香叶醇-D6 | 66063-44-3

• 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
• 中文名称: 香叶醇-D6
• 英文名称: (8,9-2H6)geraniol
• 英文别名: [8,8,8-2H3]-3-methyl-7-([2H3]methyl)octa-2E,6-dien-1-ol；(2E)-[8,8,8,10,10,10-²H₆]-3,7-dimethyl-2,6-octadien-1-ol；(E)-3-methyl-7-(methyl-d3)octa-2,6-dien-8,8,8-d3-1-ol；geraniol-8,8,8,9,9,9-d6；Geraniol-D6；(2E)-8,8,8-trideuterio-3-methyl-7-(trideuteriomethyl)octa-2,6-dien-1-ol
• CAS: 66063-44-3
• 化学式: C₁₀H₁₈O
• 分子量: 160.205
• InChiKey: GLZPCOQZEFWAFX-VXNAPGOLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  11
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  香叶醇-D6 在 manganese(IV) oxide 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 以42%的产率得到(2E)-[8,8,8,10,10,10-²H₆]-3,7-dimethyl-2,6-octadien-1-al
  参考文献：
  名称：

  模仿蚜虫的类虹膜植物中的类虹膜性信息素生物合成

  摘要：

  （1 R，4a S，7 S，7a R）-荆芥内酯（1）和（4a S，7 S，7a R）-荆芥内酯（2）在植物中的生物合成涉及类环烯合酶（ISY），这是一种非典型的还原环化酶催化将8-氧代香叶醛还原为（S）-8-氧代鞘氨醇的反应性烯醇，并催化该烯醇中间体的非酶促反应或通过与荆芥内酯相关的短链脱氢酶（NEPS）的环化反应生成荆芥内酯。在这项研究中，我们调查了生物合成体内的1和2中的豌豆蚜，苯乙腈（Acyrthosiphon pisum），使用同位素标记的单萜类化合物库作为分子探针。从香叶醇和橙花醇合成氘标记的探针的局部施用导致产量的2 ħ 4 -lactol 1和2 ħ 4内酯2。然而，使用由（S）-香茅酚合成的标记探针，氘掺入并不明显。这些结果表明，动物，特别是蚜虫中的虹膜生物合成可能遵循与植物所表征的大致相似的途径。

  DOI：

  10.1002/chem.202001356
• 作为产物：
  描述：

  (E)-2-((3-methyl-7-(methyl-d3)octa-2,6-dien-1-yl-8,8,8-d3)oxy)tetrahydro-2H-pyran 在 对甲苯磺酸 作用下， 以 乙醇 为溶剂， 以36 %的产率得到香叶醇-D6
  参考文献：
  名称：

  [EN] DEUTERATED PHENOL DERIVATIVES, PREPARATION METHOD THEREFOR, AND USE THEREOF
  [FR] DÉRIVÉS DE PHÉNOL DEUTÉRÉS, LEUR PROCÉDÉ DE PRÉPARATION ET LEUR UTILISATION
  [ZH] 氘代苯酚衍生物及其制备方法和用途

  摘要：

  本申请涉及化合物A的氘代化合物或者其药物可接受的盐或立体异构体，其中所述化合物A中的一个或多个氢被氘取代，该化合物用于治疗中枢神经系统相关的疾病。

  公开号：

  WO2022218382A1

文献信息

• Selective Isomerization of Epoxides to Allylic Alcohols Catalyzed by TiO₂-Supported Gold Nanoparticles
  作者：Christos Raptis、Hermenegildo Garcia、Manolis Stratakis

  DOI：10.1002/anie.200805838

  日期：2009.4.14

  ReacTiO2ns for rings: Gold nanoparticles supported on TiO2 are used as a novel heterogeneous catalyst for the isomerization of epoxides to allylic alcohols by a concerted mechanism (see scheme). The reaction proceeds in high yields and the product selectivity is often remarkable.

