ChemSpider 2D Image | Methoxsalen | C12H8O4

Methoxsalen

  • Molecular FormulaC12H8O4
  • Average mass216.189 Da
  • Monoisotopic mass216.042252 Da
  • ChemSpider ID3971

More details:

Featured data source
The Merck Index Online

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

196453 [Beilstein]
206-066-9 [EINECS]
298-81-7 [RN]
6-Hydroxy-7-methoxy-5-benzofuranacrylic Acid d-Lactone
7H-Furo[3,2-g][1]benzopyran-7-one, 9-methoxy- [ACD/Index Name]
8-Methoxy[furano-3',2':6,7-coumarin]
8-Methoxypsoralen
8-MOP
9-Methoxy-7H-furo[3,2-g]chromen-7-on [German] [ACD/IUPAC Name]
9-Methoxy-7H-furo[3,2-g]chromen-7-one [ACD/IUPAC Name]
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Validated by Experts, Validated by Users, Non-Validated, Removed by Users

DRG 0088 [DBID]
MFCD00005009 [DBID]
NCI C55903 [DBID]
U4VJ29L7BQ [DBID]
Xanthotoxin; IN-113; IN00113 [DBID]
A1783/0075596 [DBID]
AIDS001590 [DBID]
AIDS-001590 [DBID]
BRN 0196453 [DBID]
C01864 [DBID]
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  • Spectroscopy
  • Experimental Physico-chemical Properties
  • Predicted Physico-chemical Properties
  • Miscellaneous

    • Toxicity:

      Organic Compound; Aromatic Hydrocarbon; Ether; Ester; Drug; Food Toxin; Furocoumarin; Plant Toxin; Photosensitizing Agent; Cross-Linking Reagent; Metabolite; Natural Compound; Pigmenting Agent Toxin, Toxin-Target Database T3D0836

    • Safety:

      45-46-22-41 Alfa Aesar A17108
      53-20-26-36/39-45 Alfa Aesar A17108
      D05AD02 Wikidata Q408570
      D05BA02 Wikidata Q408570
      Danger Alfa Aesar A17108
      H340-H350-H318-H302 Alfa Aesar A17108
      P280-P281-P305+P351+P338-P310-P405-P501a Alfa Aesar A17108
      WARNING: Irreversible damage risk, protect skin/eyes/lungs. Alfa Aesar A17108

    • Target Organs:

      DNA photosenstizing TargetMol T1548

    • Chemical Class:

      A member of the class of psoralens that is 7<element>H</element>-furo[3,2-<ital>g</ital>]chromen-7-one in which the 9 position is substituted by a methoxy group. It is a constituent of the fruits of < ital>Ammi majus</ital>. Like other psoralens, trioxsalen causes photosensitization of the skin. It is administered topically or orally in conjunction with UV-A for phototherapy treatment of vitiligo a nd severe psoriasis. ChEBI CHEBI:18358
      A member of the class of psoralens that is 7H-furo[3,2-g]chromen-7-one in which the 9 position is substituted by a methoxy group. It is a constituent of the fruits of Ammi majus. Like other psoralens, trioxsalen causes photosensitization of the skin. It is administered topically or orally in conjunction with UV-A for phototherapy treatment of vitiligo and severe psoriasis. ChEBI https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:18358, CHEBI:18358

    • Bio Activity:

      Cytochrome P450 MedChem Express HY-30151
      DNA TargetMol T1548
      Metabolism/Protease; MedChem Express HY-30151
      Methoxsalen (8-Methoxypsoralen) is a potent tricyclic furocoumarin suicide inhibitor of CYP (cytochrome P-450), is an agent used to treat psoriasis, eczema, vitiligo and some cutaneous Lymphomas in co njunction with exposing the skin to sunlight. MedChem Express
      Methoxsalen (8-Methoxypsoralen) is a potent tricyclic furocoumarin suicide inhibitor of CYP (cytochrome P-450), is an agent used to treat psoriasis, eczema, vitiligo and some cutaneous Lymphomas in conjunction with exposing the skin to sunlight.;Target: CYP (cytochrome P-450)Methoxsalen is a drug used to treat psoriasis, eczema, vitiligo, and some cutaneous lymphomas in conjunction with exposing the skin to UVA light from lamps or sunlight. Methoxsalen modifies the way skin cells receive the UVA radiation, allegedly clearing up the disease. The dosage comes in 10 mg tablets, which are taken in the amount of 30 mg 75 minutes before a PUVA (psoralen + UVA) light treatment. Chemically, methoxsalen belongs to a class of organic natural molecules known asfuranocoumarins. They consist of coumarin annulated with furan.Administration of intra peritoneal (ip) methoxsalen significantly increased nicotine's Cmax, prolonged the plasma half-life (fourfold decrease) of nicotine, and increased MedChem Express HY-30151
      Others TargetMol T1548
  • Gas Chromatography

