Cyclohexanol, 1-methyl-4-(1-methylethylidene)-

Formula: C₁₀H₁₈O
Molecular weight: 154.2493
IUPAC Standard InChI: InChI=1S/C10H18O/c1-8(2)9-4-6-10(3,11)7-5-9/h11H,4-7H2,1-3H3
IUPAC Standard InChIKey: NNRLDGQZIVUQTE-UHFFFAOYSA-N
CAS Registry Number: 586-81-2
Chemical structure:
This structure is also available as a 2d Mol file
Other names: γ-Terpineol; 1-Methyl-4-(1-methylethylidene)cyclohexanol; 1-methyl-4-(1-methylethylidene)cyclohexan-1-ol
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Information on this page:
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, non-polar column, isothermal

Column type	Active phase	Temperature (C)	I	Reference	Comment
Capillary	SE-30	120.	1185.	Tudor and Moldovan, 1999
Capillary	SE-30	100.	1185.4	Tudor, 1997	40. m/0.35 mm/0.35 μm
Packed	SE-30	100.	1181.	Pías and Gascó, 1975	Ar, Chromosorb W AW DMCS HP (80-100 mesh); Column length: 1. m
Packed	SE-30	120.	1187.	Pías and Gascó, 1975	Ar, Chromosorb W AW DMCS HP (80-100 mesh); Column length: 1. m
Packed	SE-30	140.	1195.	Pías and Gascó, 1975	Ar, Chromosorb W AW DMCS HP (80-100 mesh); Column length: 1. m

Kovats' RI, non-polar column, temperature ramp

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Column type	Active phase	I	Reference	Comment
Capillary	PTE-5	1178.	Gudzic, Dordevic, et al., 2001	60. m/0.32 mm/0.39 μm, H2, 4.3 K/min; T_start: 60. C; T_end: 285. C

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

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Column type	Active phase	I	Reference	Comment
Packed	SE-30	1183.	Ramsey, Lee, et al., 1980	He, Chromosorb G HP (80-100 mesh); Column length: 1.5 m; Program: not specified

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

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Column type	Active phase	I	Reference	Comment
Capillary	SPB-5	1192.	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	CP Sil 5 CB	1177.	Pino, Marbot, et al., 2002	50. m/0.32 mm/0.4 μm, He, 60. C @ 10. min, 3. K/min, 280. C @ 60. min

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

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Column type	Active phase	I	Reference	Comment
Capillary	HP-5MS	1217.6	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)
Capillary	5 % Phenyl methyl siloxane	1199.	Sacchetti, Maietti, et al., 2005	30. m/0.32 mm/0.15 μm, He; Program: 45C => 1C/min => 100C => 5C/min => 250C (10min)

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

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Column type	Active phase	I	Reference	Comment
Capillary	ZB-Wax	1696.	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

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

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Column type	Active phase	I	Reference	Comment
Capillary	DB-Wax	1683.	Ferrari, Lablanquie, et al., 2004	60. m/0.25 mm/0.25 μm, He; Program: 35C(0.7min) => 20C/min => 70C => 4C/min => 240C

