(6R)-2-trans-2,6-dimethyl-6-hydroxy-2,7-octadienoic acid | 83945-54-4

• 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-trans-2,6-dimethyl-6-hydroxy-2,7-octadienoic acid
• 英文别名: (6S),(2E)-6-hydroxy-2,6-dimethyl-2,7-octadienoic acid；(2E,6R)-6-hydroxy-2,6-dimethyl-2,7-octadienoic acid；(6R,2E)-2,6-dimethyl-6-hydroxy-2,7-octadienoic acid；6(R)-hydroxy-2,6-dimethyl-2(E)-7-octadienoic acid；(6R)-menthiafolic acid；(-)-linalool-1-oic acid；(2E,6R)-6-hydroxy-2,6-dimethylocta-2,7-dienoic acid
• CAS: 83945-54-4
• 化学式: C₁₀H₁₆O₃
• 分子量: 184.235
• InChiKey: SSKWMOQUUQAJGV-PCGIRMHASA-N

物化性质

• 沸点：
  346.5±42.0 °C(Predicted)
• 密度：
  1.057±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  13
• 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：
  57.5
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (6R)-2-trans-2,6-dimethyl-6-hydroxy-2,7-octadienoic acid 在 lithium aluminium tetrahydride 作用下， 以 乙醚 为溶剂， 反应 0.17h， 以53%的产率得到R-(-)-8-hydroxylinalool
  参考文献：
  名称：

  来自 Viburnum phlebotrichum 的苦味单萜葡萄糖苷

  摘要：

  摘要 从荚蒾叶甲醇提取物中分离出三种已知的苦单萜葡萄糖苷。

  DOI：

  10.1016/0031-9422(82)80159-3
• 作为产物：
  描述：

  isorhamnetin 3-O-β-D-glucopyranosyl-7-O-[(6R,2E)-2,6-dimethyl-6-hydroxy-2,7-octadienoyl-(1→ 3)]-α-L-rhamnopyranoside 在 水 、 碳酸氢钠 作用下， 反应 2.0h， 生成 (6R)-2-trans-2,6-dimethyl-6-hydroxy-2,7-octadienoic acid
  参考文献：
  名称：

  Inhibitory Effects of the Constituents of <i>Hippophae rhamnoides</i> on 3T3-L1 Cell Differentiation and Nitric Oxide Production in RAW264.7 Cells

  摘要：

  从沙棘叶中分离出三种新的黄酮醇苷，沙棘苷 A–C (1–3)，以及 27 种已知成分。它们的结构通过光谱分析确定。研究了它们对 3T3-L1 前脂肪细胞分化和成熟脂肪细胞中甘油三酯积累以及 RAW264.7 细胞中一氧化氮产生的抑制活性。

  DOI：

  10.1248/cpb.c12-00835

文献信息

• Synthesis of (E)-2,6-dimethyl-6-hydroxyocta-2,7-dienoic acid and the corresponding amide (“acacialactam”) in optically active form
  作者：Miguel Carda、Juan Murga、Florenci González、J Alberto Marco

  DOI：10.1016/0040-4020(95)00025-4

  日期：1995.2

  The total synthesis of the title compounds in optically active form from geraniol as the starting material is described. The physical and spectral properties of the synthetic amide are identical with those of the natural compound acacialactam, this fact confirming that the structure proposed for the latter compound is not correct. The configuration of the single stereogenic carbon atom in the natural

  描述了由香叶醇作为起始原料以光学活性形式的标题化合物的全合成。合成酰胺的物理和光谱性质与天然化合物阿拉伯胶内酰胺的相同，这一事实证实了对于后一种化合物提出的结构是不正确的。在天然酰胺单立体碳原子的构型被示出为小号。
• Structure and Synthesis of a New Monoterpenoidal Carboxamide from the Seeds of the Thai Medicinal Plant Acacia concinna.
  作者：Toshikazu SEKINE、Nobuaki FUKASAWA、Fumio IKEGAMI、Kazuki SAITO、Yuichi FUJII、Isamu MURAKOSHI

