Cyclohexanol, 5-methyl-2-(1-methylethyl)-, (1α,2β,5β)-

Formula: C₁₀H₂₀O
Molecular weight: 156.2652
IUPAC Standard InChI: InChI=1S/C10H20O/c1-7(2)9-5-4-8(3)6-10(9)11/h7-11H,4-6H2,1-3H3/t8-,9-,10+/m1/s1
IUPAC Standard InChIKey: NOOLISFMXDJSKH-BBBLOLIVSA-N
CAS Registry Number: 490-99-3
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: Menthol, trans-1,3,cis-1,4-; Isomenthol; Isomentol; 2-Isopropyl-5-methylcyclohexanol, (1α,2β,5β)-
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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, non-polar column, temperature ramp

Column type	Active phase	I	Reference	Comment
Capillary	BP-1	1174.	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	1174.	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	HP-5	1182.	Kitic, Palic, et al., 2001	25. m/0.32 mm/0.52 μm, H2, 4. K/min; T_start: 40. C; T_end: 240. C

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

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Column type	Active phase	I	Reference	Comment
Capillary	SF-96	1182.	Malingré and Maarse, 1974	Column length: 150. m; Column diameter: 0.75 mm; Program: not specified

Kovats' RI, polar column, isothermal

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Column type	Active phase	Temperature (C)	I	Reference	Comment
Capillary	Carbowax 20M	130.	1667.	Malingré and Maarse, 1974	Column length: 150. m; Column diameter: 0.75 mm

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

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Column type	Active phase	I	Reference	Comment
Capillary	SE-54	1178.	Simionatto, Porto, et al., 2005	25. m/0.25 mm/0.2 μm, H2, 4. K/min; T_start: 50. C; T_end: 250. C
Capillary	HP-5MS	1221.	Garland, Menary, et al., 2004	30. m/0.22 mm/0.25 μm, N2, 60. C @ 1. min, 20. K/min, 290. C @ 10. min
Capillary	SE-52	1155.	Duru, Cakir, et al., 2002	25. m/0.32 mm/0.15 μm, N2, 45. C @ 5. min, 3. K/min, 200. C @ 20. min
Capillary	SPB-Sulfur	1182.2	de Lacy Costello, Evans, et al., 2001	30. m/0.32 mm/4. μm, 40. C @ 12.5 min, 4. K/min; T_end: 200. C
Capillary	HP-5	1192.	Song, Sawamura, et al., 2000	30. m/0.25 mm/0.25 μm, He, 2. K/min; T_start: 70. C; T_end: 230. C

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

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Column type	Active phase	I	Reference	Comment
Capillary	SE-52	1188.	Guerrini, Sacchetti, et al., 2006	30. m/0.32 mm/0.15 μm, He; Program: 45C => 1C/min => 100C => 5C/min => 250C (10min)
Capillary	SE-52	1192.	Mondello, Dugo, et al., 1995	60. m/0.32 mm/0.40 μm, He; Program: 45 C (6 min) 3 C/min -> 111 0C 2 C/min -> 160 C 3 C/min -> 300 C (15 min)

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

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Column type	Active phase	I	Reference	Comment
Capillary	Carbowax 20M	1655.	Mondello, Dugo, et al., 1995	60. m/0.32 mm/0.425 μm, He, 45. C @ 3. min, 3. K/min, 300. C @ 20. min

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

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Column type	Active phase	I	Reference	Comment
Capillary	CP-Wax 52CB	1639.	Romeo, Ziino, et al., 2007	60. m/0.25 mm/0.25 μm, He; Program: 45C(5min) => 10C/min => 80C => 2C/min => 240C