Normal alkane RI, non-polar column, temperature ramp

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Column type	Active phase	I	Reference	Comment
Capillary	HP-5 MS	1199.	Phungpanya, Thongpoon, et al., 2012	30. m/0.25 mm/0.25 μm, Helium, 2. K/min; T_start: 50. C; T_end: 180. C
Capillary	HP-5	1198.	Monsef-Esfahani, Miri, et al., 2010	30. m/0.25 mm/0.25 μm, Helium, 50. C @ 5. min, 3. K/min; T_end: 240. C
Capillary	HP-5 MS	1195.	Pripdeevech, Chumpolsri, et al., 2010	30. m/0.25 mm/0.25 μm, Helium, 2. K/min; T_start: 100. C; T_end: 220. C
Capillary	HP-5 MS	1203.	Radulovic, Blagojevic, et al., 2010	30. m/0.25 mm/0.25 μm, Helium, 5. K/min, 290. C @ 10. min; T_start: 70. C
Capillary	DB-5 MS	1207.	Patil, Jayaprakasha, et al., 2009	60. m/0.25 mm/0.25 μm, Helium, 40. C @ 12. min, 2. K/min, 330. C @ 30. min
Capillary	DB-5	1159.	Yadegarinia, Gachkar, et al., 2006	30. m/0.25 mm/0.25 μm, He, 4. K/min; T_start: 40. C; T_end: 250. C
Capillary	SPB-5	1205.	Cornu, Kondjoyan, et al., 2005	60. m/0.32 mm/1. μm, He, 40. C @ 5. min, 3. K/min; T_end: 230. C
Capillary	DB-5	1199.	Morteza-Semnani and Saeedi, 2005	30. m/0.25 mm/0.25 μm, He, 60. C @ 4. min, 4. K/min; T_end: 220. C
Capillary	DB-1	1170.	Mahalwal and Ali, 2003	30. m/0.25 mm/0.25 μm, N2, 4. K/min; T_start: 80. C; T_end: 250. C
Capillary	HP-5	1188.	Velickovic, Ristic, et al., 2003	25. m/0.32 mm/0.53 μm, Helium, 4. K/min; T_start: 40. C; T_end: 280. C
Capillary	HP-5	1188.	Velickovic, Ristic, et al., 2003	25. m/0.32 mm/0.53 μm, Helium, 4. K/min; T_start: 40. C; T_end: 280. C
Capillary	HP-5	1188.	Velickovic, Ristic, et al., 2003	25. m/0.32 mm/0.53 μm, Helium, 4. K/min; T_start: 40. C; T_end: 280. C
Capillary	HP-5	1189.	Velickovic, Ristic, et al., 2003	25. m/0.32 mm/0.53 μm, Helium, 4. K/min; T_start: 40. C; T_end: 280. C
Capillary	DB-1	1169.	Palá-Paúl, Pérez-Alonso, et al., 2001	30. m/0.25 mm/0.25 μm, N2, 4. K/min; T_start: 80. C; T_end: 225. C
Capillary	DB-1	1169.	Palá-Paúl, Pérez-Alonso, et al., 1999	50. m/0.25 mm/0.25 μm, He, 4. K/min; T_start: 70. C; T_end: 240. C
Capillary	OV-101	1187.	Zenkevich, Kosman, et al., 1999	He, 6. K/min; Column length: 25. m; Column diameter: 0.20 mm; T_start: 80. C; T_end: 240. C

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

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Column type	Active phase	I	Reference	Comment
Capillary	DB-1	1201.	Rao, Maia, et al., 2007	30. m/0.25 mm/0.25 μm, Helium; Program: 35 0C 4 0C/min -> 180 0C 10 0C/min -> 250 0C
Capillary	CP Sil 8 CB	1196.	Judzentiene and Buzelyte, 2006	50. m/0.32 mm/0.25 μm, He; Program: 60C(2min) => 5C/min => 160C(1min) => 10C/min => 250C (5min)
Capillary	SE-52	1199.	Tognolini, Barocelli, et al., 2006	30. m/0.32 mm/0.15 μm, He; Program: 45C => 1C/min => 100C => 5C/min => 250C (10min)
Capillary	DB-5MS	1197.	Bagci and Baser, 2005	30. m/0.25 mm/0.25 μm; Program: 70C(2min) => 10C/min => 150C(15min) => 5C/min => 240C
Capillary	SE-30	1161.	Vinogradov, 2004	Program: not specified
Capillary	SE-30	1174.	Vinogradov, 2004	Program: not specified
Capillary	SE-30	1178.	Li, Wu, et al., 2002	He; Column length: 60. m; Column diameter: 0.25 mm; Program: 50 0C (5 min) 5 0C/min -> 165 0C 4 0C/min -> 230 0C
Capillary	SE-30	1177.	Li, Wu, et al., 2002	He; Column length: 60. m; Column diameter: 0.25 mm; Program: not specified
Capillary	DB-5	1180.	Isidorov, Zenkevich, et al., 1997	Program: not specified
Capillary	Polydimethyl siloxanes	1174.	Zenkevich, 1997	Program: not specified
Capillary	OV-1	1146.	De Pooter and Schamp, 1987	35. m/0.50 mm/1.5 μm; Program: not specified
Capillary	OV-101	1160.	Shibamoto, 1987	Program: not specified
Other	Methyl Silicone	1183.	Ardrey and Moffat, 1981	Program: not specified

