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2(3H)-Furanone, 5-methyl-


Phase change 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 as indicated in comments:
BS - Robert L. Brown and Stephen E. Stein
AC - William E. Acree, Jr., James S. Chickos

Reduced pressure boiling point

Tboil (K) Pressure (atm) Reference Comment
329.20.016Weast and Grasselli, 1989BS
329.0.016American Tokyo Kasei, 1988BS

Enthalpy of vaporization

DeltavapH (kcal/mol) Temperature (K) Method Reference Comment
9.63339.AStephenson and Malanowski, 1987Based on data from 324. - 442. K.; AC

Reaction 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: Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein

Note: Please consider using the reaction search for this species. This page allows searching of all reactions involving this species. A general reaction search form is also available. Future versions of this site may rely on reaction search pages in place of the enumerated reaction displays seen below.

Individual Reactions

dihydro-5-methylenefuran-2(3H)-one = 2(3H)-Furanone, 5-methyl-

By formula: C5H6O2 = C5H6O2

Quantity Value Units Method Reference Comment
Deltar-2.0 ± 0.26kcal/molKinTaskinen, 1994liquid phase; solvent: Cyclohexane

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 compiled by: Sharon G. Lias, Rhoda D. Levin, and Sherif A. Kafafi

Ionization energy determinations

IE (eV) Method Reference
9.62 ± 0.05EIThorstad, Undheim, et al., 1975

IR Spectrum

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Data compiled by: Coblentz Society, Inc.

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


Mass spectrum (electron ionization)

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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

Spectrum

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Mass spectrum
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Additional Data

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Owner NIST Mass Spectrometry Data Center
Collection (C) 2014 copyright by the U.S. Secretary of Commerce
on behalf of the United States of America. All rights reserved.
Origin Japan AIST/NIMC Database- Spectrum MS-NW-5756
NIST MS number 234785

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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, temperature ramp

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Column type Active phase I Reference Comment
CapillaryDB-1835.Takeoka, Perrino, et al., 199660. m/0.25 mm/0.25 «mu»m, 30. C @ 4. min, 2. K/min; Tend: 220. C
CapillaryDB-1836.Takeoka, Perrino, et al., 199660. m/0.25 mm/0.25 «mu»m, 30. C @ 4. min, 2. K/min; Tend: 220. C

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

View large format table.

Column type Active phase I Reference Comment
CapillaryDB-Petro830.1Pang T., Zhu S., et al., 200750. m/0.2 mm/0.5 «mu»m, 2. K/min; Tstart: 50. C; Tend: 270. C
CapillaryDB-Petro830.1Pang T., Zhu S., et al., 200750. m/0.2 mm/0.5 «mu»m, 2. K/min; Tstart: 50. C; Tend: 270. C
CapillaryBPX-5885.Aaslyng, Elmore, et al., 199850. m/0.32 mm/0.50 «mu»m, He, 4. K/min; Tstart: 40. C; Tend: 280. C

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

View large format table.

Column type Active phase I Reference Comment
CapillaryCarbowax1416.Baltes w. and Bochmann G., 1987Column diameter: 0.3 mm; Program: not specified
CapillaryCarbowax1416.Baltes w. and Bochmann G., 1987Column diameter: 0.3 mm; Program: not specified
CapillaryCarbowax1417.Baltes w. and Bochmann G., 1987Column diameter: 0.3 mm; Program: not specified
CapillaryCarbowax1423.Baltes w. and Bochmann G., 1987Column diameter: 0.3 mm; Program: not specified

Normal alkane RI, non-polar column, temperature ramp

View large format table.

