Cyclohexanol, 5-methyl-2-(1-methylethyl)-, (1α,2α,5β)-
- Formula: C10H20O
- Molecular weight: 156.2652
- IUPAC Standard InChIKey: NOOLISFMXDJSKH-UHFFFAOYSA-N
- CAS Registry Number: 491-01-0
- 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. - Species with the same structure:
- Stereoisomers:
- Cyclohexanol, 5-methyl-2-(1-methylethyl)-, (1α,2β,5α)-
- Cyclohexanol, 5-methyl-2-(1-methylethyl)-, [1R-(1α,2α,5β)]-
- Levomenthol
- Cyclohexanol, 5-methyl-2-(1-methylethyl)-, [1S-(1α,2α,5β)]-
- Cyclohexanol, 5-methyl-2-(1-methylethyl)-, [1S-(1α,2β,5β)]-
- Cyclohexanol, 5-methyl-2-(1-methylethyl)-, (1α,2β,5β)-
- Cyclohexanol, 5-methyl-2-(1-methylethyl)-, (1α,2α,5α)-
- Cyclohexanol, 5-methyl-2-(1-methylethyl)-, (1α,2β,5α)-
- Other names: Menthol, trans-1,3,trans-1,4-; Neo-Menthol
- Information on this page:
- Other data available:
- Options:
Gas Chromatography
Go To: Top, References, Notes
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, isothermal
Column type | Active phase | Temperature (C) | I | Reference | Comment |
---|---|---|---|---|---|
Capillary | SE-30 | 120. | 1153. | Tudor and Moldovan, 1999 | |
Capillary | SE-30 | 100. | 1152.8 | Tudor, 1997 | 40. m/0.35 mm/0.35 μm |
Kovats' RI, non-polar column, temperature ramp
Column type | Active phase | I | Reference | Comment |
---|---|---|---|---|
Capillary | BP-1 | 1157. | Rajeswara Rao, 2002 | 25. m/0.5 mm/0.25 μm, N2, 5. K/min, 220. C @ 10. min; Tstart: 60. C |
Capillary | BP-1 | 1157. | Rao B.R.R., 2002 | 25. m/0.5 mm/0.25 μm, 5. K/min, 220. C @ 10. min; Tstart: 60. C |
Capillary | OV-1 | 1153. | Bicchi, Frattini, et al., 1988 | 23. m/0.32 mm/0.3 μm, H2, 3. K/min; Tstart: 50. C; Tend: 200. C |
Kovats' RI, non-polar column, custom temperature program
Column type | Active phase | I | Reference | Comment |
---|---|---|---|---|
Capillary | BP-1 | 1152. | Dwivedi, Khan, et al., 2004 | 25. m/0.25 mm/0.25 μm, N2; Program: 60C => 5C/min => 220C(5min) => 3C/min => 245C(5min) |
Kovats' RI, polar column, temperature ramp
Column type | Active phase | I | Reference | Comment |
---|---|---|---|---|
Capillary | Supelcowax-20M | 1557. | Bicchi, Frattini, et al., 1988 | 23. m/0.32 mm/0.30 μm, H2, 50. C @ 1. min, 3. K/min; Tend: 200. C |
Van Den Dool and Kratz RI, non-polar column, temperature ramp
Column type | Active phase | I | Reference | Comment |
---|---|---|---|---|
Capillary | BP-1 | 1161. | Blanc, Bradesi, et al., 2006 | 50. m/0.22 mm/0.25 μm, 2. K/min, 220. C @ 20. min; Tstart: 60. C |
Capillary | DB-5 | 1176. | Agnihotri, Agarwal, et al., 2005 | 30. m/0.25 mm/0.25 μm, He, 90. C @ 2. min, 4. K/min; Tend: 220. C |
Capillary | HP-5MS | 1165. | Demetzos, Angelopoulou, et al., 2002 | 30. m/0.25 mm/0.25 μm, 50. C @ 5. min, 3. K/min; Tend: 280. C |
Capillary | BP-1 | 1156. | Baldovini, Ristorcelli, et al., 2000 | 50. m/0.22 mm/0.25 μm, 2. K/min, 220. C @ 20. min; Tstart: 60. C |
