gamma-氨基丁酸-棕榈酰胺 | 58725-44-3

• 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
• 中文名称: gamma-氨基丁酸-棕榈酰胺
• 英文名称: 4RO16
• 英文别名: N-palmitoyl GABA；GABA-palmitamide；4-(hexadecanoylamino)butanoic acid
• CAS: 58725-44-3
• 化学式: C₂₀H₃₉NO₃
• 分子量: 341.535
• InChiKey: YLKMEQOADSECIK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.7
• 重原子数：
  24
• 可旋转键数：
  18
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  66.4
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2,4,6,8,10-dodecapentaenol 、 gamma-氨基丁酸-棕榈酰胺 在 4-二甲氨基吡啶 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 5.0h， 生成
  参考文献：
  名称：

  Fluorescent Polyene Ceramide Analogues as Membrane Probes

  摘要：

  Three ceramide analogues have been synthesized, with sphingosine-like chains containing five conjugated double bonds. Pentaene I has an N-palmitoyl acyl chain, while the other two pentaenes contain also a doxyl radical, respectively, at C5 (Penta5dox) and at C16 (Penta16dox) positions of the N-acyl chain. Pentaene I maximum excitation and emission wavelengths in a phospholipid bilayer are 353 and 478 nm, respectively. Pentaene I does not segregate from the other lipids in the way natural ceramide does, but rather mixes with them in a selective way according to the lipid phases involved. Fluorescence confocal microscopy studies show that when lipid domains in different physical states coexist, Pentaene I emission is higher in gel than in fluid domains, and in liquid-ordered than in liquid-disordered areas. Electron paramagnetic resonance of the pentaene doxyl probes confirms that these molecules are sensitive to the physical state of the bilayer. Calorimetric and fluorescence quenching experiments suggest that the lipids under study orient themselves in lipid bilayers with their polar moieties located at the lipid water interface. The doxyl radical in the N-acyl chain quenches the fluorescence of the pentaene group when in close proximity. Because of this property, Penta16dox can detect gel fluid transitions in phospholipids. The availability of probes for lipids in the gel phase is important in view of novel evidence for the existence of gel microdomains in cell membranes.

  DOI：

  10.1021/la505017x
• 作为产物：
  描述：

  4-氨基丁酸 、 棕榈酰氯 在 sodium hydroxide 作用下， 以 四氢呋喃 为溶剂， 反应 3.0h， 以58%的产率得到gamma-氨基丁酸-棕榈酰胺
  参考文献：
  名称：

  Inhibition of Group IVA Cytosolic Phospholipase A₂ by Novel 2-Oxoamides in Vitro, in Cells, and in Vivo

  摘要：

  The Group IVA cytosolic phospholipase A(2) (GIVA PLA(2)) is a particularly attractive target for drug development because it is the rate-limiting provider of proinflammatory mediators. We previously reported the discovery of novel 2-oxoamides that inhibit GIVA PLA(2) [Kokotos, G.; et al. J. Med. Chem. 2002, 45, 2891-2893]. In the present work, we have further explored this class of inhibitors and found that the 2-oxoamide functionality is more potent when it contains a long 2-oxoacyl residue and a free carboxy group. Long-chain 2-oxoamides based on gamma-aminobutyric acid and gamma-norleucine are potent inhibitors of GIVA PLA(2). Such inhibitors act through a fast and reversible mode of inhibition in vitro, are able to block the production of arachidonic acid and prostaglandin E-2 in cells, and demonstrate potent in vivo antiinflammatory and analgesic activity.

  DOI：

  10.1021/jm030485c

文献信息

• Organic compounds
  申请人：Givaudan S.A.

  公开号：US10836712B2

  公开（公告）日：2020-11-17

  A flavour composition comprising a compound according to the formula (I) or edible salts thereof, wherein R1 is an alkyl residue containing 6 to 20 carbon atoms, or an alkene residue containing from 9 to 25 carbon atoms with 1 to 6 double bonds, R1 together with the carbonyl group to which it is attached is a residue of a carboxylic acid, and NR2R3, in which R3 is H or together with R2 and the N-atom to which they are attached, a 5-membered ring, is a residue of an amino acid, in particular a proteinogenic amino acid, ornithine, gamma-aminobutyric acid or beta alanine, or a 1-amino cycloalkyl carboxylic acid.

  一种包含符合式(I)的化合物或其可食用盐的风味组合物，其中R1是含有6至20个碳原子的烷基残基，或者含有9至25个碳原子且具有1至6个双键的烯烃残基，R1与其连接的羰基一起是羧酸的残基，NR2R3中，R3为H或与R2和它们连接的N原子一起是一个5元环的残基，是一种氨基酸的残基，特别是一种蛋白质原性氨基酸、鸟氨酸、γ-氨基丁酸或β-丙氨酸，或者是一种1-氨基环烷基羧酸的残基。
• N-Acyl-Amino Acid Derivatives for Improvement of the Flavour Profile Edible Compositions
  申请人：Givaudan S.A.

