8-oxolinalool | 118014-46-3

• 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
• 英文名称: 8-oxolinalool
• 英文别名: (6E)-8-oxolinalool；(2E)-6-hydroxy-2,6-dimethylocta-2,7-dienal
• CAS: 118014-46-3
• 化学式: C₁₀H₁₆O₂
• 分子量: 168.236
• InChiKey: HRVZNWRZLYDLBU-RMKNXTFCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  12
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.5
• 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-oxolinalool 在 甲醇 、 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 反应 0.5h， 以87%的产率得到lilac aldehyde
  参考文献：
  名称：

  猕猴桃：水果和花卉中的挥发性化合物

  摘要：

  在对几种猕猴桃基因型的花和果实的挥发性成分进行研究时，检测到 240 多种化合物。从每个基因型的个体组织中提取了大约 60-70 种不同的化合物。两种不同的挥发性取样方法（顶空和溶剂）有利于不同类别的化合物，这取决于它们在花或果实基质中的挥发性和溶解度。从花中提取的化合物主要包括芳樟醇衍生物，包括丁香醛 (12a-d) 和醇 (13a-d)、2,6-二甲基-6-羟基辛基-2,7-二烯醛 (8)、8-羟基芳樟醇 (9 )、倍半萜烯和苯化合物，它们被认为是苯丙氨酸和酪氨酸的代谢物。水果样品的提取物中含有一些单萜，但以丁酸乙酯、己酸乙酯、2-甲基丁酸酯和2-甲基丙酸酯，由醛类己醛和己-E2-烯醛组成。还检测到了许多未鉴定的化合物，其中 8 种来自花的密切相关，它们要么是一种化合物的异构体，要么是两种或两种以上密切相关的化合物。这是关于猕猴桃中存在一系列芳樟醇衍生物的首次报告。

  DOI：

  10.1016/s0031-9422(03)00142-0
• 作为产物：
  描述：

  芳樟醇 在 selenium(IV) oxide 作用下， 以 1,4-二氧六环 为溶剂， 反应 1.5h， 以19%的产率得到8-oxolinalool
  参考文献：
  名称：

  猕猴桃：水果和花卉中的挥发性化合物

  摘要：

  在对几种猕猴桃基因型的花和果实的挥发性成分进行研究时，检测到 240 多种化合物。从每个基因型的个体组织中提取了大约 60-70 种不同的化合物。两种不同的挥发性取样方法（顶空和溶剂）有利于不同类别的化合物，这取决于它们在花或果实基质中的挥发性和溶解度。从花中提取的化合物主要包括芳樟醇衍生物，包括丁香醛 (12a-d) 和醇 (13a-d)、2,6-二甲基-6-羟基辛基-2,7-二烯醛 (8)、8-羟基芳樟醇 (9 )、倍半萜烯和苯化合物，它们被认为是苯丙氨酸和酪氨酸的代谢物。水果样品的提取物中含有一些单萜，但以丁酸乙酯、己酸乙酯、2-甲基丁酸酯和2-甲基丙酸酯，由醛类己醛和己-E2-烯醛组成。还检测到了许多未鉴定的化合物，其中 8 种来自花的密切相关，它们要么是一种化合物的异构体，要么是两种或两种以上密切相关的化合物。这是关于猕猴桃中存在一系列芳樟醇衍生物的首次报告。

  DOI：

  10.1016/s0031-9422(03)00142-0

文献信息

• Cloning and expression of a member of a new cytochrome P-450 family: cytochrome P-450lin (CYP111) from Pseudomonas incognita
  作者：J D Ropp、I C Gunsalus、S G Sligar

  DOI：10.1128/jb.175.18.6028-6037.1993

  日期：1993.9

  Cytochrome P-450lin catalyzes the 8-methyl hydroxylation of linalool as the first committed step of its utilization by Pseudomonas incognita as the sole carbon source. By using a polymerase chain reaction-based cloning strategy, a 2.1-kb DNA fragment containing the cytochrome P-450lin gene (linC) was isolated. An open reading frame of 406 amino acids has been identified as that of P-450lin on the basis of amino acid sequence data from peptides of the native protein. Heterologous expression of functional holoprotein is exhibited by Escherichia coli transformed with pUC18 containing the subcloned linC gene under constitutive transcriptional control of the lac promoter. The G+C content of linC was found to be 55% overall and 58% in the third codon position. An optimized amino acid sequence alignment of P-450lin with cytochrome P-450cam shows that the two enzymes have only 25% identity. P-450lin was found to exhibit the expected conservation in the axial cysteine heme ligand-containing peptide and the threonine region postulated to form an O2-binding pocket (T. L. Poulos, B. C. Finzel, and A. J. Howard, J. Mol. Biol. 195:687-700, 1987). The low amino acid sequence identity between P-450lin and all other P-450 sequences has shown that P-450lin is the first member of the CYP111 P-450 gene family.

