8(Z)-heptadecenoic acid | 7432-41-9

• 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: 8(Z)-heptadecenoic acid
• 英文别名: cis-8-Heptadecenoic acid；(Z)-heptadec-8-enoic acid
• CAS: 7432-41-9
• 化学式: C₁₇H₃₂O₂
• 分子量: 268.44
• InChiKey: ZBIGLIMGCLJKHN-KTKRTIGZSA-N

物化性质

• 熔点：
  5.5-7.0 °C
• 沸点：
  389.4±21.0 °C(Predicted)
• 密度：
  0.902±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.9
• 重原子数：
  19
• 可旋转键数：
  14
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.82
• 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：

  8(Z)-heptadecenoic acid 在 silica gel 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 2.5h， 生成 3-<(7Z)-hexadecenyl>-4-methylfuran-2,5-dione
  参考文献：
  名称：

  Poigny, Stephane; Guyot, Michele; Samadi, Mohammad, Journal of the Chemical Society. Perkin transactions I, 1997, # 15, p. 2175 - 2177

  摘要：

  DOI：
• 作为产物：
  描述：

  2-羟基油酸 在 lead(IV) acetate 、 sodium chlorite 、 sodium dihydrogenphosphate 、 2-甲基-2-丁烯 作用下， 以 水 、 叔丁醇 、 苯 为溶剂， 反应 1.08h， 生成 8(Z)-heptadecenoic acid
  参考文献：
  名称：

  Inhibition of Oleamide Hydrolase Catalyzed Hydrolysis of the Endogenous Sleep-Inducing Lipid cis-9-Octadecenamide

  摘要：

  Oleamide (1, cis-9-octadecenamide) is a naturally occurring brain constituent that. has been shown to accumulate and disappear under conditions of sleep deprivation and sleep recovery, respectively. Synthetic 1 has been found to induce sleep in a structurally specific manner at nanomolar quantities. Hydrolysis of 1 by an enzyme (oleamide hydrolase) present in the cell membrane rapidly degrades oleamide to oleic acid (cis-9-octadecenoic acid). Such observations suggest 1 may constitute a prototypical member of a class of fatty acid primary amide biological signaling molecules in which the diversity and selectivity of function are derived from the length of the alkane chain as well as the position, stereochemistry, and degree of unsaturation. A series of inhibitors of oleamide hydrolase were designed and prepared which were expected to derive their properties through interactions with the putative active site cysteine residue within oleamide hydrolase. This approach yielded a series of rapid, selective, and highly potent inhibitors (K-i = 13 mu M to 1 nM) which in addition to their potential therapeutic value may serve as useful tools to define the biological role of oleamide.

  DOI：

  10.1021/ja954064z

文献信息

• ALPHA-HYDROXYLATED FATTY-ACID METABOLITES, MEDICAL USES OF SAME AND USE AS BIOMARKERS
  申请人：Universitat de les Illes Balears

  公开号：EP4098649A2

  公开（公告）日：2022-12-07

  Described are fatty acids with one or more unsaturations, having an odd hydrocarbon chain, the fatty acids having the chemical structure of the therapeutically active metabolites of even-chain mono- or polyunsaturated alpha-hydroxylated fatty acids. Also described are compositions comprising said fatty acids, medical uses thereof, and the use thereof as indicators of the efficacy of and/or response to the treatment of a patient with the even-chain mono- or polyunsaturated alpha-hydroxylated fatty acids from which they are derived.

  所述脂肪酸具有一种或多种不饱和脂肪酸，具有奇数烃链，这些脂肪酸具有偶数链单不饱和或多不饱和α-羟基化脂肪酸的治疗活性代谢产物的化学结构。此外，还描述了包含所述脂肪酸的组合物、其医疗用途，以及将其用作偶链单不饱和或多不饱和α-羟基化脂肪酸治疗患者的疗效和/或反应的指标，这些脂肪酸就是从偶链单不饱和或多不饱和α-羟基化脂肪酸中提取的。
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  作者：Marcel S.F. Lie Ken Jie、C.C. Lam

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