Methoxsalen

Formula: C₁₂H₈O₄
Molecular weight: 216.1895
IUPAC Standard InChI: InChI=1S/C12H8O4/c1-14-12-10-8(4-5-15-10)6-7-2-3-9(13)16-11(7)12/h2-6H,1H3
IUPAC Standard InChIKey: QXKHYNVANLEOEG-UHFFFAOYSA-N
CAS Registry Number: 298-81-7
Chemical structure:
This structure is also available as a 2d Mol file or as a computed 3d SD file
The 3d structure may be viewed using Java or Javascript.
Other names: 7H-Furo[3,2-g][1]benzopyran-7-one, 9-methoxy-; Ammoidin; Meladinin; Meloxine; Methoxa-Dome; Oxsoralen; Xanthotoxin; Xanthotoxine; 8-Methoxy-[furano-3'.2':6.7-coumarin]; 8-Methoxypsoralen; 8-Methoxypsoralene; 8-MOP; Ammodin; Meladinine; Meladoxen; New-Meladinin; NCI-C55903; Oxypsoralen; Puvalen; 5-Benzofuranacrylic acid, 6-hydroxy-7-methoxy-, δ-lactone; 8-Methoxy-2',3',6,7-furocoumarin; 8-Methoxy-4',5',6,7-furocoumarin; 8-MP; 9-Methoxy-7H-furo[3,2-g][1]benzopyran-7-one; 8-Methoxy-6,7-furanocoumarin; Puvamet; Methoxaten; 8-Methoxyfuranocoumarin; 9-Methoxy-7H-furo(3,2-g)benzopyran-7-one; Oxsoralen-Ultra; Oxsoralen lotion; Proralone-mop; Psoralon-mop; Uvadex; Zanthotoxin; 9-methoxypsoralen; Geroxalen; 9-Methoxy-7H-furo[3,2-g]chromen-7-one; Deltapsoralen; Methoxsalene; Vitpso; NSC 45923; 9-methoxyfuro[3,2-g]chromen-7-one
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Other data available:
- Mass spectrum (electron ionization)
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Gas Chromatography

Data compiled by: NIST Mass Spectrometry Data Center, William E. Wallace, director

Van Den Dool and Kratz RI, non-polar column, temperature ramp

Column type	Active phase	I	Reference	Comment
Capillary	OV-101	1990.	Yang, Sugisawa, et al., 1992	N2, 2. K/min; Column length: 50. m; Column diameter: 0.25 mm; T_start: 80. C; T_end: 200. C
Packed	SE-30	1980.	Perrigo and Peel, 1981	N2, Chromosorb W, 130. C @ 2. min, 8. K/min, 290. C @ 8. min; Column length: 1.8 m

Normal alkane RI, non-polar column, temperature ramp

View large format table.

Column type	Active phase	I	Reference	Comment
Capillary	HP-5MS	2034.	Cho, Abd El-Aty, et al., 2007	30. m/0.25 mm/0.25 μm, He, 50. C @ 4. min, 5. K/min, 280. C @ 10. min
Capillary	DB-5	2040.	Feger, Brandauer, et al., 2006	15. m/0.25 mm/0.5 μm, He, 50. C @ 1. min, 10. K/min, 320. C @ 5. min
Capillary	HP-5MS	2034.	Kim, Abd El-Aty, et al., 2006	30. m/0.25 mm/0.25 μm, He, 50. C @ 4. min, 5. K/min, 280. C @ 10. min
Capillary	HP-5MS	2034.	Kim, El-Aty, et al., 2006	30. m/0.25 mm/0.25 μm, He, 50. C @ 4. min, 5. K/min, 280. C @ 10. min
Capillary	DB-5	2038.6	Gawdzik, Mardarowicz, et al., 1996	30. m/0.25 mm/0.25 μm, 60. C @ 2. min, 4. K/min, 300. C @ 5. min
Capillary	OV-101	1990.	Tamura, Yang, et al., 1993	2. K/min; Column length: 50. m; Column diameter: 0.25 mm; T_start: 80. C; T_end: 200. C

Normal alkane RI, non-polar column, custom temperature program

View large format table.

Column type	Active phase	I	Reference	Comment
Capillary	HP-5 MS	2022.	Schmidt, Noletto, et al., 2006	30. m/0.25 mm/0.25 μm, Helium; Program: 40 0C (10 min) 3 0C/min -> 200 0C 2 0C/min -> 220 0C
Other	Methyl Silicone	1980.	Ardrey and Moffat, 1981	Program: not specified

References

Go To: Top, Gas Chromatography, Notes

Yang, Sugisawa, et al., 1992
Yang, R.; Sugisawa, H.; Nakatani, H.; Tamura, H.; Takagi, N., Comparison of odor quality in peel oils of acid citrus, Nippon Shokuhin Kogyo Gakkaishi, 1992, 39, 1, 16-24, https://doi.org/10.3136/nskkk1962.39.16 . [all data]

Perrigo and Peel, 1981
Perrigo, B.J.; Peel, H.W., The use of retention indices and temperature-programmed gas chromatography in analytical toxicology, J. Chromatogr. Sci., 1981, 19, 5, 219-226, https://doi.org/10.1093/chromsci/19.5.219 . [all data]

Cho, Abd El-Aty, et al., 2007
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., 2007, 44, 5, 1154-1158, https://doi.org/10.1016/j.jpba.2007.03.011 . [all data]

Feger, Brandauer, et al., 2006
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., 2006, 54, 6, 2242-2252, https://doi.org/10.1021/jf052267t . [all data]

Kim, Abd El-Aty, et al., 2006
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, 2006, 1116, 1-2, 259-264, https://doi.org/10.1016/j.chroma.2006.03.060 . [all data]

Kim, El-Aty, et al., 2006
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, 2006, 20, 11, 1267-1273, https://doi.org/10.1002/bmc.696 . [all data]

Gawdzik, Mardarowicz, et al., 1996
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., 1996, 19, 4, 237-240, https://doi.org/10.1002/jhrc.1240190416 . [all data]

Tamura, Yang, et al., 1993
Tamura, H.; Yang, R.-H.; Sugisawa, H., Aroma profiles of peel oils of acid citrus, ACS Sym. Ser., 1993, 525, 121-136. [all data]

Schmidt, Noletto, et al., 2006
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, 2006, 12, 3, 43-65, https://doi.org/10.1300/J044v12n03_04 . [all data]

Ardrey and Moffat, 1981
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., 1981, 220, 3, 195-252, https://doi.org/10.1016/S0021-9673(00)81925-1 . [all data]

Notes

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Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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