2H-Pyran, tetrahydro-4-methyl-2-(2-methyl-1-propenyl)-

Formula: C₁₀H₁₈O
Molecular weight: 154.2493
IUPAC Standard InChI: InChI=1S/C10H18O/c1-8(2)6-10-7-9(3)4-5-11-10/h6,9-10H,4-5,7H2,1-3H3/t9-,10-/m1/s1
IUPAC Standard InChIKey: CZCBTSFUTPZVKJ-NXEZZACHSA-N
CAS Registry Number: 16409-43-1
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.
Stereoisomers:
Other names: Rose oxide; 2H-Pyran, tetrahydro-4-methyl-2-(2-methylpropenyl)-; Rosoxide; Rose oxide L; Pyran, tetrahydro-2-(2-methyl-1-propenyl)-4-methyl-; Pyran, 2-(2-methyl-1-propenyl)-4-methyltetrahydro-; 4-Methyl-2-(2-methyl-1-propenyl)tetrahydro-2H-pyran; Rosenoxide; Tetrahydro-4-methyl-2-[2-methyl-1-propenyl]-2H-pyran; 2H-Pyran, tetrahydro-4-methyl-2-(2-methyl-1-propen-1-yl)-; Pyran, tetrahydro-4-methyl-2-(2-methylpropenyl)-; cis Rose oxide; Rose oxide , I; tetrahydro-4-methyl-2-(2-methylprop-1-enyl)pyran
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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

Kovats' RI, polar column, isothermal

Column type	Active phase	Temperature (C)	I	Reference	Comment
Capillary	Carbowax 20M	90.	1368.	Moore and Brown, 1976	N2

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

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Column type	Active phase	I	Reference	Comment
Capillary	HP-5MS	1112.3	Zhao, Liang, et al., 2005	30. m/0.25 mm/0.25 μm, He, 2. K/min; T_start: 80. C; T_end: 290. C
Capillary	HP-5MS	1112.7	Zhao, Liang, et al., 2005	30. m/0.25 mm/0.25 μm, He, 4. K/min; T_start: 80. C; T_end: 290. C
Capillary	HP-5MS	1112.7	Zhao, Liang, et al., 2005	30. m/0.25 mm/0.25 μm, He, 6. K/min; T_start: 80. C; T_end: 290. C

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

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Column type	Active phase	I	Reference	Comment
Capillary	DB-Wax	1337.	Varming, Andersen, et al., 2006	30. m/0.25 mm/0.25 μm, He, 40. C @ 10. min, 6. K/min, 240. C @ 25. min
Capillary	DB-Wax	1363.	Brophy, Goldsack, et al., 2004	60. m/0.32 mm/0.25 μm, He, 3. K/min; T_start: 32. C; T_end: 220. C
Capillary	ZB-Wax	1338.	Ledauphin, Saint-Clair, et al., 2004	30. m/0.25 mm/0.15 μm, He, 35. C @ 10. min, 1.8 K/min, 220. C @ 10. min
Capillary	DB-Wax	1339.	Varming, Andersen, et al., 2004	30. m/0.25 mm/0.25 μm, He, 40. C @ 10. min, 6. K/min, 240. C @ 25. min
Capillary	DB-Wax	1390.	Claudela, Dirningera, et al., 2002	60. m/0.32 mm/0.5 μm, He, 2.7 K/min, 235. C @ 30. min; T_start: 67. C

Normal alkane RI, non-polar column, isothermal

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Column type	Active phase	Temperature (C)	I	Reference	Comment
Capillary	DB-5	25.	1111.	Hemmateenejad, Jawadnia, et al., 2007

Normal alkane RI, non-polar column, temperature ramp

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Column type	Active phase	I	Reference	Comment
Capillary	RTX-5	1115.	Setkova, Risticevic, et al., 2007	10. m/0.18 mm/0.2 μm, He, 40. C @ 0.5 min, 50. K/min, 275. C @ 0.5 min
Capillary	FSOT-RSL-200	1108.	Jirovetz, Eller, et al., 2006	30. m/0.32 mm/0.25 μm, Hydrogen, 40. C @ 5. min, 6. K/min, 280. C @ 5. min
Capillary	HP-5 MS	1099.	Shang, Hu, et al., 2001	30. m/0.25 mm/0.25 μm, Helium, 50. C @ 2. min, 5. K/min, 250. C @ 5. min
Capillary	DB-5	1112.	Reverchon, Porta, et al., 1997	30. m/0.25 mm/0.25 μm, He, 50. C @ 5. min, 2. K/min; T_end: 250. C