Van Den Dool and Kratz RI, non-polar column, custom temperature program
Column type | Active phase | I | Reference | Comment |
---|---|---|---|---|
Capillary | SE-52 | 1161. | Lorenzo, Paz, et al., 2002 | 30. m/0.32 mm/0.42 μm, H2; Program: 60C(8min) => 3C/min => 180C => 20C/min => 250C(10min) |
Van Den Dool and Kratz RI, polar column, temperature ramp
Column type | Active phase | I | Reference | Comment |
---|---|---|---|---|
Capillary | BP-20 | 1601. | Blanc, Bradesi, et al., 2006 | 50. m/0.22 mm/0.25 μm, 2. K/min, 220. C @ 20. min; Tstart: 60. C |
Capillary | DB-Wax | 1574. | 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 | BP-20 | 1594. | Baldovini, Ristorcelli, et al., 2000 | 50. m/0.22 mm/0.25 μm, 2. K/min, 220. C @ 20. min; Tstart: 60. C |
Van Den Dool and Kratz RI, polar column, custom temperature program
Column type | Active phase | I | Reference | Comment |
---|---|---|---|---|
Capillary | Carbowax 20M | 1599. | Lorenzo, Paz, et al., 2002 | 25. m/0.32 mm/0.25 μm, H2; Program: 40C(8min) => 3C/min => 180C => 20C/min => 230C |
Normal alkane RI, non-polar column, temperature ramp
Column type | Active phase | I | Reference | Comment |
---|---|---|---|---|
Capillary | HP-5 | 1166. | Bertoli, Lepnardi, et al., 2011 | 30. m/0.25 mm/0.25 μm, Helium, 3. K/min; Tstart: 60. C; Tend: 240. C |
Capillary | HP-5MS | 1170. | Bozin B., Mlmica-Dukic N., et al., 2007 | 30. m/0.25 mm/0.25 μm, He, 3. K/min; Tstart: 60. C; Tend: 280. C |
Capillary | HP-5MS | 1170. | Bozin, Mimicá-Dukic, et al., 2006 | 30. m/0.25 mm/0.25 μm, He, 3. K/min; Tstart: 60. C; Tend: 280. C |
Capillary | DB-5 | 1164. | Salehi, Sefidkon, et al., 2005 | 30. m/0.25 mm/0.25 μm, He, 60. C @ 4. min, 3. K/min; Tend: 220. C |
Capillary | DB-1 | 1160. | Salehi, Sonboli, et al., 2005 | 60. m/0.25 mm/0.25 μm, He, 5. K/min, 250. C @ 10. min; Tstart: 60. C |
Capillary | PE-5 | 1198. | Singh, Raina, et al., 2005 | 30. m/0.32 mm/0.25 μm, H2, 60. C @ 2. min, 5. K/min, 230. C @ 4. min |
Capillary | BP-1 | 1154. | Gupta, Mallavarapu, et al., 2001 | 30. m/0.25 mm/0.25 μm, N2, 5. K/min; Tstart: 60. C; Tend: 220. C |
Capillary | OV-101 | 1151. | Orav and Kann, 2001 | He, 2. K/min; Column length: 50. m; Column diameter: 0.2 mm; Tstart: 50. C; Tend: 250. C |
Capillary | OV-1 | 1159. | Oberhofer, Nikiforov, et al., 1999 | 25. m/0.25 mm/0.25 μm, H2, 40. C @ 5. min, 3. K/min, 220. C @ 5. min |
Capillary | BP-1 | 1156. | Rao, Bhattacharya, et al., 1999 | N2, 5. K/min, 220. C @ 10. min; Column length: 25. m; Column diameter: 0.5 mm; Tstart: 60. C |
Capillary | DB-1 | 1156. | Stashenko, Puertas, et al., 1996 | 60. m/0.25 mm/0.25 μm, He, 50. C @ 5. min, 2.5 K/min; Tend: 250. C |
Capillary | OV-101 | 1154. | De Pooter and Schamp, 1986 | 30. m/0.5 mm/0.8 μm, He, 2. K/min; Tstart: 40. C; Tend: 220. C |
Capillary | OV-101 | 1154. | De Pooter and Schamp, 1986 | 30. m/0.5 mm/0.8 μm, He, 2. K/min; Tstart: 40. C; Tend: 220. C |
