(2R,4R)-4-Methyl-2-(2-methylprop-1-en-1-yl)tetrahydro-2H-pyran

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+/m0/s1
IUPAC Standard InChIKey: CZCBTSFUTPZVKJ-VHSXEESVSA-N
CAS Registry Number: 5258-11-7
Chemical structure:
This structure is also available as a 2d Mol file
Species with the same structure:
- trans-Rose oxide
Stereoisomers:
- 2H-Pyran, tetrahydro-4-methyl-2-(2-methyl-1-propenyl)-
- cis-Rose oxide
Other names: trans-Rose oxide; Rose oxide trans; (E)-Rose oxide; (t)-Rose oxide
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Gas Chromatography

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

Kovats' RI, non-polar column, temperature ramp

Column type	Active phase	I	Reference	Comment
Capillary	HP-5MS	1117.	Jalali-Heravi, Zekavat, et al., 2006	60. m/0.25 mm/0.25 μm, He, 40. C @ 1. min, 3. K/min, 250. C @ 20. min
Capillary	SPB-5	1130.	Gauvin, Lecomte, et al., 2004	60. m/0.32 mm/1. μm, He, 4. K/min, 200. C @ 30. min; T_start: 60. C
Capillary	DB-5	1140.	Baranauskiene, Venskutonis, et al., 2003	50. m/0.32 mm/0.25 μm, He, 50. C @ 2. min, 5. K/min, 280. C @ 10. min
Capillary	Cross-Linked Methylsilicone	1115.	Rajeswara Rao, Kaul, et al., 2002	50. m/0.2 mm/0.25 μm, He, 4. K/min; T_start: 100. C; T_end: 280. C
Capillary	BP-1	1107.	Rajeswara Rao, 2002	25. m/0.5 mm/0.25 μm, N2, 5. K/min, 220. C @ 10. min; T_start: 60. C
Capillary	BP-1	1107.	Rao B.R.R., 2002	25. m/0.5 mm/0.25 μm, 5. K/min, 220. C @ 10. min; T_start: 60. C
Capillary	BP-1	1115.	Jain, Aggarwal, et al., 2001	25. m/0.55 mm/0.25 μm, N2, 5. K/min, 220. C @ 15. min; T_start: 60. C
Capillary	BP-1	1116.	Rao, Kaul, et al., 2000	N2, 5. K/min, 220. C @ 10. min; Column length: 25. m; Column diameter: 0.5 mm; T_start: 60. C
Capillary	BP-1	1116.	Rao, Sastry, et al., 2000	25. m/0.50 mm/0.25 μm, N2, 5. K/min, 220. C @ 10. min; T_start: 60. C
Capillary	DB-5	1127.	Adams, 1999	30. m/0.26 mm/0.25 μm, He, 3. K/min; T_start: 60. C; T_end: 246. C
Capillary	BP-1	1115.	Kulkarni, Mallavarapu, et al., 1998	N2, 5. K/min; Column length: 25. m; Column diameter: 0.25 mm; T_start: 60. C; T_end: 220. C

Kovats' RI, non-polar column, custom temperature program

View large format table.

Column type	Active phase	I	Reference	Comment
Capillary	HP-5	1127.	Shellie and Marriott, 2003	30. m/0.25 mm/0.25 μm, He; Program: not specified

Kovats' RI, polar column, temperature ramp

View large format table.

Column type	Active phase	I	Reference	Comment
Capillary	HP-Wax	1386.	Gauvin, Lecomte, et al., 2004	50. m/0.2 mm/0.4 μm, He, 4. K/min, 230. C @ 30. min; T_start: 60. C
Capillary	Carbowax 20M	1358.	Kulkarni, Mallavarapu, et al., 1998	N2, 5. K/min; Column length: 25. m; Column diameter: 0.25 mm; T_start: 60. C; T_end: 200. C

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

View large format table.

Column type	Active phase	I	Reference	Comment
Capillary	Equity-5	1149.	Rocha, Coelho, et al., 2007	60. m/0.25 mm/1. μm, He, 40. C @ 1. min, 5. K/min, 260. C @ 15. min
Capillary	HP-5	1127.	Shellie and Marriott, 2003	30. m/0.25 mm/0.25 μm, He, 3. K/min; T_start: 40. C; T_end: 240. 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	DB-5	1126.	Boulanger, Chassagne, et al., 1999	30. m/0.25 mm/0.25 μm, H2; Program: 40C(5min) => 2C/min => 220C => 5C/min => 250C(15min)
Capillary	DB-5	1127.	Boulanger, Chassagne, et al., 1999	30. m/0.25 mm/0.25 μm, H2; Program: 40C(5min) => 2C/min => 220C => 5C/min => 250C(15min)

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

View large format table.

