5-Cholesten-3-β-ol-7-one, TMS
- Formula: C33H60O2Si2
- Molecular weight: 544.9993
- IUPAC Standard InChI: InChI=1S/C33H60O2Si2/c1-23(2)13-12-14-24(3)27-15-16-28-31-29(18-20-33(27,28)5)32(4)19-17-26(34-36(6,7)8)21-25(32)22-30(31)35-37(9,10)11/h22-24,26-29H,12-21H2,1-11H3/t24?,26-,27?,28?,29?,32?,33?/m1/s1
- IUPAC Standard InChIKey: GRQGMVRZMUHBDW-MMEKYXELSA-N
- Chemical structure:
This structure is also available as a 2d Mol file - Stereoisomers:
- Other names: 3B-Hydroxy-5-cholesten-7-one, TMS; 7-Ketocholesterol, TMS; 7-Oxocholesterol, 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, temperature ramp
| Column type | Active phase | I | Reference | Comment |
|---|---|---|---|---|
| Capillary | Methyl Silicone | 3389. | 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, custom temperature program
| Column type | Active phase | I | Reference | Comment |
|---|---|---|---|---|
| Capillary | Ultra-1 | 3370. | 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 | 3375. | Axelson and Larsson, 1996 | 25. m/0.32 mm/0.17 μm; Program: 50C (3min) => (rapidly) => 185C => 5C/min => 280C |
References
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Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
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]
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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