3-十三烷基十六酸 | 180476-36-2

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 中文名称: 3-十三烷基十六酸
• 英文名称: 3-tridecylhexadecanoic acid
• CAS: 180476-36-2
• 化学式: C₂₉H₅₈O₂
• 分子量: 438.778
• InChiKey: NVVMUWWSJZPFJE-UHFFFAOYSA-N

物化性质

• 沸点：
  545.2±18.0 °C(Predicted)
• 密度：
  0.873±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  14.1
• 重原子数：
  31
• 可旋转键数：
  26
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.97
• 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：

  3-十三烷基十六酸 在 lithium aluminium tetrahydride 、 4 A molecular sieve 、 硫酸 、 三氟化硼乙醚 作用下， 以 乙醚 为溶剂， 反应 3.0h， 生成 (2S,4S,5R,6R)-4-Acetoxy-5-acetylamino-2-[(2R,3S,4S,5R,6R)-3,5-bis-benzoyloxy-2-benzoyloxymethyl-6-(3-tridecyl-hexadecyloxy)-tetrahydro-pyran-4-yloxy]-6-((1S,2R)-1,2,3-triacetoxy-propyl)-tetrahydro-pyran-2-carboxylic acid methyl ester
  参考文献：
  名称：

  Synthetic Studies on Sialoglycoconjugates 88: Synthesis of Ganglioside GM₃and GM₄Analogs Containing 2- OR 3-Branched Fatty-Alkyl Residues in Place of Ceramide

  摘要：

  Each of four ganglioside GM(4) and GM(3) analogues containing 2- or 3-branched fatty alkyl residues in place of ceramide have been synthesized. Coupling of O-(methyl 5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-D-glycero-alpha-D-galacto-2-nonulopyranosylonate)-(2-->3) -2,4,6-tri-O-benzoyl-alpha-D-galactopyranosyl trichloroacetimidate (13) or O-(methyl 5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-D-glycero-alpha-D-galacto-2- nonulopyranosylonate)-(2-->3)-O-(2,4-di-O-acetyl-6-O-benzoyl-beta-D-galactopyranosyl)-(1-->4)-3 -O-acetyl-2,4-di-O-benzoyl-alpha-D-glucopyranosyl trichloroacetimidate (14) with 2- or 3-branched fatty-alkyl-1-ols (9-12), prepared from the corresponding branched fatty acids by methyl esterification and reduction, using BF3 . OEt(2) gave the corresponding ganglioside analogues (15, 17, 19, 21, 23, 25, 27, 29) in good yields, which were coverted, via O-deacylation and de-esterification, into the tide compounds.

  DOI：

  10.1080/07328309608005679
• 作为产物：
  描述：

  14-二十七酮 在 platinum(IV) oxide 、 氢气 、 sodium hydride 、 potassium hydroxide 作用下， 以 四氢呋喃 、 甲醇 、 氯仿 、 水 、 mineral oil 、 正丁醇 为溶剂， 100.0 ℃ 、101.33 kPa 条件下， 反应 46.0h， 生成 3-十三烷基十六酸
  参考文献：
  名称：

  Development of Vizantin, a Safe Immunostimulant, Based on the Structure–Activity Relationship of Trehalose-6,6′-dicorynomycolate

  摘要：

  Vizantin, 6,6'-bis-O-(3-nonyldodecanoy1)-alpha,alpha'-trehalose, was developed as a safe immunostimulator on the basis of a structure-activity relationship (SAR) study with trehalose 6,6'-dicorynomycolate (TDCM). It was possible to synthesize vizantin on a large scale more easily than in the case of TDCM, and the compound exhibited more potent prophylactic effect on experimental lung metastasis of B16-F0 melanoma cells. Because vizantin stimulated human macrophages, it is a promising candidate for clinical application.

  DOI：

  10.1021/jm3016443

文献信息

• Chemical Hybridization of Vizantin and Lipid A to Generate a Novel LPS Antagonist
  作者：Hirofumi Yamamoto、Masataka Oda、Marina Kanno、Shota Tamashiro、Ikuko Tamura、Toshihiko Yoneda、Naoto Yamasaki、Hisanori Domon、Mayo Nakano、Hironobu Takahashi、Yutaka Terao、Yusuke Kasai、Hiroshi Imagawa

  DOI：10.1248/cpb.c15-00828

  日期：——

  Lipopolysaccharide (LPS) antagonists have attracted considerable interest as promising candidates for the treatment of severe sepsis triggered by Gram-negative bacteria. In this article, we describe the development of a novel LPS antagonist based on chemical hybridization of vizantin and the hydrophobic molecular unit of LPS (lipid A). Vizantin, 6,6′-bis-O-(3-nonyldodecanoyl)-α,α′-trehalose, was designed as an immunostimulator from a structure–activity relationship (SAR) study with trehalose 6,6′-dicorynomycolate (TDCM). Our recent study indicated that vizantin displays adjuvant activity by specifically binding to the Toll-like receptor 4 (TLR4)/MD2 protein complex. Because lipid A unit (or LPS) is also known to trigger an inflammatory response via the same TLR4/MD2 complex as vizantin, we designed a hybrid compound of vizantin and lipid A with the aim of developing a novel biofunctional glycolipid. Focusing on the antagonism to Escherichia coli LPS in an in vitro model with human macrophages (THP-1 cells), we identified a potent LPS antagonist among the synthesized hybrid compounds. The novel LPS antagonist effectively inhibited LPS-induced release of tumor necrosis factor-alpha (TNF-α) in a dose-dependent manner with an IC50 value of 3.8 nM, making it a candidate for the treatment drug of Gram-negative sepsis and/or septic shock.