Column type Active phase I Reference Comment
CapillaryHP-5 MS869.Radulovic, Blagojevic, et al., 201030. m/0.25 mm/0.25 «mu»m, Helium, 5. K/min, 290. C @ 10. min; Tstart: 70. C
CapillaryZB-5867.Harrison and Priest, 200930. m/0.25 mm/0.25 «mu»m, Helium, 40. C @ 1. min, 6. K/min, 280. C @ 9. min
CapillaryHP-5 MS865.Kim and Chung, 200930. m/0.25 mm/0.25 «mu»m, Helium, 35. C @ 5. min, 2. K/min, 195. C @ 30. min
Capillary5 % Phenyl methyl siloxane864.Zellner, Bicchi, et al., 200830. m/0.25 mm/0.25 «mu»m, 3. K/min; Tstart: 50. C; Tend: 250. C
CapillarySPB-5861.Pino, Marquez, et al., 200630. m/0.25 mm/0.25 «mu»m, Helium, 60. C @ 2. min, 4. K/min, 250. C @ 20. min
CapillaryZB-5884.Jürgens and Dötterl, 200460. m/0.25 mm/0.25 «mu»m, He, 40. C @ 4.6 min, 6. K/min, 260. C @ 1. min
CapillaryDB-5901.Georgilopoulos and Gallois, 198830. m/0.35 mm/1.0 «mu»m, Hydrogen, 2. K/min; Tstart: 45. C; Tend: 220. C

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

View large format table.

Column type Active phase I Reference Comment
CapillaryPolydimethyl siloxane with 5 % Ph groups874.Robinson, Adams, et al., 2012Program: not specified
CapillaryPolydimethyl siloxane with 5 % Ph groups885.Robinson, Adams, et al., 2012Program: not specified
CapillaryDB-5 MS873.Cajka, Hajslova, et al., 200730. m/0.25 mm/0.25 «mu»m, Helium; Program: 45 0C (0.75 min) 10 0C/min -> 200 0C 30 0C/min -> 245 0C (1.25 min)

Normal alkane RI, polar column, temperature ramp

View large format table.

Column type Active phase I Reference Comment
CapillaryDB-Wax1429.Umano, Hagi, et al., 1995He, 40. C @ 2. min, 2. K/min; Column length: 60. m; Column diameter: 0.25 mm; Tend: 200. C
CapillaryCarbowax 20M1390.Vernin, Metzger, et al., 1992He, 3. K/min; Column length: 50. m; Column diameter: 0.33 mm; Tstart: 60. C; Tend: 200. C

Normal alkane RI, polar column, custom temperature program

View large format table.

Column type Active phase I Reference Comment
CapillaryHP-Innowax1430.Narain, Galvao, et al., 200730. m/0.25 mm/0.25 «mu»m, Helium; Program: 30 0C (5 min) 5 0C/min -> 100 0C (5 min) 1 0C/min -> 130 0C 10 0C/min -> 195 0C (45 min)
CapillaryCarbowax 20M1430.Vinogradov, 2004Program: not specified

References

Go To: Top, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, IR Spectrum, Mass spectrum (electron ionization), Gas Chromatography, NIST Free Links, Notes

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

Weast and Grasselli, 1989
CRC Handbook of Data on Organic Compounds, 2nd Editon, Weast,R.C and Grasselli, J.G., ed(s)., CRC Press, Inc., Boca Raton, FL, 1989, 1. [all data]

American Tokyo Kasei, 1988
American Tokyo Kasei, TCI American Organic Chemical 88/89 Catalog, American Tokyo Kasei, Portland, OR, 1988, 1610. [all data]

Stephenson and Malanowski, 1987
Stephenson, Richard M.; Malanowski, Stanislaw, Handbook of the Thermodynamics of Organic Compounds, 1987, https://doi.org/10.1007/978-94-009-3173-2 . [all data]

Taskinen, 1994
Taskinen, E., Relative thermodynamic stabilities of «gamma»-methylene-«gamma»-butyrolactone and «alpha»-angelicalactone, Tetrahedron, 1994, 50, 1885-1888. [all data]

Thorstad, Undheim, et al., 1975
Thorstad, O.; Undheim, K.; Cederlund, B.; Hornfeldt, A.-B., Ionisation potentials in tautomeric analysis of 2-hydroxy derivatives of thiophenes, selenophenes, and furans, Acta Chem. Scand. Ser. B:, 1975, 29, 647. [all data]

Takeoka, Perrino, et al., 1996
Takeoka, G.; Perrino, C., Jr.; Buttery, R., Volatile constituents of used frying oils, J. Agric. Food Chem., 1996, 44, 3, 654-660, https://doi.org/10.1021/jf950430m . [all data]