Normal alkane RI, non-polar column, custom temperature program
Column type | Active phase | I | Reference | Comment |
---|---|---|---|---|
Capillary | SE-52 | 1166. | Tognolini, Barocelli, et al., 2006 | 30. m/0.32 mm/0.15 μm, He; Program: 45C => 1C/min => 100C => 5C/min => 250C (10min) |
Capillary | SE-30 | 1157. | Vinogradov, 2004 | Program: not specified |
Capillary | Polydimethyl siloxanes | 1157. | Zenkevich, 1997 | Program: not specified |
Capillary | OV-101 | 1159. | Shibamoto, 1987 | Column length: 60. m; Column diameter: 0.25 mm; Program: not specified |
Packed | OV-101 | 1159. | 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
Column type | Active phase | I | Reference | Comment |
---|---|---|---|---|
Capillary | CP-Wax | 1570. | Ka, Choi, et al., 2005 | 30. m/0.32 mm/0.25 μm, He, 40. C @ 2. min, 5. K/min; Tend: 180. C |
Capillary | DB-Wax | 1586. | Salehi, Sonboli, et al., 2005 | 30. m/0.25 mm/0.25 μm, He, 4. K/min, 250. C @ 10. min; Tstart: 40. C |
Capillary | Carbowax 20M | 1559. | Kasali, Oyedeji, et al., 2001 | 30. m/0.25 mm/0.25 μm, He, 4. K/min; Tstart: 50. C; Tend: 215. C |
Capillary | PEG-20M | 1590. | Orav and Kann, 2001 | He, 2. K/min; Column length: 50. m; Column diameter: 0.2 mm; Tstart: 70. C; Tend: 220. C |
Capillary | BP-20 | 1560. | Rao, Bhattacharya, et al., 1999 | N2, 5. K/min; Column length: 25. m; Column diameter: 0.5 mm; Tstart: 60. C; Tend: 200. C |
Capillary | HP-Innowax FSC | 1604. | 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 |
Capillary | DB-Wax | 1551. | Stashenko, Puertas, et al., 1996 | 60. m/0.25 mm/0.25 μm, He, 50. C @ 5. min, 2.5 K/min; Tend: 180. C |
Capillary | Carbowax 20M | 1559. | Shibamoto, 1987 | 2. K/min; Column length: 50. m; Column diameter: 0.25 mm; Tstart: 80. C; Tend: 200. C |
Normal alkane RI, polar column, custom temperature program
Column type | Active phase | I | Reference | Comment |
---|---|---|---|---|
Capillary | Carbowax 20M | 1589. | Vinogradov, 2004 | Program: not specified |
References
Go To: Top, Gas Chromatography, Notes
Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
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]
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]
Bicchi, Frattini, et al., 1988
Bicchi, C.; Frattini, C.; Nano, G.M.; D'Amato, A.,
On column injection-dual channel analysis of essential oils,
J. Hi. Res. Chromatogr. Chromatogr. Comm., 1988, 11, 1, 56-60, https://doi.org/10.1002/jhrc.1240110115
. [all data]
Dwivedi, Khan, et al., 2004
Dwivedi, S.; Khan, M.; Srivastava, S.K.; Syamasunnder, K.V.; Srivastava, A.,
Essential oil composition of different accessions of Mentha × piperita L. grown on the northern plains of India,
Flavour Fragr. J., 2004, 19, 5, 437-440, https://doi.org/10.1002/ffj.1333
. [all data]
Blanc, Bradesi, et al., 2006
Blanc, M.-C.; Bradesi, P.; Goncalves, M.J.; Salgueiro, L.; Casanova, J.,
