(3R)-7-hydroxycitronellol | 122612-23-1

• 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: (3R)-7-hydroxycitronellol
• 英文别名: (R)-3,7-dimethyl-octane-1,7-diol；(+)-7-hydroxy-dihydro-citronellol；(+)(R)-2,6-dimethyl-octanediol-(2,8)；(+)(R)-2,6-Dimethyl-octandiol-(2,8)；(+)-2,6-Dimethyl-octan-2,8-diol；(r)-3,7-Dimethyl-octane-1,7-diol；(3R)-3,7-dimethyloctane-1,7-diol
• CAS: 122612-23-1
• 化学式: C₁₀H₂₂O₂
• 分子量: 174.283
• InChiKey: FPCCDPXRNNVUOM-SECBINFHSA-N

物化性质

• 沸点：
  264.1±8.0 °C(Predicted)
• 密度：
  0.921±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  12
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  40.5
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (3R)-7-hydroxycitronellol 在 戴斯-马丁氧化剂 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以34%的产率得到(+)-7-羟基-3,7-二甲基辛醛
  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
• 作为产物：
  描述：

  (R)-(+)-β-香茅醇 在 platinum(IV) oxide 氢氧化钾 、 氢气 作用下， 以 甲醇 、 乙酸乙酯 为溶剂， 20.0 ℃ 、97.19 kPa 条件下， 反应 1.5h， 生成 (3R)-7-hydroxycitronellol
  参考文献：
  名称：

  Etudes sur lesmatièresvégétales挥发物CLXXIX。合成DES顺-等反式- [2-甲基-2-丙烯-1-]基-2-甲基-4-tétrahydropyrannes

  摘要：

  通过氧合（+）-β-香茅醇乙酸制备的氢过氧化物的还原得到（+）-2,3-环氧-二氢香茅醇的乙酸盐和（+）-脱氢香茅醇的（+）-2,6的乙酸盐-（二甲基-八--1,3-二烯-8-醇在后一种中占主导），以及（+）-2,6-二甲基-八-3-烯-2,8-二醇的那些（其中反式异构体占主导地位）。

  DOI：

  10.1002/hlca.19610440705

文献信息

• Etudes sur les matières végétales volatiles CLXXIX. Synthèses des<i>cis</i>- et<i>trans</i>-[méthyl-2-propène-1]-yl-2-méthyl-4-tétrahydropyrannes
  作者：Yves-René Naves、Paul Tullen

  DOI：10.1002/hlca.19610440705

  日期：——

  Reduction of the hydroperoxides prepared by oxygenation of (+)-β-citronellyl acetate affords the acetate of (+)-2,3-epoxy-dihydrocitronellol and the acetates of the (+)-dehydrocitronellols (the (+)-2,6-dimethyl-octa-1,3-diene-8-ols predominating in the latter), as well as those of the (+)-2,6-dimethyl-oct-3-ene-2,8-diols (where the trans- isomer predominates).

  通过氧合（+）-β-香茅醇乙酸制备的氢过氧化物的还原得到（+）-2,3-环氧-二氢香茅醇的乙酸盐和（+）-脱氢香茅醇的（+）-2,6的乙酸盐-（二甲基-八--1,3-二烯-8-醇在后一种中占主导），以及（+）-2,6-二甲基-八-3-烯-2,8-二醇的那些（其中反式异构体占主导地位）。
• Naves, Helvetica Chimica Acta, 1946, vol. 29, p. 1454
  作者：Naves

  DOI：——

  日期：——
• 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：——
• Sabetay; Palfray, Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences, 1934, vol. 198, p. 1514
  作者：Sabetay、Palfray

  DOI：——

  日期：——
• The Odorant (<i>R</i>)-Citronellal Attenuates Caffeine Bitterness by Inhibiting the Bitter Receptors TAS2R43 and TAS2R46
  作者：Barbara Suess、Anne Brockhoff、Wolfgang Meyerhof、Thomas Hofmann

  DOI：10.1021/acs.jafc.6b03554

  日期：2018.3.14

  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.