Levomenthol
- Formula: C10H20O
- Molecular weight: 156.2652
- IUPAC Standard InChIKey: NOOLISFMXDJSKH-AEJSXWLSSA-N
- CAS Registry Number: 2216-51-5
- 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:
- Cyclohexanol, 5-methyl-2-(1-methylethyl)-
- Cyclohexanol, 5-methyl-2-(1-methylethyl)-, (1α,2β,5α)-
- Cyclohexanol, 5-methyl-2-(1-methylethyl)-, [1R-(1α,2α,5β)]-
- 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,5β)-
- Cyclohexanol, 5-methyl-2-(1-methylethyl)-, (1α,2α,5α)-
- Cyclohexanol, 5-methyl-2-(1-methylethyl)-, (1α,2β,5α)-
- Other names: Cyclohexanol, 5-methyl-2-(1-methylethyl)-, [1R-(1α,2β,5α)]-; L-(-)-Menthol; Menthol, (1R,3R,4S)-(-)-; (-)-Menthol; (R)-(-)-Menthol; U.S.P. Menthol; 1R-Menthol; (1R,2S,5R)-(-)-Menthol; (-)-Menthyl alcohol; (1R-(1-α,2-β,5-α))-5-Methyl-2-(1-methylethyl)cyclohexanol; L-Menthol; (1R)-(-)-Menthol; (1R,2S,5R)-2-Isopropyl-5-methylcyclohexanol; Cyclohexanol, 5-methyl-2-(1-methylethyl)-, (1R,2S,5R)-; NSC 62788; 1-Menthol; (1R,3R,4S)-(-)-menthol
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Phase change data
Go To: Top, Gas Chromatography, References, Notes
Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
Data compiled as indicated in comments:
BS - Robert L. Brown and Stephen E. Stein
TRC - Thermodynamics Research Center, NIST Boulder Laboratories, Chris Muzny director
AC - William E. Acree, Jr., James S. Chickos
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
Tboil | 485.2 | K | N/A | Aldrich Chemical Company Inc., 1990 | BS |
Tboil | 489.6 | K | N/A | Weast and Grasselli, 1989 | BS |
Quantity | Value | Units | Method | Reference | Comment |
Tfus | 314.65 | K | N/A | Zeiss and Tsutsui, 1953 | Uncertainty assigned by TRC = 1.5 K; TRC |
Tfus | 315.4 | K | N/A | White and Bishop, 1940 | Uncertainty assigned by TRC = 0.5 K; TRC |
Quantity | Value | Units | Method | Reference | Comment |
ΔvapH° | 56.6 | kJ/mol | GC | Hoskovec, Grygarová, et al., 2005 | Based on data from 323. to 433. K.; AC |
Enthalpy of vaporization
ΔvapH (kJ/mol) | Temperature (K) | Method | Reference | Comment |
---|---|---|---|---|
59.1 | 387. | A | Stephenson and Malanowski, 1987 | Based on data from 372. to 488. K.; AC |
58.2 | 344. | N/A | Stull, 1947 | Based on data from 329. to 485. K.; AC |
Enthalpy of sublimation
ΔsubH (kJ/mol) | Temperature (K) | Method | Reference | Comment |
---|---|---|---|---|
95.8 ± 4.8 | 289. | HSA | Chickos, Garin, et al., 1981 | Based on data from 279. to 299. K.; AC |
Enthalpy of fusion
ΔfusH (kJ/mol) | Temperature (K) | Method | Reference | Comment |
---|---|---|---|---|
11.88 | 316.2 | DTA | Chickos, Garin, et al., 1981 | AC |
Gas Chromatography
Go To: Top, Phase change data, 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 | ZB-1 | 100. | 1158.58 | Hoskovec, Grygarová, et al., 2005 | 30. m/0.32 mm/0.25 μm, He |
Capillary | ZB-1 | 110. | 1161.95 | Hoskovec, Grygarová, et al., 2005 | 30. m/0.32 mm/0.25 μm, He |
Capillary | ZB-1 | 120. | 1165.41 | Hoskovec, Grygarová, et al., 2005 | 30. m/0.32 mm/0.25 μm, He |
Capillary | ZB-1 | 130. | 1169.1 | Hoskovec, Grygarová, et al., 2005 | 30. m/0.32 mm/0.25 μm, He |
Capillary | ZB-1 | 140. | 1172.79 | Hoskovec, Grygarová, et al., 2005 | 30. m/0.32 mm/0.25 μm, He |
Capillary | ZB-1 | 150. | 1176.76 | Hoskovec, Grygarová, et al., 2005 | 30. m/0.32 mm/0.25 μm, He |
Capillary | ZB-1 | 160. | 1180.78 | Hoskovec, Grygarová, et al., 2005 | 30. m/0.32 mm/0.25 μm, He |