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

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Column type	Active phase	I	Reference	Comment
Capillary	HP-5	1107.	Custer, 2009	25. m/0.32 mm/0.17 μm, Helium; Program: 60 0C (5 min) 4 0C/min -> 220 0C 11 0C/min -> 280 0C (15 min)
Capillary	HP-5	1108.	Custer, 2009	25. m/0.32 mm/0.17 μm, Helium; Program: not specified
Capillary	DB-1	1102.	Delort and Jaquier, 2009	60. m/0.25 mm/0.25 μm, Helium; Program: 50 0C (5 min) 3 0C/min -> 120 0C 5 0C/min -> 250 0C (3 min) 15 0C/min -> 300 0C (20 min)
Capillary	HP-5	1109.	Zhao, Li, et al., 2008	30. m/0.25 mm/0.25 μm; Program: 40 0C (2 min) 5 0C/min -> 80 0C 7 oC/min -> 160 0C 9 0C/min -> 200 0C 20 0C/min -> 280 0C (10 min)
Capillary	HP-5	1111.	Zhao, Li, et al., 2008	30. m/0.25 mm/0.25 μm; Program: not specified
Capillary	DB-5	1108.	Nivinsliene, Butkiene, et al., 2007	50. m/0.32 mm/0.25 μm, Helium; Program: 60 0C (1 min) 5 0C/min -> 160 0C 10 0C/min -> 250 0C
Capillary	HP-5 MS	1100.	Shang, Hu, et al., 2001	30. m/0.25 mm/0.25 μm, Helium; Program: not specified

Normal alkane RI, polar column, temperature ramp

View large format table.

Column type	Active phase	I	Reference	Comment
Capillary	DB-Wax	1381.	Zeng, Xie, et al., 2011	30. m/0.25 mm/0.25 μm, Helium, 40. C @ 2. min, 4. K/min, 230. C @ 4.5 min
Capillary	DB-Wax	1313.	Zhao, Xu, et al., 2009	30. m/0.25 mm/0.25 μm, Helium, 40. C @ 2. min, 3. K/min, 230. C @ 5. min
Capillary	DB-Wax	1350.	Umano, Nakahara, et al., 1999	60. m/0.25 mm/0.25 μm, He, 40. C @ 2. min, 2. K/min; T_end: 200. C
Capillary	SP-1000	1352.	Brophy, Goldsack, et al., 1996	He, 3. K/min; Column length: 85. m; Column diameter: 0.50 mm; T_start: 65. C; T_end: 225. C

Normal alkane RI, polar column, custom temperature program

View large format table.

Column type	Active phase	I	Reference	Comment
Capillary	DB-Wax	1338.	Zhao, Xu, et al., 2009	30. m/0.25 mm/0.25 μm, Helium; Program: not specified

References

Go To: Top, Gas Chromatography, Notes

Moore and Brown, 1976
Moore, B.P.; Brown, W.V., 3,4,5-Trimethoxybenzylhydrazine - an efficient subtraction reagent for aldehydes and ketones in gas chromatography, J. Chromatogr., 1976, 121, 2, 279-284, https://doi.org/10.1016/S0021-9673(00)85024-4 . [all data]

Zhao, Liang, et al., 2005
Zhao, C.-X.; Liang, Y.-Z.; Fang, H.-Z.; Li, X.-N., Temperature-programmed retention indices for gas chromatography-mass spectroscopy analysis of plant essential oils, J. Chromatogr. A, 2005, 1096, 1-2, 76-85, https://doi.org/10.1016/j.chroma.2005.09.067 . [all data]

Varming, Andersen, et al., 2006
Varming, C.; Andersen, M.L.; Poll, L., Volatile Monoterpenes in Black Currant (Ribes nigrum L.) Juice: Effects of Heating and Enzymatic Treatment by β-Glucosidase, J. Agric. Food Chem., 2006, 54, 6, 2298-2302, https://doi.org/10.1021/jf051938k . [all data]

Brophy, Goldsack, et al., 2004
Brophy, J.J.; Goldsack, R.J.; O'Sullivan, W., Chemistry of the Australian gymnosperms. Part VII. The leaf oils of the genus Actinostrobus, Biochem. Syst. Ecol., 2004, 32, 10, 867-873, https://doi.org/10.1016/j.bse.2004.05.001 . [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]

Varming, Andersen, et al., 2004
Varming, C.; Andersen, M.L.; Poll, L., Influence of thermal treatment on black currant (Ribes nigrum L.) juice aroma, J. Agric. Food Chem., 2004, 52, 25, 7628-7636, https://doi.org/10.1021/jf049435m . [all data]

Claudela, Dirningera, et al., 2002
Claudela, P.; Dirningera, N.; Etievant, P., Effects of water on gas chromatographic column efficiency measurements applied to on-column injections of volatile aroma compounds, J. Sep. Sci., 2002, 25, 5-6, 365-370, https://doi.org/10.1002/1615-9314(20020401)25:5/6<365::AID-JSSC365>3.0.CO;2-Y . [all data]