    • Retention Index (Kovats):

      1901 (estimated with error: 89) NIST Spectra mainlib_188900, replib_233931, replib_246230

    • Retention Index (Normal Alkane):

      1990 (Program type: Ramp; Column cl... (show more) ass: Standard non-polar; Column diameter: 0.25 mm; Column length: 50 m; Column type: Capillary; Heat rate: 2 K/min; Start T: 80 C; End T: 200 C; CAS no: 298817; Active phase: OV-101; Data type: Normal alkane RI; Authors: Tamura, H.; Yang, R.-H.; Sugisawa, H., Aroma profiles of peel oils of acid citrus, ACS Sym. Ser., 525, 1993, 121-136.) NIST Spectra nist ri
      1980 (Program type: Ramp; Column cl... (show more) ass: Standard non-polar; Column type: Other; CAS no: 298817; Active phase: Methyl Silicone; Data type: Normal alkane RI; Authors: Ardrey, R.E.; Moffat, A.C., Gas-liquid chromatographic retention indices of 1318 substances of toxicological interest on SE-30 or OV-1 stationary phase, J. Chromatogr., 220, 1981, 195-252.) NIST Spectra nist ri
      2034 (Program type: Ramp; Column cl... (show more) ass: Semi-standard non-polar; Column diameter: 0.25 mm; Column length: 30 m; Column type: Capillary; Heat rate: 5 K/min; Start T: 50 C; End T: 280 C; End time: 10 min; Start time: 4 min; CAS no: 298817; Active phase: HP-5MS; Carrier gas: He; Phase thickness: 0.25 um; Data type: Normal alkane RI; Authors: Cho, S.-K.; Abd El-Aty, A.M.; Choi, J.-H.; Kim, M.R.; Shim, J.H., Optimized conditions for the extraction of secondary volatile metabolites in Angelica roots by accelerated solvent extraction, J. Pharm. Biomed. Anal., 44, 2007, 1154-1158., Program type: Ramp; Column cl... (show more) ass: Semi-standard non-polar; Column diameter: 0.25 mm; Column length: 30 m; Column type: Capillary; Heat rate: 5 K/min; Start T: 50 C; End T: 280 C; End time: 10 min; Start time: 4 min; CAS no: 298817; Active phase: HP-5MS; Carrier gas: He; Phase thickness: 0.25 um; Data type: Normal alkane RI; Authors: Kim, M.R.; Abd El-Aty, A.M.; Kim, I.S.; Shim, J.H., Determination of volatile flavor components in danggui cultivars by solvent free injection and hydrodistillation followed by gas chromatographic-mass spectrometric analysis, J. Chromatogr. A, 1116, 2006, 259-264., Program type: Ramp; Column cl... (show more) ass: Semi-standard non-polar; Column diameter: 0.25 mm; Column length: 30 m; Column type: Capillary; Heat rate: 5 K/min; Start T: 50 C; End T: 280 C; End time: 10 min; Start time: 4 min; CAS no: 298817; Active phase: HP-5MS; Carrier gas: He; Phase thickness: 0.25 um; Data type: Normal alkane RI; Authors: Kim, M.R.; El-Aty, A.M.A.; Choi, J.-H.; Lee, K.B.; Shim, J.H., Identification of volatile components in Angelica species using supercritical-CO2 fluid extraction and solid phase microextraction coupled to gas chromatography-mass spectrometry, Biomedical Chromatography, 20, 2006, 1267-1273.) NIST Spectra nist ri
      2040 (Program type: Ramp; Column cl... (show more) ass: Semi-standard non-polar; Column diameter: 0.25 mm; Column length: 15 m; Column type: Capillary; Heat rate: 10 K/min; Start T: 50 C; End T: 320 C; End time: 5 min; Start time: 1 min; CAS no: 298817; Active phase: DB-5; Carrier gas: He; Phase thickness: 0.5 um; Data type: Normal alkane RI; Authors: Feger, W.; Brandauer, H.; Gabris, P.; Ziegler, H., Nonvolatiles of Commercial Lime and Grapefruit Oils Separated by High-Speed Countercurrent Chromatography, J. Agric. Food Chem., 54, 2006, 2242-2252.) NIST Spectra nist ri
      2022 (Program type: Complex; Column... (show more) class: Semi-standard non-polar; Column diameter: 0.25 mm; Column length: 30 m; Column type: Capillary; Description: 40 0C (10 min) ^ 3 0C/min -> 200 0C ^ 2 0C/min -> 220 0C; CAS no: 298817; Active phase: HP-5 MS; Carrier gas: Helium; Phase thickness: 0.25 um; Data type: Normal alkane RI; Authors: Schmidt, J.M.; Noletto, J.A.; Vogler, B.; Setzer, W.N., Abaco Bush Medicine: Chemical composition of the essential oils of four aromatic medicinal plants from Abaco Island, Bahamas, J. Herbs, Spices & Medicinal Plants, 12(3), 2006, 43-65.) NIST Spectra nist ri
      2038.6 (Program type: Ramp; Column cl... (show more) ass: Semi-standard non-polar; Column diameter: 0.25 mm; Column length: 30 m; Column type: Capillary; Heat rate: 4 K/min; Start T: 60 C; End T: 300 C; End time: 5 min; Start time: 2 min; CAS no: 298817; Active phase: DB-5; Phase thickness: 0.25 um; Data type: Normal alkane RI; Authors: Gawdzik, J.; Mardarowicz, M.; Suprynowicz, Z.; Kawka, S.; Wolski, T., Supercritical fluid extraction of essential oils from the fruits of Archangelica off. Hoffm. and their characterization by GC/MS, J. Hi. Res. Chromatogr., 19, 1996, 237-240.) NIST Spectra nist ri

