3-hydroxy-N-(4-hydroxy-3-methoxybenzyl)octanamide | 1331858-67-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 3-hydroxy-N-(4-hydroxy-3-methoxybenzyl)octanamide
• 英文别名: A6G,aza-[6]-gingerol；3-hydroxy-N-[(4-hydroxy-3-methoxyphenyl)methyl]octanamide
• CAS: 1331858-67-3
• 化学式: C₁₆H₂₅NO₄
• 分子量: 295.379
• InChiKey: OPIQNMDVTYVMIB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  21
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  78.8
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  3-(tert-butyldimethylsilyloxy)-N-(4-hydroxy-3-methoxybenzyl)octanamide 在 对甲苯磺酸 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以72%的产率得到3-hydroxy-N-(4-hydroxy-3-methoxybenzyl)octanamide
  参考文献：
  名称：

  Synthesis of a New [6]-Gingerol Analogue and Its Protective Effect with Respect to the Development of Metabolic Syndrome in Mice Fed a High-Fat Diet

  摘要：

  To determine the effects of a [6]-gingerol analogue (6G), a major chemical component of the ginger rhizome, and its stable analogue after digestion in simulated gastric fluid, aza-[6]-gingerol (A6G), on diet-induced body fat accumulation, we synthesized 6G and A6G. Mice were fed either a control regular rodent chow, a high-fat diet (HFD), or a HFD supplemented with 6G and A6G. Magnetic resonance imaging adiposity parameters of the 6G- and A6G-treated mice were compared with those of control mice. Supplementation with 6G and A6G significantly reduced body weight gain, fat accumulation, and circulating levels of insulin and leptin. The mRNA levels of sterol regulatory element-binding protein 1c (SREBP-1c) and acetyl-CoA carboxylase 1 in the liver were significantly lower in mice fed A6G than in HFD control mice. Our findings indicate that A6G, rather than 6G, enhances energy metabolism and reduces the extent of lipogenesis by downregulating SREBP-1c and its related molecules, which leads to the suppression of body fat accumulation.

  DOI：

  10.1021/jm200662c

文献信息

• Synthesis of a New [6]-Gingerol Analogue and Its Protective Effect with Respect to the Development of Metabolic Syndrome in Mice Fed a High-Fat Diet
  作者：Mayumi Okamoto、Hiroyuki Irii、Yu Tahara、Hiroyuki Ishii、Akiko Hirao、Haruhide Udagawa、Masaki Hiramoto、Kazuki Yasuda、Atsuo Takanishi、Shigenobu Shibata、Isao Shimizu

  DOI：10.1021/jm200662c

  日期：2011.9.22

  To determine the effects of a [6]-gingerol analogue (6G), a major chemical component of the ginger rhizome, and its stable analogue after digestion in simulated gastric fluid, aza-[6]-gingerol (A6G), on diet-induced body fat accumulation, we synthesized 6G and A6G. Mice were fed either a control regular rodent chow, a high-fat diet (HFD), or a HFD supplemented with 6G and A6G. Magnetic resonance imaging adiposity parameters of the 6G- and A6G-treated mice were compared with those of control mice. Supplementation with 6G and A6G significantly reduced body weight gain, fat accumulation, and circulating levels of insulin and leptin. The mRNA levels of sterol regulatory element-binding protein 1c (SREBP-1c) and acetyl-CoA carboxylase 1 in the liver were significantly lower in mice fed A6G than in HFD control mice. Our findings indicate that A6G, rather than 6G, enhances energy metabolism and reduces the extent of lipogenesis by downregulating SREBP-1c and its related molecules, which leads to the suppression of body fat accumulation.