Normal alkane RI, polar column, temperature ramp

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Column type	Active phase	I	Reference	Comment
Capillary	DB-Wax	1695.	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	HP-Innowax FSC	1684.	Baser, Kirimer, et al., 1997	He, 60. C @ 10. min, 4. K/min, 240. C @ 10. min; Column length: 60. m; Column diameter: 0.25 mm

Normal alkane RI, polar column, custom temperature program

View large format table.

Column type	Active phase	I	Reference	Comment
Capillary	DB-Wax	1683.	Zhao, Xu, et al., 2009	30. m/0.25 mm/0.25 μm, Helium; Program: not specified
Capillary	Carbowax 20M	1655.	Vinogradov, 2004	Program: not specified

References

Go To: Top, Gas Chromatography, Notes

Tudor and Moldovan, 1999
Tudor, E.; Moldovan, D., Temperature Dependence of the Retention Index for Perfumery Compounds on a Se-30 Glass Capillary Column. II. The Hyperbolic Equation, J. Chromatogr., 1999, 848, 1-2, 215-227, https://doi.org/10.1016/S0021-9673(99)00412-4 . [all data]

Tudor, 1997
Tudor, E., Temperature dependence of the retention index for perfumery compounds on a SE-30 glass capillary column. I. Linear equations, J. Chromatogr. A, 1997, 779, 1-2, 287-297, https://doi.org/10.1016/S0021-9673(97)00453-6 . [all data]

Pías and Gascó, 1975
Pías, J.B.; Gascó, L., GC Retention Data of Alcohols and Benzoyl Derivatives of Alcohols, J. Chromatogr. - Chrom. Data, 1975, d14-d16. [all data]

Gudzic, Dordevic, et al., 2001
Gudzic, B.; Dordevic, S.; Palic, R.; Stojanovic, G., Essential oils of Hypericum olympicum L. and Hypericum perforatum L., Flavour Fragr. J., 2001, 16, 3, 201-203, https://doi.org/10.1002/ffj.978 . [all data]

Ramsey, Lee, et al., 1980
Ramsey, J.D.; Lee, T.D.; Osselton, M.D.; Moffat, A.C., Gas-liquid chromatographic retention indices of 296 non-drug substances on SE-30 or OV-1 likely to be encountered in toxicological analyses, J. Chromatogr., 1980, 184, 2, 185-206, https://doi.org/10.1016/S0021-9673(00)85641-1 . [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]

Pino, Marbot, et al., 2002
Pino, J.A.; Marbot, R.; Vázquez, C., Characterization of volatile in Cosa Rican Guava [Psidium friedrichsthalianum (Berg) Niedenzu] fruit, J. Agric. Food Chem., 2002, 50, 21, 6023-6026, https://doi.org/10.1021/jf011456i . [all data]

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

Sacchetti, Maietti, et al., 2005
Sacchetti, G.; Maietti, S.; Muzzoli, M.; Scaglianti, M.; Manfredini, S.; Radice, M.; Bruni, R., Comparative evaluation of 11 essential oils of different origin as functional antioxidants, antiradicals and antimicrobials in foods, Food Chem., 2005, 91, 4, 621-632, https://doi.org/10.1016/j.foodchem.2004.06.031 . [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]

Ferrari, Lablanquie, et al., 2004
Ferrari, G.; Lablanquie, O.; Cantagrel, R.; Ledauphin, J.; Payot, T.; Fournier, N.; Guichard, E., Determination of key odorant compounds in freshly distilled cognac using GC-O, GC-MS, and sensory evaluation, J. Agric. Food Chem., 2004, 52, 18, 5670-5676, https://doi.org/10.1021/jf049512d . [all data]

Phungpanya, Thongpoon, et al., 2012
Phungpanya, C.; Thongpoon, C.; Pripdeevech, P.; Machan, T., Analysis of aroma volatiles from fresh leaves of Plectranthus amboinicus using solid phase microextraction (SPME) technique, Pure and Applied Chemistry International Conference 2012 (PACCON 2012), 2012, 16701672. [all data]

