cholesteryl oleate | 1256491-32-3

• 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: cholesteryl oleate
• 英文别名: Cholesteryl octadec-9-enoate；[(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] octadec-9-enoate
• CAS: 1256491-32-3
• 化学式: C₄₅H₇₈O₂
• 分子量: 651.113
• InChiKey: RJECHNNFRHZQKU-XNTGVSEISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  16.6
• 重原子数：
  47
• 可旋转键数：
  22
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  cholesteryl oleate 在 臭氧 、 L-脯氨酸 作用下， 以 甲醇 、 氯仿 、 水 、 乙腈 为溶剂， 反应 2.34h， 生成 5β-hydroxyl-B-norcholestane-6β-carboxaldehyde-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

文献信息

• AMPHIPATHIC MOLECULES AS CHOLESTEROL AND OTHER LIPID UPTAKE INHIBITORS
  申请人：——

  公开号：US20010005714A1

  公开（公告）日：2001-06-28

  Cholesterol biosynthesis can be inhibited by suitable inhibitors, such as the statins. However, hypercholesterolaemia, whether familial or diet-induced, and more generally hyperlipidaemia are not adequately addressed by cholesterol biosynthesis inhibitors alone, since the body's cholesterol is acquired by uptake from the diet as well as by endogenous synthesis. Lipid is also taken up from the gut. This problem is addressed by providing one or more molecules having amphipathic regions to inhibit the uptake of cholesterol, and other lipids, from the gut. Obesity may also be treated or prevented in this way, as may atherosclerosis. Examples of suitable molecules having amphipathic regions include natural or variant apoproteins and other proteins and peptides having an amphipathic &agr;-helix composed of at least about 15 amino acids.

  胆固醇生物合成可以通过适当的抑制剂，如他汀类药物，来进行抑制。然而，无论是家族性还是饮食诱导的高胆固醇血症，以及更普遍的高脂血症，单靠胆固醇生物合成抑制剂并不能充分解决，因为人体的胆固醇既通过饮食摄入获得，也通过内源合成获得。脂质也从肠道摄取。通过提供一个或多个具有两性区域的分子来抑制从肠道摄取胆固醇和其他脂质，可以解决这个问题。肥胖也可以通过这种方式治疗或预防，动脉粥样硬化也可以。具有两性区域的适当分子的示例包括天然或变异的载脂蛋白和其他具有至少约15个氨基酸组成的两性α-螺旋的蛋白和肽。
• [EN] RAS BINDING PEPTIDES AND METHODS OF USE<br/>[FR] PEPTIDES DE LIAISON À RAS ET MÉTHODES D'UTILISATION
  申请人：RA PHARMACEUTICALS INC

  公开号：WO2017181061A1

  公开（公告）日：2017-10-19

  The present invention provides Ras modulators including inhibitors and/or antagonists of Ras, Ras binding, and Ras-dependent cell signaling activity. Also provided are methods of utilizing the Ras modulators as therapeutics.

  本发明提供了Ras调节剂，包括Ras的抑制剂和/或拮抗剂，以及Ras结合和Ras依赖的细胞信号活性。还提供了利用这些Ras调节剂作为治疗药物的方法。
• NON-NATURALLY OCCURRING LIPOPROTEIN PARTICLE
  申请人：——

  公开号：US20020147304A1

  公开（公告）日：2002-10-10

  Non-naturally occurring receptor competent LDL particle comprising at least one peptide component wherein the said peptide component comprises at least a binding site for an Apo B protein receptor and at least one lipophilic substituent.

  非自然存在的受体适配LDL颗粒，包括至少一个肽组分，其中所述肽组分至少包括一个与Apo B蛋白受体结合位点和至少一个疏水取代基。
• Non-naturally occurring lipoprotein particle
  申请人：University of Strathclyde

  公开号：US20040235730A1

  公开（公告）日：2004-11-25

  Non-naturally occurring lipoprotein particles, process for preparing such particles and uses thereof.

  非自然发生的脂蛋白颗粒，制备这种颗粒的方法及其用途。
• COSMETIC COMPOSITION FOR ANTI-AGING OR ALLEVIATING SKIN REDNESS, AND MEDICINAL COMPOSITION FOR PREVENTING AND TREATING SKIN INFLAMMATORY DISEASES, CONTAINING COMPOUND INDUCING INCREASE IN EXPRESSION OF ADIPONECTIN
  申请人：Incospharm Corporation

  公开号：US20180303733A1

  公开（公告）日：2018-10-25

  Provided are a cosmetic composition for anti-aging or alleviating skin redness, and a medicinal composition for treating and preventing skin inflammatory diseases caused by light, containing a compound inducing an increase in expression of adiponectin or a pharmaceutically acceptable salt thereof.

  提供了一种用于抗衰老或缓解皮肤红肿的化妆品组合物，以及一种用于治疗和预防由光线引起的皮肤炎症性疾病的药用组合物，其中含有一种诱导脂联素表达增加的化合物或其药用可接受的盐。