24β_F-hydroxy-cholest-4-en-3-one | 61092-05-5

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 类固醇和类固醇衍生物
• 英文名称: 24β_F-hydroxy-cholest-4-en-3-one
• 英文别名: 24β_F-Hydroxy-cholest-4-en-3-on；24(S)-hydroxy-4-cholestene-3-one；(24S)-24-Hydroxycholest-4-en-3-one；(8S,9S,10R,13R,14S,17R)-17-[(2R,5S)-5-hydroxy-6-methylheptan-2-yl]-10,13-dimethyl-1,2,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-3-one
• CAS: 61092-05-5
• 化学式: C₂₇H₄₄O₂
• 分子量: 400.645
• InChiKey: KRBFVEHJMZFIPE-OAKHZPDASA-N

物化性质

• 沸点：
  515.6±19.0 °C(Predicted)
• 密度：
  1.03±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  7
• 重原子数：
  29
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  24β_F-hydroxy-cholest-4-en-3-one 、 N-氯-N-吡啶基乙酰肼 以 甲醇 、 水 、 溶剂黄146 为溶剂， 反应 0.5h， 生成
  参考文献：
  名称：

  Analysis of derivatised steroids by matrix-assisted laser desorption/ionisation and post-source decay mass spectrometry

  摘要：

  Neutral steroids are difficult to analyse using desorption ionisation methods coupled with mass spectrometry (MS). However, steroids with an unhindered ketone group can readily be derivatised with the Girard P (GP) reagent to give GP hydrazones. Steroid GP hydrazones contain a quaternary nitrogen atom and are readily desorbed in the matrix-assisted laser desorption/ionisation (MALDI) process, giving an improvement in sensitivity of two orders of magnitude. Steroids without a ketone group, but with a 3 beta-hydroxy-Delta(5) function, can be readily converted to 3-OXO-Delta(4) steroids and subsequently derivatised to GP hydrazones for MALDI analysis. In addition to giving strong [M](+) ions upon MALDI, steroid GP hydrazones give informative post-source decay (PSD) spectra. By using the accurate mass of the precursor-ion measured by MALDI-MS, in combination with the structural information encoded in its PSD spectrum, steroid structures can readily be determined. (c) 2005 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.steroids.2005.08.002
• 作为产物：
  描述：

  (3Β,24S)-胆甾-5-烯-3,24-二醇 在 cholesterol oxidase 作用下， 以 aq. phosphate buffer 为溶剂， 反应 1.0h， 生成 24β_F-hydroxy-cholest-4-en-3-one
  参考文献：
  名称：

  Highly automated nano-LC/MS-based approach for thousand cell-scale quantification of side chain-hydroxylated oxysterols

  摘要：

  Iso-octyl chain-hydroxylated oxysterols were determined in attomoles per 10,000 cells concentrations in 10,000-80,000 cultured pancreatic adenocarcinoma cells, using a sensitive, highly automated nano-LC-ESI-MS-based method. Identified oxysterols included 24S hydroxycholesterol (24S-OHC), 25 hydroxycholesterol (25-OHC), and 27 hydroxycholesterol (27-OHC), while 20S hydroxycholesterol and 22S hydroxycholesterol were not detected. Lower mass limit of quantification was 23 fg (65 amol) for 25-OHC and 27-OHC (100 times lower than our previous method) and 54 fg (135 amol) for 24S-OHC, after derivatization into Girard T hydrazones and online sample cleanup using simplified and robust automatic filtration and filter back flushing solid phase extraction LC/MS/MS. The instrument configuration was easily installed using a commercial nano-LC/MS system. Recoveries in spiked sample were 96, 97, and 77% for 24S-OHC, 25-OHC, and 27-OHC, with within- and between-day repeatabilities of 1-21% and 2-20% relative SD, respectively. The study demonstrates the potential of nano-LC in lipidomics/sterolomics.

  DOI：

  10.1194/jlr.d048801

文献信息

• Ercoli; de Ruggieri, Gazzetta Chimica Italiana, 1953, vol. 83, p. 720,723
  作者：Ercoli、de Ruggieri

  DOI：——

  日期：——
• Analysis of derivatised steroids by matrix-assisted laser desorption/ionisation and post-source decay mass spectrometry
  作者：Muhammad Atif Khan、Yuqin Wang、Sibylle Heidelberger、Gunvor Alvelius、Suya Liu、Jan Sjövall、William J. Griffiths

  DOI：10.1016/j.steroids.2005.08.002

  日期：2006.1

  Neutral steroids are difficult to analyse using desorption ionisation methods coupled with mass spectrometry (MS). However, steroids with an unhindered ketone group can readily be derivatised with the Girard P (GP) reagent to give GP hydrazones. Steroid GP hydrazones contain a quaternary nitrogen atom and are readily desorbed in the matrix-assisted laser desorption/ionisation (MALDI) process, giving an improvement in sensitivity of two orders of magnitude. Steroids without a ketone group, but with a 3 beta-hydroxy-Delta(5) function, can be readily converted to 3-OXO-Delta(4) steroids and subsequently derivatised to GP hydrazones for MALDI analysis. In addition to giving strong [M](+) ions upon MALDI, steroid GP hydrazones give informative post-source decay (PSD) spectra. By using the accurate mass of the precursor-ion measured by MALDI-MS, in combination with the structural information encoded in its PSD spectrum, steroid structures can readily be determined. (c) 2005 Elsevier Inc. All rights reserved.
• Highly automated nano-LC/MS-based approach for thousand cell-scale quantification of side chain-hydroxylated oxysterols
  作者：Hanne Roberg-Larsen、Kaja Lund、Tore Vehus、Nina Solberg、Caroline Vesterdal、Dorna Misaghian、Petter Angell Olsen、Stefan Krauss、Steven Ray Wilson、Elsa Lundanes

  DOI：10.1194/jlr.d048801

  日期：2014.7

  Iso-octyl chain-hydroxylated oxysterols were determined in attomoles per 10,000 cells concentrations in 10,000-80,000 cultured pancreatic adenocarcinoma cells, using a sensitive, highly automated nano-LC-ESI-MS-based method. Identified oxysterols included 24S hydroxycholesterol (24S-OHC), 25 hydroxycholesterol (25-OHC), and 27 hydroxycholesterol (27-OHC), while 20S hydroxycholesterol and 22S hydroxycholesterol were not detected. Lower mass limit of quantification was 23 fg (65 amol) for 25-OHC and 27-OHC (100 times lower than our previous method) and 54 fg (135 amol) for 24S-OHC, after derivatization into Girard T hydrazones and online sample cleanup using simplified and robust automatic filtration and filter back flushing solid phase extraction LC/MS/MS. The instrument configuration was easily installed using a commercial nano-LC/MS system. Recoveries in spiked sample were 96, 97, and 77% for 24S-OHC, 25-OHC, and 27-OHC, with within- and between-day repeatabilities of 1-21% and 2-20% relative SD, respectively. The study demonstrates the potential of nano-LC in lipidomics/sterolomics.