(6R)-(+)-2,6-dimethyl-8-hydroxy-2-octenal | 234434-63-0

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: (6R)-(+)-2,6-dimethyl-8-hydroxy-2-octenal
• 英文别名: (2E,6R)-8-hydroxy-2,6-dimethyl-2-octenal；(E,6R)-8-hydroxy-2,6-dimethyloct-2-enal
• CAS: 234434-63-0
• 化学式: C₁₀H₁₈O₂
• 分子量: 170.252
• InChiKey: DQQMOUVABPRNEO-RAJVOEEQSA-N

物化性质

• 沸点：
  279.0±23.0 °C(Predicted)
• 密度：
  0.934±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  12
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.7
• 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：

  (6R)-(+)-2,6-dimethyl-8-hydroxy-2-octenal 在 sodium hydroxide 、 silver nitrate 作用下， 生成 6,7-dihydrofoliamenthoic acid methyl ester
  参考文献：
  名称：

  Acylated Iridoid Glycosides from Buddleja japonica HEMSL.

  摘要：

  从日本紫苑（Buddleja japonica HEMSL.）中分离出了十六种新的酰基化马兜铃苷，称为buddlejosides A1-A16，同时还分离出了四种已知的马兜铃苷；它们分别是6-香草酰-ajugol、6-阿魏酰-ajugol、verbascoside A和6-O-[α-L-(4-O-阿魏酰)-rhamnopyranosyl]-catalpol。这些新化合物的结构是基于化学和光谱证据确定的。Buddlejosides A1是与单萜酸酰化的ajugol衍生物，A2是sinusol，A3-A16是与肉桂酸衍生物和醋酸酰化的6-鼠李糖基-catalpol衍生物。

  DOI：

  10.1248/cpb.39.2944
• 作为产物：
  描述：

  (R)-(+)-β-香茅醇 在 selenium(IV) oxide 作用下， 以 乙醇 为溶剂， 反应 2.0h， 以15 mg的产率得到(6R)-(+)-2,6-dimethyl-8-hydroxy-2-octenal
  参考文献：
  名称：

  Acylated Iridoid Glycosides from Buddleja japonica HEMSL.

  摘要：

  从日本紫苑（Buddleja japonica HEMSL.）中分离出了十六种新的酰基化马兜铃苷，称为buddlejosides A1-A16，同时还分离出了四种已知的马兜铃苷；它们分别是6-香草酰-ajugol、6-阿魏酰-ajugol、verbascoside A和6-O-[α-L-(4-O-阿魏酰)-rhamnopyranosyl]-catalpol。这些新化合物的结构是基于化学和光谱证据确定的。Buddlejosides A1是与单萜酸酰化的ajugol衍生物，A2是sinusol，A3-A16是与肉桂酸衍生物和醋酸酰化的6-鼠李糖基-catalpol衍生物。

  DOI：

  10.1248/cpb.39.2944

文献信息

• Chiral synthetic intermediates via asymmetric hydrogenation of .alpha.-methyl-.alpha.,.beta.-unsaturated aldehydes by bakers' yeast
  作者：Paola Gramatica、Paolo Manitto、Laura Poli

  DOI：10.1021/jo00223a038

  日期：1985.11
• GRAMATICA, P.;MANITTO, P.;POLI, L., J. ORG. CHEM., 1985, 50, N 23, 4625-4628
  作者：GRAMATICA, P.、MANITTO, P.、POLI, L.

  DOI：——

  日期：——
• Acylated Iridoid Glycosides from Buddleja japonica HEMSL.
  作者：Toshio MIYASE、Chiko AKAHORI、Hiromi KOHSAKA、Akira UENO

  DOI：10.1248/cpb.39.2944

  日期：——

  Sixteen new acylated iridoid glycosides, called buddlejosides A1-A16, were isolated from Buddleja japonica HEMSL., together with four known iridoid glycosides; 6-vanilloyl-ajugol, 6-feruloyl-ajugol, verbascoside A, and 6-O-[α-L-(4-O-feruloyl)-rhamnopyranosyl]-catalpol. Structures of the new compounds were determined on the basis of chemical and spectroscopic evidence. Buddlejosides A1 was an ajugol derivative acylated with monoterpenic acid, A2 was an sinuatol and A3-A16 were 6-rhamnopyranosyl-catalpol derivatives acylated with cinnamic acid derivative and acetic acid.

  从日本紫苑（Buddleja japonica HEMSL.）中分离出了十六种新的酰基化马兜铃苷，称为buddlejosides A1-A16，同时还分离出了四种已知的马兜铃苷；它们分别是6-香草酰-ajugol、6-阿魏酰-ajugol、verbascoside A和6-O-[α-L-(4-O-阿魏酰)-rhamnopyranosyl]-catalpol。这些新化合物的结构是基于化学和光谱证据确定的。Buddlejosides A1是与单萜酸酰化的ajugol衍生物，A2是sinusol，A3-A16是与肉桂酸衍生物和醋酸酰化的6-鼠李糖基-catalpol衍生物。
• (2<i>E</i>,6<i>R</i>)-8-Hydroxy-2,6-dimethyl-2-octenoic Acid, a Novel<i>Anti</i>-osteoporotic Monoterpene, Isolated from<i>Cistanche salsa</i>
  作者：Kohji YAMAGUCHI、Chikara SHINOHARA、Sachiko KOJIMA、Mikiko SODEOKA、Tomoko TSUJI

  DOI：10.1271/bbb.63.731

  日期：1999.1

  (2E,6R)-8-Hydroxy-2,6-dimethyl-2-octenoic acid [(R)-HDOA], a novel monoterpene from Cistanche salsa, a Chinese herb, was found to be an anti-osteoporotic compound. The extract of Cistanche salsa significantly suppressed the bone weight loss in ovariectomized mice, a postmenopausal osteoporosis model. The active substance was then purified by using this osteoporotic model and the chemical structure was determined. The active compound from Cistanche salsa, (R)-HDOA, suppressed the decrease of bone weight and the mechanical strength in the ovariectomized mice. Furthermore, (R)- and (S)-HDOA were synthesized and the activity of each was evaluated. (R)-HDOA suppressed the bone weight loss, although (S)-HDOA did not showed any activity.

  (2E,6R)-8-羟基-2,6-二甲基-2-辛烯酸[(R)-HDOA]是从中国草药肉苁蓉中发现的一种新型单萜化合物，具有抗骨质疏松特性。肉苁蓉提取物显著抑制了卵巢切除小鼠（一种绝经后骨质疏松模型）的骨重量损失。通过利用这一骨质疏松模型对该活性物质进行纯化，并确定了其化学结构。肉苁蓉中的活性化合物(R)-HDOA抑制了卵巢切除小鼠骨重量的减少和力学强度的下降。进一步合成了(R)-和(S)-HDOA，并对它们各自的活性进行了评估。(R)-HDOA抑制了骨重量损失，而(S)-HDOA未显示出任何活性。