Cholesterol
- Formula: C27H46O
- Molecular weight: 386.6535
- IUPAC Standard InChI: InChI=1S/C27H46O/c1-18(2)7-6-8-19(3)23-11-12-24-22-10-9-20-17-21(28)13-15-26(20,4)25(22)14-16-27(23,24)5/h9,18-19,21-25,28H,6-8,10-17H2,1-5H3/t19?,21-,22?,23?,24?,25?,26?,27?/m1/s1
- IUPAC Standard InChIKey: HVYWMOMLDIMFJA-VUDDDUNTSA-N
- CAS Registry Number: 57-88-5
- Chemical structure:
This structure is also available as a 2d Mol file - Stereoisomers:
- Other names: Cholest-5-en-3-ol (3β)-; (-)-Cholesterol; Cholest-5-en-3β-ol; Cholesterin; Cholesterol base H; Cholesteryl alcohol; Cordulan; Dusoline; Dusoran; Dythol; Hydrocerin; Kathro; Lanol; Nimco cholesterol base H; Nimco cholesterol base No. 712; Provitamin D; Tegolan; Wool alcohols B. P.; 3β-Hydroxycholest-5-ene; 5-Cholesten-3β-ol; Cholestrin; Cholestrol; Super hartolan; 5,6-Cholesten-3β-ol; Δ5-Cholesten-3-β-ol; Cholesterine; Dastar; Fancol CH; (3β)-Cholest-5-en-3-ol; Cholest-5-en-3beta-ol; Lidinite; NSC 8798; Cholest-5-en-3-ol; 5-Cholesten-3B-ol; Cholest-5-en-3b-ol
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Condensed phase thermochemistry data
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: Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔfH°solid | -161.3 ± 0.98 | kcal/mol | Ccb | Johnson, 1975 | |
| Quantity | Value | Units | Method | Reference | Comment |
| ΔcH°solid | -3949.33 ± 0.93 | kcal/mol | Ccb | Johnson, 1975 | Corresponding ΔfHºsolid = -161.3 kcal/mol (simple calculation by NIST; no Washburn corrections) |
| ΔcH°solid | -3966. ± 16. | kcal/mol | Ccb | Paoli, Garrigues, et al., 1969 | Corresponding ΔfHºsolid = -145. kcal/mol (simple calculation by NIST; no Washburn corrections) |
Phase change data
Go To: Top, Condensed phase thermochemistry 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 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
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
DH - Eugene S. Domalski and Elizabeth D. Hearing
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| Tboil | 633.2 | K | N/A | Aldrich Chemical Company Inc., 1990 | BS |
| Quantity | Value | Units | Method | Reference | Comment |
| Tfus | 420.2 | K | N/A | Davis, Porter, et al., 1970 | Uncertainty assigned by TRC = 0.5 K; TRC |
| Quantity | Value | Units | Method | Reference | Comment |
| ΔvapH° | 36.7 ± 0.2 | kcal/mol | CGC | Nichols, Kweskin, et al., 2006 | AC |
| Quantity | Value | Units | Method | Reference | Comment |
| ΔsubH° | 27.40 | kcal/mol | V | Hickman, Hecker, et al., 1937 | ALS |
Enthalpy of vaporization
| ΔvapH (kcal/mol) | Temperature (K) | Method | Reference | Comment |
|---|---|---|---|---|
| 27.46 | 426. | A | Stephenson and Malanowski, 1987 | Based on data from 411. to 447. K.; AC |
Enthalpy of sublimation
| ΔsubH (kcal/mol) | Temperature (K) | Method | Reference | Comment |
|---|---|---|---|---|
| 34.1 ± 0.2 | 386. to 414. | ME | Oja, Chen, et al., 2009 | AC |
Enthalpy of fusion
| ΔfusH (kcal/mol) | Temperature (K) | Method | Reference | Comment |
|---|---|---|---|---|
| 6.81 | 421.7 | DSC | Chen, Su, et al., 2009 | AC |
| 6.00 | 423.2 | DSC | Peng, Jiangjun, et al., 2008 | Based on data from 300. to 440. K.; AC |
| 5.045 | 423.2 | DSC | Kaloustian, Pauli, et al., 2003 | AC |
| 6.33 | 422.5 | N/A | IWAHASHI, MINAMI, et al., 2001 | AC |
| 6.79 | 422.3 | AC | Miltenburg, Genderen, et al., 1998 | AC |
| 6.551 | 420.2 | N/A | Domalski and Hearing, 1996 | AC |
Enthalpy of phase transition
| ΔHtrs (kcal/mol) | Temperature (K) | Initial Phase | Final Phase | Reference | Comment |
|---|---|---|---|---|---|
| 0.5975 | 304.8 | crystaline, II | crystaline, I | Petropavlov, Tsygankova, et al., 1988 | DH |
Entropy of phase transition
| ΔStrs (cal/mol*K) | Temperature (K) | Initial Phase | Final Phase | Reference | Comment |
|---|---|---|---|---|---|
| 2.0 | 304.8 | crystaline, II | crystaline, I | Petropavlov, Tsygankova, et al., 1988 | DH |
References
Go To: Top, Condensed phase thermochemistry data, Phase change data, Notes
Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
Johnson, 1975
Johnson, W.H.,
The enthalpies of combustion and formation of cholesterol [cholest-5-en-3-ol (3β)],
