Chemical Properties of Cyclohexanol, 5-methyl-2-(1-methylethyl)-, (1«alpha»,2«beta»,5«alpha»)- (CAS 89-78-1)

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

InChI Key

NOOLISFMXDJSKH-KXUCPTDWSA-N

Formula

C10H20O

SMILES

CC1CCC(C(C)C)C(O)C1

Molecular Weight¹

156.27

CAS

89-78-1

Other Names

• (-)-menthol
• (.+-.)-menthol
• (.+/-.)-Menthol
• (1R,2S,5R)-2-isopropyl-5-methylcyclohexan-1-ol
• (1R,2S,5R)-5-methyl-2-(1-methylethyl)cyclohexanol
• 2-Isopropyl-5-methylcyclohexanol
• 2-Isopropyl-5-methylcyclohexanol, (1«alpha»,2«beta»,5«alpha»)-
• 3-p-Menthanol
• 5-Methyl-2-(1-methylethyl)cyclohexanol
• 5-Methyl-2-(1-methylethyl)cyclohexanol, (1«alpha»,2«beta»,5«alpha»)-
• 5«alpha»-Methyl-2«beta»-(1«alpha»-methylethyl)cyclohexanol
• Cyclohexanol, 2-isopropyl-5-methyl-
• Cyclohexanol, 2-isopropyl-5-methyl-, (1«alpha»,2«beta»,5«alpha»)-
• Cyclohexanol, 5-methyl-2-(1-methylethyl)-, (1R,2S,5R)-rel-
• Cyclohexanol, 5-methyl-2-(1-methylethyl)-, (1«alpha»,2«beta»,5«alpha»)-(.+/-.)-
• DL-menthol
• Diterpene
• Fancol menthol
• Fisherman's friend lozenges
• Hexahydrothymol
• L-menthol
• Menthacamphor
• Menthol
• Menthol terpine hydrate
• Menthol, cis-1,3,trans-1,4-
• Menthomenthol
• NCI-C50000
• NSC 2603
• Peppermint camphor
• Racemic menthol
• Therapeutic mineral ice
• component of Dermoplast
• component of Minut-rub
• component of Robitussin cough drops
• component of Sarna
• component of Theragesic
• levomenthol
• p-Menthan-3-ol
• rac-Menthol
• racementhol
• rel-(1R,2S,5R)-2-isopropyl-5-methylcyclohexan-1-ol
• rel-(1R,2S,5R)-5-methyl-2-(1-methylethyl)cyclohexanol

• C_p,gas : Ideal gas heat capacity (J/mol×K).
• C_sat : Molar heat capacity at saturation pressure (J/mol×K).
• η : Dynamic viscosity (Pa×s).
• Δ_fH°_gas : Enthalpy of formation at standard conditions (kJ/mol).
• Δ_fusH° : Enthalpy of fusion at standard conditions (kJ/mol).
• Δ_fusH : Enthalpy of fusion at a given temperature (kJ/mol).
• Δ_subH : Enthalpy of sublimation at a given temperature (kJ/mol).
• Δ_vapH° : Enthalpy of vaporization at standard conditions (kJ/mol).
• Δ_vapH : Enthalpy of vaporization at a given temperature (kJ/mol).
• IE : Ionization energy (eV).
• logP_oct/wat : Octanol/Water partition coefficient.
• McVol : McGowan's characteristic volume (ml/mol).
• P_vap : Vapor pressure (kPa).
• I_np : Non-polar retention indices.
• I_p : Polar retention indices.
• T_boil : Normal Boiling Point Temperature (K).
• T_boilr : Boiling point at reduced pressure (K).
• T_c : Critical Temperature (K).
• T_fus : Normal melting (fusion) point (K).
• T_triple : Triple Point Temperature (K).
• ¹: Molecular weight from the IUPAC atomic weights tables.