Monsef-Esfahani, Miri, et al., 2010
Monsef-Esfahani, H.R.; Miri, A.; Amini, M.; Amanzadeh, Y.; Hadjiakhoondi, A.; Hajiaghaee, R.; Ajani, Y., Seasonal variations in the chemical composition, antioxidant activity and total phenolic content of Teucrium persicum Boiss. essential oils, Res. J. Biol. Sci., 2010, 5, 7, 492-498, https://doi.org/10.3923/rjbsci.2010.492.498 . [all data]

Pripdeevech, Chumpolsri, et al., 2010
Pripdeevech, P.; Chumpolsri, W.; Suttiarporn, P.; Wongpornchai, S., The chemical composition and antioxidant activities of Basil from Thailand using retention indices and comprehensive two-dimensional gas chromatography, J. Seb. Chem. Soc., 2010, 75, 11, 1503-1513, https://doi.org/10.2298/JSC100203125P . [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]

Patil, Jayaprakasha, et al., 2009
Patil, J.R.; Jayaprakasha, G.K.; Murthy, K.N.C.; Tichy, S.E.; Chetti, M.B.; Patil, B.S., Apoptosis-mediated proliferation inhibition of human colon cancer cells by volatile principles of Citrus auratifolia, Food Chem., 2009, 114, 4, 1351-1358, https://doi.org/10.1016/j.foodchem.2008.11.033 . [all data]

Yadegarinia, Gachkar, et al., 2006
Yadegarinia, D.; Gachkar, L.; Rezaei, M.B.; Taghizadeh, M.; Astaneh, S.A.; Rasooli, I., Biochemical activities of Iranian Mentha piperita L. and Myrtus communis L. essential oils, Phytochemistry, 2006, 67, 12, 1249-1255, https://doi.org/10.1016/j.phytochem.2006.04.025 . [all data]

Cornu, Kondjoyan, et al., 2005
Cornu, A.; Kondjoyan, N.; Martin, B.; Verdier-Metz, I.; Pradel, P.; Berdague, J.-L.; Coulon, J.-B., Terpene profiles in Cantal and Saint-Nectairetype cheese made from raw or pasteurised milk, J. Sci. Food Agric., 2005, 85, 12, 2040-2046, https://doi.org/10.1002/jsfa.2214 . [all data]

Morteza-Semnani and Saeedi, 2005
Morteza-Semnani, K.; Saeedi, M., The essential oil composition of Phlomis bruguieri Desf. from Iran, Flavour Fragr. J., 2005, 20, 3, 344-346, https://doi.org/10.1002/ffj.1459 . [all data]

Mahalwal and Ali, 2003
Mahalwal, V.S.; Ali, M., Volatile constituents of Cymbopogon nardus (Linn.) rendle, Flavour Fragr. J., 2003, 18, 1, 73-76, https://doi.org/10.1002/ffj.1144 . [all data]

Velickovic, Ristic, et al., 2003
Velickovic, A.S.; Ristic, M.S.; Velickovic, D.T.; Ilic, S.; Mitic, N.D., The possibilities of the application of some species of sage (Salvia L.) as auxiliaries in the treatment of some diseases, J. Serb. Chem. Soc., 2003, 68, 6, 435-445, https://doi.org/10.2298/JSC0306435V . [all data]

Palá-Paúl, Pérez-Alonso, et al., 2001
Palá-Paúl, J.; Pérez-Alonso, M.J.; Velasco-Negueruela, A.; Palá-Paúl, R.; Sanz, J.; Conejero, Fco., Seasonal variation in chemical constituents of Santolina rosmarinifolia L. ssp. rosmarinifolia, Biochem. Syst. Ecol., 2001, 29, 7, 663-672, https://doi.org/10.1016/S0305-1978(01)00032-1 . [all data]

