Cyclohexene, 1-methyl-4-(1-methylethyl)-
- Formula: C10H18
- Molecular weight: 138.2499
- IUPAC Standard InChIKey: FAMJUFMHYAFYNU-UHFFFAOYSA-N
- CAS Registry Number: 5502-88-5
- 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. - Species with the same structure:
- Other names: p-Menth-1-ene; Carvomenthene; 1-p-Menthene; 1-Methyl-4-isopropylcyclohexene; δ1-p-Menthene; 1-Methyl-4-isopropyl-1-cyclohexene; 4-Isopropyl-1-methylcyclohexene; 1-Methyl-4-(1-methylethyl)cyclohexene; 4-Isopropyl-1-methyl-1-cyclohexene; p-1-Menthene; p-Ment-1-ene; NSC 96749; 1-Menthene
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Gas phase thermochemistry data
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Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
Data compiled by: Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔfH°gas | -26.48 ± 0.76 | kcal/mol | Ccb | Kalechits, Luk'yanova, et al., 1990 |
Condensed phase thermochemistry data
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Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
Data compiled by: Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔfH°liquid | -38.19 ± 0.76 | kcal/mol | Ccb | Kalechits, Luk'yanova, et al., 1990 | |
Quantity | Value | Units | Method | Reference | Comment |
ΔcH°liquid | -1517.2 ± 0.74 | kcal/mol | Ccb | Kalechits, Luk'yanova, et al., 1990 | Corresponding ΔfHºliquid = -38.19 kcal/mol (simple calculation by NIST; no Washburn corrections) |
Phase change data
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, 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:
TRC - Thermodynamics Research Center, NIST Boulder Laboratories, Chris Muzny director
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
DRB - Donald R. Burgess, Jr.
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
Tboil | 443. | K | N/A | Pines, Olberg, et al., 1952 | Uncertainty assigned by TRC = 4. K; TRC |
Tboil | 450. | K | N/A | Smith, Fuzek, et al., 1949 | Uncertainty assigned by TRC = 1. K; TRC |
Tboil | 443. | K | N/A | Knoevenagel, 1897 | Uncertainty assigned by TRC = 5. K; position of side chains on ring not determined; TRC |
Quantity | Value | Units | Method | Reference | Comment |
ΔvapH° | 11.72 ± 0.079 | kcal/mol | C | Kalechits, Luk'yanova, et al., 1990 | ALS |
ΔvapH° | 11.7 | kcal/mol | N/A | Kalechits, Luk'yanova, et al., 1990 | DRB |
Gas Chromatography
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, 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 | SE-30 | 130. | 1036. | Bredael, 1982 | Column length: 100. m; Column diameter: 0.5 mm |
Capillary | SE-30 | 80. | 1019. | Bredael, 1982 | Column length: 100. m; Column diameter: 0.5 mm |
Capillary | SE-30 | 80. | 1005.7 | Albaigés and Guardino, 1980 | He; Column length: 64. m; Column diameter: 0.25 mm |
Capillary | Squalane | 80. | 1019.9 | Albaigés and Guardino, 1980 | He; Column length: 100. m; Column diameter: 0.25 mm |
Capillary | Apiezon L | 100. | 1049. | Morishita, Okano, et al., 1980 | Column length: 45. m; Column diameter: 0.25 mm |
Packed | SE-30 | 160. | 985. | Hedin, Thompson, et al., 1972 | N2, Chromosorb W; Column length: 6.145 m |
Kovats' RI, non-polar column, temperature ramp
Column type | Active phase | I | Reference | Comment |
---|---|---|---|---|
Capillary | DB-5 | 1032. | Buchin, Salmon, et al., 2002 | 60. m/0.32 mm/1. μm, He, 40. C @ 5. min, 3. K/min, 230. C @ 2. min |
Capillary | CP Sil 5 CB | 1017. | Kasali, Adio, et al., 2002 | He, 3. K/min; Column length: 25. m; Column diameter: 0.25 mm; Tstart: 50. C; Tend: 230. C |
Capillary | DB-1 | 1020. | Mevy, Bessiere, et al., 2002 | He, 3. K/min; Column length: 25. m; Column diameter: 0.2 mm; Tstart: 60. C; Tend: 220. C |
Capillary | HP-5 | 1026. | Ramos, Siani, et al., 2000 | 30. m/0.32 mm/0.25 μm, He, 3. K/min; Tstart: 70. C; Tend: 250. C |
Capillary | Methyl Silicone | 1017.7 | Rao, Rajanikanth, et al., 1989 | 4. K/min, 250. C @ 15. min; Column length: 12. m; Column diameter: 0.5 mm; Tstart: 70. C |
Kovats' RI, polar column, isothermal
Column type | Active phase | Temperature (C) | I | Reference | Comment |
---|---|---|---|---|---|