Column type	Active phase	I	Reference	Comment
Capillary	CP-Wax 52CB	1341.	Jensen, Christensen, et al., 2000	50. m/0.25 mm/0.2 μm, He, 30. C @ 1.3 min, 2. K/min; T_end: 220. C
Capillary	DB-Wax	1362.	Möllenbeck, König, et al., 1997	25. m/0.25 mm/0.25 μm, He, 50. C @ 3. min, 4. K/min; T_end: 240. C

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

View large format table.

Column type	Active phase	I	Reference	Comment
Capillary	CP-Wax 52CB	1341.	Kaack, Christensen, et al., 2005	50. m/0.25 mm/0.2 μm, He; Program: 33C(1.5min) => 1.5C/min => 60C(4min) => 2C/min => 100C => 8C/min => 220C(15min)

Normal alkane RI, non-polar column, temperature ramp

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Column type	Active phase	I	Reference	Comment
Capillary	HP-5 MS	1115.	Karlsson, Birgersson, et al., 2009	30. m/0.25 mm/0.25 μm, Hydrogen, 30. C @ 5. min, 8. K/min, 230. C @ 10. min
Capillary	HP-5MS	1115.	Vichi, Riu-Aumatell, et al., 2007	30. m/0.25 mm/0.25 μm, He, 40. C @ 5. min, 3. K/min, 250. C @ 10. min
Capillary	HP-5MS	1127.	Mimica-Dukic, Bozin, et al., 2004	30. m/0.25 mm/0.25 μm, He, 3. K/min; T_start: 60. C; T_end: 280. C
Capillary	DB-1	1130.	Perez-Alonso, Velasco-Negueruela, et al., 2003	50. m/0.25 mm/0.25 μm, N2, 4. K/min; T_start: 95. C; T_end: 240. C
Capillary	BP-1	1116.	Gupta, Mallavarapu, et al., 2001	30. m/0.25 mm/0.25 μm, N2, 5. K/min; T_start: 60. C; T_end: 220. C
Capillary	SPB-1	1127.	Wong and Lai, 1996	50. m/0.2 mm/0.33 μm, He, 40. C @ 3. min, 3. K/min, 200. C @ 30. min
Capillary	DB-1	1128.	Nishimura, 1995	60. m/0.25 mm/0.25 μm, He, 3. K/min; T_start: 80. C; T_end: 210. C

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

View large format table.

Column type	Active phase	I	Reference	Comment
Capillary	SE-30	1110.	Vinogradov, 2004	Program: not specified
Capillary	SE-30	1110.	Vinogradov, 2004	Program: not specified
Capillary	CP Sil 5 CB	1115.	Weyerstahl, Marschall, et al., 1998	He; Column length: 25. m; Phase thickness: 0.39 μm; Program: not specified
Capillary	Polydimethyl siloxanes	1110.	Zenkevich, 1997	Program: not specified
Packed	OV-101	1114.	Swigar and Silverstein, 1981	N2, Chromosorb G 60-80mesh DMCS; Column length: 2.5 m; Program: not specified

Normal alkane RI, polar column, temperature ramp

View large format table.

Column type	Active phase	I	Reference	Comment
Capillary	DB-Wax	1350.	Karlsson, Birgersson, et al., 2009	30. m/0.25 mm/0.25 μm, Hydrogen, 30. C @ 5. min, 8. K/min, 230. C @ 10. min
Capillary	Supelcowax-10	1417.	Vichi, Riu-Aumatell, et al., 2007	30. m/0.25 mm/0.25 μm, He, 40. C @ 5. min, 3. K/min, 250. C @ 10. min
Capillary	Carbowax 20M	1370.	Babu and Kaul, 2005	60. m/0.25 mm/0.25 μm, N2, 40. C @ 2. min, 10. K/min, 190. C @ 15. min
Capillary	Stabilwax	1367.	Jirovetz, Buchbauer, et al., 2005	30. m/0.32 mm/0.5 μm, 40. C @ 5. min, 6. K/min, 280. C @ 5. min
Capillary	PE-Wax	1355.	Ram, Kumar, et al., 2005	50. m/0.32 mm/0.25 μm, H2, 4. K/min, 220. C @ 2. min; T_start: 60. C
Capillary	DB-Wax	1371.	Werkhoff, Güntert, et al., 1998	60. m/0.32 mm/0.25 μm, H2, 3. K/min; T_start: 60. C; T_end: 220. C
Capillary	Supelcowax-10	1367.	Wong and Lai, 1996	60. m/0.25 mm/0.25 μm, He, 40. C @ 3. min, 3. K/min, 200. C @ 30. min

Normal alkane RI, polar column, custom temperature program

View large format table.

