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

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-KXUCPTDWSA-N
CAS Registry Number: 89-78-1
Chemical structure:
This structure is also available as a 2d Mol file
Species with the same structure:
- Cyclohexanol, 5-methyl-2-(1-methylethyl)-, (1α,2β,5α)-
Stereoisomers:
Other names: Menthol, cis-1,3,trans-1,4-; Hexahydrothymol; Menthacamphor; Menthol; Menthomenthol; Peppermint camphor; dl-Menthol; p-Menthan-3-ol; Cyclohexanol, 2-isopropyl-5-methyl-; NCI-C50000; 5-Methyl-2-(1-methylethyl)cyclohexanol; 2-Isopropyl-5-methylcyclohexanol; l-Menthol; 3-p-Menthanol; 5α-Methyl-2β-(1α-methylethyl)cyclohexanol; component of Dermoplast; Fancol menthol; Fisherman's friend lozenges; Menthol terpine hydrate; component of Minut-rub; Racemic menthol; component of Robitussin cough drops; component of Sarna; component of Theragesic; Therapeutic mineral ice; Cyclohexanol, 2-isopropyl-5-methyl-, (1α,2β,5α)-; 2-Isopropyl-5-methylcyclohexanol, (1α,2β,5α)-; 5-Methyl-2-(1-methylethyl)cyclohexanol, (1α,2β,5α)-; (.+/-.)-Menthol; Cyclohexanol, 5-methyl-2-(1-methylethyl)-, (1R,2S,5R)-rel-; NSC 2603; Racementhol; rac-Menthol; Diterpene
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Other data available:
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Normal alkane RI, polar column, temperature ramp

Go To: Top, References, Notes

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

Column type	Capillary	Capillary	Capillary	Capillary	Capillary
Active phase	VF-Wax MS	CP-Wax	DB-Wax	HP-Innowax	DB-Wax
Column length (m)	60.	60.	30.	30.	60.
Carrier gas	Helium	Helium	He	Helium	He
Substrate
Column diameter (mm)	0.25	0.25	0.25	0.25	0.25
Phase thickness (μm)	0.25	0.25	0.25	0.25	0.5
T_start (C)	60.	50.	30.	40.	50.
T_end (C)	220.	230.	210.	250.	230.
Heat rate (K/min)	3.	6.	5.	2.	3.
Initial hold (min)	5.	2.		5.	2.
Final hold (min)	25.	15.			20.
I	1641.	1639.	1645.	1652.	1636.
Reference	Duarte, Dias, et al., 2010	Mo, Fan, et al., 2009	Kumazawa, Itobe, et al., 2008	Formisano, Rigano, et al., 2007	Cai, Lin, et al., 2006
Comment	MSDC-RI	MSDC-RI	MSDC-RI	MSDC-RI	MSDC-RI

Column type	Capillary	Capillary	Capillary	Capillary	Capillary
Active phase	CP-Wax	DB-Wax	ZB-Wax	DB-Wax	DB-Wax
Column length (m)	30.	30.	30.	30.	30.
Carrier gas	He	He	Helium	He	He
Substrate
Column diameter (mm)	0.32	0.25	0.32	0.25	0.25
Phase thickness (μm)	0.25	0.25	0.25	0.25	0.25
T_start (C)	40.	40.	40.	90.	50.
T_end (C)	180.	250.	250.	220.	230.
Heat rate (K/min)	5.	4.	5.	7.	3.
Initial hold (min)	2.		2.	2.	2.
Final hold (min)		10.	5.	5.	20.
I	1636.	1589.	1631.	1628.	1641.
Reference	Ka, Choi, et al., 2005	Salehi, Sonboli, et al., 2005	N/A	Agnihotri, Thappa, et al., 2004	Lin, Cai, et al., 2003
Comment	MSDC-RI	MSDC-RI	MSDC-RI	MSDC-RI	MSDC-RI