Essential oil of Dittrichia viscosa ssp. viscosa: analysis by 13C-NMR and antimicrobial activity,
Flavour Fragr. J., 2006, 21, 2, 324-332, https://doi.org/10.1002/ffj.1605
. [all data]
Agnihotri, Agarwal, et al., 2005
Agnihotri, V.K.; Agarwal, S.G.; Dhar, P.L.; Thappa, R.K.; Baleshwar; Kapahi, B.K.; Saxena, R.K.; Qazi, G.N.,
Essential oil composition of Mentha pulegium L. growing wild in the north-western Himalayas India,
Flavour Fragr. J., 2005, 20, 6, 607-610, https://doi.org/10.1002/ffj.1497
. [all data]
Demetzos, Angelopoulou, et al., 2002
Demetzos, C.; Angelopoulou, D.; Perdetzoglou, D.,
A comparative study of the essential oils of Cistus salviifolius in several populations of Crete (Greece),
Biochem. Syst. Ecol., 2002, 30, 7, 651-665, https://doi.org/10.1016/S0305-1978(01)00145-4
. [all data]
Baldovini, Ristorcelli, et al., 2000
Baldovini, N.; Ristorcelli, D.; Tomi, F.; Casanova, J.,
Infraspecific variability of the essential oil of Calamintha nepeta from Corsica (France),
Flavour Fragr. J., 2000, 15, 1, 50-54, https://doi.org/10.1002/(SICI)1099-1026(200001/02)15:1<50::AID-FFJ871>3.0.CO;2-F
. [all data]
Lorenzo, Paz, et al., 2002
Lorenzo, D.; Paz, D.; Dellacassa, E.; Davies, P.; Vila, R.; Cañigueral, S.,
Essential oils of Mentha pulegium and Mentha rotundifolia from Uruguay,
Braz. Arch. Biol. Technol., 2002, 45, 4, 519-524, https://doi.org/10.1590/S1516-89132002000600016
. [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]
Bertoli, Lepnardi, et al., 2011
Bertoli, A.; Lepnardi, M.; Krzyzanowska, J.; Oleszek, W.; Pistelli, L.,
Mentha longifolia in vitro cultures as safe source of flavouring ingradients,
Acta Biochem. Polonica, 2011, 58, 4, 581-587. [all data]
Bozin B., Mlmica-Dukic N., et al., 2007
Bozin B.; Mlmica-Dukic N.; Samojlik I.; Jovin E.,
Antimicrobial and antioxidant properties of rosemary and sage (Rosmarinus officinalis L. and Salvia officinalis L., lamiaceae) essential oils,
J. Agric. Food Chem., 2007, 55, 19, 7879-7885, https://doi.org/10.1021/jf0715323
. [all data]
Bozin, Mimicá-Dukic, et al., 2006
Bozin, B.; Mimicá-Dukic, N.; Simin, N.; Anackov, G.,
Characterization of the volatile composition of essential oils of some lamiaceae spices and the antimicrobial and antioxidant activities of the entire oils,
J. Agric. Food Chem., 2006, 54, 5, 1822-1828, https://doi.org/10.1021/jf051922u
. [all data]
Salehi, Sefidkon, et al., 2005
Salehi, P.; Sefidkon, F.; Bazzaz Tolami, L.; Sonboli, A.,
Essential oil composition of Salvia palaestina Benth. from Iran,
Flavour Fragr. J., 2005, 20, 5, 525-527, https://doi.org/10.1002/ffj.1448
. [all data]
Salehi, Sonboli, et al., 2005
Salehi, P.; Sonboli, A.; Eftekhar, F.; Nejad-Ebrahimi, S.; Yousefzadi, M.,
Essential Oil Composition, Antibacterial and Antioxidant Activity of the Oil and Various Extracts of Ziziphora clinopodioides subsp. rigida (BOISS.) RECH. f. from Iran,
