Furan, 2,5-dimethyl-

• Formula: C₆H₈O
• Molecular weight: 96.1271
• IUPAC Standard InChI: InChI=1S/C6H8O/c1-5-3-4-6(2)7-5/h3-4H,1-2H3 Copy

  
• IUPAC Standard InChIKey: GSNUFIFRDBKVIE-UHFFFAOYSA-N Copy
• CAS Registry Number: 625-86-5
• 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: 2,5-Dimethylfuran; 2,5-Dimethylfurane
• Permanent link for this species. Use this link for bookmarking this species for future reference.
• Information on this page:
  • Gas phase thermochemistry data
  • Gas phase ion energetics data
  • Gas Chromatography
  • References
  • Notes
• Other data available:
  • Phase change data
  • IR Spectrum
  • Mass spectrum (electron ionization)
  • UV/Visible spectrum
• Data at other public NIST sites:
  • Gas Phase Kinetics Database
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Gas phase thermochemistry data

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Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.

Data compiled by: Glushko Thermocenter, Russian Academy of Sciences, Moscow

Constant pressure heat capacity of gas

Gas phase ion energetics data

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Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.

Data evaluated as indicated in comments:
HL - Edward P. Hunter and Sharon G. Lias

Data compiled as indicated in comments:
LBLHLM - Sharon G. Lias, John E. Bartmess, Joel F. Liebman, John L. Holmes, Rhoda D. Levin, and W. Gary Mallard

View reactions leading to C₆H₈O⁺ (ion structure unspecified)

Ionization energy determinations

Gas Chromatography

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Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.

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

Kovats' RI, non-polar column, isothermal

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Kovats' RI, non-polar column, temperature ramp

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Kovats' RI, polar column, isothermal

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Kovats' RI, polar column, temperature ramp

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

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

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

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Van Den Dool and Kratz RI, polar column, custom temperature program

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Normal alkane RI, non-polar column, temperature ramp

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

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Normal alkane RI, polar column, temperature ramp

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Normal alkane RI, polar column, custom temperature program

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References

Go To: Top, Gas phase thermochemistry data, Gas phase ion energetics data, Gas Chromatography, Notes

Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.

Thermodynamics Research Center, 1997
Thermodynamics Research Center, Selected Values of Properties of Chemical Compounds., Thermodynamics Research Center, Texas A&M University, College Station, Texas, 1997. [all data]

Green J.H.S., 1977
Green J.H.S., Spectroscopic and thermodynamic properties of furan derivatives. I. 2- and 2,5-substituted compounds, Spectrochim. Acta, 1977, A33, 843-848. [all data]

Hunter and Lias, 1998
Hunter, E.P.; Lias, S.G., Evaluated Gas Phase Basicities and Proton Affinities of Molecules: An Update, J. Phys. Chem. Ref. Data, 1998, 27, 3, 413-656, https://doi.org/10.1063/1.556018 . [all data]

Veszpremi, Nyulaszi, et al., 1987
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Misharina, Beletsky, et al., 1994
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Golovnya, Misharina, et al., 1992
Golovnya, R.V.; Misharina, T.A.; Beletskiy, I.V., Influence of methyl, formyl and acetyl groups on retention of substituted furans and thiophenes in capillary GC, Chromatographia, 1992, 34, 9/10, 497-501, https://doi.org/10.1007/BF02290243 . [all data]

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Pino, J.A.; Marbot, R.; Bello, A., Volatile compounds of Psidium salutare (H.B.K.) Berg. fruit, J. Agric. Food Chem., 2002, 50, 18, 5146-5148, https://doi.org/10.1021/jf0116303 . [all data]

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Ames, J.M.; Guy, R.C.E.; Kipping, G.J., Effect of pH and temperature on the formation of volatile compounds in cysteine/reducing sugar/starch mixtures during extrusion cooking, J. Agric. Food Chem., 2001, 49, 4, 1885-1894, https://doi.org/10.1021/jf0012547 . [all data]