Column type	Capillary	Capillary	Capillary	Capillary	Capillary
Active phase	TC-Wax	HP-Innowax	PEG-20M	DB-Wax	HP Innowax FSP
Column length (m)	60.	50.	50.	60.	60.
Carrier gas			He	Nitrogen	He
Substrate
Column diameter (mm)	0.25	0.2	0.2	0.25	0.25
Phase thickness (μm)		0.2			0.25
T_start (C)	80.	50.	70.	40.	60.
T_end (C)	240.	220.	220.	200.	220.
Heat rate (K/min)	3.	4.	2.	2.
Initial hold (min)		5.		10.	10.
Final hold (min)					10.
I	1637.	1614.	1637.	1651.	1651.
Reference	Miyazawa, Yamafuji, et al., 2003	Stashenko, Jaramillo, et al., 2003	Orav and Kann, 2001	Tamura, Boonbumrung, et al., 2000	Kaya, Baser, et al., 1999
Comment	MSDC-RI	MSDC-RI	MSDC-RI	MSDC-RI	MSDC-RI

Column type	Capillary	Capillary	Capillary	Capillary	Capillary
Active phase	HP-Innowax	Carbowax	BP-20	TC-Wax	Carbowax 20M
Column length (m)	60.	50.	25.	60.	50.
Carrier gas	He	N2	N2
Substrate
Column diameter (mm)	0.25	0.2	0.5	0.25	0.25
Phase thickness (μm)	0.25
T_start (C)	60.	80.	60.	80.	80.
T_end (C)	220.	200.	200.	240.	200.
Heat rate (K/min)		1.	5.	3.	2.
Initial hold (min)	10.			5.
Final hold (min)		20.
I	1651.	1612.	1640.	1642.	1600.
Reference	Kaya, Baser, et al., 1999, 2	Menon, Chacko, et al., 1999	Rao, Bhattacharya, et al., 1999	Shuichi, Masazumi, et al., 1996	Shibamoto, 1987
Comment	MSDC-RI	MSDC-RI	MSDC-RI	MSDC-RI	MSDC-RI

Column type	Packed
Active phase	Carbowax 20M
Column length (m)	2.
Carrier gas	Hydrogen
Substrate	Gas-Chrom Z (80-100 mesh)
Column diameter (mm)
Phase thickness (μm)
T_start (C)	65.
T_end (C)	220.
Heat rate (K/min)	4.
Initial hold (min)
Final hold (min)
I	1631.
Reference	Stancher and Pertoldi, 1967
Comment	MSDC-RI

References

Go To: Top, Normal alkane RI, polar column, temperature ramp, Notes

Duarte, Dias, et al., 2010
Duarte, W.F.; Dias, D.R.; Oliveira, J.M.; Teixeira, J.A.; de Almeida e Silva, J.B.; Schwan, R.F., Characterization of different fruit wines made from cacao,cupuassu, gabiroba, jaboticaba and umbu, Food Sci. Technol., 2010, 43, 1564-1572. [all data]

Mo, Fan, et al., 2009
Mo, X.; Fan, W.; Xu, Y., Changes in volatile compounds of Chinese rice wine wheat qu during fermentation and storage, J. of the Institute of Brewing, 2009, 115, 4, 300-307, https://doi.org/10.1002/j.2050-0416.2009.tb00385.x . [all data]

Kumazawa, Itobe, et al., 2008
Kumazawa, K.; Itobe, T.; Nishimura, O.; Hamaguchi, T., A new approach to estimate the in-mouth release characteristics of odorants in chewing gum, Food Science and Technology Research, 2008, 14, 3, 269-276, https://doi.org/10.3136/fstr.14.269 . [all data]

Formisano, Rigano, et al., 2007
Formisano, C.; Rigano, D.; Napolitano, F.; Senatore, F.; Arnold, N.A.; Piozzi, F.; Rosselli, S., Volatile constituents of Calamintha ariganifolia Boiss. growing wild in Lebanon, Natural Product Communications, 2007, 2, 12, 1253-1256. [all data]

Cai, Lin, et al., 2006
Cai, J.; Lin, P.; Zhu, X.; Su, Q., Comparative analysis of clary sage (S. sclarea L.) oil volatiles by GC-FTIR and GC-MS, Food Chem., 2006, 99, 2, 401-407, https://doi.org/10.1016/j.foodchem.2005.07.041 . [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]