Capillary | ZB-1 | 50. | 1143.95 | Hoskovec, Grygarová, et al., 2005 | 30. m/0.32 mm/0.25 μm, He |
Capillary | ZB-1 | 60. | 1146.99 | Hoskovec, Grygarová, et al., 2005 | 30. m/0.32 mm/0.25 μm, He |
Capillary | ZB-1 | 70. | 1149.57 | Hoskovec, Grygarová, et al., 2005 | 30. m/0.32 mm/0.25 μm, He |
Capillary | ZB-1 | 80. | 1152.38 | Hoskovec, Grygarová, et al., 2005 | 30. m/0.32 mm/0.25 μm, He |
Capillary | ZB-1 | 90. | 1155.38 | Hoskovec, Grygarová, et al., 2005 | 30. m/0.32 mm/0.25 μm, He |
Van Den Dool and Kratz RI, non-polar column, temperature ramp
Column type | Active phase | I | Reference | Comment |
---|---|---|---|---|
Capillary | DB-1 | 1150.4 | Sun and Stremple, 2003 | 30. m/0.25 mm/0.25 μm, He, 3. K/min; Tstart: 40. C; Tend: 325. C |
Van Den Dool and Kratz RI, non-polar column, custom temperature program
Column type | Active phase | I | Reference | Comment |
---|---|---|---|---|
Capillary | SE-52 | 1178. | 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 | DB-Wax | 1626. | Choi, 2003 | 60. m/0.25 mm/0.25 μm, N2, 70. C @ 2. min, 2. K/min, 230. C @ 20. min |
Capillary | DB-Wax | 1652. | Choi and Sawamura, 2000 | 60. m/0.25 mm/0.25 μm, N2, 70. C @ 2. min, 2. K/min, 230. C @ 20. min |
Van Den Dool and Kratz RI, polar column, custom temperature program
Column type | Active phase | I | Reference | Comment |
---|---|---|---|---|
Capillary | CP-Wax 52CB | 1596. | Romeo, Ziino, et al., 2007 | 60. m/0.25 mm/0.25 μm, He; Program: 45C(5min) => 10C/min => 80C => 2C/min => 240C |
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 | DB-5 | 1172. | Sefidkon and Jamzad, 2005 | He, 4. K/min; Column length: 30. m; Column diameter: 0.25 mm; Tstart: 40. C; Tend: 240. C |
Capillary | OV-101 | 1171. | Egolf and Jurs, 1993 | 2. K/min; Column length: 50. m; Column diameter: 0.22 mm; Tstart: 80. C; Tend: 200. C |
Normal alkane RI, polar column, temperature ramp
Column type | Active phase | I | Reference | Comment |
---|---|---|---|---|
Capillary | DB-Wax | 1639. | Lee, Umano, et al., 2005 | 30. m/0.25 mm/0.25 μm, He, 3. K/min, 180. C @ 40. min; Tstart: 50. C |
Capillary | DB-Wax | 1651. | Choi, 2004 | 60. m/0.25 mm/0.25 μm, N2, 70. C @ 2. min, 2. K/min, 230. C @ 20. min |
Capillary | DB-Wax | 1642. | Umano, Nakahara, et al., 1999 | 60. m/0.25 mm/0.25 μm, He, 40. C @ 2. min, 2. K/min; Tend: 200. C |
Capillary | Carbowax 20M | 1612. | Egolf and Jurs, 1993 | 2. K/min; Column length: 80. m; Column diameter: 0.2 mm; Tstart: 70. C; Tend: 170. C |
References
Go To: Top, Phase change data, Gas Chromatography, Notes
Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
Aldrich Chemical Company Inc., 1990
Aldrich Chemical Company Inc.,
Catalog Handbook of Fine Chemicals, Aldrich Chemical Company, Inc., Milwaukee WI, 1990, 1. [all data]
Weast and Grasselli, 1989
CRC Handbook of Data on Organic Compounds, 2nd Editon, Weast,R.C and Grasselli, J.G., ed(s)., CRC Press, Inc., Boca Raton, FL, 1989, 1. [all data]
Zeiss and Tsutsui, 1953
Zeiss, H.H.; Tsutsui, M.,
The Carbon-Oxygen Absorption Band in the Infrared Spectra of Alcohols,
J. Am. Chem. Soc., 1953, 75, 897. [all data]
White and Bishop, 1940
White, A.H.; Bishop, W.S.,
Dielectric Evidence of Molecular Rotation in the Crystals of Certain Non-aromatic Compounds,
J. Am. Chem. Soc., 1940, 62, 8-16. [all data]
Hoskovec, Grygarová, et al., 2005