Pang T., Zhu S., et al., 2007
Pang T.; Zhu S.; Lu X.; Xu G., Identification of unknown compounds on the basis of retention index data in comprehensive two-dimensional gas chromatography, J. Sep. Sci., 2007, 30, 6, 868-874, https://doi.org/10.1002/jssc.200600471 . [all data]

Aaslyng, Elmore, et al., 1998
Aaslyng, M.D.; Elmore, J.S.; Mottram, D.S., Comparison of the aroma characteristics of acid-hydrolyzed and enzyme-hydrolyzed vegetable proteins produced from soy, J. Agric. Food Chem., 1998, 46, 12, 5225-5231, https://doi.org/10.1021/jf9806816 . [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]

Radulovic, Blagojevic, et al., 2010
Radulovic, N.; Blagojevic, P.; Palic, R., Comparative study of the leaf volatiles of Arctostaphylos uva-ursi (L.) Spreng. and Vaccinium vitis-idaea L. (Ericaceae), Molecules, 2010, 15, 9, 6168-6185, https://doi.org/10.3390/molecules15096168 . [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]

Kim and Chung, 2009
Kim, J.-S.; Chung, H.Y., GC-MS analysis of the volatile components in dried boxthorn (Lycium chimensis) Fruit, J. Korean Soc. Appl. Biol. Chem., 2009, 52, 5, 516-524, https://doi.org/10.3839/jksabc.2009.088 . [all data]

Zellner, Bicchi, et al., 2008
Zellner, B.d'A.; Bicchi, C.; Dugo, P.; Rubiolo, P.; Dugo, G.; Mondello, L., Linear retention indices in gas chromatographic analysis: a review, Flavour Fragrance J., 2008, 23, 5, 297-314, https://doi.org/10.1002/ffj.1887 . [all data]

Pino, Marquez, et al., 2006
Pino, J.A.; Marquez, E.; Marbot, R., Volatile constituents from tea of roselle (Hibiscus sabdariffa L.), Rev. CENIC Ciencias Quimicas, 2006, 37, 3, 127-129. [all data]

Jürgens and Dötterl, 2004
Jürgens, A.; Dötterl, S., Chemical composition of anther volatiles in Ranunculaceae: genera-specific profiles in Aemone, Aquilegia, Caltha, Pulsatilla, Ranunculus, and Trollius species, American Journal of Botany, 2004, 91, 12, 1969-1980, https://doi.org/10.3732/ajb.91.12.1969 . [all data]

Georgilopoulos and Gallois, 1988
Georgilopoulos, D.N.; Gallois, A.N., Flavour compounds of a commercial concentrated blackberry juice, Food Chem., 1988, 28, 2, 141-148, https://doi.org/10.1016/0308-8146(88)90143-4 . [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]

Cajka, Hajslova, et al., 2007
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]

Umano, Hagi, et al., 1995
Umano, K.; Hagi, Y.; Nakahara, K.; Shyoji, A.; Shibamoto, T., Volatile chemicals formed in the headspace of a heated D-glucose/L-cysteine Maillard model system, J. Agric. Food Chem., 1995, 43, 8, 2212-2218, https://doi.org/10.1021/jf00056a046 . [all data]

Vernin, Metzger, et al., 1992
Vernin, G.; Metzger, J.; Boniface, C.; Murello, M.-H.; Siouffi, A.; Larice, J.-L.; Parkanyi, C., Kinetics and thermal degradation of the fructose-methionine Amadori intermediates. GC-MS/SPECMA data bank identification of volatile aroma compounds, Carbohyd. Res., 1992, 230, 1, 15-29, https://doi.org/10.1016/S0008-6215(00)90510-X . [all data]

Narain, Galvao, et al., 2007
Narain, N.; Galvao, M. deS.; Ferreira, D.DaS.; Navarro, D.M.A.F., Flavor biogeneration in Mangaba (Hancornia speciosa Gomes) fruit, BioEng. Campinas, 2007, 1, 1, 25-31. [all data]

Vinogradov, 2004
Vinogradov, B.A., Production, composition, properties and application of essential oils, 2004, retrieved from http://viness.narod.ru. [all data]


Notes

Go To: Top, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, IR Spectrum, Mass spectrum (electron ionization), Gas Chromatography, NIST Free Links, References