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ChemSpider 2D Image | Bergapten | C12H8O4

Bergapten

  • Molecular FormulaC12H8O4
  • Average mass216.189 Da
  • Monoisotopic mass216.042252 Da
  • ChemSpider ID2265

More details:



Featured data source



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

207-604-5 [EINECS]
484-20-8 [RN]
4-Methoxy-7H-furo[3,2-g][1]benzopyran-7-one
4-Methoxy-7H-furo[3,2-g]chromen-7-on [German] [ACD/IUPAC Name]
4-Methoxy-7H-furo[3,2-g]chromen-7-one [ACD/IUPAC Name]
4-Méthoxy-7H-furo[3,2-g]chromén-7-one [French] [ACD/IUPAC Name]
4-Methoxyfuro[3,2-g]benzopyrane-7-one
4-Methoxy-furo[3,2-g]chromen-7-one
5-19-06-00004 [Beilstein]
5-Methoxypsoralen
More...

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

19560 [DBID]
4FVK84C92X [DBID]
bergapten; IN-88; IN00088 [DBID]
275727_ALDRICH [DBID]
65320_FLUKA [DBID]
ACon0_000984 [DBID]
ACon1_001979 [DBID]
AIDS031096 [DBID]
AIDS-031096 [DBID]
BAS 00674110 [DBID]
More...
  • Spectroscopy
  • Experimental Physico-chemical Properties
  • Predicted Physico-chemical Properties
  • Miscellaneous
    • Appearance:

      white to off-white crystalline solid OU Chemical Safety Data (No longer updated) More details
    • Stability:

      Stable. Combustible. Incompatible with strong oxidizing agents.May be light sensitive. OU Chemical Safety Data (No longer updated) More details
    • Toxicity:

      ORL-RAT LD50 > 30,000 mg kg-1, ORL-MUS LD50 8100 mg kg-1, ORL-GPG LD50 9000 mg kg-1 OU Chemical Safety Data (No longer updated) More details
    • Safety:

      Danger Biosynth Q-100536
      GHS08 Biosynth Q-100536
      H334; H340; H350 Biosynth Q-100536
      P201; P261; P308+P313 Biosynth Q-100536
      Safety glasses, adequate ventilation. Handled as a potential carcinogen. OU Chemical Safety Data (No longer updated) More details
    • Target Organs:

      Cross-linking DNA TargetMol T2143
    • Chemical Class:

      A 5-methoxyfurocoumarin that is psoralen substituted by a methoxy group at position 5. ChEBI CHEBI:18293, https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:18293
      coumarin Microsource [00300546]
    • Drug Status:

      INN Microsource [00300546]
    • Compound Source:

      Major constit. of bergamot oil (Citrus bergamia), also from Heracleum giganteum and Ammi majus. Widely distributed in the Rutaceae and Umbelliferae Zerenex Molecular [ZBioX-0680]
      widespread in Umbelliferae Microsource [00300546]
    • Bio Activity:

      5-Methoxypsoralen, a naturally occurring linear furocoumarin, has been successfully used in combination with ultraviolet (UV) A irradiation [psoralen plus UV (PUVA)] to manage psoriasis and vitiligo; inhibit proliferation in the human hepatocellular carcinoma cell line. MedChem Express
      5-Methoxypsoralen, a naturally occurring linear furocoumarin, has been successfully used in combination with ultraviolet (UV) A irradiation [psoralen plus UV (PUVA)] to manage psoriasis and vitiligo; inhibit proliferation in the human hepatocellular carcinoma cell line.; IC50 value: ; Target: anti cancer; in vitro: 5-MOP increased the activity of NATand also increased the further metabolism of AAF at 24 h in the rat stomach. MedChem Express HY-N0370
      5-Methoxypsoralen, a naturally occurring linear furocoumarin, has been successfully used in combination with ultraviolet (UV) A irradiation [psoralen plus UV (PUVA)] to manage psoriasis and vitiligo; inhibit proliferation in the human hepatocellular carcinoma cell line.;IC50 value: ;Target: anti cancer;In vitro: 5-MOP increased the activity of NATand also increased the further metabolism of AAF at 24 h in the rat stomach. In the rat colon, no statistically significant changes caused by 5-MOP were observed in NAT activity, but 5-MOP increased the further metabolism of AAF at 24 to 72 h. 5-MOP decreased the activity of NAT only at 72-h incubation in SC-M1 cells. In COLO 205 cells, however, 5-MOP decreased the activity of NAT between 24 h and 72 h [2]. 5-methoxypsoralen resulted in IL-8 inhibition at 10 microM concentration, without effects on cell proliferation. In synthesis, 5-methoxypsoralen can be taken into consideration to investigate mechanisms of neutrophil chemotactic signall MedChem Express HY-N0370
      Antipsoriatic; Zerenex Molecular [ZBioX-0680]
      DNA TargetMol T2143
      DNA Damage/DNA Repair TargetMol T2143
      Others MedChem Express HY-N0370
  • Gas Chromatography
    • Retention Index (Kovats):