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]

Agnihotri, Thappa, et al., 2004
Agnihotri, V.K.; Thappa, R.K.; Meena, B.; Kapahi, B.K.; Saxena, R.K.; Qazi, G.N.; Agarwal, S.G., Essential oil composition of aerial parts of Angelica glauca growing wild in North-West Himalaya (India), Phytochemistry, 2004, 65, 16, 2411-2413, https://doi.org/10.1016/j.phytochem.2004.07.004 . [all data]

Lin, Cai, et al., 2003
Lin, P.; Cai, J.; Li, J.; Sang, W.; Su, Q., Constituents of the essential oil of Hemerocallis flava day lily, Flavour Fragr. J., 2003, 18, 6, 539-541, https://doi.org/10.1002/ffj.1264 . [all data]

Miyazawa, Yamafuji, et al., 2003
Miyazawa, M.; Yamafuji, C.; Kurose, K.; Ishikawa, Y., Volatile components of the rhizomes of Cirsium japonicum DC, Flavour Fragr. J., 2003, 18, 1, 15-17, https://doi.org/10.1002/ffj.1135 . [all data]

Stashenko, Jaramillo, et al., 2003
Stashenko, E.E.; Jaramillo, B.E.; Martínez, J.R., Comparación de la composición química y de la actividad antioxidante in vitro de los metabolitos secundarios volátiles de plantas de la familia verbenaceae, Rev. Acad. Colomb. Cienc. Exactas Fis. Nat., 2003, 27, 105, 579-597. [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]

Tamura, Boonbumrung, et al., 2000
Tamura, H.; Boonbumrung, S.; Yoshizawa, T.; Varanyanond, W., Volatile components of the essential oil in the pulp of four yellow mangoes (Mangifera indica L.) in Thailand, Food Sci. Technol. Res., 2000, 6, 1, 68-73, https://doi.org/10.3136/fstr.6.68 . [all data]

Kaya, Baser, et al., 1999
Kaya, A.; Baser, K.H.C.; Koca, F., Essential oils of Acinos troodi (Post) Leblebici subsp. vardaranus Leblebici and subsp. grandiflorus Hartvig Strid, Flavour Fragr. J., 1999, 14, 1, 50-54, https://doi.org/10.1002/(SICI)1099-1026(199901/02)14:1<50::AID-FFJ783>3.0.CO;2-7 . [all data]

Kaya, Baser, et al., 1999, 2
Kaya, A.; Baser, K.H.C.; Tümen, G.; Koca, F., The essential oil of Acinos suaveolens (Sm.) G. Don fil. Acinos arvensis (Lam.) Dandy and Acinos rotundifolius Pers. growing wild in Turkey, Flavour Fragr. J., 1999, 14, 1, 60-64, https://doi.org/10.1002/(SICI)1099-1026(199901/02)14:1<60::AID-FFJ785>3.0.CO;2-0 . [all data]

Menon, Chacko, et al., 1999
Menon, A.N.; Chacko, S.; Narayanan, C.S., Free and glycosidically bound volatiles of cardamom (Eletteria cardamomum Maton var. miniscula Burkill), Flavour Fragr. J., 1999, 14, 1, 65-68, https://doi.org/10.1002/(SICI)1099-1026(199901/02)14:1<65::AID-FFJ789>3.0.CO;2-A . [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]

Shuichi, Masazumi, et al., 1996
Shuichi, H.; Masazumi, N.; Hiromu, K.; Kiyoshi, F., Comparison of volatile compounds berween the crude drugs, Onji-tsutsu and Onji-niki, Nippon nogei kagaku kaishi, 1996, 70, 2, 151-160. [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]

Stancher and Pertoldi, 1967
Stancher, B.; Pertoldi, M.G., Characterization of commercial materials used in synthetic essential oil production. Identification and gas-chromatographic determination of impurities, Rassegna chimica, 1967, 19, 3, 99-109. [all data]

Notes

Go To: Top, Normal alkane RI, polar column, temperature ramp, References

Symbols used in this document:

T_end Final temperature

T_start Initial temperature
Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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