Hoskovec, Michal; Grygarová, Dana; Cvacka, Josef; Streinz, Ludvík; Zima, Jirí; Verevkin, Sergey P.; Koutek, Bohumír,
Determining the vapour pressures of plant volatiles from gas chromatographic retention data,
Journal of Chromatography A, 2005, 1083, 1-2, 161-172, https://doi.org/10.1016/j.chroma.2005.06.006
. [all data]
Stephenson and Malanowski, 1987
Stephenson, Richard M.; Malanowski, Stanislaw,
Handbook of the Thermodynamics of Organic Compounds, 1987, https://doi.org/10.1007/978-94-009-3173-2
. [all data]
Stull, 1947
Stull, Daniel R.,
Vapor Pressure of Pure Substances. Organic and Inorganic Compounds,
Ind. Eng. Chem., 1947, 39, 4, 517-540, https://doi.org/10.1021/ie50448a022
. [all data]
Chickos, Garin, et al., 1981
Chickos, J.S.; Garin, D.L.; Hitt, M.; Schilling, G.,
Some solid state properties of enantiomers and their racemates,
Tetrahedron, 1981, 37, 12, 2255-2259, https://doi.org/10.1016/S0040-4020(01)97981-5
. [all data]
Sun and Stremple, 2003
Sun, G.; Stremple, P.,
Retention index characterization of flavor, fragrance, and many other compounds on DB-1 and DB-XLB, 2003, retrieved from http://www.chem.agilent.com/cag/cabu/pdf/b-0279.pdf. [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]
Choi, 2003
Choi, H.-S.,
Character impact odorants of Citrus Hallabong [(C. unshiu Marcov × C. sinensis Osbeck) × C. reticulata Blanco] cold-pressed peel oil,
J. Agric. Food Chem., 2003, 51, 9, 2687-2692, https://doi.org/10.1021/jf021069o
. [all data]
Choi and Sawamura, 2000
Choi, H.-S.; Sawamura, M.,
Composition of the essential oil of Citrus tamurana Hort. ex Tanaka (Hyuganatsu),
J. Agric. Food Chem., 2000, 48, 10, 4868-4873, https://doi.org/10.1021/jf000651e
. [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]
Sefidkon and Jamzad, 2005
Sefidkon, F.; Jamzad, Z.,
Chemical composition of the essential oil of three Iranian Satureja species (S. mutica, S. macrantha and S. intermedia),
Food Chem., 2005, 91, 1, 1-4, https://doi.org/10.1016/j.foodchem.2004.01.027
. [all data]
Egolf and Jurs, 1993
Egolf, L.M.; Jurs, P.C.,
Quantitative structure-retention and structure-odor intensity relationships for a diverse group of odor-active compounds,
Anal. Chem., 1993, 65, 21, 3119-3126, https://doi.org/10.1021/ac00069a027
. [all data]
Lee, Umano, et al., 2005
Lee, S.-J.; Umano, K.; Shibamoto, T.; Lee, K.-G.,
Identification of volatile components in basil (Ocimum basilicum L.) and thyme leaves (Thymus vulgaris L.) and their antioxidant properties,
Food Chem., 2005, 91, 1, 131-137, https://doi.org/10.1016/j.foodchem.2004.05.056
. [all data]
Choi, 2004
Choi, H.-S.,
Volatile constituents of satsuma mandarins growing in Korea,
Flavour Fragr. J., 2004, 19, 5, 406-412, https://doi.org/10.1002/ffj.1283
. [all data]
Umano, Nakahara, et al., 1999
Umano, K.; Nakahara, K.; Shoji, A.; Shibamoto, T.,
Aroma chemicals isolated and identified from leaves of aloe arborescens Mill. Var. natalensis Berger,
J. Agric. Food Chem., 1999, 47, 9, 3702-3705, https://doi.org/10.1021/jf990116i
. [all data]
Notes
Go To: Top, Phase change data, Gas Chromatography, References
- Symbols used in this document:
Tboil Boiling point Tfus Fusion (melting) point ΔfusH Enthalpy of fusion ΔsubH Enthalpy of sublimation ΔvapH Enthalpy of vaporization ΔvapH° Enthalpy of vaporization at standard conditions - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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