2-methyl-2-oleamidopropanoic acid

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 2-methyl-2-oleamidopropanoic acid
• 英文别名: dimethyl oleoyl glycine；HU596；2-methyl-2-[[(Z)-octadec-9-enoyl]amino]propanoic acid
• 化学式: C₂₂H₄₁NO₃
• 分子量: 367.572
• InChiKey: XFLXJCCWLJSPFC-QXMHVHEDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.2
• 重原子数：
  26
• 可旋转键数：
  17
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  66.4
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  油酰氯 、 2-甲基丙氨酸 在 sodium hydroxide 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 7.0h， 以28%的产率得到2-methyl-2-oleamidopropanoic acid
  参考文献：
  名称：

  [EN] N-ACYLATED 2-AMINOISOBUTYRIC ACID COMPOUNDS AND FLAVOUR COMPOSITIONS CONTAINING THEM
  [FR] COMPOSÉS D'ACIDES 2-AMINO-ISOBUTYRIQUES N-ACYLÉS ET COMPOSITIONS AROMATISANTES LES CONTENANT

  摘要：

  一种化合物，其化学式为（I）或其可食用盐，[此处应插入公式] 其中R与其附着的羰基团一起是羧酸的残基。这些化合物可用于食品和饮料等可食用组合物中，以使或改变所述组合物的口感和口感。

  公开号：

  WO2015050536A1

文献信息

• [EN] N-ACYLATED 2-AMINOISOBUTYRIC ACID COMPOUNDS AND FLAVOUR COMPOSITIONS CONTAINING THEM<br/>[FR] COMPOSÉS D'ACIDES 2-AMINO-ISOBUTYRIQUES N-ACYLÉS ET COMPOSITIONS AROMATISANTES LES CONTENANT
  申请人：GIVAUDAN SA

  公开号：WO2015050536A1

  公开（公告）日：2015-04-09

  A compound according to the formula (I) or edible salts thereof, [Formula should be inserted here] Wherein R together with the carbonyl group to which it is attached is a residue of a carboxylic acid. Said compounds may be used in edible compositions such as foods and beverages to impart or modify flavour and mouth feel to said compositions.

  一种化合物，其化学式为（I）或其可食用盐，[此处应插入公式] 其中R与其附着的羰基团一起是羧酸的残基。这些化合物可用于食品和饮料等可食用组合物中，以使或改变所述组合物的口感和口感。
• Organic compounds
  申请人：GIVAUDAN S.A.

  公开号：US11122826B2

  公开（公告）日：2021-09-21

  A compound according to the formula (I) or edible salts thereof, Wherein R together with the carbonyl group to which it is attached is a residue of a carboxylic acid. Said compounds may be used in edible compositions such as foods and beverages to impart or modify flavour and mouth feel to said compositions.

  符合式 (I) 的化合物或其食用盐、 其中，R 及其所连接的羰基是羧酸的残基。所述化合物可用于食品和饮料等可食用成分中，以赋予或改变所述成分的风味和口感。
• N-ACYLATED 2-AMINOISOBUTYRIC ACID COMPOUNDS AND FLAVOUR COMPOSITIONS CONTAINING THEM
  申请人：Givaudan S.A.

  公开号：EP3052472A1

  公开（公告）日：2016-08-10
• Improvements in or Relating to Organic Compounds
  申请人：WANG Yili

  公开号：US20160213038A1

  公开（公告）日：2016-07-28

  A compound according to the formula (I) or edible salts thereof, Wherein R together with the carbonyl group to which it is attached is a residue of a carboxylic acid. Said compounds may be used in edible compositions such as foods and beverages to impart or modify flavour and mouth feel to said compositions.
• Oleoyl alanine (HU595): a stable monomethylated oleoyl glycine interferes with acute naloxone precipitated morphine withdrawal in male rats
  作者：Samantha M. Ayoub、Reem Smoum、Mathew Farag、Harkirat Atwal、Stephen A. Collins、Erin M. Rock、Cheryl L. Limebeer、Fabiana Piscitelli、Fabio Arturo Iannotti、Aron H. Lichtman、Francesco Leri、Vincenzo Di Marzo、Raphael Mechoulam、Linda A. Parker

  DOI：10.1007/s00213-020-05570-4

  日期：2020.9

  Rationale Oleoyl glycine, a little studied fatty acid amide similar in structure to anandamide, interferes with nicotine addiction in mice and acute naloxone-precipitated morphine withdrawal (MWD) in rats. Because endogenous oleoyl glycine is subject to rapid enzymatic deactivation, we evaluated the potential of more stable analogs to interfere with opiate withdrawal. Objectives The potential of monomethylated oleoyl glycine (oleoyl alanine, HU595) to interfere with somatic and aversive effects of acute naloxone-precipitated MWD, its duration, and mechanism of action was assessed in male Sprague Dawley rats. The potential of dimethylated oleoyl glycine (HU596) to interfere with the aversive effects of naloxone-precipitated MWD was also investigated. Results Oleoyl alanine (HU595) interfered with somatic and aversive effects produced by naloxone-precipitated MWD at equivalent doses (1 and 5 mg/kg, i.p.) as we have reported for oleoyl glycine; however, oleoyl alanine produced a longer lasting (60 min) interference, yet did not produce rewarding or aversive effects on its own and did not modify locomotor activity. HU596 was not effective. The interference with aversive effects of naloxone-precipitated MWD by oleoyl alanine was prevented by both a PPAR alpha antagonist and a CB(1)receptor antagonist. Accordingly, the compound was found to inhibit FAAH and activate PPAR alpha in vitro. Finally, oleoyl alanine also reduced acute naloxone-precipitated MWD anhedonia, as measured by decreased saccharin preference. Conclusions Oleoyl alanine (also an endogenous fatty acid) may be a more stable and effective treatment for opiate withdrawal than oleoyl glycine.