Normal alkane RI, non-polar column, temperature ramp

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Column type	Active phase	I	Reference	Comment
Capillary	DB-1	1162.	Mirjalili, Salehi, et al., 2010	25. m/0.25 mm/0.25 μm, Nitrogen, 60. C @ 1. min, 4. K/min, 250. C @ 10. min
Capillary	HP-5 MS	1177.	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	1197.	Baranauskiene R., Bylaite E., et al., 2007	50. m/0.32 mm/0.25 μm, He, 50. C @ 2. min, 5. K/min, 280. C @ 10. min
Capillary	DB-5	1179.	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	DB-1	1182.	Salehi, Sonboli, et al., 2005	60. m/0.25 mm/0.25 μm, He, 5. K/min, 250. C @ 10. min; T_start: 60. C
Capillary	DB-5MS	1182.	paz Lima, Silva, et al., 2004	30. m/0.25 mm/0.25 μm, He, 3. K/min; T_start: 60. C; T_end: 240. C
Capillary	DB-5MS	1178.	Cherchi, Deidda, et al., 2001	30. m/0.25 mm/0.25 μm, He, 3. K/min; T_start: 60. C; T_end: 240. C
Capillary	BP-1	1184.	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	OV-101	1171.	Orav and Kann, 2001	He, 2. K/min; Column length: 50. m; Column diameter: 0.2 mm; T_start: 50. C; T_end: 250. C
Capillary	DB-5	1141.	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
Capillary	OV-101	1178.	De Pooter and Schamp, 1986	30. m/0.5 mm/0.8 μm, He, 2. K/min; T_start: 40. 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	Siloxane, 5 % Ph	1185.	VOC BinBase, 2012	Program: not specified
Capillary	Polydimethyl siloxane, 5 % phenyl	1185.	Skogerson, Wohlgemuth, et al., 2011	Program: not specified
Capillary	DB-1	1178.	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	DB-1	1154.	Mendes, Trindade, et al., 2009	30. m/0.25 mm/0.25 μm, Hydrogen; Program: 45 0C 3 0C/min -> 175 0C 15 0C/min -> 300 0C (10 min)
Capillary	SE-52	1183.	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-5	1182.	Blank, Fontes, et al., 2005	30. m/0.25 mm/0.25 μm, He; Program: 80 0C (1 min) 3 0C/min -> 180 0C 10 0C/min -> 300 0C (3 min)
Capillary	SE-30	1182.	Vinogradov, 2004	Program: not specified
Capillary	Polydimethyl siloxanes	1176.	Zenkevich, 1997	Program: not specified
Packed	OV-101	1174.	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

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Column type	Active phase	I	Reference	Comment
Capillary	DB-Wax	1653.	Salehi, Sonboli, et al., 2005	30. m/0.25 mm/0.25 μm, He, 4. K/min, 250. C @ 10. min; T_start: 40. C
Capillary	PEG-20M	1660.	Orav and Kann, 2001	He, 2. K/min; Column length: 50. m; Column diameter: 0.2 mm; T_start: 70. C; T_end: 220. C
Capillary	Supelcowax-10	1684.	Campeanu, Burcea, et al., 1998	60. m/0.32 mm/0.5 μm, H2, 35. C @ 5. min, 5. K/min, 250. C @ 20. min
Capillary	HP-Innowax FSC	1678.	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

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Column type	Active phase	I	Reference	Comment
Capillary	Carbowax 20M	1667.	Vinogradov, 2004	Program: not specified

References

Go To: Top, Gas Chromatography, Notes

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]

Kitic, Palic, et al., 2001
Kitic, D.; Palic, R.; Ristic, M.; Sojanovic, G.; Jovanovic, T., The volatile constituents of Calamintha sylvatica Bromf. subsp. sylvatica, Flavour Fragr. J., 2001, 16, 4, 257-258, https://doi.org/10.1002/ffj.995 . [all data]

Malingré and Maarse, 1974
Malingré, T.M.; Maarse, H., Composition of the essential oil of Mentha aquatica, Phytochemistry, 1974, 13, 8, 1531-1535, https://doi.org/10.1016/0031-9422(74)80322-5 . [all data]

Simionatto, Porto, et al., 2005
Simionatto, E.; Porto, C.; da Silva, U.F.; Squizani, A.; Dalcol, I.I.; Morel, A.F., Composition and antimicrobial activity of the essential oil from Aloysia sellowii, J. Braz. Chem. Soc., 2005, 16, 6B, 1458-1462, https://doi.org/10.1590/S0103-50532005000800028 . [all data]

Garland, Menary, et al., 2004
Garland, S.M.; Menary, R.C.; Davies, N.W.; Oliver, G.S., Practical approaches to the analyses for pesticide residues in essential oils, A report for the Rural Industries Research and Development Corporation, RIRDC Publication No. 04/109, Rural Industries Research and Development Corporation, Barton, ACT, 2004. [all data]

Duru, Cakir, et al., 2002
Duru, M.E.; Cakir, A.; Harmandar, M., Composition of the volatile oils isolated from the leaves of Liquidambar orientalis Mill. var. orientalis and L. orientalis var. integriloba from Turkey, Flavour Fragr. J., 2002, 17, 2, 95-98, https://doi.org/10.1002/ffj.1050 . [all data]

de Lacy Costello, Evans, et al., 2001
de Lacy Costello, B.P.J.; Evans, P.; Ewen, R.J.; Gunson, H.E.; Jones, P.R.H.; Ratcliffe, N.M.; Spencer-Phillips, P.T.N., Gas chromatography-mass spectrometry analyses of volatile organic compounds from potato tubers inoculated with Phytophthora infestans or Fusarium coeruleum, Plant Pathol., 2001, 50, 4, 489-496, https://doi.org/10.1046/j.1365-3059.2001.00594.x . [all data]

Song, Sawamura, et al., 2000
Song, H.S.; Sawamura, M.; Ito, T.; Kawashimo, K.; Ukeda, H., Quantitative determination of characteric flavour of Citrus junos (yuzu) peel oil, Flavour Fragr. J., 2000, 15, 4, 245-250, https://doi.org/10.1002/1099-1026(200007/08)15:4<245::AID-FFJ904>3.0.CO;2-V . [all data]