  公开号：US20150086694A1

  公开（公告）日：2015-03-26

  The use of a compound according to formula (I) or the edible salts thereof in an edible composition to mask or modulate an undesired taste or off-taste contained in the edible composition wherein R 1 is an alkyl residue containing 6 to 20 carbon atoms, or an alkene residue containing from 9 to 25 carbon atoms with 1 to 6 double bonds, R 1 together with the carbonyl group to which it is attached is a residue of a carboxylic acid, and NR 2 R 3 , in which R 3 is H or together with R 2 and the N-atom to which they are attached, a 5-membered ring, is a residue of an amino acid, in particular a proteinogenic amino acid, ornithine, gamma-aminobutyric acid or beta alanine, or a 1-amino cycloalkyl carboxylic acid.

  根据公式（I）或其可食用盐在可食用组合物中的使用，以掩盖或调节可食用组合物中所含的不良味道或异味，其中R1是含6至20个碳原子的烷基残基，或含有1至6个双键的9至25个碳原子的烯烃残基，R1与其附着的羰基基团一起是羧酸的残基，而NR2R3中，R3为H或与R2和它们所附着的N原子一起，形成一个5元环，是氨基酸的残基，特别是蛋白质原氨基酸、鸟氨酸、γ-氨基丁酸或β-丙氨酸，或1-氨基环烷基羧酸的残基。
• N-acyl derivatives of gamma amino-butyric acid and beta alanine as food flavouring compounds
  申请人：Givaudan S.A.

  公开号：US10645955B2

  公开（公告）日：2020-05-12

  A flavour composition comprising a compound according to the formula (I) and edible salts thereof, wherein R1 is an alkyl residue containing 6 to 20 carbon atoms, or an alkene residue containing from 9 to 25 carbon atoms with 1 to 6 double bonds, R1 together with the carbonyl group to which it is attached is a residue of a carboxylic acid, and m is 0 or 1.

  一种香料组合物，包含符合式（I）的化合物 及其食用盐、 其中 R1 是含有 6 至 20 个碳原子的烷基残基，或含有 9 至 25 个碳原子并带有 1 至 6 个双键的烯基残基，R1 与所连接的羰基一起是羧酸残基，以及 m 为 0 或 1。
• N-acyl-amino acid derivatives for improvement of the flavor profile of edible compositions
  申请人：Givaudan S.A.

  公开号：US10856563B2

  公开（公告）日：2020-12-08

  The use of a compound according to formula (I) or the edible salts thereof in an edible composition to mask or modulate an undesired taste or off-taste contained in the edible composition wherein R1 is an alkyl residue containing 6 to 20 carbon atoms, or an alkene residue containing from 9 to 25 carbon atoms with 1 to 6 double bonds, R1 together with the carbonyl group to which it is attached is a residue of a carboxylic acid, and NR2R3, in which R3 is H or together with R2 and the N-atom to which they are attached, a 5-membered ring, is a residue of an amino acid, in particular a proteinogenic amino acid, ornithine, gamma-aminobutyric acid or beta alanine, or a 1-amino cycloalkyl carboxylic acid.

  在可食用组合物中使用式(I)化合物或其食用盐，以掩盖或调节可食用组合物中所含的不良味道或异味 其中 R1 是含有 6 至 20 个碳原子的烷基残基，或含有 9 至 25 个碳原子并带有 1 至 6 个双键的烯基残基，R1 与所连接的羰基一起是羧酸残基，以及 NR2R3、是氨基酸残基，特别是蛋白氨基酸、鸟氨酸、γ-氨基丁酸或 β-丙氨酸，或 1-氨基环烷基羧酸。
• In or relating to organic compounds
  申请人：Givaudan SA

  公开号：US11524933B2

  公开（公告）日：2022-12-13

  A flavour composition comprising a compound according to the formula (I) or edible salts thereof, wherein R 1 is alkyl residue containing 6 to 20 carbon atoms, or an alkene residue containing from 9 to 25 carbon atoms with 1 to 6 double bonds, R 1 together with the carbonyl to which it is attached is a residue carboxylic acid, and NR 2 R 3 , in which R 3 is H or together with R 2 and the N-atom to which they are attached, a 5-membered ring, is a residue of an amino acid, in particular proteinogenic amino acid, ornithine, gamma-aminobutyric acid or beta alanine, or a 1-amino cycloalkyl carboxylic acid.

  一种香料组合物，包含根据式 (I) 的化合物或其食用盐、 其中 R 1 是含有 6 至 20 个碳原子的烷基残基，或含有 9 至 25 个碳原子并带有 1 至 6 个双键的烯基残基，R 1 连同其所连接的羰基是羧酸残基，而 NR 2 R 3 ，其中 R 3 是 H 或与 R 2 是氨基酸残基，特别是蛋白氨基酸、鸟氨酸、γ-氨基丁酸或 β-丙氨酸，或 1-氨基环烷基羧酸。