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)
  • Gas Chromatography
  • References
  • Notes
• Other data available:
  • UV/Visible spectrum
• Options:
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• NIST / TRC Web Thermo Tables, professional edition (thermophysical and thermochemical data)

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Condensed phase thermochemistry data

Go To: Top, Phase change data, IR Spectrum, Mass spectrum (electron ionization), 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 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

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), Gas Chromatography, 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]

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]

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]

van Gelder, Jonker, et al., 1988
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]

Japp, Gill, et al., 1987
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]

Keiser, Yazlovetsky, et al., 1986
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]

Quilliam and Westmore, 1978
Quilliam, M.A.; Westmore, J.B., Sterically crowded trialkylsilyl derivatives for chromatography and mass spectrometry of biologically-important compounds, Anal. Chem., 1978, 50, 1, 59-68, https://doi.org/10.1021/ac50023a020 . [all data]

Knights, 1966
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]

Ramsey, Lee, et al., 1980
Ramsey, J.D.; Lee, T.D.; Osselton, M.D.; Moffat, A.C., Gas-liquid chromatographic retention indices of 296 non-drug substances on SE-30 or OV-1 likely to be encountered in toxicological analyses, J. Chromatogr., 1980, 184, 2, 185-206, https://doi.org/10.1016/S0021-9673(00)85641-1 . [all data]

Berninger, Grunnagel, et al., 1975
Berninger, H.; Grunnagel, R.; Mall, S.; Moller, M.R., Gas chromatographic identification of unknown substances from body fluids by menas of retention indices, Beitr. Gerichtl. Med., 1975, 33, 185-191. [all data]

Steiner, Steidle, et al., 2005
Steiner, S.; Steidle, J.L.M.; Ruther, J., Female sex pheromone in immature insect males - a case of pre-emergence chemical mimicry?, Behavioral Ecology and Sociobiology, 2005, 58, 2, 111-120, https://doi.org/10.1007/s00265-005-0930-x . [all data]

Tokuda, Saitoh, et al., 1988
Tokuda, H.; Saitoh, E.; Kimura, Y.; Takano, S., Automated analysis of various compounds with a wide range of boiling points by capillary gas chromatgraphy based on retention indices, J. Chromatogr., 1988, 454, 109-120, https://doi.org/10.1016/S0021-9673(00)88606-9 . [all data]

Perrigo, Peel, et al., 1985
Perrigo, B.J.; Peel, H.W.; Ballantyne, D.J., Use of Dual-Column Fused-Silica Capillary Gas Chromatography in Combination with Detector Response Factors for Analytical Toxicology., J. Chromatogr., 1985, 341, 81-88, https://doi.org/10.1016/S0378-4347(00)84011-6 . [all data]

Perrigo, Ballantyne, et al., 1984
Perrigo, B.J.; Ballantyne, D.J.; Peel, H.W., Condierations in developing a data base for drugs on a DBI capillary column, J. Can. Soc. Forensic Sci., 1984, 17, 2, 41-49, https://doi.org/10.1080/00085030.1984.10757360 . [all data]

Anderson and Stafford, 1983
Anderson, W.H.; Stafford, D.T., Applications of capillary gas chromatography in routine toxicological analyses, J. Hi. Res. Chromatogr. Chromatogr. Comm., 1983, 6, 5, 247-254, https://doi.org/10.1002/jhrc.1240060506 . [all data]

Perrigo and Peel, 1981
Perrigo, B.J.; Peel, H.W., The use of retention indices and temperature-programmed gas chromatography in analytical toxicology, J. Chromatogr. Sci., 1981, 19, 5, 219-226, https://doi.org/10.1093/chromsci/19.5.219 . [all data]

Baidarovtseva, Rudenko, et al., 1976
Baidarovtseva, M.A.; Rudenko, B.A.; Kuleshova, M.I.; Kucherov, V.F., Gas-chromatographic separation of free sterols using steam as the mobile phase, Chem. Nat. Compd. (Engl. Transl.), 1976, 11, 6, 765-767, https://doi.org/10.1007/BF00568465 . [all data]

Steiger, Haberer, et al., 2011
Steiger, S.; Haberer, W.; Muller, J.K., Social environment determines degree of chemical signalling (Supplemented matherials), Biol. Lett., 2011, 7, 6, 822-824, https://doi.org/10.1098/rsbl.2011.0457 . [all data]

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Peel, H.W.; Perrigo, B., A practical gas chromatographic screening procedure for toxicological analysis, Can. Soc. Forens. Sci. J., 1976, 9, 2, 69-74, https://doi.org/10.1080/00085030.1976.10757247 . [all data]

Peel and Perrigo, 1975
Peel, H.W.; Perrigo, B., A practical gas chromatographic screening procedure for toxicological analysis, Can.Soc.Forens.Sci.J., 1975, 9, 2, 69-74, https://doi.org/10.1080/00085030.1976.10757247 . [all data]

Steiger, Peschke, et al., 2007
Steiger, S.; Peschke, K.; Francke, W.; Muller, J.K., The smell of parents: breeding status influences cuticular hydrocarbon pattern in the burying beetle Nicrophorus vespilloides, Proc. Roy. Soc. B, 2007, 274, 1622, 2211-2220, https://doi.org/10.1098/rspb.2007.0656 . [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]

Ardrey and Moffat, 1981
Ardrey, R.E.; Moffat, A.C., Gas-liquid chromatographic retention indices of 1318 substances of toxicological interest on SE-30 or OV-1 stationary phase, J. Chromatogr., 1981, 220, 3, 195-252, https://doi.org/10.1016/S0021-9673(00)81925-1 . [all data]

Notes

Go To: Top, Condensed phase thermochemistry data, Phase change data, IR Spectrum, Mass spectrum (electron ionization), Gas Chromatography, 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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