J. Res. Natl. Bur. Stand. Sect. A:, 1975, 79, 493-496. [all data]
Paoli, Garrigues, et al., 1969
Paoli, D.; Garrigues, J.-C.; Patin, H.,
Combustion microcalorimetry: application to steroids,
C. R. Acad. Sci. Paris, 1969, 268, 780-783. [all data]
Aldrich Chemical Company Inc., 1990
Aldrich Chemical Company Inc.,
Catalog Handbook of Fine Chemicals, Aldrich Chemical Company, Inc., Milwaukee WI, 1990, 1. [all data]
Davis, Porter, et al., 1970
Davis, G.J.; Porter, R.S.; Barrall, E.M.,
Evaluation of Thermal Transitions in Some Cholesteryl Esters of Saturated Aliphatic Acids,
Mol. Cryst. Liq. Cryst., 1970, 10, 1-2, 1, https://doi.org/10.1080/15421407008083482
. [all data]
Nichols, Kweskin, et al., 2006
Nichols, Gary; Kweskin, Sasha; Frericks, Margaret; Reiter, Sarah; Wang, Gin; Orf, Jennifer; Carvallo, Brett; Hillesheim, Dorothea; Chickos, James,
Evaluation of the Vaporization, Fusion, and Sublimation Enthalpies of the 1-Alkanols: The Vaporization Enthalpy of 1-, 6-, 7-, and 9-Heptadecanol, 1-Octadecanol, 1-Eicosanol, 1-Docosanol, 1-Hexacosanol, and Cholesterol at T = 298.15 K by Correlation Gas Chromatography,
J. Chem. Eng. Data, 2006, 51, 2, 475-482, https://doi.org/10.1021/je0503857
. [all data]
Hickman, Hecker, et al., 1937
Hickman, K.C.D.; Hecker, J.C.; Embree, N.D.,
Direct determination of low vapor pressures,
Ind. Eng. Chem., 1937, 9, 264-267. [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]
Oja, Chen, et al., 2009
Oja, Vahur; Chen, Xu; Hajaligol, Mohammad R.; Chan, W. Geoffrey,
Sublimation Thermodynamic Parameters for Cholesterol, Ergosterol, β-Sitosterol, and Stigmasterol,
J. Chem. Eng. Data, 2009, 54, 3, 730-734, https://doi.org/10.1021/je800395m
. [all data]
Chen, Su, et al., 2009
Chen, Wei; Su, Baogen; Xing, Huabin; Yang, Yiwen; Ren, Qilong,
Solubilities of cholesterol and desmosterol in binary solvent mixtures of n-hexane+ethanol,
Fluid Phase Equilibria, 2009, 287, 1, 1-6, https://doi.org/10.1016/j.fluid.2009.08.016
. [all data]
Peng, Jiangjun, et al., 2008
Peng, L.; Jiangjun, X.; Fangquan, M.; Xi, L.; Chaocan, Z.,
Study on the thermodynamic properties of cholesterol,
J Therm Anal Calorim, 2008, 93, 2, 485-488, https://doi.org/10.1007/s10973-007-8675-6
. [all data]
Kaloustian, Pauli, et al., 2003
Kaloustian, J.; Pauli, A-M; Lechene de la Porte, P.; Lafont, H.; Portugal, H.,
Journal of Thermal Analysis and Calorimetry, 2003, 71, 2, 341-351, https://doi.org/10.1023/A:1022818902212
. [all data]
IWAHASHI, MINAMI, et al., 2001
IWAHASHI, Makio; MINAMI, Hideyuki; SUZUKI, Takeshi; KOYANAGI, Masaru; YAO, Haruhiko; EMA, Kenji; ASHIZAWA, Kazuhide,
Thermodynamic Properties of Steroids: 5-cholesten-3.BETA.-ol, 5.ALPHA.-cholestan-3.BETA.-ol, and 5.BETA.-cholestan-3.ALPHA.-ol.,
J. Oleo Sci., 2001, 50, 9, 693-699, https://doi.org/10.5650/jos.50.693
. [all data]
Miltenburg, Genderen, et al., 1998
Miltenburg, J.C. van; Genderen, A.C.G. van; den Berg, G.J.K. van,
Design improvements in adiabatic calorimetry,
Thermochimica Acta, 1998, 319, 1-2, 151-162, https://doi.org/10.1016/S0040-6031(98)00402-X
. [all data]
Domalski and Hearing, 1996
Domalski, Eugene S.; Hearing, Elizabeth D.,
Heat Capacities and Entropies of Organic Compounds in the Condensed Phase. Volume III,
J. Phys. Chem. Ref. Data, 1996, 25, 1, 1, https://doi.org/10.1063/1.555985
. [all data]
Petropavlov, Tsygankova, et al., 1988
Petropavlov, N.N.; Tsygankova, I.G.; Teslenko, L.A.,
Microcalorimetric investigation of polymorphic transitions in organic crystals,
Sov. Phys. Crystallogr., 1988, 33(6), 853-855. [all data]
Notes
Go To: Top, Condensed phase thermochemistry data, Phase change data, References
- Symbols used in this document:
Tboil Boiling point Tfus Fusion (melting) point ΔHtrs Enthalpy of phase transition ΔStrs Entropy of phase transition ΔcH°solid Enthalpy of combustion of solid at standard conditions ΔfH°solid Enthalpy of formation of solid at standard conditions ΔfusH Enthalpy of fusion ΔsubH Enthalpy of sublimation ΔsubH° Enthalpy of sublimation at standard conditions 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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