Guerrini, Sacchetti, et al., 2006
Guerrini, A.; Sacchetti, G.; Muzzoli, M.; Rueda, G.M.; Medici, A.; Besco, E.; Bruni, R., Composition of the Volatile Fraction of Ocotea bofo Kunth (Lauraceae) Calyces by GC-MS and NMR Fingerprinting and Its Antimicrobial and Antioxidant Activity, J. Agric. Food Chem., 2006, 54, 20, 7778-7788, https://doi.org/10.1021/jf0605493 . [all data]

Mondello, Dugo, et al., 1995
Mondello, L.; Dugo, P.; Basile, A.; Dugo, G., Interactive use of linear retention indices, on polar and apolar columns, with a MS-library for reliable identification of complex mixtures, J. Microcolumn Sep., 1995, 7, 6, 581-591, https://doi.org/10.1002/mcs.1220070605 . [all data]

Romeo, Ziino, et al., 2007
Romeo, V.; Ziino, M.; Giuffrrida, D.; Condurso, C.; Verzera, A., Flavour profile of capers (Capparis spinosa L.) from the Eolian Archipelago by HS-SPME/GC?MS, Food Chem., 2007, 101, 3, 1272-1278, https://doi.org/10.1016/j.foodchem.2005.12.029 . [all data]

Mirjalili, Salehi, et al., 2010
Mirjalili, M.H.; Salehi, P.; Sonboli, A.; HAdian, J.; Ebrahimi, S.N.; Yousefzadi, M., The composition and antibacterial activity of the essential oil of Levisticum officinale Koch flowers and fruits at different developmental stages, J. Serb. Chem. Soc., 2010, 75, 12, 1661-1669, https://doi.org/10.2298/JSC100524126M . [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]

Baranauskiene R., Bylaite E., et al., 2007
Baranauskiene R.; Bylaite E.; Venskutonis R.P., Flavor retention of peppermint (Mentha piperita L.) essential oil spray-dried in modified starches during encapsulation and storage, J. Agric. Food Chem., 2007, 55, 8, 3027-3036, https://doi.org/10.1021/jf062508c . [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]

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]

paz Lima, Silva, et al., 2004
paz Lima, M.; Silva, T.M.D.; da Silva, J.D.; Zoghbi, M.G.B.; Andrade, E.H.A., Essential oil composition of leaf and fine stem of Aniba canelilla (Kunth) Mez from Manaus, Brazil., Acta Amazonica, 2004, 34, 2, 329-330, https://doi.org/10.1590/S0044-59672004000200019 . [all data]

Cherchi, Deidda, et al., 2001
Cherchi, G.; Deidda, D.; de Gioannis, B.; Marongiu, B.; Pompei, R.; Porcedda, S., Extraction of Santolina insularis essential oil by supercritical carbon dioxide: influence of some process parameters and biological activity, Flavour Fragr. J., 2001, 16, 1, 35-43, https://doi.org/10.1002/1099-1026(200101/02)16:1<35::AID-FFJ942>3.0.CO;2-Y . [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]

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]

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]

VOC BinBase, 2012
VOC BinBase, The volatile compound BinBase (VOC BinBase), 2012, retrieved from http://fiehnlab.ucdavis.edu/projects/VocBinBase and http://binbase.sourceforge.net. [all data]

Skogerson, Wohlgemuth, et al., 2011
Skogerson, K.; Wohlgemuth, G.; Fiehn, O., VocBinNase, 2011, retrieved from http://fiehnlab.ucdavis.edu/projects//VocBinBase. [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]

Mendes, Trindade, et al., 2009
Mendes, M.D.; Trindade, H.; Figueiredo, A.C.; Barroso, J.G.; Fontinha, S.S.; Pedro, L.G., Volatile and molecular characterization of two Portuguese endemic species: Angelica lignescens and Melanoselinium decipiens, Biochen. Systematics Ecol., 2009, 37, 2, 98-105, https://doi.org/10.1016/j.bse.2008.12.006 . [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]

Blank, Fontes, et al., 2005
Blank, A.F.; Fontes, S.M.; Carvalho Filho, J.L.S.; Alves, P.B.; Silva-Mann, R.; Mendonça, M.C.; Arrigoni-Blank, M.F.; Rodrigues, M.O., Influence of harvest times and drying of leaves on the essential oil of Melissa officinalis L. cultivated in two environments, Rev. Bras. Pl. Med., Botucatu, 2005, 8, 1, 73-78. [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]

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

Campeanu, Burcea, et al., 1998
Campeanu, G.; Burcea, M.; Doneanu, C.; Namolosanu, I.; Visan, L., GC/MS characterization of the volatiles isolated from the wines obtained from the indigenous cultivar Feteasca Regala, Analusis, 1998, 26, 2, 93-97, https://doi.org/10.1051/analusis:1998117 . [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

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Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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