Hemmateenejad, Jawadnia, et al., 2007
Hemmateenejad, B.; Jawadnia, K.; Elyasi, M., Quantitative structure - retention relationship for the Kovats retention indices of a large set of terpenes: a comdined data splitting-feature selection strategy, Anal. Chim. Acta, 2007, 592, 1, 72-81, https://doi.org/10.1016/j.aca.2007.04.009 . [all data]

Setkova, Risticevic, et al., 2007
Setkova, L.; Risticevic, S.; Pawliszyn, J., Rapid headspace solid-phase microextraction-gas chromatographic?time-of-flight mass spectrometric method for qualitative profiling of ice wine volatile fraction II: Classification of Canadian and Czech ice wines using statistical evaluation of the data, J. Chromatogr. A, 2007, 1147, 2, 224-240, https://doi.org/10.1016/j.chroma.2007.02.052 . [all data]

Jirovetz, Eller, et al., 2006
Jirovetz, L.; Eller, G.; Buchbauer, G.; Schmidt, E.; Denkova, Z.; Stoyanova, A.S.; Nikolova R.; Geissler, M., Chemical composition, antimicrobial activities and odor descriptions of some essential oils with characteristic floral-rosy scent and of their principal aroma compounds, Recent. Res. Devel. Agronomy Horticulture, 2006, 2, 1-12. [all data]

Shang, Hu, et al., 2001
Shang, C.; Hu, Y.; Deng, C.; Hu, K., Rapid determination of volatile constituents of Michelia alba flowers by gas chromatography - mass spectrometry with solid-phase microextraction, J. Chromatogr. A, 2001, 942, 1-2, 283-288, https://doi.org/10.1016/S0021-9673(01)01382-6 . [all data]

Reverchon, Porta, et al., 1997
Reverchon, E.; Porta, G.D.; Gorgoglione, D., Supercritical CO₂ extraction of volatile oil from rose concrete, Flavour Fragr. J., 1997, 12, 1, 37-41, https://doi.org/10.1002/(SICI)1099-1026(199701)12:1<37::AID-FFJ605>3.0.CO;2-V . [all data]

Custer, 2009
Custer, Y., GC Volatile Components Analysis of Different Parts of Litchi chinensis (Dissertation), 2009. [all data]

Delort and Jaquier, 2009
Delort, E.; Jaquier, A., Novel terpenyl esters from Australian finger lime (Citrus australasica) peel extract, Flav. Fragr. J., 2009, 24, 3, 123-132, https://doi.org/10.1002/ffj.1922 . [all data]

Zhao, Li, et al., 2008
Zhao, Y.; Li, J.; Xu, Y.; Duan, H.; Fan, W.; Zhao, G., EXtraction, preparation and identification of volatile compounds in Changyu XO brandy, Chinese J. Chromatogr., 2008, 26, 2, 212-222, https://doi.org/10.1016/S1872-2059(08)60014-0 . [all data]

Nivinsliene, Butkiene, et al., 2007
Nivinsliene, O.; Butkiene, R.; Gudalevic, A.; Mockute, D.; Meskauskiene, V.; Grigaliunaite, B., Influence of urban environment on chemical composition of Tilia cordata essential oil, Chemija, 2007, 18, 1, 44-49. [all data]

Zeng, Xie, et al., 2011
Zeng, Z.; Xie, R.; Zhang, T.; Zhang, H.; Chen, J.Y., Analysis of volatile compositions of Magnolia biondii Pamp by steam distillation and Headspace solid phase micro-extraction, J. Oleo Sci., 2011, 60, 12, 591-596, https://doi.org/10.5650/jos.60.591 . [all data]

Zhao, Xu, et al., 2009
Zhao, Y.; Xu, Y.; Li, J.; Fan, W.; Jiang, W., Profile of volatile compounds in 11 brandies by headspace solid-phase microextraction followed by gas chromatography-mass spectrometry, J. Food. Sci., 2009, 74, 2, c90-c99, https://doi.org/10.1111/j.1750-3841.2008.01029.x . [all data]

Umano, Nakahara, et al., 1999
Umano, K.; Nakahara, K.; Shoji, A.; Shibamoto, T., Aroma chemicals isolated and identified from leaves of aloe arborescens Mill. Var. natalensis Berger, J. Agric. Food Chem., 1999, 47, 9, 3702-3705, https://doi.org/10.1021/jf990116i . [all data]

Brophy, Goldsack, et al., 1996
Brophy, J.J.; Goldsack, R.J.; Bean, A.R.; Forster, P.I.; Fookes, C.J.R., The leaf essential oils of the genus Syncarpia ten. (Myrtaceae), Flavour Fragr. J., 1996, 11, 6, 361-366, https://doi.org/10.1002/(SICI)1099-1026(199611)11:6<361::AID-FFJ591>3.0.CO;2-T . [all data]

Notes

Go To: Top, Gas Chromatography, References

Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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