      1901 (estimated with error: 89) NIST Spectra mainlib_290666, replib_215756
      2061 (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: 3 K/min; Start T: 50 C; End T: 250 C; End time: 5 min; Start time: 10 min; CAS no: 484208; Active phase: HP-5MS; Carrier gas: He; Phase thickness: 0.25 um; Data type: Kovats RI; Authors: Asuming, W.A.; Beauchamp, P.S.; Descalzo, J.T.; Dev, B.C.; Dev, V.; Frost, S.; Ma, C.W., Essential oil composition of four Lomatium Raf. species and their chemotaxonomy, Biochem. Syst. Ecol., 33, 2005, 17-26.) NIST Spectra nist ri
    • Retention Index (Normal Alkane):

      2062 (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: 484208; 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
      2060.7 (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: 484208; 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
      2025.9 (Program type: Ramp; Column cl... (show more) ass: Semi-standard non-polar; Column diameter: 0.32 mm; Column length: 25 m; Column type: Capillary; Heat rate: 3 K/min; Start T: 100 C; End T: 230 C; End time: 20 min; Start time: 3 min; CAS no: 484208; Active phase: SE-54; Carrier gas: He; Data type: Normal alkane RI; Authors: Chouchi, D.; Barth, D., Rapid Identification of Some Coumarin Derivatives in Deterpenated Citrus Peel Oil by Gas Chromatography, J. Chromatogr. A, 672, 1994, 177-183.) NIST Spectra nist ri
    • Retention Index (Linear):

      2048 (Program type: Ramp; Column cl... (show more) ass: Standard non-polar; Column type: Capillary; CAS no: 484208; Active phase: DB-1; Data type: Linear RI; Authors: Rouseff, R.; Smoot, J.; Valim, F.; Dreher, G.; Mahattanatawee, k.; Bell, W.; Blaze, M., Flavor Database, 2002.) NIST Spectra nist ri
      2080 (Program type: Ramp; Column cl... (show more) ass: Semi-standard non-polar; Column diameter: 0.1 mm; Column length: 10 m; Column type: Capillary; Heat rate: 12.3 K/min; Start T: 50 C; End T: 350 C; CAS no: 484208; Active phase: RTX-5; Carrier gas: He; Phase thickness: 0.1 um; Data type: Linear RI; Authors: Mondello, L.; Zappia, G.; Dugo, P.; Dugo, G.; Bonaccorsi, I.; Dugo, G., Identification of complex samples by Fast-GC/MS using linear retention indices in conjunction with the MS-library, 2000.) NIST Spectra nist ri
      2075 (Program type: Complex; Column... (show more) class: Semi-standard non-polar; Column diameter: 0.32 mm; Column length: 60 m; Column type: Capillary; Description: 45 C (6 min) ^ 3 C/min -> 111 0C ^ 2 C/min -> 160 C ^ 3 C/min -> 300 C (15 min); CAS no: 484208; Active phase: SE-52; Carrier gas: He; Phase thickness: 0.40 um; Data type: Linear RI; Authors: Mondello, L.; Dugo, P.; Basile, A.; Dugo, G., Interactive use of linear retention indices, on polar and apolar columns, with a MS-library for reliable identification of complex mixtures, J. Microcolumn Sep., 7(6), 1995, 581-591.) NIST Spectra nist ri

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

Density: 1.4±0.1 g/cm3
Boiling Point: 412.4±45.0 °C at 760 mmHg
Vapour Pressure: 0.0±1.0 mmHg at 25°C
Enthalpy of Vaporization: 66.5±3.0 kJ/mol
Flash Point: 203.2±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: 2.00
ACD/LogD (pH 5.5): 2.04
ACD/BCF (pH 5.5): 21.07
ACD/KOC (pH 5.5): 308.36
ACD/LogD (pH 7.4): 2.04
ACD/BCF (pH 7.4): 21.07
ACD/KOC (pH 7.4): 308.36
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) =  1.93
       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):  7.54E-007  (Modified Grain method)
    MP  (exp database):  188 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):  810.5
       log Kow used: 1.93 (expkow database)
       no-melting pt equation used

 Water Sol Estimate from Fragments:
    Wat Sol (v1.01 est) =  92.623 mg/L

 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]:  2.646E-010 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  1.93  (exp database)
  Log Kaw used:  -5.786  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  7.716
      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  ): 7.716
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  0.000587 
       Octanol/air (Koa) model:  1.28E-005 
   Fraction sorbed to airborne particulates (phi):
       Junge-Pankow model     :  0.0208 
       Mackay model           :  0.0449 
       Octanol/air (Koa) model:  0.00102 

 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 = 0.786 (BCF = 6.111)
       log Kow used: 1.93 (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:               2.19  percent
    Total biodegradation:        0.09  percent
    Total sludge adsorption:     2.09  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       0.182           2.04         1000       
   Water     30.6            360          1000       
   Soil      69.1            720          1000       
   Sediment  0.1             3.24e+003    0          
     Persistence Time: 455 hr




                    

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