(R)-7-hydroxycitronellic acid

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羟基酸及其衍生物
• 英文名称: (R)-7-hydroxycitronellic acid
• 英文别名: (R)-7-hydroxy-3,7-dimethyl-octanoic acid；(R)-7-Hydroxy-3,7-dimethyl-octansaeure；(+)(R)-2-Hydroxy-2.6-dimethyl-octansaeure-(8)；(+)(R)-Hydroxydihydrocitronellsaeure；(+)(R)-Oxydihydrocitronellsaeure；(3R)-7-hydroxy-3,7-dimethyloctanoic acid
• 化学式: C₁₀H₂₀O₃
• 分子量: 188.267
• InChiKey: LBBSPQOXZLKDOD-MRVPVSSYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  13
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  57.5
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  (R)-(+)-香茅酸 在 硫酸 作用下， 以 水 为溶剂， 反应 3.0h， 以66%的产率得到(R)-7-hydroxycitronellic acid
  参考文献：
  名称：

  The Odorant (R)-Citronellal Attenuates Caffeine Bitterness by Inhibiting the Bitter Receptors TAS2R43 and TAS2R46

  摘要：

  Sensory studies showed the volatile fraction of lemon grass and its main constituent, the odor-active citronellal, to significantly decrease the perceived bitterness of a black tea infusion as well as caffeine solutions. Seven citronellal-related derivatives were synthesized and shown to inhibit the perceived bitterness of caffeine in a structure-dependent manner. The aldehyde function at carbon 1, the (R)-configuration of the methyl-branched carbon 3, and a hydrophobic carbon chain were found to favor the bitter inhibitory activity of citronellal; for example, even low concentrations of 25 ppm were observed to reduce bitterness perception of caffeine solution (6 mmol/L) by 32%, whereas (R)-citronellic acid (100 pm) showed a reduction of only 21% and (R)-citronellol (100 pm) was completely inactive. Cell-based functional experiments, conducted with the human bitter taste receptors TAS2R7, TAS2R10, TAS2R14, TAS2R43, and TAS2R46 reported to be sensitive to caffeine, revealed (R)citronellal to completely block caffeine-induced calcium signals in TAS2R43-expressing cells, and, to a lesser extent, in TAS2R46-expressing cells. Stimulation of TAS2R43-expressing cells with structurally different bitter agonists identified (R)-citronellal as a general allosteric inhibitor of TAS2R43. Further structure/activity studies indicated 3-methyl-branched aliphatic aldehydes with a carbon chain of >= 4 C atoms as best TAS2R43 antagonists. Whereas odor taste interactions have been mainly interpreted in the literature to be caused by a central neuronal integration of odors and tastes, rather than by peripheral events at the level of reception, the findings of this study open up a new dimension regarding the interaction of the two chemical senses.

  DOI：

  10.1021/acs.jafc.6b03554

文献信息

• Palfray; Sabetay; Rangel, Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences, 1941, vol. 212, p. 912
  作者：Palfray、Sabetay、Rangel

  DOI：——

  日期：——
• Ishikawa; Suga, Kagaku Kenkyusho Hokoku, 1950, vol. 26, p. 258
  作者：Ishikawa、Suga

  DOI：——

  日期：——