Ames, Guy, et al., 2001, 2
Ames, J.M.; Guy, R.C.E.; Kipping, G.J., Effect of pH, temperature, and moisture on the formation of volatile compounds in glycine/glucose model systems, J. Agric. Food Chem., 2001, 49, 9, 4315-4323, https://doi.org/10.1021/jf010198m . [all data]

Kim, 2001
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Misharina, Golovnya, et al., 1993
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Elmore, J.S.; Mottram, D.S.; Enser, M.; Wood, J.D., Effect of the polyunsaturated fatty acid composition of beef muscle on the profile of aroma volatiles, J. Agric. Food Chem., 1999, 47, 4, 1619-1625, https://doi.org/10.1021/jf980718m . [all data]

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Nielsen, Larsen, et al., 2004
Nielsen, G.S.; Larsen, L.M.; Poll, L., Formation of aroma compounds during long-term frozen storage of unblanched leek (Allium ampeloprasum Var. Bulga) as affected by packaging atmosphere and slice thickness, J. Agric. Food Chem., 2004, 52, 5, 1234-1240, https://doi.org/10.1021/jf0306183 . [all data]

Nielsen, Larsen, et al., 2004, 2
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Nielsen and Poll, 2004
Nielsen, G.S.; Poll, L., Determination of odor active aroma compounds in freshly cut leek (Allium ampeloprasum Var. Bulga) and in long-term stored frozen unblanched and blanched leek slices by gas chromatography olfactometry analysis, J. Agric. Food Chem., 2004, 52, 6, 1642-1646, https://doi.org/10.1021/jf030682k . [all data]

Nielsen, Larsen, et al., 2003
Nielsen, G.S.; Larsen, L.M.; Poll, L., Formation of aroma compounds and lipoxygenase (EC 1.13.11.12) activity in unblanced leek (Allium ampeloprasum Var. Bulga) slices during long-term frozen storage, J. Agric. Food Chem., 2003, 51, 7, 1970-1976, https://doi.org/10.1021/jf020921o . [all data]

Baltes and Mevissen, 1988
Baltes, W.; Mevissen, L., Model reactions on roast aroma formation. VI. Volatile reaction products from the reaction of phenylalanine with glucose during cooking and roasting, Z. Lebensm. Unters. Forsch., 1988, 187, 3, 209-214, https://doi.org/10.1007/BF01043341 . [all data]

Alasalvar, Shahidi, et al., 2003
Alasalvar, C.; Shahidi, F.; Cadwallader, K.R., Comparison of natural and roasted Turkish Tombul hazelnut (Corylus avellana L.) volatiles and flavor by DHA/GC/MS and descriptive sensory analysis, J. Agric. Food Chem., 2003, 51, 17, 5067-5072, https://doi.org/10.1021/jf0300846 . [all data]

Baltes w. and Bochmann G., 1987
Baltes w.; Bochmann G., Model reactions on roast aroma formation. II. Mass spectrometric identification of furans and furanones from the reaction of serine and threonine with sucrose under the conditions of coffee roasting, Z. Lebensm. Unters. Forsch., 1987, 184, 179-186. [all data]

Kotowska, Zalikowski, et al., 2012
Kotowska, U.; Zalikowski, M.; Isidorov, V.A., HS-SPME/GC-MS analysis of volatile and semi-volatile organic compounds emitted from municipal sewage sludge, Environ. Monit. Asses., 2012, 184, 5, 2893-2907, https://doi.org/10.1007/s10661-011-2158-8 . [all data]

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Cais-Sokolinska, D.; Majcher, M.; Pikul, J.; Bielinska, S.; Czauderma, M.; Wojtowski, J., The effect of Camelia sativa cake diet supplementation on sensory and volatile profiles of ewe's milk, African J. Biotechnol., 2011, 10, 37, 7245-7252. [all data]

Harrison and Priest, 2009
Harrison, B.M.; Priest, F.G., Composition of peaks used in the preparation of malt for Scotch Whisky production - influence of geographical source and extraction depth, J. Agric. Food Chem., 2009, 57, 6, 2385-2391, https://doi.org/10.1021/jf803556y . [all data]

