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 Copy

  
• IUPAC Standard InChIKey: HVYWMOMLDIMFJA-VUDDDUNTSA-N Copy
• CAS Registry Number: 57-88-5
• Chemical structure:
  This structure is also available as a 2d Mol file
• Stereoisomers:
  • Cholest-5-en-3-ol, (3α)-
• 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
• Permanent link for this species. Use this link for bookmarking this species for future reference.
• Information on this page:
  • Condensed phase thermochemistry data
  • Phase change data
  • IR Spectrum
  • Mass spectrum (electron ionization)
  • UV/Visible spectrum
  • Gas Chromatography
  • References
  • Notes
• Options:
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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

Phase change 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 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

Enthalpy of vaporization

Enthalpy of sublimation

Enthalpy of fusion

Enthalpy of phase transition

Entropy of phase transition

IR Spectrum

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Data compiled by: Coblentz Society, Inc.

• SOLID (KBr DISC) VS KBr $$SEE 5095 FOR SOLUTION; PERKIN-ELMER 21 (GRATING); DIGITIZED BY COBLENTZ SOCIETY (BATCH I) FROM HARD COPY; 2 cm^-1 resolution
• SOLID (MINERAL OIL MULL); Not specified, most likely a prism, grating, or hybrid spectrometer.; DIGITIZED BY NIST FROM HARD COPY; 4 cm^-1 resolution
• SOLUTION 1% (CS2 FOR 2-15 microns, AND C2Cl4 FOR 5.5-7.2 microns) $$SEE 5106 FOR KBr DISC; PERKIN-ELMER 21 (GRATING); DIGITIZED BY COBLENTZ SOCIETY (BATCH I) FROM HARD COPY; 2 cm^-1 resolution

Mass spectrum (electron ionization)

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

Spectrum

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Additional Data

UV/Visible spectrum

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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: Victor Talrose, Alexander N. Yermakov, Alexy A. Usov, Antonina A. Goncharova, Axlexander N. Leskin, Natalia A. Messineva, Natalia V. Trusova, Margarita V. Efimkina

Spectrum

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Additional Data

Gas Chromatography

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

Kovats' RI, non-polar column, isothermal

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Kovats' RI, non-polar column, custom temperature program

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Van Den Dool and Kratz RI, non-polar column, temperature ramp

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Normal alkane RI, non-polar column, isothermal

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Normal alkane RI, non-polar column, temperature ramp

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Normal alkane RI, non-polar column, custom temperature program

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References

Go To: Top, Condensed phase thermochemistry data, Phase change data, IR Spectrum, Mass spectrum (electron ionization), UV/Visible spectrum, Gas Chromatography, NIST Subscription Links, 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 (3_β)], J. Res. Natl. Bur. Stand. Sect. A:, 1975, 79, 493-496. [all data]

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Paoli, D.; Garrigues, J.-C.; Patin, H., Combustion microcalorimetry: application to steroids, C. R. Acad. Sci. Paris, 1969, 268, 780-783. [all data]

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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]

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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]

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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]

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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]

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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]

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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]

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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]

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Venner, H., Chem. Ber., 1956, 89, 1634. [all data]

Keiser, Retunskii, et al., 1990
Keiser, L.S.; Retunskii, V.N.; Yazlovetskii, I.G., Gas chromatographic identification of sterols in insects. Estimation of retention data reproducibility, Zh. Anal. Khim., 1990, 45, 1767-1773. [all data]

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van Gelder, W.M.J.; Jonker, H.H.; Huizing, H.J.; Scheffer, J.J.C., Capillary gas chromatography of steroidal alkaloids from Solanaceae. Retention indices and simultaneous flame ionization/nitrogen-specific detection, J. Chromatogr., 1988, 442, 133-145, https://doi.org/10.1016/S0021-9673(00)94463-7 . [all data]

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Japp, M.; Gill, R.; Osselton, M.D., Comparison of drug retention indices determined on packed, wide bore capillary and narrow bore capillary columns, J. Forensic Sci., 1987, 32, 6, 1574-1586. [all data]

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Keiser, L.S.; Yazlovetsky, I.G.; Retunsky, V.N., Gas-chromatographic indentification of sterols in insects with the use of two-dimentional three-phase diagrams plotted on the basis of logarithmic retention indices, J. Anal. Chem. USSR (Engl. Transl.), 1986, 41, 9, 1166-1172. [all data]

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Knights, B.A., Application of retention indices to steroid gas chromatography, J. Gas Chromatogr., 1966, 4, 9, 329-331, https://doi.org/10.1093/chromsci/4.9.329 . [all data]

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Notes

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• 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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