2H-Pyran, 2-ethenyltetrahydro-2,6,6-trimethyl-

Formula: C₁₀H₁₈O
Molecular weight: 154.2493
IUPAC Standard InChI: InChI=1S/C10H18O/c1-5-10(4)8-6-7-9(2,3)11-10/h5H,1,6-8H2,2-4H3
IUPAC Standard InChIKey: NETOHYFTCONTDT-UHFFFAOYSA-N
CAS Registry Number: 7392-19-0
Chemical structure:
This structure is also available as a 2d Mol file
Species with the same structure:
- Geranic oxide
- Linalool-3,7-oxide
Stereoisomers:
- Dehydroxylinalooloxide A
Other names: 2H-Pyran, tetrahydro-2,2,6-trimethyl-6-vinyl-; 2,2,6-Trimethyl-6-vinyltetrahydropyran; 2,6,6-Trimethyl-2-vinyltetrahydropyran; 2,2,6-Trimethyl-6-vinyltetrahydro-2H-pyran; 2,6,6-Trimethyl-2-ethenyltetrahydro-2H-pyran; 2,6,6-Trimethyl-2-ethenyltetrahydropyran; 2,6,6-Trimethyl-2-vinyl-tetrahydropyrane; 2-Vinyltetrahydro-2,6,6-trimethyl-2H-pyran; Linalool 3,7-oxide; 2,2,6-Trimethyl-6-vinyltetrahydrofuran; 2,6,6-Trimethyl-2-ethenyltetrahydro-2-pyran; 2,6,6-trimethoxy-2-vinyltetrahydropyran
Information on this page:
Other data available:
- Mass spectrum (electron ionization)
Options:
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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	SPB-1	960.	Chisholm, Wilson, et al., 2003	25. m/0.25 mm/0.25 μm, 35. C @ 10. min, 4. K/min; T_end: 225. C
Capillary	SPB-5	971.	Pino, Marbot, et al., 2003	30. m/0.25 mm/0.25 μm, He, 60. C @ 2. min, 4. K/min, 250. C @ 20. min
Capillary	SPB-1	960.	Chisholm, Wilson, et al., 2001	15. m/0.25 mm/0.25 μm, 35. C @ 3. min, 6. K/min, 225. C @ 10. min
Capillary	SPB-1	960.	Chen, Huang, et al., 1998	60. m/0.32 mm/0.25 μm, N2, 4. K/min, 200. C @ 20. min; T_start: 40. C

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

View large format table.

Column type	Active phase	I	Reference	Comment
Capillary	HP-5MS	971.3	Andriamaharavo, 2014	30. m/0.25 mm/0.25 μm, He; Program: 60C (1 min) => 5 C/min => 210C => 10 C/min => 280C (15 min)

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

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Column type	Active phase	I	Reference	Comment
Capillary	ZB-Wax	1096.	Ledauphin, Saint-Clair, et al., 2004	30. m/0.25 mm/0.15 μm, He, 35. C @ 5. min, 5. K/min, 220. C @ 10. min
Capillary	Supelcowax	1113.	Chisholm, Wilson, et al., 2003	25. m/0.25 mm/0.25 μm, 35. C @ 5. min, 4. K/min, 225. C @ 10. min
Capillary	DB-Wax	1109.	Fröhlich, Duque, et al., 1989	30. m/0.25 mm/0.25 μm, He, 50. C @ 3. min, 4. K/min; T_end: 250. C
Capillary	DB-Wax	1112.	Fröhlich, Duque, et al., 1989	30. m/0.25 mm/0.25 μm, He, 50. C @ 3. min, 4. K/min; T_end: 250. C

Normal alkane RI, non-polar column, temperature ramp

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Column type	Active phase	I	Reference	Comment
Capillary	OV-1	963.	Hu, Liang, et al., 2010	30. m/0.25 mm/0.25 μm, Helium, 50. C @ 3. min, 5. K/min, 250. C @ 2. min
Capillary	SPB-5	969.	Pino, Marquez, et al., 2006	30. m/0.25 mm/0.25 μm, Helium, 60. C @ 2. min, 4. K/min, 250. C @ 20. min
Capillary	CP Sil 8 CB	961.	Wang and Guo-Y. -L., 2004	30. m/0.25 mm/0.25 μm, He, 50. C @ 3. min, 10. K/min, 200. C @ 2. min
Capillary	DB-5	979.	Georgilopoulos and Gallois, 1988	30. m/0.35 mm/1.0 μm, Hydrogen, 2. K/min; T_start: 45. C; T_end: 220. C

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

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Column type	Active phase	I	Reference	Comment
Capillary	HP-5	972.	Demyttenaere, Dagher, et al., 2003	30. m/0.25 mm/0.25 μm, He; Program: 40C(1min) => 5C/min => 180C => 10C/min => 220C(2min)
Capillary	HP-5MS	972.	Demyttenaere, Dagher, et al., 2002	30. m/0.25 mm/0.25 μm, He; Program: 40C(1min) => 5C/min => 220C => 10C/min => 240C(2min)
Capillary	DB-1	957.	Takeoka, Flath, et al., 1988	30. m/0.25 mm/0.25 μm, H2; Program: 30C (2min) => 2C/min => 150C => 4C/min => 250C

Normal alkane RI, polar column, temperature ramp

View large format table.