Physical Properties

Property	Value	Unit	Source
ΔfH°gas	-347.50	kJ/mol	Relay (1.0) Calculated Property
ΔfusH°	16.20	kJ/mol	Joback Calculated Property
ΔvapH°	74.01	kJ/mol	Relay (1.0) Calculated Property
IE	9.15	eV	Relay (1.0) Calculated Property
logPoct/wat	2.440		Crippen Calculated Property
McVol	146.770	ml/mol	McGowan Calculated Property
Inp	[198.32; 1194.00]
Inp	1166.60		NIST
Inp	1174.00		NIST
Inp	1180.00		NIST
Inp	1185.00		NIST
Inp	1169.00		NIST
Inp	1169.00		NIST
Inp	1173.00		NIST
Inp	1173.00		NIST
Inp	1141.00		NIST
Inp	1172.00		NIST
Inp	1174.00		NIST
Inp	1162.00		NIST
Inp	1163.00		NIST
Inp	1161.00		NIST
Inp	1168.00		NIST
Inp	1173.00		NIST
Inp	1178.00		NIST
Inp	1160.00		NIST
Inp	1160.00		NIST
Inp	1160.00		NIST
Inp	1141.00		NIST
Inp	1173.00		NIST
Inp	1165.00		NIST
Inp	1170.00		NIST
Inp	1150.20		NIST
Inp	1175.00		NIST
Inp	1173.00		NIST
Inp	1140.00		NIST
Inp	1181.00		NIST
Inp	1180.78		NIST
Inp	1180.91		NIST
Inp	1156.00		NIST
Inp	1167.00		NIST
Inp	1153.30		NIST
Inp	1153.30		NIST
Inp	1153.30		NIST
Inp	1169.00		NIST
Inp	1175.00		NIST
Inp	1172.00		NIST
Inp	1178.00		NIST
Inp	1186.00		NIST
Inp	1170.00		NIST
Inp	1172.00		NIST
Inp	1180.00		NIST
Inp	1182.00		NIST
Inp	1172.00		NIST
Inp	1154.00		NIST
Inp	1178.00		NIST
Inp	1171.00		NIST
Inp	1194.00		NIST
Inp	1172.00		NIST
Inp	1185.00		NIST
Inp	1185.00		NIST
Inp	1172.00		NIST
Inp	1175.00		NIST
Inp	1191.00		NIST
Inp	1149.00		NIST
Inp	1186.00		NIST
Inp	1188.00		NIST
Inp	1179.00		NIST
Inp	1172.00		NIST
Inp	1173.70		NIST
Inp	1166.00		NIST
Inp	1191.00		NIST
Inp	1160.00		NIST
Inp	1174.00		NIST
Inp	1171.00		NIST
Inp	1172.00		NIST
Inp	1151.00		NIST
Inp	1152.00		NIST
Inp	1153.00		NIST
Inp	1155.00		NIST
Inp	1168.00		NIST
Inp	1186.00		NIST
Inp	1186.00		NIST
Inp	1173.00		NIST
Inp	1173.00		NIST
Inp	1150.00		NIST
Inp	1165.00		NIST
Inp	1163.00		NIST
Inp	1163.00		NIST
Inp	1156.00		NIST
Inp	1169.00		NIST
Inp	1169.00		NIST
Inp	1171.00		NIST
Inp	1175.00		NIST
Inp	1173.00		NIST
Inp	1184.00		NIST
Inp	1184.00		NIST
Inp	1150.00		NIST
Inp	1178.00		NIST
Inp	1175.00		NIST
Inp	1172.00		NIST
Inp	1151.00		NIST
Inp	1160.00		NIST
Inp	1182.00		NIST
Inp	1182.00		NIST
Inp	1172.00		NIST
Inp	1173.00		NIST
Inp	1172.00		NIST
Inp	1171.00		NIST
Inp	1171.00		NIST
Inp	1182.00		NIST
Inp	1148.00		NIST
Inp	1166.00		NIST
Inp	1174.00		NIST
Inp	1165.00		NIST
Inp	1173.00		NIST
Inp	1160.00		NIST
Inp	1171.00		NIST
Inp	1171.00		NIST
Inp	1171.00		NIST
Inp	1158.00		NIST
Inp	Outlier 198.32		NIST
Inp	1166.60		NIST
Inp	1173.00		NIST
Inp	1175.00		NIST
Inp	1182.00		NIST
Inp	1171.00		NIST
Inp	1165.00		NIST
Inp	1185.00		NIST
Inp	1141.00		NIST
Inp	1163.00		NIST
Ip	[1589.00; 1652.00]
Ip	1641.00		NIST
Ip	1636.00		NIST
Ip	1637.00		NIST
Ip	1651.00		NIST
Ip	1631.00		NIST
Ip	1640.00		NIST
Ip	1642.00		NIST
Ip	1619.00		NIST
Ip	1632.00		NIST
Ip	1631.00		NIST
Ip	1618.00		NIST
Ip	1651.00		NIST
Ip	1632.00		NIST
Ip	1612.00		NIST
Ip	1630.00		NIST
Ip	1637.00		NIST
Ip	1636.00		NIST
Ip	1642.00		NIST
Ip	1646.00		NIST
Ip	1627.00		NIST
Ip	1615.00		NIST
Ip	1644.00		NIST
Ip	1637.00		NIST
Ip	1641.00		NIST
Ip	1639.00		NIST
Ip	1645.00		NIST
Ip	1652.00		NIST
Ip	1636.00		NIST
Ip	1636.00		NIST
Ip	Outlier 1589.00		NIST
Ip	1631.00		NIST
Ip	1628.00		NIST
Ip	1641.00		NIST
Ip	1637.00		NIST
Ip	1614.00		NIST
Ip	1637.00		NIST
Ip	1651.00		NIST
Ip	1651.00		NIST
Ip	1651.00		NIST
Ip	1612.00		NIST
Ip	1640.00		NIST
Ip	1642.00		NIST
Ip	Outlier 1600.00		NIST
Ip	1631.00		NIST
Ip	1649.00		NIST
Ip	1635.00		NIST
Ip	1637.00		NIST
Ip	1638.00		NIST
Ip	1608.00		NIST
Ip	1652.00		NIST
Ip	1612.00		NIST
Ip	1638.00		NIST
Ip	1636.00		NIST
Ip	1612.00		NIST
Ip	1642.00		NIST
Ip	1649.00		NIST
Ip	1652.00		NIST
Tboil	[489.45; 489.65]	K
Tboil	489.50	K	KDB
Tboil	489.45 ± 0.60	K	NIST
Tboil	489.55 ± 0.40	K	NIST
Tboil	489.65 ± 0.30	K	NIST
Tboil	489.55 ± 0.50	K	NIST
Tboil	489.60 ± 0.50	K	NIST
Tboil	489.60 ± 0.50	K	NIST
Tc	[694.00; 694.00]	K
Tc	694.00	K	KDB
Tc	694.00 ± 5.00	K	NIST
Tfus	[314.00; 315.90]	K
Tfus	315.90	K	(Solid + liquid) equilibrium phase diagrams in binary mixtures containing terpenes: New experimental data and analysis of several modelling strategies with modified UNIFAC (Dortmund) and PC-SAFT equation of state
Tfus	315.00	K	KDB
Tfus	314.00 ± 0.60	K	NIST
Tfus	315.15 ± 0.50	K	NIST
Ttriple	305.70	K	Polymorphism and thermophysical properties of L- and DL-menthol