  细胞色素P-450lin催化芳樟醇的8-甲基羟化反应，作为Pseudomonas incognita唯一的碳源利用的第一步。通过使用聚合酶链反应克隆策略，分离出一个2.1 kb的DNA片段，其中包含细胞色素P-450lin基因（linC）。基于来自原生蛋白质肽段的氨基酸序列数据，已经确定了一个包含406个氨基酸的开放阅读框架，即P-450lin。在lac启动子的构成转录控制下，含有亚克隆的linC基因的pUC18转化的大肠杆菌表现出功能性全蛋白的异源表达。发现linC的G+C含量总体为55％，第三密码子位置为58％。P-450lin与细胞色素P-450cam的优化氨基酸序列比对表明，这两种酶只有25％的同源性。发现P-450lin在含有轴向半胱氨酸血红素配体的肽段和推测形成O2结合口袋的苏氨酸区域中表现出预期的保守性。P-450lin与所有其他P-450序列之间的低氨基酸序列同源性表明，P-450lin是CYP111 P-450基因家族的第一个成员。
• Singh, Ashima; Sharma; Singh, Jasvinder, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2009, vol. 48, # 3, p. 452 - 454
  作者：Singh, Ashima、Sharma、Singh, Jasvinder

  DOI：——

  日期：——
• Narcissus trevithian and Narcissus geranium: Analysis and synthesis of compounds
  作者：Hans M. van Dort、Paul P. Jagers、Roel. ter Heide、Anton J. A. van der Weerdt

  DOI：10.1021/jf00035a047

  日期：1993.11

  The essential oils of two narcissus varieties, Narcissus trevithian and Narcissus geranium, obtained by extraction of flowers followed by high vacuum distillation of the absolute, were analyzed by GC/MS. After separation in fractions, unknown compounds were isolated by preparative GLC and their structures established by NMR/IR spectroscopy. The synthesis of a number of new compounds, found for the first time in narcissus oil, is described. The two narcissus species are compared with respect to their main components and odor quality. All compounds found so far in narcissus varieties are listed.
• Chirality and biosynthesis of lilac compounds in Actinidia arguta flowers
  作者：A.J. Matich、B.J. Bunn、D.J. Comeskey、M.B. Hunt、D.D. Rowan

  DOI：10.1016/j.phytochem.2007.03.023

  日期：2007.7

  Biosynthesis of lilac compounds in 'Hortgem Tahi' kiwifruit (Actinidia arguta) flowers was investigated by treating inflorescences with d(5)-linalool. The incorporation of the deuterium label into 8-hydroxylinalool, 8-oxolinalool, the lilac aldehydes, alcohols, and alcohol epoxides was followed by GGMS and enantioselective GC-MS. Both (R)- and (S)-linalool were produced naturally by the flowers, but 8-hydroxylinalool, 8-oxolinalool, and the lilac aldehydes and alcohols occurred predominantly as the (S) and 5'(S)-diastereoisomers, respectively. The enantio selective step in the biosynthesis of the lilac aldehydes and alcohols was concluded to be the oxidation of linalool to (S)-8-hydroxylinalool. In contrast, the lilac alcohol epoxides had a 5'(R):(S) ratio, the same as for linalool, which suggests that either these compounds are not synthesised from the 5'(S)-configured lilac aldehydes and alcohols, or that if indeed they are, then it is by an enantioselective step that favours utilisation of the 5'(R)-configured compounds. (c) 2007 Elsevier Ltd. All rights reserved.
• Ullah A.J.; Murray R.I.; Bhattacharyya P.K., J Biol Chem, 1990, 0021-9258, 1345-51
  作者：Ullah A.J.、Murray R.I.、Bhattacharyya P.K.、Wagner G.C.、Gunsalus I.C.

  DOI：——

  日期：——