Column type	Active phase	I	Reference	Comment
Capillary	CP-Wax 52 CB	1341.	Kaack and Christensen, 2008	50. m/0.25 mm/0.29 μm, Helium; Program: 33 0C (1 min) 2 0C/min -> 130 0C 10 0C/min -> 220 0C
Capillary	Carbowax 20M	1366.	Vinogradov, 2004	Program: not specified
Capillary	Carbowax 20M	1370.	Vinogradov, 2004	Program: not specified
Capillary	DB-Wax	1379.	Weyerstahl, Marschall, et al., 1998	N2; Column length: 60. m; Phase thickness: 0.25 μm; Program: not specified

References

Go To: Top, Gas Chromatography, Notes

Jalali-Heravi, Zekavat, et al., 2006
Jalali-Heravi, M.; Zekavat, B.; Sereshti, H., Characterization of essential oil components of Iranian geranium oil using gas chromatography-mass spectrometry combined with chemometric resolution techniques, J. Chromatogr. A, 2006, 1114, 1, 154-163, https://doi.org/10.1016/j.chroma.2006.02.034 . [all data]

Gauvin, Lecomte, et al., 2004
Gauvin, A.; Lecomte, H.; Smadja, J., Comparative investigations of the essential oils of two scented geranium (Pelargonium spp.) cultivars grown on Reunion Island, Flavour Fragr. J., 2004, 19, 5, 455-460, https://doi.org/10.1002/ffj.1354 . [all data]

Baranauskiene, Venskutonis, et al., 2003
Baranauskiene, R.; Venskutonis, R.P.; Demyttenaere, J.C.R., Sensory and instrumental evaluation of catnip (Nepeta cataria L.) aroma, J. Agric. Food Chem., 2003, 51, 13, 3840-3848, https://doi.org/10.1021/jf021187b . [all data]

Rajeswara Rao, Kaul, et al., 2002
Rajeswara Rao, B.R.; Kaul, P.N.; Syamasundar, K.V.; Ramesh, S., Water soluble fractions of rose scented geranium (Pelargonium species) essential oil, Bioresour. Technol., 2002, 84, 3, 243-246, https://doi.org/10.1016/S0960-8524(02)00057-3 . [all data]

Rajeswara Rao, 2002
Rajeswara Rao, B.R., Biomass yield, essential oil yield and essential oil composition of rose-scented geranium (Pelargonium species) as influenced by row spacings and intercropping with cornmint (Mentha arvensis L.f. piperascens Malinv. ex Holmes), Ind. Crops Prod., 2002, 16, 2, 133-144, https://doi.org/10.1016/S0926-6690(02)00038-9 . [all data]

Rao B.R.R., 2002
Rao B.R.R., Biomass yield, essential oil yield and essential oil composition of rose-scented geranium (Pelargonium species) as influenced by row spacings and intercropping with cornmint (Mentha arvensis L.f. piperascens Malinv. ex Holmes), Industrial Crops and Products, 2002, 16, 2, 133-144, https://doi.org/10.1016/S0926-6690(02)00038-9 . [all data]

Jain, Aggarwal, et al., 2001
Jain, N.; Aggarwal, K.K.; Syamasundar, K.V.; Srivastava, S.K.; Kumar, S., Essential oil composition of geranium (Pelargonium sp.) from the plains of Northern India, Flavour Fragr. J., 2001, 16, 1, 44-46, https://doi.org/10.1002/1099-1026(200101/02)16:1<44::AID-FFJ943>3.0.CO;2-X . [all data]

Rao, Kaul, et al., 2000
Rao, B.R.R.; Kaul, P.N.; Mallavarapu, G.R.; Ramesh, S., First observation of little leaf disease and its impact on the yield and composition of the essential oil of rose-scented geranium (Pelargonium sp.), Flavour Fragr. J., 2000, 15, 3, 137-140, https://doi.org/10.1002/1099-1026(200005/06)15:3<137::AID-FFJ880>3.0.CO;2-A . [all data]

Rao, Sastry, et al., 2000
Rao, B.R.R.; Sastry, K.P.; Saleem, S.M.; Rao, E.V.S.P.; Syamasundar, K.V.; Ramesh, S., Volatile flower oils of three genotypes of rose-scented geranium (Pelargonium sp.), Flavour Fragr. J., 2000, 15, 2, 105-107, https://doi.org/10.1002/(SICI)1099-1026(200003/04)15:2<105::AID-FFJ875>3.0.CO;2-G . [all data]