    • Retention Index (Linear):

      1990 (Program type: Ramp; Column cl... (show more) ass: Standard non-polar; Column diameter: 0.25 mm; Column length: 50 m; Column type: Capillary; Heat rate: 2 K/min; Start T: 80 C; End T: 200 C; CAS no: 298817; Active phase: OV-101; Carrier gas: N2; Data type: Linear RI; Authors: Yang, R.; Sugisawa, H.; Nakatani, H.; Tamura, H.; Takagi, N., Comparison of odor quality in peel oils of acid citrus, Nippon Shokuhin Kogyo Gakkaishi, 39(1), 1992, 16-24.) NIST Spectra nist ri
      1980 (Program type: Ramp; Column cl... (show more) ass: Standard non-polar; Column length: 1.8 m; Column type: Packed; Heat rate: 8 K/min; Start T: 130 C; End T: 290 C; End time: 8 min; Start time: 2 min; CAS no: 298817; Active phase: SE-30; Carrier gas: N2; Substrate: Chromosorb W; Data type: Linear RI; Authors: Perrigo, B.J.; Peel, H.W., The use of retention indices and temperature-programmed gas chromatography in analytical toxicology, J. Chromatogr. Sci., 19, 1981, 219-226.) NIST Spectra nist ri

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

Density: 1.4±0.1 g/cm3
Boiling Point: 414.8±45.0 °C at 760 mmHg
Vapour Pressure: 0.0±1.0 mmHg at 25°C
Enthalpy of Vaporization: 66.8±3.0 kJ/mol
Flash Point: 204.7±28.7 °C
Index of Refraction: 1.635
Molar Refractivity: 56.6±0.3 cm3
#H bond acceptors: 4
#H bond donors: 0
#Freely Rotating Bonds: 1
#Rule of 5 Violations: 0
ACD/LogP: 1.93
ACD/LogD (pH 5.5): 1.98
ACD/BCF (pH 5.5): 18.79
ACD/KOC (pH 5.5): 284.15
ACD/LogD (pH 7.4): 1.98
ACD/BCF (pH 7.4): 18.79
ACD/KOC (pH 7.4): 284.15
Polar Surface Area: 49 Å2
Polarizability: 22.4±0.5 10-24cm3
Surface Tension: 52.0±3.0 dyne/cm
Molar Volume: 158.0±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) =  2.14
    Log Kow (Exper. database match) =  2.00
       Exper. Ref:  (in press)

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  372.53  (Adapted Stein & Brown method)
    Melting Pt (deg C):  125.53  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  2.15E-006  (Modified Grain method)
    MP  (exp database):  148 deg C
    Subcooled liquid VP: 3.83E-005 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):  706.2
       log Kow used: 2.00 (expkow database)
       no-melting pt equation used
     Water Sol (Exper. database match) =  47.6 mg/L (30 deg C)
        Exper. Ref:  YALKOWSKY,SH & DANNENFELSER,RM (1992)

 Water Sol Estimate from Fragments:
    Wat Sol (v1.01 est) =  92.623 mg/L
    Wat Sol (Exper. database match) =  47.60
       Exper. Ref:  YALKOWSKY,SH & DANNENFELSER,RM (1992)

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

 Henrys Law Constant (25 deg C) [HENRYWIN v3.10]:
   Bond Method :   4.00E-008  atm-m3/mole
   Group Method:   Incomplete
 Henrys LC [VP/WSol estimate using EPI values]:  8.660E-010 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  2.00  (exp database)
  Log Kaw used:  -5.786  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  7.786
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :   0.9507
   Biowin2 (Non-Linear Model)     :   0.9981
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   2.8035  (weeks       )
   Biowin4 (Primary Survey Model) :   3.8419  (days        )
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :   0.6454
   Biowin6 (MITI Non-Linear Model):   0.6201
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model):  0.6730
 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):  0.00511 Pa (3.83E-005 mm Hg)
  Log Koa (Koawin est  ): 7.786
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  0.000587 
       Octanol/air (Koa) model:  1.5E-005 
   Fraction sorbed to airborne particulates (phi):
       Junge-Pankow model     :  0.0208 
       Mackay model           :  0.0449 
       Octanol/air (Koa) model:  0.0012 

 Atmospheric Oxidation (25 deg C) [AopWin v1.92]:
   Hydroxyl Radicals Reaction:
      OVERALL OH Rate Constant = 106.3808 E-12 cm3/molecule-sec
      Half-Life =     0.101 Days (12-hr day; 1.5E6 OH/cm3)
      Half-Life =     1.207 Hrs
   Ozone Reaction:
      OVERALL Ozone Rate Constant =     2.100000 E-17 cm3/molecule-sec
      Half-Life =     0.546 Days (at 7E11 mol/cm3)
      Half-Life =     13.097 Hrs
   Fraction sorbed to airborne particulates (phi): 0.0328 (Junge,Mackay)
    Note: the sorbed fraction may be resistant to atmospheric oxidation

 Soil Adsorption Coefficient (PCKOCWIN v1.66):
      Koc    :  652.6
      Log Koc:  2.815 

 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 = 0.840 (BCF = 6.918)
       log Kow used: 2.00 (expkow database)

 Volatilization from Water:
    Henry LC:  4E-008 atm-m3/mole  (estimated by Bond SAR Method)
    Half-Life from Model River: 2.152E+004  hours   (896.8 days)
    Half-Life from Model Lake : 2.349E+005  hours   (9788 days)

 Removal In Wastewater Treatment:
    Total removal:               2.25  percent
    Total biodegradation:        0.10  percent
    Total sludge adsorption:     2.15  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       0.178           2.04         1000       
   Water     29.7            360          1000       
   Soil      70              720          1000       
   Sediment  0.105           3.24e+003    0          
     Persistence Time: 462 hr

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