Palá-Paúl, Pérez-Alonso, et al., 1999
Palá-Paúl, J.; Pérez-Alonso, M.J.; Velasco-Negueruela, A.; Ramos-Vázquez, P.; Gómez-Contreras, F.; Sanz, J., Essential oil of Santolina rosmarinifolia L. ssp. rosmarinifolia: first isolation of capillene, a diacetylene derivative, Flavour Fragr. J., 1999, 14, 2, 131-134, https://doi.org/10.1002/(SICI)1099-1026(199903/04)14:2<131::AID-FFJ794>3.0.CO;2-7 . [all data]

Zenkevich, Kosman, et al., 1999
Zenkevich, I.G.; Kosman, V.M.; Tkachenko, K.G., Some Features of Quantitative Analysis of Essential Oil's Components in High Performance Liquid Chromatography, Rastitelnye Resursy (Plant resources), 1999, 35, 1, 128-137. [all data]

Rao, Maia, et al., 2007
Rao, V.S.; Maia, J.L.; Oliveira, F.A.; Lemos, T.L.G.; Chaves, M.H.; Santos, F.A., Composition and antinociceptive activity of the essential oil from Protium heptaphyllum resin, Natural Product Communications, 2007, 2, 12, 1199-1202. [all data]

Judzentiene and Buzelyte, 2006
Judzentiene, A.; Buzelyte, J., Chemical composition of essential oils of Artemisia vulgaris L. (mugwort) from North Lithuania, Chemija, 2006, 17, 1, 12-15. [all data]

Tognolini, Barocelli, et al., 2006
Tognolini, M.; Barocelli, E.; Ballabeni, V.; Bruni, R.; Bianchi, A.; Chiavarini, M.; Impicciatore, M., Comparative screening of plant essential oils: Phenylpropanoid moiety as basic core for antiplatelet activity, Life Sciences, 2006, 78, 13, 1419-1432, https://doi.org/10.1016/j.lfs.2005.07.020 . [all data]

Bagci and Baser, 2005
Bagci, E.; Baser, K.H.C., Study of the essential oils of Thymus haussknechtii Velen and Thymus kotschyanus Boiss. et Hohen var. kotschyanus (Lamiaceae) taxa from the eastern Anatolian region in Turkey, Flavour Fragr. J., 2005, 20, 2, 199-202, https://doi.org/10.1002/ffj.1397 . [all data]

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

Li, Wu, et al., 2002
Li, C.; Wu, H.; Yang, L.; ren, Y., Study of the composition of ginger oil from Laifeng, Flavour Fragr. Cosmetics, 2002, 5, 15-17. [all data]

Isidorov, Zenkevich, et al., 1997
Isidorov, V.; Zenkevich, I.; Sacharevich, T., Calculation of Gas Chromatographic Retention Indices for Monoterpenes and Terpenoids from Their Physico-Chemical Constants, Chem. Anal. (Warsaw), 1997, 42, 627-634. [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]

De Pooter and Schamp, 1987
De Pooter, H.L.; Schamp, N.M., The Essential Oil of Mentha X villosa nm. alopecuroides, Flavour Fragr. J., 1987, 2, 4, 163-165, https://doi.org/10.1002/ffj.2730020405 . [all data]

Shibamoto, 1987
Shibamoto, T., Retention Indices in Essential Oil Analysis in Capillary Gas Chromatography in Essential Oil Analysis, Sandra, P.; Bicchi, C., ed(s)., Hutchig Verlag, Heidelberg, New York, 1987, 259-274. [all data]

Ardrey and Moffat, 1981
Ardrey, R.E.; Moffat, A.C., Gas-liquid chromatographic retention indices of 1318 substances of toxicological interest on SE-30 or OV-1 stationary phase, J. Chromatogr., 1981, 220, 3, 195-252, https://doi.org/10.1016/S0021-9673(00)81925-1 . [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]

Baser, Kirimer, et al., 1997
Baser, K.H.C.; Kirimer, N.; Duman, H., Composition of the essential oil of Micromeria dolichodontha P. H. Davis, Flavour Fragr. J., 1997, 12, 4, 289-291, https://doi.org/10.1002/(SICI)1099-1026(199707)12:4<289::AID-FFJ640>3.0.CO;2-A . [all data]

Notes

Go To: Top, Gas Chromatography, References

Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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