DBID]
21748_FLUKA [DBID]
21750_FLUKA [DBID]
360376_ALDRICH [DBID]
Bio1_000468 [DBID]
Bio1_000957 [DBID]
Bio1_001446 [DBID]
Bio2_000268 [DBID]
Bio2_000748 [DBID]
BRN 2816484 [DBID]
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  • Experimental Physico-chemical Properties
  • Predicted Physico-chemical Properties
  • Miscellaneous
    • Appearance:

      crystalline white powder Oxford University Chemical Safety Data (No longer updated) More details
    • Stability:

      Stable. Incompatible with strong oxidizing agents. Oxford University Chemical Safety Data (No longer updated) More details
    • Toxicity:

      ORL-RAT LD50 150 mg kg-1, SKN-MUS LD50 > 512 mg kg-1 Oxford University Chemical Safety Data (No longer updated) More details
    • Safety:

      25-37/38-41-42/43 LKT Labs [C0266]
      Danger Biosynth C-1700
      GHS06; GHS08 Biosynth C-1700
      H301 H315 H317 H318 H334 H335 LKT Labs [C0266]
      H301; H311; H315; H319; H331; H335; H371 Biosynth C-1700
      IRRITANT Matrix Scientific 098839
      Safety glasses, gloves, good ventilation. Oxford University Chemical Safety Data (No longer updated) More details
      T LKT Labs [C0266]
      UN 2811 6.1/PG 2 LKT Labs [C0266]
    • Target Organs:

      TRP/TRPV Channel agonist TargetMol T1062
    • Compound Source:

      Capsicum spp Microsource [01501128]
      Pungent principle of various Capsicum spp. (Solanaceae) Zerenex Molecular [ZBioX-0487]
    • Bio Activity:

      . Zerenex Molecular [ZBioX-0487]
      Apoptosis MedChem Express HY-10448
      Apoptosis inducer MedChem Express HY-10448
      Apoptosis inducer TRP Channel MedChem Express HY-10448
      Apoptosis; Membrane Tranporter/Ion Channel; MedChem Express HY-10448
      Capsaicin, the active component of chili peppers, is a member of the vanilloid family, binds to a receptor called the vanilloid receptor subtype 1 (VR1). MedChem Express HY-10448, http://www.medchemexpress.com/Dapagliflozin.html
      Capsaicin, the active component of chili peppers, is a member of the vanilloid family, binds to a receptor called the vanilloid receptor subtype 1 (VR1). Capsaicin is able to kill prostate cancer and lung cancer cells by causing them to undergo apoptosis.;IC50 Value: 150 uM (MTT assay in FaDu cells) [1];In vitro: Treatment of A172 cells withcapsaicin inhibited cell growth and induced apoptosis through down-regulation of Bcl-2 and activation of caspase-3. Interestingly, synergistic induction of morphological alternation was observed when A172 cells were treated with capsaicin [2]. After the addition of capsaicin, the levels of reactive oxygen species were reduced slightly in the earlier stage of treatment. Interestingly, an elevation of intracellular calcium ion concentration was detected in the MCF-7 cells [3].;In vivo: Intraperitoneal administration of CAP (10mg/kg body weight) to Swiss albino mice suppressed the development of lung carcinoma by amending the protein expressions of MedChem Express HY-10448
      Ion Channels Tocris Bioscience 462
      Membrane Transporter/Ion Channel TargetMol T1062
      Prototypic vanilloid receptor agonist Tocris Bioscience 0462
      Prototypic vanilloid receptor agonist (pEC50 values are 7.97 and 7.10 at rat and human VR1 receptors respectively). Excites a subset of primary afferent sensory neurons, with subsequent antinociceptiv e and anti-inflammatory effects. Reversibly inhibits aggregation of platelets. Also available as part of the Vanilloid TRPV1 Receptor Tocriset™. Tocris Bioscience 0462
      Prototypic vanilloid receptor agonist (pEC50 values are 7.97 and 7.10 at rat and human VR1 receptors respectively). Excites a subset of primary afferent sensory neurons, with subsequent antinociceptive and anti-inflammatory effects. Reversibly inhibits aggregation of platelets. Also available as part of the Vanilloid TRPV1 Receptor Tocriset?. Tocris Bioscience 462
      Transient Receptor Potential Channels Tocris Bioscience 462
      TRPV Tocris Bioscience 462
      TRPV1 receptor TargetMol T1062
  • Gas Chromatography

