15-hydroxy-pentadecanoic acid ethyl ester | 101791-21-3

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: 15-hydroxy-pentadecanoic acid ethyl ester
• 英文别名: 15-Hydroxy-pentadecansaeure-aethylester；ethyl 15-hydroxypentadecanoate
• CAS: 101791-21-3
• 化学式: C₁₇H₃₄O₃
• 分子量: 286.455
• InChiKey: LFARJIYYLAWPJQ-UHFFFAOYSA-N

物化性质

• 沸点：
  374.7±15.0 °C(Predicted)
• 密度：
  0.923±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  20
• 可旋转键数：
  16
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.94
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  15-hydroxy-pentadecanoic acid ethyl ester 在 lithium aluminium tetrahydride 、 4-甲基苯磺酸吡啶 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 生成 15-((tetrahydro-2H-pyran-2-yl)oxy)pentadecan-1-ol
  参考文献：
  名称：

  Z-Selective intramolecular Horner–Wadsworth–Emmons reaction for the synthesis of macrocyclic alkenes

  摘要：

  The Z-selective intramolecular Horner-Wadsworth-Emmons reaction of the substrates 7-12 (RO)(2)P(O)CHR'CO(2)Et (R' = (CH(2))(n)CHO) (R = Ph or o-tBuC(6)H(4)) gives the 13-18-membered cyclic alkenes selectively (up to Z:E = 97:3) in good yields using NaH in THF under high dilution conditions. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2011.01.043
• 作为产物：
  描述：

  环十五内酯 、 乙醇 在 sodium ethanolate 作用下， 以86%的产率得到15-hydroxy-pentadecanoic acid ethyl ester
  参考文献：
  名称：

  Z-Selective intramolecular Horner–Wadsworth–Emmons reaction for the synthesis of macrocyclic alkenes

  摘要：

  The Z-selective intramolecular Horner-Wadsworth-Emmons reaction of the substrates 7-12 (RO)(2)P(O)CHR'CO(2)Et (R' = (CH(2))(n)CHO) (R = Ph or o-tBuC(6)H(4)) gives the 13-18-membered cyclic alkenes selectively (up to Z:E = 97:3) in good yields using NaH in THF under high dilution conditions. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2011.01.043

文献信息

• Carbon Chain Length Modulates MDA‐MB‐231 Breast Cancer Cell Killing Mechanisms by Mitochondrially Targeted Aryl−Urea Fatty Acids
  作者：Michael Murray、Ariane Roseblade、Yongjuan Chen、Kirsi Bourget、Tristan Rawling

  DOI：10.1002/cmdc.201900577

  日期：2020.1.17

  anticancer agents. We designed an aryl-urea fatty acid (1 g; 16([4-chloro-3-(trifluoromethyl)phenyl]carbamoyl}amino)hexadecanoic acid) that disrupted the mitochondrion and decreased MDA-MB-231 breast cancer cell viability. To optimize the aryl-ureas the present study evaluated mitochondrial targeting by 1 g analogues containing alkyl chains between 10-17 carbons. Using the dye JC-1, the C12-C17 analogues

  靶向肿瘤细胞线粒体可以产生新型抗癌药。我们设计了一种芳基脲脂肪酸（1 g； 16（[4-氯-3-（三氟甲基）苯基]氨基甲酰基}氨基）十六烷酸）破坏线粒体并降低MDA-MB-231乳腺癌细胞的活力。为了优化芳基脲，本研究评估了1 g含10-17个碳原子之间烷基链的类似物的线粒体靶向性。使用染料JC-1，C12-C17类似物可有效破坏线粒体膜电位（IC50为3.5±1.2至7.6±1.1μM）并破坏ATP的产生；较短的类似物活性较低。7-氨基放线菌素D / annexin V染色和流式细胞仪显示这些试剂在不同程度上激活了坏死和细胞凋亡的杀伤机制（7-氨基放线菌素D / annexin V染色比为4.3-6.0）。的确，1 g及其C17类似物分别优先激活坏死和凋亡（比率2.1和16）。综上所述，烷基链长是芳基脲对线粒体靶向的决定因素，可以改变以开发出以调节方式激活细胞凋亡或坏死的类似物。
• [EN] FATTY ACID ANALOGUES AND METHODS OF USE<br/>[FR] ANALOGUES D'ACIDES GRAS ET PROCÉDÉS D'UTILISATION
  申请人：BELITE BIO LLC

  公开号：WO2019222414A1

  公开（公告）日：2019-11-21

  Provided herein are compounds, pharmaceutical compositions, and methods of treatment for various diseases or conditions, such as cancer. In one aspect, the method comprises the treatment of metastatic cancers. Compounds and methods provided herein are also used for the treatment of diseases such as inflammatory disease, cardiovascular disease, autoimmune disease, and dry eye syndrome. Further provided herein are dietary supplement formulations and methods for supporting a healthy lifestyle.

