9-oxononanoyl cholesterol | 144396-42-9

• 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: 9-oxononanoyl cholesterol
• 英文别名: [(3S,8S,9S,10R,13R,14S,17R)-10,13-dimethyl-17-[(2R)-6-methylheptan-2-yl]-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-yl] 9-oxononanoate
• CAS: 144396-42-9
• 化学式: C₃₆H₆₀O₃
• 分子量: 540.871
• InChiKey: QKNMAEQWRIBQQQ-MKQVXYPISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.8
• 重原子数：
  39
• 可旋转键数：
  15
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  9-oxononanoyl cholesterol 在 臭氧 作用下， 以 甲醇 、 氯仿 为溶剂， 反应 0.17h， 生成 5-oxo-5,6-secocholestan-6-al-3β-(9-oxononanoate)
  参考文献：
  名称：

  Occurrence of cytotoxic 9-oxononanoyl secosterol aldehydes in human low-density lipoprotein

  摘要：

  The reaction products of three major cholesteryl esters, cholesteryl palmitate (C16:0-CE), cholesteryl oleate (C18:1-CE), and cholesteryl linoleate (C18:2-CE), present in human low-density lipoprotein (LDL) treated with ozone were isolated and characterized. In vitro ozonization of C16:0-CE was found to form the palmitoyl ester of secosterol-A (3 beta-hydroxy-5-oxo-5,6-secocholestan-6-al) and its aldolization product secosterol-B (3 beta-hydroxy-5 beta-hydroxy-B-norcholestane-6 beta-carboxaldehyde). On the other hand, when C18:1-CE and C18:2-CE were oxidized by ozone, the aldehyde 9-oxononanoyl cholesterol (9-ONC) was formed as a primary product, which was then further oxidized to form 9-oxononanoyl secosterol-A (9-ON-secoA) and 9-oxononanoyl secosterol-B (9-ON-secoB). The compounds 9-ON-secoA and -B, but not 9-ONC, were found to exhibit strong cytotoxicity against human leukemia HL-60 cells. An LC-ESI-MS/MS method was developed for the detection of these cholesteryl ester ozonolysis products by derivatizing them with dansyl hydrazine. Using this method, we found for the first time that low concentrations of 9-ON-secoA and -B, but not palmitoyl secosterols, were present in human LDL. These novel oxidized cholesterol esters, 9ON-secoA and -B, probably play important roles in the pathogenesis of several inflammatory disorders such as cancer, diabetes, atherosclerosis, and neurodegenerative diseases. (C) 2013 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.freeradbiomed.2013.01.029
• 作为产物：
  描述：

  cholesteryl oleate 在 臭氧 作用下， 以 甲醇 、 氯仿 为溶剂， 反应 0.17h， 生成 9-oxononanoyl cholesterol
  参考文献：
  名称：

  Occurrence of cytotoxic 9-oxononanoyl secosterol aldehydes in human low-density lipoprotein

  摘要：

  The reaction products of three major cholesteryl esters, cholesteryl palmitate (C16:0-CE), cholesteryl oleate (C18:1-CE), and cholesteryl linoleate (C18:2-CE), present in human low-density lipoprotein (LDL) treated with ozone were isolated and characterized. In vitro ozonization of C16:0-CE was found to form the palmitoyl ester of secosterol-A (3 beta-hydroxy-5-oxo-5,6-secocholestan-6-al) and its aldolization product secosterol-B (3 beta-hydroxy-5 beta-hydroxy-B-norcholestane-6 beta-carboxaldehyde). On the other hand, when C18:1-CE and C18:2-CE were oxidized by ozone, the aldehyde 9-oxononanoyl cholesterol (9-ONC) was formed as a primary product, which was then further oxidized to form 9-oxononanoyl secosterol-A (9-ON-secoA) and 9-oxononanoyl secosterol-B (9-ON-secoB). The compounds 9-ON-secoA and -B, but not 9-ONC, were found to exhibit strong cytotoxicity against human leukemia HL-60 cells. An LC-ESI-MS/MS method was developed for the detection of these cholesteryl ester ozonolysis products by derivatizing them with dansyl hydrazine. Using this method, we found for the first time that low concentrations of 9-ON-secoA and -B, but not palmitoyl secosterols, were present in human LDL. These novel oxidized cholesterol esters, 9ON-secoA and -B, probably play important roles in the pathogenesis of several inflammatory disorders such as cancer, diabetes, atherosclerosis, and neurodegenerative diseases. (C) 2013 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.freeradbiomed.2013.01.029

文献信息

• Occurrence of cytotoxic 9-oxononanoyl secosterol aldehydes in human low-density lipoprotein
  作者：Noriyuki Miyoshi、Nozomi Iwasaki、Susumu Tomono、Tatsuya Higashi、Hiroshi Ohshima

  DOI：10.1016/j.freeradbiomed.2013.01.029

  日期：2013.7

  The reaction products of three major cholesteryl esters, cholesteryl palmitate (C16:0-CE), cholesteryl oleate (C18:1-CE), and cholesteryl linoleate (C18:2-CE), present in human low-density lipoprotein (LDL) treated with ozone were isolated and characterized. In vitro ozonization of C16:0-CE was found to form the palmitoyl ester of secosterol-A (3 beta-hydroxy-5-oxo-5,6-secocholestan-6-al) and its aldolization product secosterol-B (3 beta-hydroxy-5 beta-hydroxy-B-norcholestane-6 beta-carboxaldehyde). On the other hand, when C18:1-CE and C18:2-CE were oxidized by ozone, the aldehyde 9-oxononanoyl cholesterol (9-ONC) was formed as a primary product, which was then further oxidized to form 9-oxononanoyl secosterol-A (9-ON-secoA) and 9-oxononanoyl secosterol-B (9-ON-secoB). The compounds 9-ON-secoA and -B, but not 9-ONC, were found to exhibit strong cytotoxicity against human leukemia HL-60 cells. An LC-ESI-MS/MS method was developed for the detection of these cholesteryl ester ozonolysis products by derivatizing them with dansyl hydrazine. Using this method, we found for the first time that low concentrations of 9-ON-secoA and -B, but not palmitoyl secosterols, were present in human LDL. These novel oxidized cholesterol esters, 9ON-secoA and -B, probably play important roles in the pathogenesis of several inflammatory disorders such as cancer, diabetes, atherosclerosis, and neurodegenerative diseases. (C) 2013 Elsevier Inc. All rights reserved.