Adams, 1999
Adams, R.P., Systematics of multi-seeded eastern hemisphere Juniperus based on leaf essential oils and RAPD DNA fingerprinting, Biochem. Syst. Ecol., 1999, 27, 7, 709-725, https://doi.org/10.1016/S0305-1978(99)00016-2 . [all data]

Kulkarni, Mallavarapu, et al., 1998
Kulkarni, R.N.; Mallavarapu, G.R.; Baskaran, K.; Ramesch, S.; Kumar, S., Composition of the essential oils of two isomenthone-rich variants of geranium (Pelargonium sp.), Flavour Fragr. J., 1998, 13, 6, 389-392, https://doi.org/10.1002/(SICI)1099-1026(199811/12)13:6<389::AID-FFJ757>3.0.CO;2-2 . [all data]

Shellie and Marriott, 2003
Shellie, R.A.; Marriott, P.J., Comprehensive two-dimensional gas chromatography-mass spectrometry analysis of Pelargonium graveolens essential oil using rapid scanning quadrupole mass spectrometry, Analyst, 2003, 128, 7, 879-883, https://doi.org/10.1039/b304371a . [all data]

Rocha, Coelho, et al., 2007
Rocha, S.M.; Coelho, E.; Zrostlikova, J.; Delgadillo, I.; Coimbra b, M.A., Comprehensive two-dimensional gas chromatography with time-of-flight mass spectrometry of monoterpenoids as a powerful tool for grape origin traceability, J. Chromatogr. A, 2007, 1161, 1-2, 292-299, https://doi.org/10.1016/j.chroma.2007.05.093 . [all data]

Boulanger, Chassagne, et al., 1999
Boulanger, R.; Chassagne, D.; Crouzet, J., Free and bound flavour components of amazonian fruits. 1: Bacuri, Flavour Fragr. J., 1999, 14, 5, 303-311, https://doi.org/10.1002/(SICI)1099-1026(199909/10)14:5<303::AID-FFJ834>3.0.CO;2-C . [all data]

Jensen, Christensen, et al., 2000
Jensen, K.; Christensen, L.P.; Hansen, M.; Jørgensen, U.; Kaack, K., Olfactory and quantitative analysis of volatiles in elderberry (Sambucus nigra L) juice processed from seven cultivars, J. Sci. Food Agric., 2000, 81, 2, 237-244, https://doi.org/10.1002/1097-0010(20010115)81:2<237::AID-JSFA809>3.0.CO;2-H . [all data]

Möllenbeck, König, et al., 1997
Möllenbeck, S.; König, T.; Schreier, P.; Schwab, W.; Rajaonarivony, J.; Ranarivelo, L., Chemical composition and analyses of enantiomers of essential oils from Madagascar, Flavour Fragr. J., 1997, 12, 2, 63-69, https://doi.org/10.1002/(SICI)1099-1026(199703)12:2<63::AID-FFJ614>3.0.CO;2-Z . [all data]

Kaack, Christensen, et al., 2005
Kaack, K.; Christensen, L.P.; Hughes, M.; Eder, R., The relationship between sensory quality and volatile compounds in raw juice processed from elderberries ( Sambucus nigra L.), Eur. Food Res. Technol., 2005, 221, 3-4, 244-254, https://doi.org/10.1007/s00217-005-1141-4 . [all data]

Karlsson, Birgersson, et al., 2009
Karlsson, M.F.; Birgersson, G.; Prado, A.M.C.; Bosa, F.; Bengtsson, M.; Witzgall, P., Plant Odor Analysis of Potato: Responce of Guatemalan Moth to Above- and Background Potato Volatiles, J. Agric. Food Chem., 2009, 57, 13, 5903-5909, https://doi.org/10.1021/jf803730h . [all data]

Vichi, Riu-Aumatell, et al., 2007
Vichi, S.; Riu-Aumatell, M.; Mora-Pons, M.; Guadayol, J.M.; Buxaderas, S.; López-Tamames, E., Analytical, Nutritional and Clinical Methods. HS-SPME coupled to GC/MS for quality control of Juniperus communis L. berries used for gin aromatization, Food Chem., 2007, 105, 4, 1748-1754, https://doi.org/10.1016/j.foodchem.2007.03.026 . [all data]

Mimica-Dukic, Bozin, et al., 2004
Mimica-Dukic, N.; Bozin, B.; Sokovic, M.; Simin, N., Antimicrobial and antioxidant activities of Melissa officinalis L. (Lamiaceae) essential oil, J. Agric. Food Chem., 2004, 52, 9, 2485-2489, https://doi.org/10.1021/jf030698a . [all data]