  用于环的ReacTiO 2 ns：负载在TiO 2上的金纳米颗粒用作新型异质催化剂，可通过协同机制将环氧化物异构化为烯丙基醇（参见方案）。该反应以高产率进行，并且产物选择性通常是显着的。
• Metabolism of geraniol in grape berry mesocarp of L. cv. Scheurebe: demonstration of stereoselective reduction, /-isomerization, oxidation and glycosylation
  作者：F LUAN、A MOSANDL、A MUNCH、M WUST

  DOI：10.1016/j.phytochem.2004.12.017

  日期：2005.2

  The metabolism of deuterium labeled geraniol in grape mesocarp of Vitis vinifera L. cv. Scheurebe was studied by in vivo-feeding experiments. Stereoselective reduction to (S)-citronellol, E/Z-isomerization to nerol, oxidation to neral/geranial and glycosylation of the corresponding monoterpene alcohols could be demonstrated. Time course studies including the determination of conversion rates revealed

  Vitis vinifera L. cv. 葡萄中果皮中氘标记香叶醇的代谢。通过体内喂养实验研究了 Scheurebe。可以证明立体选择性还原为 (S)-香茅醇、E/Z 异构化为橙花醇、氧化为橙花/香叶醛和相应单萜醇的糖基化。包括转化率测定在内的时间进程研究表明，单萜的这些二次转化的活性取决于成熟阶段，并且可以通过成熟期末的急剧增加与初级单萜合酶活性的发展区分开来。还证明了从葡萄浆果中果皮中标记的香叶醇对强效气味顺式-(2S,4R)-玫瑰氧化物进行立体选择性生物合成。由于 (S)-香茅醇是 cis-(2S, 4R)-玫瑰氧化物 可以得出结论，尤其是成熟期的最后部分对于这种强效气味的产生很重要。这一发现证实了一个结论，即通过将果实长时间留在葡萄藤上，可以在浆果中建立更高浓度的风味化合物。
• Regiospecificity and isotope effects associated with the methyl-methylene eliminations in the enzyme-catalyzed biosynthesis of (R)- and (S)-limonene
  作者：Hyung Jung Pyun、Robert M. Coates、Kurt C. Wagschal、Paul McGeady、Rodney B. Croteau

  DOI：10.1021/jo00067a037

  日期：1993.7

  [8-H-3]-, [8,8,9,9-H-2(4)]-, and [1-H-3,8,9-H-2(6)] geranyl diphosphates (1-t, 1-d4, and 1-d6,t) were synthesized and used as substrates for several monoterpene cyclases to determine the regiospecificity and isotope effects attending the terminating proton transfers in the enzyme-catalyzed biosynthesis of (R)- and (S)-limonene. Degradation of enantiomeric [H-3]limonenes produced by cyclization Of 1-t with the (+)- and (-)-pinene cyclases (synthases) from Salvia officinalis demonstrated that the eliminations occur at both the cis- (55-65%) and trans-methyl (45-35%) groups. In contrast, the terminating eliminations in the formation of (+)- and (-)-limonene catalyzed by limonene cyclasses from Citrus sinensis and Perilla frutescens, respectively, were shown by degradation to occur exclusively (greater-than-or-equal-to 97-98%) at the cis terminal methyl group. The intramolecular isotope effects for the methyl-methylene elimination in limonene biosynthesis catalyzed by (+)- and (-)-pinene cyclases from S. officinalis were found to be k(H)/k(D) = 2.3 +/- 0.2 and 5.9 +/- 0.5, respectively, by GC/MS determinations of [H-2]-limonene derived from enzymatic cyclizations of 1-d4. Similar experiments with (-)-limonene cyclase from Mentha spicata resulted in k(H)/k(D) = 4.0 +/- 0.4. Incubations of 1-d6,t with pinene and bornyl PP cyclases from S. officinalis exhibited significant remote isotope effects (k(H)/k(D) = 1.16-1.27) on the total rate of monoterpene formation which suggest that the initial cyclization step of the enzyme-bound linalyl diphosphate intermediate is an important component of the overall rate of the enzymatic reactions. The isotope effects on the partitioning of the alpha-terpinyl carbocation intermediate between bicyclization and elimination to limonene were determined from the effects of deuterium substitution on the product ratios derived from enzymatic cyclization of 1-d6,t. The small size of these product isotope effects (k(H)/k(D)) = 1.2-1.7) is attributed to a conformational inversion of the alpha-terpinyl ion to a half-chair conformer prior to proton elimination to limonene, thereby rendering the bicyclizations relatively immune to the intrinsic deuterium isotope effect. The regiospecific proton transfers from the cis terminal methyl group effected by the limonene cyclases from Citrus and Perilla are attributed to the minimization of charge separation in the transition state.
• CARR, GRAHAM;DEAN, CHRISTOPHER;WHITTAKER, DAVID, J. CHEM. SOC. PERKIN TRANS. PT 2,(1989) N, C. 71-76
  作者：CARR, GRAHAM、DEAN, CHRISTOPHER、WHITTAKER, DAVID

  DOI：——

  日期：——