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

Density: 1.0±0.1 g/cm3
Boiling Point: 469.7±55.0 °C at 760 mmHg
Vapour Pressure: 0.0±1.2 mmHg at 25°C
Enthalpy of Vaporization: 77.1±3.0 kJ/mol
Flash Point: 237.9±31.5 °C
Index of Refraction: 1.508
Molar Refractivity: 88.5±0.5 cm3
#H bond acceptors: 4
#H bond donors: 2
#Freely Rotating Bonds: 9
#Rule of 5 Violations: 0
ACD/LogP: 4.27
ACD/LogD (pH 5.5): 2.41
ACD/BCF (pH 5.5): 21.80
ACD/KOC (pH 5.5): 153.12
ACD/LogD (pH 7.4): 2.43
ACD/BCF (pH 7.4): 22.87
ACD/KOC (pH 7.4): 160.64
Polar Surface Area: 62 Å2
Polarizability: 35.1±0.5 10-24cm3
Surface Tension: 35.0±7.0 dyne/cm
Molar Volume: 297.0±7.0 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) =  4.00

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  465.44  (Adapted Stein & Brown method)
    Melting Pt (deg C):  196.46  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  1.32E-008  (Modified Grain method)
    MP  (exp database):  65 deg C
    Subcooled liquid VP: 3.12E-008 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):  4.409
       log Kow used: 4.00 (estimated)
       no-melting pt equation used

 Water Sol Estimate from Fragments:
    Wat Sol (v1.01 est) =  88.896 mg/L

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

 Henrys Law Constant (25 deg C) [HENRYWIN v3.10]:
   Bond Method :   1.04E-013  atm-m3/mole
   Group Method:   Incomplete
 Henrys LC [VP/WSol estimate using EPI values]:  1.203E-009 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  4.00  (KowWin est)
  Log Kaw used:  -11.371  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  15.371
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :   1.0600
   Biowin2 (Non-Linear Model)     :   0.9892
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   2.4683  (weeks-months)
   Biowin4 (Primary Survey Model) :   3.7293  (days-weeks  )
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :   0.3192
   Biowin6 (MITI Non-Linear Model):   0.1645
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model): -0.2143
 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):  4.16E-006 Pa (3.12E-008 mm Hg)
  Log Koa (Koawin est  ): 15.371
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  0.721 
       Octanol/air (Koa) model:  577 
   Fraction sorbed to airborne particulates (phi):
       Junge-Pankow model     :  0.963 
       Mackay model           :  0.983 
       Octanol/air (Koa) model:  1 

 Atmospheric Oxidation (25 deg C) [AopWin v1.92]:
   Hydroxyl Radicals Reaction:
      OVERALL OH Rate Constant = 113.6632 E-12 cm3/molecule-sec [Cis-isomer]
      OVERALL OH Rate Constant = 121.2632 E-12 cm3/molecule-sec [Trans-isomer]
      Half-Life =    1.129 Hrs (12-hr day; 1.5E6 OH/cm3) [Cis-isomer]
      Half-Life =    1.058 Hrs (12-hr day; 1.5E6 OH/cm3) [Trans-isomer]
   Ozone Reaction:
      OVERALL Ozone Rate Constant =    13.000000 E-17 cm3/molecule-sec [Cis-]
      OVERALL Ozone Rate Constant =    20.000000 E-17 cm3/molecule-sec [Trans-]
      Half-Life =     2.116 Hrs (at 7E11 mol/cm3) [Cis-isomer]
      Half-Life =     1.375 Hrs (at 7E11 mol/cm3) [Trans-isomer]
   Reaction With Nitrate Radicals May Be Important!
   Fraction sorbed to airborne particulates (phi): 0.973 (Junge,Mackay)
    Note: the sorbed fraction may be resistant to atmospheric oxidation

 Soil Adsorption Coefficient (PCKOCWIN v1.66):
      Koc    :  4.373E+004
      Log Koc:  4.641 

 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 = 2.377 (BCF = 238.4)
       log Kow used: 4.00 (estimated)

 Volatilization from Water:
    Henry LC:  1.04E-013 atm-m3/mole  (estimated by Bond SAR Method)
    Half-Life from Model River: 9.839E+009  hours   (4.099E+008 days)
    Half-Life from Model Lake : 1.073E+011  hours   (4.472E+009 days)

 Removal In Wastewater Treatment:
    Total removal:              30.06  percent
    Total biodegradation:        0.32  percent
    Total sludge adsorption:    29.74  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       1.78e-006       1.09         1000       
   Water     10.9            900          1000       
   Soil      86.5            1.8e+003     1000       
   Sediment  2.58            8.1e+003     0          
     Persistence Time: 1.89e+003 hr




                    

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