Perez-Alonso, Velasco-Negueruela, et al., 2003
Perez-Alonso, M.J.; Velasco-Negueruela, A.; Palá-Paúl, J.; Sanz, J., Variations in the essential oil composition of Artemisia pedemontana gathered in Spain: chemotype camphor-1,8-cineole and chemotype davanone, Biochem. Syst. Ecol., 2003, 31, 1, 77-84, https://doi.org/10.1016/S0305-1978(02)00082-0 . [all data]

Gupta, Mallavarapu, et al., 2001
Gupta, R.; Mallavarapu, G.R.; Banerjee, S.; Kumar, S., Characteristics of an isomenthone-rich somaclonal mutant isolated in a geraniol-rich rose-scented geranium accession of Pelargonium graveolens, Flavour Fragr. J., 2001, 16, 5, 319-324, https://doi.org/10.1002/ffj.1002 . [all data]

Wong and Lai, 1996
Wong, K.C.; Lai, F.Y., Volatile constituents from the fruits of four Syzygium species grown in Malaysia, Flavour Fragr. J., 1996, 11, 1, 61-66, https://doi.org/10.1002/(SICI)1099-1026(199601)11:1<61::AID-FFJ539>3.0.CO;2-1 . [all data]

Nishimura, 1995
Nishimura, O., Identification of the characteristic odorants in fresh rhizomes of ginger (Zingiber officinale Roscoe) using aroma extract dilution analysis and modified multidimensional gas chromatography-mass spectroscopy, J. Agric. Food Chem., 1995, 43, 11, 2941-2945, https://doi.org/10.1021/jf00059a031 . [all data]

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

Weyerstahl, Marschall, et al., 1998
Weyerstahl, P.; Marschall, H.; Weirauch, M.; Thefeld, K.; Surburg, H., Constituents of commercial Labdanum oil, Flavour Fragr. J., 1998, 13, 5, 295-318, https://doi.org/10.1002/(SICI)1099-1026(1998090)13:5<295::AID-FFJ751>3.0.CO;2-I . [all data]

Zenkevich, 1997
Zenkevich, I.G., Analytical Parameters of Components of Essential Oils for their Chromatographic and Chromato-Spectral Identificaiton. Oxsigenated derivatives of Mono- and Sesquiterpene Hydrocarbons, Rastit, Resursy (Rus.), 1997, 33, 1, 16-28. [all data]

Swigar and Silverstein, 1981
Swigar, A.A.; Silverstein, R.M., Monoterpenes, Aldrich Chemical Company, Milwaukee, WI, USA, 1981, 130. [all data]

Babu and Kaul, 2005
Babu, K.G.D.; Kaul, V.K., Variation in essential oil composition of rose-scented geranium (Pelargonium sp.) distilled by different distillation techniques, Flavour Fragr. J., 2005, 20, 2, 222-231, https://doi.org/10.1002/ffj.1414 . [all data]

Jirovetz, Buchbauer, et al., 2005
Jirovetz, L.; Buchbauer, G.; Stoyanova, A.; Balinova, A.; Guangjiun, Z.; Xihan, M., Solid phase microextraction/gas chromatographic and olfactory analysis of the scent and fixative properties of the essential oil of Rosa damascena L. from China, Flavour Fragr. J., 2005, 20, 1, 7-12, https://doi.org/10.1002/ffj.1375 . [all data]

Ram, Kumar, et al., 2005
Ram, P.; Kumar, B.; Naqvi, A.A.; Verma, R.S.; Patra, N.K., Post-harvest storage effect on quantity and quality of rose-scented geranium (Pelargonium sp. cv. 'Bourbon') oil in Uttaranchal, Flavour Fragr. J., 2005, 20, 6, 666-668, https://doi.org/10.1002/ffj.1544 . [all data]

Werkhoff, Güntert, et al., 1998
Werkhoff, P.; Güntert, M.; Krammer, G.; Sommer, H.; Kaulen, J., Vacuum headspace method in aroma research: flavor chemistry of yellow passion fruits, J. Agric. Food Chem., 1998, 46, 3, 1076-1093, https://doi.org/10.1021/jf970655s . [all data]

Kaack and Christensen, 2008
Kaack, K.; Christensen, L.P., Effect of packing materials and storage time on volatile compounds in tea processes from flowers of black elder (Sambucus nigra L.), Eur. Food Res. Technol., 2008, 227, 4, 1259-1273, https://doi.org/10.1007/s00217-008-0844-8 . [all data]

Notes

Go To: Top, Gas Chromatography, References

Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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