Column type	Active phase	I	Reference	Comment
Capillary	Carbowax 20M	1109.	Engel and Tressl, 1983	2. K/min; Column length: 50. m; Column diameter: 0.32 mm; T_start: 70. C; T_end: 180. C
Capillary	Carbowax 20M	1095.	Yamaguchi and Shibamoto, 1980	N2, 1. K/min; Column length: 50. m; Column diameter: 0.28 mm; T_start: 80. C; T_end: 170. C

Normal alkane RI, polar column, custom temperature program

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Column type	Active phase	I	Reference	Comment
Capillary	Carbowax 20M	1091.	Vinogradov, 2004	Program: not specified

References

Go To: Top, Gas Chromatography, Notes

Chisholm, Wilson, et al., 2003
Chisholm, M.G.; Wilson, M.A.; Gaskey, G.M., Characterization of aroma volatiles in key lime essential oils (Cirtrus aurantifolia Swingle), Flavour Fragr. J., 2003, 18, 2, 106-115, https://doi.org/10.1002/ffj.1172 . [all data]

Pino, Marbot, et al., 2003
Pino, J.; Marbot, R.; Rosado, A.; Vázquez, C., Volatile constituents of fruits of Garcinia dulcis Kurz. from Cuba, Flavour Fragr. J., 2003, 18, 4, 271-274, https://doi.org/10.1002/ffj.1187 . [all data]

Chisholm, Wilson, et al., 2001
Chisholm, M.G.; Wilson, M.A.; Gaskey, G.M.; Jell, J.A.; Cass, D.M., Jr., Chapter 9. The identification of aroma compounds in key lime oil using solid-phase microextraction and gas chromatography-olfactometry, Am. Chem. Soc. Symp. Ser., 2001, 782, 100-112. [all data]

Chen, Huang, et al., 1998
Chen, S.-H.; Huang, T.-C.; Ho, C.-T.; Tsai, P.-J., Extraction, analysis, and study on the volatiles in roselle tea, J. Agric. Food Chem., 1998, 46, 3, 1101-1105, https://doi.org/10.1021/jf970720y . [all data]

Andriamaharavo, 2014
Andriamaharavo, N.R., Retention Data. NIST Mass Spectrometry Data Center., NIST Mass Spectrometry Data Center, 2014. [all data]

Ledauphin, Saint-Clair, et al., 2004
Ledauphin, J.; Saint-Clair, J.-F.; Lablanquie, O.; Guichard, H.; Founier, N.; Guichard, E.; Barillier, D., Identification of trace volatile compounds in freshly distilled calvados and cognac using preparative separations coupled with gas chromatography-mass spectrometry, J. Agric. Food Chem., 2004, 52, 16, 5124-5134, https://doi.org/10.1021/jf040052y . [all data]

Fröhlich, Duque, et al., 1989
Fröhlich, O.; Duque, C.; Schreier, P., Volatile constituents of curuba (Passiflora mollissima) fruit, J. Agric. Food Chem., 1989, 37, 2, 421-425, https://doi.org/10.1021/jf00086a033 . [all data]

Hu, Liang, et al., 2010
Hu, C.-D.; Liang, Y.-Z.; Guo, F.-Q.; Li, X.-R.; Wang, W.-P., Determination of essential oil composition from Osmanthus fragrans tea by GC-MS combined with a chemometric resolution method, Molecules, 2010, 15, 5, 3683-3693, https://doi.org/10.3390/molecules15053683 . [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]

Wang and Guo-Y. -L., 2004
Wang, H.-Y.; Guo-Y. -L., Rapid analysis of the volatile compounds in the rhizomes of Rhodiola sachalinensis and Rhodiola sacra by static headspace-gas chromatography-tandem mass spectrometry, Anal. Letters, 2004, 37, 10, 2151-2161, https://doi.org/10.1081/AL-200026690 . [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]

Demyttenaere, Dagher, et al., 2003
Demyttenaere, J.C.R.; Dagher, C.; Sandra, P.; Kallithraka, S.; Verhé, R.; de Kimpe, N., Flavour analysis of Greek white wine by solid-phase microextraction-capillary gas chromatography-mass spectrometry, J. Chromatogr. A, 2003, 985, 1-2, 233-246, https://doi.org/10.1016/S0021-9673(02)01467-X . [all data]

Demyttenaere, Dagher, et al., 2002
Demyttenaere, J.C.R.; Dagher, C.; Verhé, R.; Sandra, P., Flavour analysis of Greek white wine using solid phase microextraction - capillary GC/MS in 25th International Symposium on Capillary Chromatography, 2002, 1-16. [all data]

Takeoka, Flath, et al., 1988
Takeoka, G.R.; Flath, R.A.; Güntert, M.; Jennings, W., Nectarine volatiles: vacuum steam distillation versus headspace sampling, J. Agric. Food Chem., 1988, 36, 3, 553-560, https://doi.org/10.1021/jf00081a037 . [all data]

Engel and Tressl, 1983
Engel, K.-H.; Tressl, R., Formation of aroma components from nonvolatile precursors in passion fruit, J. Agric. Food Chem., 1983, 31, 5, 998-1002, https://doi.org/10.1021/jf00119a019 . [all data]

Yamaguchi and Shibamoto, 1980
Yamaguchi, K.; Shibamoto, T., Volatile constituents of the chestnut flower, J. Agric. Food Chem., 1980, 28, 1, 82-84, https://doi.org/10.1021/jf60227a021 . [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

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Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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