  本文提供了一些化合物、药物组合物以及用于治疗各种疾病或症状的方法，例如癌症。其中一种方法包括治疗转移性癌症。本文提供的化合物和方法也可用于治疗炎症性疾病、心血管疾病、自身免疫性疾病和干眼症等疾病。此外，本文还提供了膳食补充剂配方和维持健康生活方式的方法。
• Molecular Healing of Polymeric Materials, Coatings, Plastics, Elastomers, Composites, Laminates, Adhesives, and Sealants by Active Enzymes
  申请人：McDaniel C. Steven

  公开号：US20100210745A1

  公开（公告）日：2010-08-19

  Disclosed herein are polymeric materials such as a coating, a plastic, a laminate, a composite, an elastomer, an adhesive, or a sealant; a surface treatment such as a textile finish or a wax; a filler for such a polymeric material or a surface treatment that includes an enzyme such as an esterase (e.g., a lipolytic enzyme, a sulfuric ester hydrolase, an organophosphorus compound degradation enzyme), an enzyme (e.g., a lysozyme, a lytic transglycosylase) that degrades a cell wall and/or a cell membrane component, a biocidal or biostatic peotide, and/or a peptidase. Also disclosed herein are methods of altering a material's property such as service life, flexability, or rigidity, by incorporation of an enzyme into a material capable of being chemically crosslinked by the activity of a lipolytic enzyme, a hydrolase, and/or a urease.

  本文公开了一些聚合材料，如涂层、塑料、层压板、复合材料、弹性体、粘合剂或密封剂；一种表面处理，如纺织品涂层或蜡；一种填料，用于这样的聚合材料或表面处理，其中包括一种酶，如酯酶（例如，脂肪水解酶，硫酸酯水解酶，有机磷化合物降解酶），降解细胞壁和/或细胞膜成分的酶（例如，溶菌酶，裂解转糖基酶），生物杀菌或生物静态肽，以及/或肽酶。本文还公开了通过将酶纳入可通过脂肪水解酶、水解酶和/或脲酶的活性交联材料中来改变材料性能，如使用寿命、柔韧性或刚度的方法。
• Anti-fouling Paints and Coatings
  申请人：Reactive Surfaces LTD

  公开号：US20150191607A1

  公开（公告）日：2015-07-09

  Disclosed herein are polymeric materials such as a coating, a plastic, a laminate, a composite, an elastomer, an adhesive, or a sealant; a surface treatment such as a textile finish or a wax; a filler for such a polymeric material or a surface treatment that includes an enzyme such as an esterase (e.g., a lipolytic enzyme, a sulfuric ester hydrolase, an organophosphorus compound degradation enzyme), an enzyme (e.g., a lysozyme, a lytic transglycosylase) that degrades a cell wall and/or a cell membrane component, a biocidal or biostatic peptide, and/or a peptidase. Also disclosed herein are methods of altering a material's property such as service life, flexability, or rigidity, by incorporation of an enzyme into a material capable of being chemically crosslinked by the activity of a lipolytic enzyme, a hydrolase, and/or a urease.

  本文披露了聚合材料，例如涂层、塑料、层压材料、复合材料、弹性体、粘合剂或密封剂；表面处理，例如纺织品整理或蜡；填充剂，用于这种聚合材料或表面处理，包括酯酶（例如脂肪水解酶、硫酸酯水解酶、有机磷化合物降解酶）的酶，降解细胞壁和/或细胞膜成分的酶（例如溶菌酶、裂解转葡糖苷酶），生物杀菌或生物稳定肽，和/或肽酶。本文还披露了通过将酶并入能够通过脂肪水解酶、水解酶和/或脲酶的活性进行化学交联的材料中，改变材料性能（例如使用寿命、柔韧性或刚度）的方法。
• NOVEL PYRIDINECARBOXAMIDE DERIVATIVES
  申请人：Nisshin Flour Milling Co., Ltd.

  公开号：EP0885886A1

  公开（公告）日：1998-12-23

  Pyridinecarboxamide derivatives of the formula (wherein n represents an integer of 14 - 18, and R represents a hydrogen atom or a straight or branched C1-C4 alkyl group) or physiologically acceptable salts thereof. The compounds have excellent inhibiting activity of cerebral edema, especially ischemic cerebral edema, and inhibiting activity of delayed death of neuronal cells (an inhibiting activity of Ca-influx in neuronal cells). Cerebral edema is a pathologic condition accompanying cerebrovascular disorders, especially the acute stage of cerebrovascular disorders and then the compounds are useful as an agent for inhibiting cerebral edema or a therapeutic agent for cerebrovascular disorders. Moreover, the compounds have no hypotensive action which is considered to be side-effect in treating the acute stage cerebrovascular disorders and hardly show a behavior suppressing action so that they are an excellent therapeutic agent for, in particular, the acute stage cerebrovascular disorders. Moreover, the compounds show a cerebral protective activity (an anti-anoxic activity), an increasing activity of cerebral blood flow, and an inhibiting activity of lipid peroxidation and these activities may lead to the increased utility as a therapeutic agent for cerebrovascular disorders.

  式中的吡啶甲酰胺衍生物 (其中 n 代表 14 - 18 的整数，R 代表氢原子或直链或支链 C1-C4 烷基）或其生理上可接受的盐。 这些化合物对脑水肿，尤其是缺血性脑水肿有很好的抑制作用，对神经元细胞的延迟死亡也有很好的抑制作用（抑制神经元细胞中 Ca 的内流）。脑水肿是脑血管疾病，尤其是脑血管疾病急性期的一种病理状态，因此，这些化合物可作为抑制脑水肿的药物或脑血管疾病的治疗药物。此外，这些化合物在治疗急性期脑血管疾病时没有被认为是副作用的降压作用，也几乎没有行为抑制作用，因此是一种特别适用于急性期脑血管疾病的优良治疗剂。此外，这些化合物还显示出脑保护活性（抗缺氧活性）、增加脑血流量活性和抑制脂质过氧化活性，这些活性可能会增加其作为脑血管疾病治疗剂的效用。