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Risticevic, S.; Carasek, E.; Pawliszyn, J., Headspace solid-phase microextraction-gas chromatographic-time-of-flight mass spectrometric methodology for geographical origin verification of coffee, Anal. Chim. Acta, 2008, 617, 1-2, 72-84, https://doi.org/10.1016/j.aca.2008.04.009 . [all data]

Isidorov and Jdanova, 2002
Isidorov, V.; Jdanova, M., Volatile organic compounds from leaves litter, Chemosphere, 2002, 48, 9, 975-979, https://doi.org/10.1016/S0045-6535(02)00074-7 . [all data]

Pino, Marbot, et al., 2002, 2
Pino, J.A.; Marbot, R.; Vazquez, C., Characterization of volatiles in Loquat fruit (Eriobotrya japonica Lindl.), Revista CENIC Ciencias Quimicas, 2002, 33, 3, 115-119. [all data]

Poligné, Collignan, et al., 2001
Poligné, I.; Collignan, A.; Trystram, G., Characterization of traditional processing of pork meat into boucané, Meat Sci., 2001, 59, 4, 377-389, https://doi.org/10.1016/S0309-1740(01)00090-0 . [all data]

Orav, Kailas, et al., 1999
Orav, A.; Kailas, T.; Muurisepp, M.; Kann, J., Composition of the oil from waste tires. 2. Fraction boiling at 160-180 0C, Proc. Estonian Acad. Sci. Chem., 1999, 48, 3, 136-140. [all data]

Tai and Ho, 1998
Tai, C.-Y.; Ho, C.-T., Influence of glutathione oxidation and pH on thermal formation of Maillard-type volatile compounds, J. Agric. Food Chem., 1998, 46, 6, 2260-2265, https://doi.org/10.1021/jf971111t . [all data]

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Habu, T.; Flath, R.A.; Mon, T.R.; Morton, J.F., Volatile components of Rooibos tea (Aspalathus linearis), J. Agric. Food Chem., 1985, 33, 2, 249-254, https://doi.org/10.1021/jf00062a024 . [all data]

Robinson, Adams, et al., 2012
Robinson, A.L.; Adams, D.O.; Boss, P.K.; Heymann, H.; Solomon, P.S.; Trengove, R.D., Influence of geographic origine on the sensory characteristics and wine composition of Vitus viniferas cv. Cabernet Sauvignon wines from Australia (Supplemental data), Am. J. Enol. Vitic., 2012, 64, 4, 467-476, https://doi.org/10.5344/ajev.2012.12023 . [all data]

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Shivashankar, S.; Roy, T.K.; Moorthy, P.N.R., Headspace solid phase micro extraction and GC/MS analysis of the volatile components in seed and cake of Azadirachta indica A. juss, Chem. Bull. of Politechnika Univ. Timisoara, Romania, 2012, 57(71), 1, 1-6. [all data]

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Cajka, T.; Hajslova, J.; Cochran, J.; Holadova, K.; Klimankova, E., Solid phase microextraction - comprehensive two dimensional gas chromatography - time-of-flight mass spectrometry for the analysis of honey volatiles, J. Sep. Sci., 2007, 30, 4, 534-546, https://doi.org/10.1002/jssc.200600413 . [all data]

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Vinogradov, 2004
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Begnaud, Pérès, et al., 2003
Begnaud, F.; Pérès, C.; Berdagué, J.-L., Characterization of volatile effluents of livestock buildings by solid-phase microextraction, Int. J. Environ. Anal. Chem., 2003, 83, 10, 837-849, https://doi.org/10.1080/03067310310001603349 . [all data]

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Ciccioli, Cecinato, et al., 1994
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Narain, Galvao, et al., 2007
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Notes

Go To: Top, Gas phase thermochemistry data, Gas phase ion energetics data, Gas Chromatography, References

• Symbols used in this document:
  

  Cp,gas

  Constant pressure heat capacity of gas

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