Cheméo can also estimate Critical Pressure, Critical Volume, Standard Gibbs free energy of formation, Acentric Factor, Log10 of Water solubility in mol/l for this compound, but they fall outside the models' validated range, so they are not shown here. Open the prediction tool to compute them on demand.

Temperature Dependent Properties

Property	Value	Unit	Temperature (K)	Source
Csat	[206.10; 264.30]	J/mol×K	[253.15; 305.15]
Csat	206.10	J/mol×K	253.15	Interpretation of the global heat of melting in eutectic binary systems
Csat	214.50	J/mol×K	259.15	Interpretation of the global heat of melting in eutectic binary systems
Csat	221.90	J/mol×K	265.15	Interpretation of the global heat of melting in eutectic binary systems
Csat	228.60	J/mol×K	271.15	Interpretation of the global heat of melting in eutectic binary systems
Csat	235.60	J/mol×K	277.15	Interpretation of the global heat of melting in eutectic binary systems
Csat	242.20	J/mol×K	283.15	Interpretation of the global heat of melting in eutectic binary systems
Csat	248.10	J/mol×K	289.15	Interpretation of the global heat of melting in eutectic binary systems
Csat	253.90	J/mol×K	295.15	Interpretation of the global heat of melting in eutectic binary systems
Csat	259.90	J/mol×K	301.15	Interpretation of the global heat of melting in eutectic binary systems
Csat	264.30	J/mol×K	305.15	Interpretation of the global heat of melting in eutectic binary systems
ΔfusH	[10.25; 11.88]	kJ/mol	[301.20; 316.20]
ΔfusH	10.25	kJ/mol	301.20	NIST
ΔfusH	11.88	kJ/mol	316.20	NIST
ΔsubH	79.00 ± 4.00	kJ/mol	289.00	NIST
ΔvapH	75.00	kJ/mol	298.00	Vapor pressures and vaporization enthalpy of (-) alpha-bisabolol and (dl) menthol by correlation gas chromatography