Biol. Pharm. Bull., 2005, 28, 10, 1892-1896, https://doi.org/10.1248/bpb.28.1892
. [all data]
Singh, Raina, et al., 2005
Singh, A.K.; Raina, V.K.; Naqvi, A.A.; Patra, N.K.; Kumar, B.; Ram, P.; Khanuja, S.P.S.,
Essential oil composition and chemoarrays of menthol mint (Mentha arvensis L. f. piperascens Malinvaud ex. Holmes) cultivars,
Flavour Fragr. J., 2005, 20, 3, 302-305, https://doi.org/10.1002/ffj.1417
. [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]
Orav and Kann, 2001
Orav, A.; Kann, J.,
Determination of peppermint and orange aroma compounds in food and beverages,
Proc. Est. Acad. Sci. Chem., 2001, 50, 4, 217-225. [all data]
Oberhofer, Nikiforov, et al., 1999
Oberhofer, B.; Nikiforov, A.; Buchbauer, G.; Jirovetz, L.; Bicchi, C.,
Investigation of the alteration of the composition of various essential oils used in aroma lamp applications,
Flavour Fragr. J., 1999, 14, 5, 293-299, https://doi.org/10.1002/(SICI)1099-1026(199909/10)14:5<293::AID-FFJ829>3.0.CO;2-T
. [all data]
Rao, Bhattacharya, et al., 1999
Rao, B.R.R.; Bhattacharya, A.K.; Mallavarapu, G.R.; Ramesh, S.,
Volatile constituents of different parts of cornmint (Mentha arvensis L.),
Flavour Fragr. J., 1999, 14, 5, 262-264, https://doi.org/10.1002/(SICI)1099-1026(199909/10)14:5<262::AID-FFJ766>3.0.CO;2-6
. [all data]
Stashenko, Puertas, et al., 1996
Stashenko, E.E.; Puertas, M.A.; Combariza, M.Y.,
Volatile secondary metabolites from Spilanthes americana obtained by simultaneous steam distillation--solvent extraction and supercritical fluid extraction,
J. Chromatogr. A, 1996, 752, 1-2, 223-232, https://doi.org/10.1016/S0021-9673(96)00480-3
. [all data]
De Pooter and Schamp, 1986
De Pooter, H.L.; Schamp, N.M.,
Comparison of the Volatile Composition of Some Calamintha/Satureja Species,
Prog. Essnt. Oil. Res., 1986, 139-150. [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]
Vinogradov, 2004
Vinogradov, B.A.,
Production, composition, properties and application of essential oils, 2004, retrieved from http://viness.narod.ru. [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]
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]
Swigar and Silverstein, 1981
Swigar, A.A.; Silverstein, R.M.,
Monoterpenes, Aldrich Chemical Company, Milwaukee, WI, USA, 1981, 130. [all data]
Ka, Choi, et al., 2005
Ka, M.-H.; Choi, E.H.; Chun, H.-S.; Lee, K.-G.,
Antioxidative Activity of Volatile Extracts Isolated from Angelica tenuissimae Roots, Peppermint Leaves, Pine Needles, and Sweet Flag Leaves,
J. Agric. Food Chem., 2005, 53, 10, 4124-4129, https://doi.org/10.1021/jf047932x
. [all data]
Kasali, Oyedeji, et al., 2001
Kasali, A.A.; Oyedeji, A.O.; Ashilokun, A.O.,
Volatile leaf oil constituents of Cymbopogon citratus (DC) Stapf,
Flavour Fragr. J., 2001, 16, 5, 377-378, https://doi.org/10.1002/ffj.1019
. [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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