  脂多糖（LPS）拮抗剂作为治疗由革兰氏阴性细菌引发的严重败血症的候选药物，引起了人们的极大兴趣。在这篇文章中，我们介绍了一种新型 LPS 拮抗剂的开发情况，它基于 vizantin 与 LPS 的疏水分子单元（脂质 A）的化学杂交。Vizantin（6,6′-双-O-(3-壬基十二碳酰基)-α,α′-曲哈洛糖）是通过与 6,6′-二硼酸曲哈洛糖（TDCM）的结构-活性关系（SAR）研究而设计的一种免疫刺激剂。我们最近的研究表明，vizantin 通过与 Toll 样受体 4（TLR4）/MD2 蛋白复合物特异性结合而显示出佐剂活性。众所周知，脂质 A 单位（或 LPS）也能通过与 vizantin 相同的 TLR4/MD2 复合物触发炎症反应，因此我们设计了一种 vizantin 和脂质 A 的混合化合物，旨在开发一种新型生物功能糖脂。在以人巨噬细胞（THP-1 细胞）为对象的体外模型中，我们重点研究了大肠杆菌 LPS 的拮抗作用，并在合成的混合化合物中发现了一种强效的 LPS 拮抗剂。这种新型 LPS 拮抗剂能以剂量依赖的方式有效抑制 LPS 诱导的肿瘤坏死因子-α（TNF-α）的释放，其 IC50 值为 3.8 nM，因此可作为革兰氏阴性败血症和/或脓毒性休克的候选治疗药物。
• TREHALOSE COMPOUND, METHOD FOR PRODUCING SAME, AND PHARMACEUTICAL PRODUCT CONTAINING THE COMPOUND
  申请人：Nishizawa Mugio

  公开号：US20110218171A1

  公开（公告）日：2011-09-08

  A trehalose compound having high immunopotentiating activity and low toxicity is represented by formula (1). (In the formula, X and X′ each represents a phenyl, a naphthyl, R 1 —CHR 1 — (wherein R 1 and R 2 each represents a C 7 -C 21 alkyl group or the like) or the like; and n and n′ each independently represents an integer of 0-3). The compound exhibits a high activating effect on macrophages and neutrophils.

  具有高免疫增强活性和低毒性的海藻糖化合物由公式（1）表示。（在公式中，X和X'分别表示苯基，萘基，R1-CHR1-（其中R1和R2各代表C7-C21烷基或类似物），n和n'各自独立地表示0-3的整数）。该化合物对巨噬细胞和中性粒细胞具有高激活作用。
• Trehalose compound, method for producing same, and pharmaceutical product containing the compound
  申请人：Otsuka Chemical Co., Ltd.

  公开号：EP2567963A1

  公开（公告）日：2013-03-13

  It is an object of the present invention to provide a trehalose compound having high immunopotentiating activity and low toxicity. The compound exhibits a high activating effect on macrophages and neutrophils. The trehalose compound is represented by formula (1), wherein X represents R1-CHR2-, and X' represents R1'-CHR2'-, wherein R1, R1', R2 and R2' independently represent a C1-C21 alkyl group or a hydrogen atom, and wherein n and n' independently represent an integer of 0 to 3.

  本发明的目的是提供一种具有高免疫增强活性和低毒性的三卤糖化合物。该化合物对巨噬细胞和中性粒细胞具有很高的激活作用。 该曲卤糖化合物由式（1）表示，其中 X 代表 R1-CHR2-，X'代表 R1'-CHR2'-，其中 R1、R1'、R2 和 R2'独立地代表 C1-C21 烷基或氢原子，n 和 n'独立地代表 0 至 3 的整数。
• Synthesis and Biological Activities of Some N-Acyl-2,6-diaminopyridines and Related Linker Mode Identical Twin Drugs
  作者：Kunihiro Sumoto、Nobuko Mibu、Kazumi Yokomizo、Miyuki Saisho、Marumi Oishi、Hatsumi Aki、Takeshi Miyata

  DOI：10.3987/com-10-12105

  日期：——

  In connection with our studies on biologically active compounds in the class of N-acyl-2,6-diaminopyridines, some molecular modifications were attempted. All of the synthesized compounds were evaluated for biological activity with herpes virus type 1 (HSV-1) by a plaque reduction assay. We observed that most of the synthesized derivatives showed no significant anti-HSV-1 activity, but we found that compounds 5 and 6 with a branched long alkyl chain showed high cytotoxicity to Vero cells.
• HAIR COSMETIC COMPOSITION
  申请人：Kao Corporation

  公开号：EP0651632A1

  公开（公告）日：1995-05-10