Cholanic acid, 3α,7α-dihydroxy, Me-TMS

Formula: C₃₁H₅₈O₄Si₂
Molecular weight: 550.9608
IUPAC Standard InChI: InChI=1S/C31H58O4Si2/c1-21(11-14-28(32)33-4)24-12-13-25-29-26(16-18-31(24,25)3)30(2)17-15-23(34-36(5,6)7)19-22(30)20-27(29)35-37(8,9)10/h21-27,29H,11-20H2,1-10H3/t21-,22+,23-,24-,25+,26+,27-,29+,30+,31-/m0/s1
IUPAC Standard InChIKey: FUVKOFYYHKWFJK-CPENPXANSA-N
CAS Registry Number: 52759-80-5
Chemical structure:
This structure is also available as a 2d Mol file or as a computed 3d SD file
The 3d structure may be viewed using Java or Javascript.
Stereoisomers:
Other names: Chenodeoxycholic acid, trimethylsilyl ether-methyl ester; 3α,7α-Dihydroxy-5β-cholanic acid, methyl ester, TMS; Chenodeoxycholic acid, methyl ester, TMS; Methyl 3-α,7-α-dihydroxy-5-β-cholanoate, TMS; 3-α,7-α-Dihydroxy-5-β-cholanoic acid, MeTMS; 3α,7α-Dihydroxy-5β-cholanoic acid, methyl ester-trimethylsilyl ether; 5-β-Cholanoic acid, 3-α-7-α-diydroxy, methyl ester, TMS
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Gas Chromatography

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

Normal alkane RI, non-polar column, isothermal

Column type	Active phase	Temperature (C)	I	Reference	Comment
Capillary	OV-1	270.	3225.	Lawson and Setchell, 1988	18. m/0.20 mm/0.25 μm, He
Capillary	OV-1	275.	3216.	Lawson and Setchell, 1988	18. m/0.20 mm/0.25 μm, He

Normal alkane RI, non-polar column, temperature ramp

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Column type	Active phase	I	Reference	Comment
Capillary	CP Sil 5 CB	3244.	Batta, Aggarwal, et al., 1995	He, 100. C @ 2. min, 35. K/min; Column length: 25. m; Column diameter: 0.22 mm; T_end: 278. C
Capillary	Methyl Silicone	3198.	Ichimiya, Egestad, et al., 1991	25. m/0.32 mm/0.25 μm, He, 25. K/min; T_start: 80. C; T_end: 280. C

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

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Column type	Active phase	I	Reference	Comment
Capillary	Ultra-1	3195.	Axelson, Ellis, et al., 2000	25. m/0.32 mm/0.17 μm, H2; Program: 50 0C (3 min) -> 185 0C 5 K/min -> 280 0C
Capillary	Methyl Silicone	3199.	Meng, Reyes, et al., 1997	Program: not specified
Capillary	Methyl Silicone	3199.	Meng and Sjövall, 1997	25. m/0.32 mm/0.25 μm; Program: 60 0C 30 K/min -> 210 0C (1.5 min) 2.5 K/min -> 320 0C (20 min)
Capillary	OV-1	3225.	Iida, Momose, et al., 1987	18. m/0.20 mm/0.25 μm, He; Program: not specified

Normal alkane RI, polar column, custom temperature program

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Column type	Active phase	I	Reference	Comment
Capillary	DB-Wax	3624.	Iida, Momose, et al., 1987	15. m/0.25 mm/0.25 μm, He; Program: not specified

References

Go To: Top, Gas Chromatography, Notes

Lawson and Setchell, 1988
Lawson, A.M.; Setchell, K.D.R., Appendix of GC retention indices. List of retention indices foe methyl ester - trimethylsilyl (Me-TMS) ether derivatives of bile acids, The Bile Acids. Vol. 4, Methods and Applications, 1988, 4, 571-575. [all data]

Batta, Aggarwal, et al., 1995
Batta, A.K.; Aggarwal, S.K.; Tint, G.S.; Batta, M.; Salen, G., Capillary gas-liquid chromatography of 6-hydroxylated bile acids, J. Chromatogr. A, 1995, 704, 1, 228-233, https://doi.org/10.1016/0021-9673(95)00183-N . [all data]

Ichimiya, Egestad, et al., 1991
Ichimiya, H.; Egestad, B.; Nazer, H.; Baginski, E.S.; Clayton, P.T.; Sjövall, J., Bile acids and bile alcohols in a child with hepatic 3β-hydroxy-Δ⁵-C₂₇-steroid dehydrogenase deficiency: effects of chenodeoxycholic acid treatment, J. Lipid Res., 1991, 32, 829-841. [all data]

Axelson, Ellis, et al., 2000
Axelson, M.; Ellis, E.; Mörk, B.; Garmark, K.; Abrahamsson, A.; Björkhem, I.; Ericzon, B.-G.; Einarsson, C., Bile acid synthesis in cultured human hepatocytes: support for an alternative biosynthetic pathway to cholic acid, Hepatology, 2000, 31, 6, 1305-1312, https://doi.org/10.1053/jhep.2000.7877 . [all data]

Meng, Reyes, et al., 1997
Meng, L.-J.; Reyes, H.; Palma, J.; Hernandez, I.; Ribalta, J.; Sjövall, J., Profiles of bile acids and progesterone metabolites in the urine and serum of women with intrahepatic cholestasis of pregnancy, J. Hepatol., 1997, 27, 2, 346-357, https://doi.org/10.1016/S0168-8278(97)80181-X . [all data]

Meng and Sjövall, 1997
Meng, L.-J.; Sjövall, J., Method for combined analysis of profiles of conjugated progesterone metabolites and bile acids in serum and urine of pregnant women, J. Chromatogr. B, 1997, 688, 1, 11-26, https://doi.org/10.1016/S0378-4347(97)88051-6 . [all data]

Iida, Momose, et al., 1987
Iida, T.; Momose, T.; Tamura, T.; Matsumoto, T.; Goto, J.; Nambara, T.; Chang, F.C., Capillary gas chromatography of hydroxylated bile acid stereoisomers of the allo and normal series, J. Chromatogr., 1987, 389, 155-164, https://doi.org/10.1016/S0021-9673(01)94419-X . [all data]

Notes

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Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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