Stigmasterol

Formula: C₂₉H₄₈O
Molecular weight: 412.6908
IUPAC Standard InChI: InChI=1S/C29H48O/c1-7-21(19(2)3)9-8-20(4)25-12-13-26-24-11-10-22-18-23(30)14-16-28(22,5)27(24)15-17-29(25,26)6/h8-10,19-21,23-27,30H,7,11-18H2,1-6H3/b9-8+/t20?,21?,23-,24?,25?,26?,27?,28?,29?/m1/s1
IUPAC Standard InChIKey: HCXVJBMSMIARIN-BASBAMEESA-N
CAS Registry Number: 83-48-7
Chemical structure:
This structure is also available as a 2d Mol file
Other names: Stigmasta-5,22-dien-3-ol, (3β,22E)-; Stigmasta-5,22-dien-3β-ol; β-Stigmasterol; (24S)-5,22-Stigmastadien-3β-ol; Stigmasta-5,22-dien-3-ol, (3β)-; Stigmasterin; 5,22-Cholestadien-24-ethyl-3β-ol; Δ5,22-Stigmastadien-3β-ol; Stigmasta-5,22-dien-3-ol; NSC 8095; Phytosterol; I-Stigmasterol; (22E)-Stigmasta-5,22-dien-3-ol
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Other data available:
- Mass spectrum (electron ionization)
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Phase change data

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Data compiled by: William E. Acree, Jr., James S. Chickos

Enthalpy of sublimation

Δ_subH (kcal/mol)	Temperature (K)	Method	Reference
40.25 ± 0.33	390. to 417.	ME	Oja, Chen, et al., 2009

Gas Chromatography

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

Kovats' RI, non-polar column, isothermal

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Column type	Active phase	Temperature (C)	I	Reference	Comment
Packed	SE-30	230.	3148.	Keiser, Retunskii, et al., 1990	N2; Column length: 1.2 m
Packed	SE-30	240.	3170.	Keiser, Retunskii, et al., 1990	N2; Column length: 1.2 m
Packed	SE-30	250.	3172.	Keiser, Retunskii, et al., 1990	N2; Column length: 1.2 m
Packed	E-301	210.	3143.	Keiser, Retunskii, et al., 1990	N2; Column length: 1.2 m
Packed	E-301	220.	3138.	Keiser, Retunskii, et al., 1990	N2; Column length: 1.2 m
Packed	E-301	220.	3166.	Keiser, Retunskii, et al., 1990	N2; Column length: 1.2 m
Packed	E-301	230.	3142.	Keiser, Retunskii, et al., 1990	N2; Column length: 1.2 m
Packed	E-301	230.	3191.	Keiser, Retunskii, et al., 1990	N2; Column length: 1.2 m
Packed	E-301	240.	3164.	Keiser, Retunskii, et al., 1990	N2; Column length: 1.2 m
Capillary	CP Sil 5 CB	270.	3213.	van Gelder, Jonker, et al., 1988	50. m/0.22 mm/0.12 μm, H2
Packed	SE-30	230.	3148.	Keiser, Yazlovetsky, et al., 1986	N2; Column length: 1.2 m
Packed	SE-30	240.	3170.	Keiser, Yazlovetsky, et al., 1986	N2; Column length: 1.2 m
Packed	SE-30	250.	3172.	Keiser, Yazlovetsky, et al., 1986	N2; Column length: 1.2 m
Packed	SE-30	240.	3140.	Keiser, Yazlovetsky, et al., 1986	N2; Column length: 1.2 m
Packed	SE-30	240.	3142.	Keiser, Yazlovetsky, et al., 1986	N2; Column length: 1.2 m
Packed	SE-30	240.	3145.	Keiser, Yazlovetsky, et al., 1986	N2; Column length: 1.2 m

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

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Column type	Active phase	I	Reference	Comment
Capillary	VF-5MS	3248.6	Tret'yakov, 2008	30. m/0.25 mm/0.25 μm, He; Program: Multi-step temperature program; T(initial)=60C; T(final)=270C

Normal alkane RI, non-polar column, temperature ramp

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Column type	Active phase	I	Reference	Comment
Capillary	HP-5 MS	3170.	Xu, Han, et al., 2012	30. m/0.25 mm/0.25 μm, 60. C @ 2. min, 15. K/min, 300. C @ 10. min
Capillary	HP-5 MS	3170.	Xu, Han, et al., 2009	30. m/0.25 mm/0.25 μm, Helium, 60. C @ 2. min, 15. K/min, 300. C @ 10. min

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

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Column type	Active phase	I	Reference	Comment
Capillary		3170.	El-Shazily, Hafez, et al., 2004	Program: not specified
Capillary	OV-1	3170.	El-Shazly and Hussein, 2004	He; Column length: 15. m; Column diameter: 0.317 mm; Program: 50C(4min) => 4C/min => 90C => 10C/min => 300C(10min)

References

Go To: Top, Phase change data, Gas Chromatography, Notes

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]

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]

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]

Tret'yakov, 2008
Tret'yakov, K.V., Retention Data. NIST Mass Spectrometry Data Center., NIST Mass Spectrometry Data Center, 2008. [all data]

Xu, Han, et al., 2012
Xu, L.-L.; Han, T.; Wu, J.-Z.; Zhang, Q.-Y.; Zhang, H.; Huang, B.-K.; Rahman, K., Comparative research of chemical constituents, antifungal and antitumor properties of ether extracts of Panax ginseng and its endophytic fungus, 2012, retrieved from http://www.thefreelibrary.com/Comparative .... [all data]

Xu, Han, et al., 2009
Xu, L.-L.; Han, T.; Wu, J.-Z.; Zhang, Q.-Y.; Zhang, H.; Huang, B.-K.; Rahman, K., Comparative research of chemical constituents, antifungal and antitumor properties of ether extracts of Panax ginseng and its endophytic fungus, Phytomedicine: Int. J. Phytotherapy Phytopharmacology, 2009, 16, 6-7, 609-616, https://doi.org/10.1016/j.phymed.2009.03.014 . [all data]

El-Shazily, Hafez, et al., 2004
El-Shazily, A.M.; Hafez, S.S.; Wink, M., Comparative study of the essential oils and extracts of Achillea fragrantissima (Forssk.) Sch. Bip. and Achillea santolina L. (Asteraceae) from Egypt, Pharmazie, 2004, 59, 226-230. [all data]

El-Shazly and Hussein, 2004
El-Shazly, A.M.; Hussein, K.T., Chemical analysis and biological activities of the essential oil of Teucrium leucocladum Boiss. (Lamiaceae), Biochem. Syst. Ecol., 2004, 32, 7, 665-674, https://doi.org/10.1016/j.bse.2003.12.009 . [all data]

Notes

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Symbols used in this document:

Δ_subH Enthalpy of sublimation
Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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