5-Cholesten-3-β,27-diol, TMS
- Formula: C33H62O2Si2
- Molecular weight: 547.0152
- IUPAC Standard InChI: InChI=1S/C33H62O2Si2/c1-24(23-34-36(5,6)7)12-11-13-25(2)29-16-17-30-28-15-14-26-22-27(35-37(8,9)10)18-20-32(26,3)31(28)19-21-33(29,30)4/h14,24-25,27-31H,11-13,15-23H2,1-10H3/t24?,25-,27?,28?,29?,30?,31?,32?,33?/m1/s1
- IUPAC Standard InChIKey: XPOWNWJGSYYWLA-TZWGRJOJSA-N
- Chemical structure:
This structure is also available as a 2d Mol file - Stereoisomers:
- Other names: 27-Hydroxycholesterol, TMS; 5-Cholesten-3B(25R),26-diol, TMS; 5-Cholesten-3-β,26-diol, TMS; 26-Hydroxycholesterol, di-TMS
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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
| Column type | Active phase | Temperature (C) | I | Reference | Comment |
|---|---|---|---|---|---|
| Packed | OV-1 | 265. | 3450. | Gaskell, Smith, et al., 1975 | N2; Column length: 2. m |
Kovats' RI, non-polar column, temperature ramp
| Column type | Active phase | I | Reference | Comment |
|---|---|---|---|---|
| Capillary | Methyl Silicone | 3470. | Shoda, Axelson, et al., 1993 | 25. m/0.32 mm/0.25 μm, 30. K/min; Tstart: 60. C; Tend: 290. C |
Normal alkane RI, non-polar column, temperature ramp
| Column type | Active phase | I | Reference | Comment |
|---|---|---|---|---|
| Capillary | Methyl Silicone | 3459. | Ichimiya, Egestad, et al., 1991 | 25. m/0.32 mm/0.25 μm, He, 25. K/min; Tstart: 80. C; Tend: 280. C |
Normal alkane RI, non-polar column, custom temperature program
| Column type | Active phase | I | Reference | Comment |
|---|---|---|---|---|
| Capillary | Ultra-1 | 3450. | 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 | Ultra-1 | 3455. | Axelson and Larsson, 1996 | 25. m/0.32 mm/0.17 μm; Program: 50C (3min) => (rapidly) => 185C => 5C/min => 280C |
References
Go To: Top, Gas Chromatography, Notes
Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
Gaskell, Smith, et al., 1975
Gaskell, S.J.; Smith, A.G.; Brooks, C.J.W.,
Gas chromatography mass spectrometry of trimethylsilyl ethers of sidechain hydroxylated Δ4-3-ketosteroids. Long range trimethylsilyl group migration under electron impact,
Biomed. Mass Spectrom., 1975, 2, 3, 148-155, https://doi.org/10.1002/bms.1200020309
. [all data]
Shoda, Axelson, et al., 1993
Shoda, J.; Axelson, M.; Sjövall, J.,
Synthesis of potential C27-intermediates in bile acid biosynthesis and their deuterium-labeled analogs,
Steroids, 1993, 58, 3, 119-125, https://doi.org/10.1016/0039-128X(93)90048-R
. [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]
Axelson and Larsson, 1996
Axelson, M.; Larsson, O.,
27-Hydroxylated low density lipoprotein (LDL) cholesterol can be converted to 7α,27-Dihydroxy-4-cholesten-3-one (cytosterone) before suppressing cholesterol production in normal human fibroblasts. Evidence that an altered metabolism of LDL cholesterol can underlie a defective feedback control in malignant cells,
J. Biol. Chem., 1996, 271, 22, 12724-12736. [all data]
Notes
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- Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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