Capillary | PEG-20M | 100. | 1151. | Morishita, Okano, et al., 1980 | Column length: 75. m; Column diameter: 0.25 mm |
Van Den Dool and Kratz RI, non-polar column, temperature ramp
Column type | Active phase | I | Reference | Comment |
---|---|---|---|---|
Capillary | SE-54 | 1021. | Alma, Nitz, et al., 2004 | 30. m/0.25 mm/0.25 μm, He, 60. C @ 5. min, 2. K/min; Tend: 260. C |
Van Den Dool and Kratz RI, polar column, custom temperature program
Column type | Active phase | I | Reference | Comment |
---|---|---|---|---|
Capillary | FFAP | 1146. | Ranau, Kleeberg, et al., 2005 | 60. m/0.25 mm/0.5 μm, He; Program: 50C(3min) => 3C/min => 100C => 10C/min => 220C(13.5min) |
Normal alkane RI, non-polar column, temperature ramp
Column type | Active phase | I | Reference | Comment |
---|---|---|---|---|
Capillary | HP-5 MS | 1025. | Kim and Chung, 2009 | 30. m/0.25 mm/0.25 μm, Helium, 35. C @ 5. min, 2. K/min, 195. C @ 30. min |
Capillary | RSL-200 | 1025. | Jirovetz, Buchbauer, et al., 2005 | 30. m/0.25 mm/0.25 μm, 40. C @ 2. min, 6. K/min, 280. C @ 10. min |
Capillary | BPX-5 | 1028. | Diaz and Kite, 2002 | 5. K/min; Tstart: 40. C; Tend: 260. C |
Capillary | DB-1 | 1007. | Palá-Paúl, Pérez-Alonso, et al., 2001 | 30. m/0.25 mm/0.25 μm, N2, 4. K/min; Tstart: 80. C; Tend: 225. C |
Normal alkane RI, non-polar column, custom temperature program
Column type | Active phase | I | Reference | Comment |
---|---|---|---|---|
Capillary | Squalane | 1019. | Chen, 2008 | Program: not specified |
Capillary | SE-30 | 1022. | Vinogradov, 2004 | Program: not specified |
Capillary | Methyl Silicone | 1016. | Zenkevich, 2000 | Program: not specified |
Capillary | OV-101 | 1022. | Shibamoto, 1987 | Program: not specified |
Capillary | OV-1, SE-30, Methyl silicone, SP-2100, OV-101, DB-1, etc. | 985. | Waggott and Davies, 1984 | Hydrogen; Column length: 50. m; Column diameter: 0.32 mm; Program: not specified |
Normal alkane RI, polar column, temperature ramp
Column type | Active phase | I | Reference | Comment |
---|---|---|---|---|
Capillary | DB-Wax | 1152. | Tamura, Boonbumrung, et al., 2000 | Nitrogen, 40. C @ 10. min, 2. K/min; Column length: 60. m; Column diameter: 0.25 mm; Tend: 200. C |
Normal alkane RI, polar column, custom temperature program
Column type | Active phase | I | Reference | Comment |
---|---|---|---|---|
Capillary | Carbowax 20M | 1150. | Vinogradov, 2004 | Program: not specified |
Capillary | Carbowax 20M | 1150. | Shibamoto, 1987 | Program: not specified |
References
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, 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.
Kalechits, Luk'yanova, et al., 1990
Kalechits, G.V.; Luk'yanova, V.A.; Kozina, M.P.; Gal'chenko, G.L.,
Synthesis and thermochemical parameters of 1-p-menthene and 3-p-menthene,
J. Gen. Chem. USSR, 1990, 60, 169-172. [all data]
Pines, Olberg, et al., 1952
Pines, H.; Olberg, R.C.; Ipatieff, V.N.,
J. Am. Chem. Soc., 1952, 74, 4872. [all data]
Smith, Fuzek, et al., 1949
Smith, H.A.; Fuzek, J.F.; Meriwether, H.T.,
The Catalytic Hydrogenation of Terpenes,
J. Am. Chem. Soc., 1949, 71, 3765. [all data]
Knoevenagel, 1897
Knoevenagel, E.,
Justus Liebigs Ann. Chem., 1897, 297, 113. [all data]
Bredael, 1982
Bredael, P.,
Retention indices of hydrocarbons on SE-30,
J. Hi. Res. Chromatogr. Chromatogr. Comm., 1982, 5, 6, 325-328, https://doi.org/10.1002/jhrc.1240050610
. [all data]
Albaigés and Guardino, 1980
Albaigés, J.; Guardino, X.,
Gas chromatographic-mass spectrometric identification of alkylcyclohexanes and cyclohexenes,
Chromatographia, 1980, 13, 12, 755-762, https://doi.org/10.1007/BF02265555
. [all data]
Morishita, Okano, et al., 1980
Morishita, F.; Okano, T.; Kojima, T.,
Retention indices of monocyclic monoterpene hydrocarbons,
Bunseki Kagaku, 1980, 29, 1, 48-53, https://doi.org/10.2116/bunsekikagaku.29.48
. [all data]
Hedin, Thompson, et al., 1972
Hedin, P.A.; Thompson, A.C.; Gueldner, R.C.,
Application of a Sequential Reduction Regimen to Fractionation of Essential Oils,
Anal. Chem., 1972, 44, 7, 1254-1257, https://doi.org/10.1021/ac60315a030
. [all data]
Buchin, Salmon, et al., 2002
Buchin, S.; Salmon, J.-C.; Carnat, A.-P.; Berger, T.; Bugaud, C.; Bosset, J.O.,