Pressure Dependent Properties

Correlations

Property	Value	Unit	Temperature (K)	Source
Cp,gas	[196.22; 552.84]	J/mol×K	[273.00; 1000.00]	Joback Predicted correlation
Equation			Y = A + B·T + C·T² + D·T³ + E·T⁴ Y is Cp,gas in J/mol×K, T in K
Coefficient A			-5.63200e+01
Coefficient B			1.06286e+00
Coefficient C			-5.24000e-04
Coefficient D			7.03000e-08
Coefficient E			0.00000e+00
Temperature range, min.			273.00
Temperature range, max.			1000.00
Cp,gas	196.22	J/mol×K	273.00	Calculated Property
Cp,gas	257.23	J/mol×K	353.78	Calculated Property
Cp,gas	312.37	J/mol×K	434.56	Calculated Property
Cp,gas	361.87	J/mol×K	515.33	Calculated Property
Cp,gas	405.95	J/mol×K	596.11	Calculated Property
Cp,gas	444.84	J/mol×K	676.89	Calculated Property
Cp,gas	478.74	J/mol×K	757.67	Calculated Property
Cp,gas	507.90	J/mol×K	838.44	Calculated Property
Cp,gas	532.52	J/mol×K	919.22	Calculated Property
Cp,gas	552.84	J/mol×K	1000.00	Calculated Property

Property	Value	Unit	Temperature (K)	Source
η	[0.0043262; 0.0002277]	Pa×s	[315.01; 485.80]	Joback Predicted correlation
Equation			Y = exp(A + B/T + C·ln(T) + D·T^E) Y is η in Pa×s, T in K
Coefficient A			-1.38184e+01
Coefficient B			2.63834e+03
Coefficient C			0.00000e+00
Coefficient D			0.00000e+00
Coefficient E			0.00000e+00
Comment			Liquid phase. Joback/Reid (1987), valid from Tf to 0.7·Tc.
Temperature range, min.			315.01
Temperature range, max.			485.80
η	0.0043262	Pa×s	315.01	Calculated Property
η	0.0026881	Pa×s	333.99	Calculated Property
η	0.0017579	Pa×s	352.97	Calculated Property
η	0.0012005	Pa×s	371.94	Calculated Property
η	0.0008508	Pa×s	390.92	Calculated Property
η	0.0006225	Pa×s	409.89	Calculated Property
η	0.0004682	Pa×s	428.87	Calculated Property
η	0.0003608	Pa×s	447.85	Calculated Property
η	0.0002839	Pa×s	466.82	Calculated Property
η	0.0002277	Pa×s	485.80	Calculated Property

Property	Value	Unit	Temperature (K)	Source
Pvap	[0.13; 101.24]	kPa	[329.15; 485.15]	KDB Vapor Pressure Data
Equation			ln(Y) = A + B/T + C·ln(T) + D·T² + E/T² Y is Pvap in kPa, T in K
Coefficient A			6.60468e+01
Coefficient B			-9.08243e+03
Coefficient C			-7.05284e+00
Coefficient D			3.86441e-06
Coefficient E			0.00000e+00
Temperature range, min.			329.15
Temperature range, max.			485.15
Pvap	0.13	kPa	329.15	Calculated Property
Pvap	0.39	kPa	346.48	Calculated Property
Pvap	1.01	kPa	363.82	Calculated Property
Pvap	2.37	kPa	381.15	Calculated Property
Pvap	5.14	kPa	398.48	Calculated Property
Pvap	10.40	kPa	415.82	Calculated Property
Pvap	19.79	kPa	433.15	Calculated Property
Pvap	35.67	kPa	450.48	Calculated Property
Pvap	61.35	kPa	467.82	Calculated Property
Pvap	101.24	kPa	485.15	Calculated Property
Pvap	[0.13; 100.65]	kPa	[329.00; 485.00]	NIST
Equation			ln(Y) = A + B/(T + C) Y is Pvap in kPa, T in K
Coefficient A			1.70011e+01
Coefficient B			-5.53990e+03
Coefficient C			-3.78530e+01
Reference			Stull, 1947
Comment			Coefficents calculated by NIST from author's data.
Temperature range, min.			329.00
Temperature range, max.			485.00
Pvap	0.13	kPa	329.00	Calculated Property
Pvap	0.38	kPa	346.33	Calculated Property
Pvap	1.00	kPa	363.67	Calculated Property
Pvap	2.36	kPa	381.00	Calculated Property
Pvap	5.12	kPa	398.33	Calculated Property
Pvap	10.36	kPa	415.67	Calculated Property
Pvap	19.71	kPa	433.00	Calculated Property
Pvap	35.53	kPa	450.33	Calculated Property
Pvap	61.07	kPa	467.67	Calculated Property
Pvap	100.65	kPa	485.00	Calculated Property

Similar Compounds

Find more compounds similar to Cyclohexanol, 5-methyl-2-(1-methylethyl)-, (1«alpha»,2«beta»,5«alpha»)-.

Mixtures

• Cyclohexanol, 5-methyl-2-(1-methylethyl)-, (1«alpha»,2«beta»,5«alpha»)- + 1-Decanol
• Cyclohexanol, 5-methyl-2-(1-methylethyl)-, (1«alpha»,2«beta»,5«alpha»)- + Benzyl alcohol
• Cyclohexanol, 5-methyl-2-(1-methylethyl)-, (1«alpha»,2«beta»,5«alpha»)- + Cyclohexaneethanol
• Cyclohexanol, 5-methyl-2-(1-methylethyl)-, (1«alpha»,2«beta»,5«alpha»)- + Decane
• Cyclohexanol, 5-methyl-2-(1-methylethyl)-, (1«alpha»,2«beta»,5«alpha»)- + 2-Propanol
• Cyclohexanol, 5-methyl-2-(1-methylethyl)-, (1«alpha»,2«beta»,5«alpha»)- + 2-Propanol + methyl salicylate
• Cyclohexanol, 5-methyl-2-(1-methylethyl)-, (1«alpha»,2«beta»,5«alpha»)- + n-Decanoic acid
• Cyclohexanol, 5-methyl-2-(1-methylethyl)-, (1«alpha»,2«beta»,5«alpha»)- + n-Decanoic acid + Water
• Cyclohexanol, 5-methyl-2-(1-methylethyl)-, (1«alpha»,2«beta»,5«alpha»)- + 2-DIETHYLAMINO-N-(2,6-XYLYL)ACETAMIDE
• Cyclohexanol, 5-methyl-2-(1-methylethyl)-, (1«alpha»,2«beta»,5«alpha»)- + Pentanoic acid, 4-oxo- + Heptane

Sources

• KDB Vapor Pressure Data
• Cheméo Relay (1.0)
• Cheméo Relay (1.0, beta) Beta: served but experimental, data-limited and below our cross-validation release bar; the Joback value is recommended where available.
• Crippen Method
• Crippen Method
• (Solid + liquid) equilibrium phase diagrams in binary mixtures containing terpenes: New experimental data and analysis of several modelling strategies with modified UNIFAC (Dortmund) and PC-SAFT equation of state
• Liquid-liquid equilibria of n-heptane, methanol and deep eutectic solvents composed of carboxylic acid and monocyclic terpenes
• Thermodynamic properties of hydrophobic deep eutectic solvents and solubility of water and HMF in them: Measurements and PC-SAFT modeling
• Vapor pressures and vaporization enthalpy of (-) alpha-bisabolol and (dl) menthol by correlation gas chromatography
• Polymorphism and thermophysical properties of L- and DL-menthol
• Solute-Solvent and Solvent-Solvent Interactions of Menthol in Isopropyl Alcohol and its Binary Mixtures with Methyl Salicylate by Volumetric, Viscometric, Interferometric and Refractive Index Techniques.
• Interpretation of the global heat of melting in eutectic binary systems
• Joback Method
• KDB
• McGowan Method
• NIST Webbook

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