Identification de composés monoterpéniques, sesquiterpéniques et benzéniques dans un lait d'alpage très riche en ces substances,
Mitt. Lebensmittelunters. Hyg., 2002, 93, 199-216. [all data]
Kasali, Adio, et al., 2002
Kasali, A.A.; Adio, A.M.; Oyedeji, A.O.; Eshilokun, A.O.; Adefenwa, M.,
Volatile constituents of Boswellia serrata Roxb. (Burseraceae) bark,
Flavour Fragr. J., 2002, 17, 6, 462-464, https://doi.org/10.1002/ffj.1124
. [all data]
Mevy, Bessiere, et al., 2002
Mevy, J.P.; Bessiere, J.-M.; Dherbomez, M.; Viano, J.,
Composition and some biological activities of the essential oils from an African pasture grass: Elionurus elegans Kunth.,
J. Agric. Food Chem., 2002, 50, 15, 4240-4243, https://doi.org/10.1021/jf0115140
. [all data]
Ramos, Siani, et al., 2000
Ramos, M.F.S.; Siani, A.C.; Tappin, M.R.R.; Guimaraes, A.C.; Lahoz, J.E.; Ribeiro, J.E.L.S.,
Essential oils from oleoresins of Protium spp. of the Amazon region,
Flavour Fragr. J., 2000, 15, 6, 383-387, https://doi.org/10.1002/1099-1026(200011/12)15:6<383::AID-FFJ927>3.0.CO;2-X
. [all data]
Rao, Rajanikanth, et al., 1989
Rao, A.S.; Rajanikanth, B.; Seshadri, R.,
Volatile aroma components of Curcuma amada Roxb.,
J. Agric. Food Chem., 1989, 37, 3, 740-743, https://doi.org/10.1021/jf00087a036
. [all data]
Alma, Nitz, et al., 2004
Alma, M.H.; Nitz, S.; Kollmannsberger, H.; Digrak, M.; Efe, F.T.; Yilmaz, N.,
Chemical composition and antimicrobial activity of the essential oils from the gum of Turkish Pistachio (Pistacia vera L.),
J. Agric. Food Chem., 2004, 52, 12, 3911-3914, https://doi.org/10.1021/jf040014e
. [all data]
Ranau, Kleeberg, et al., 2005
Ranau, R.; Kleeberg, K.K.; Schlegelmilch, M.; Streese, J.; Stegmann, R.; Steinhart, H.,
Analytical determination of the suitability of different processes for the treatment of odorous waste gas,
Waste Management, 2005, 25, 9, 908-916, https://doi.org/10.1016/j.wasman.2005.07.004
. [all data]
Kim and Chung, 2009
Kim, J.-S.; Chung, H.Y.,
GC-MS analysis of the volatile components in dried boxthorn (Lycium chimensis) Fruit,
J. Korean Soc. Appl. Biol. Chem., 2009, 52, 5, 516-524, https://doi.org/10.3839/jksabc.2009.088
. [all data]
Jirovetz, Buchbauer, et al., 2005
Jirovetz, L.; Buchbauer, G.; Stoyanova, A.; Georgiev, E.V.; Damianova, S.T.,
Composition, quality control and antimicrobial activity of the essential oil of cumin (Cuminum cyminumL.) seeds from Bulgaria that had been stored for up to 36 years,
Int. J. Food Sci. Technol., 2005, 40, 3, 305-310, https://doi.org/10.1111/j.1365-2621.2004.00915.x
. [all data]
Diaz and Kite, 2002
Diaz, A.; Kite, G.C.,
A comparison of the pollination ecology of Arum maculatum and A. italicum in England,
Watsonia, 2002, 24, 171-181. [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]
Chen, 2008
Chen, H.-F.,
Quantitative prediction of gas chromatography retention indices with support vector machines, radial basis neutral networks and multiple linear regression,
Anal. Chim. Acta, 2008, 609, 1, 24-36, https://doi.org/10.1016/j.aca.2008.01.003
. [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, 2000
Zenkevich, I.G.,
Mutual Correlation between Gas Chromatographic Retention Indices of Unsaturated and Saturated Hydrocarbons found by Molecular Dynamics,
Z. Anal. Chem., 2000, 55, 10, 1091-1097. [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]
Waggott and Davies, 1984
Waggott, A.; Davies, I.W.,
Identification of organic pollutants using linear temperature programmed retention indices (LTPRIs) - Part II, 1984, retrieved from http://dwi.defra.gov.uk/research/completed-research/reports/dwi0383.pdf. [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]
Notes
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Gas Chromatography, References
- Symbols used in this document:
Tboil Boiling point ΔcH°liquid Enthalpy of combustion of liquid at standard conditions ΔfH°gas Enthalpy of formation of gas at standard conditions ΔfH°liquid Enthalpy of formation of liquid at standard conditions ΔvapH° Enthalpy of vaporization at standard conditions - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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