  DOI：10.1248/cpb.45.148

  日期：——

  A new monoterpenoidal carboxamide, concinnamide (1), has been isolated from the seeds of a Thai medicinal plant, Acacia concinna DC. (Leguminosae). Its structure has been revised to (E)-2, 6-dimethyl-6-hydroxy-2, 7-octadienamide by detailed spectroscopic and synthetic studies, though it had been preliminarily assigned as a seven-membered lactam derivative by our previous work. (-)-Concinnamide, (-)-1, was synthesized from (-)-linalool (2) by stepwise oxidation, followed by amidation to confirm the structure. The inhibitory effects of 1 and related compounds on the arachidonate 5-lipoxygenase of RBL-1 cells are also described.

  从泰国药用植物 Acacia concinna DC 的种子中分离出一种新的单萜甲酰胺，即 concinnamide (1)。 （豆科）。尽管我们之前的工作初步将其确定为七元内酰胺衍生物，但通过详细的光谱和合成研究，其结构已被修改为(E)-2,6-二甲基-6-羟基-2,7-辛二烯酰胺。 (-)-肉桂酰胺，(-)-1，由(-)-芳樟醇(2)通过逐步氧化合成，然后酰胺化以确认结构。还描述了1和相关化合物对RBL-1细胞的花生四烯酸5-脂氧合酶的抑制作用。
• Polystachyasaponin with Adjuvant Activity from Entada polystachya
  作者：Bernadete P. da Silva、José P. Parente

  DOI：10.1515/znb-2010-0514

  日期：2010.5.1

  A new complex triterpenoid saponin, polystachyasaponin, was isolated from leaves of Entada polystachya (L.) DC. (Leguminosae) by using chromatographic methods. Its structure was established as 15,16-dihydroxy-3-[[O-β -D-xylopyranosyl-(1→2)-O-α-L-arabinopyranosyl-(1→6)-2- (acetylamino)-2-deoxy-β -D-glucopyranosyl]oxy]-(3β ,15α,16α)-olean-12-en-28-oic acid O-D-apio- β -D-furanosyl-(1→3)-O-β -D-xylopyranosyl-(1→2)-O-[β -D-glucopyranosyl-(1→4)]-6-O-[(2E,6R)- 6-hydroxy-2,6-dimethyl-1-oxo-2,7-octadienyl]-β -D-glucopyranosyl ester. Structural elucidation was performed using detailed analyses of ¹H and ¹³C NMR spectra including 2D NMR spectroscopic techniques and chemical conversions. The hemolytic activity of the saponin was evaluated using in vitro assays, and its adjuvant potential on the cellular immune response against ovalbumin antigen was investigated using in vivo assays.

  一种新的复杂三萜皂苷，多穗豆皂苷，通过色谱方法从多穗豆（Entada polystachya（L.）DC.（豆科））的叶子中分离出来。其结构被确定为15,16-二羟基-3-[[O-β-D-木糖苷-(1→2)-O-α-L-阿拉伯糖苷-(1→6)-2-(乙酰氨基)-2-脱氧-β-D-葡萄糖苷基]氧]-(3β,15α,16α)-熊果-12-烯-28-酸O-D-阿匹酰-β-D-呋喃糖苷-(1→3)-O-β-D-木糖苷-(1→2)-O-[β-D-葡萄糖苷-(1→4)]-6-O-[(2E,6R)-6-羟基-2,6-二甲基-1-氧代-2,7-辛二烯基]-β-D-葡萄糖苷酯。通过详细分析1H和13C NMR光谱，包括2D NMR光谱技术和化学转化，进行了结构阐明。使用体外实验评估了皂苷的溶血活性，并使用体内实验调查了其对卵清蛋白抗原细胞免疫反应的佐剂潜力。
• Entada saponin-III, a saponin isolated from the bark of Entada phaseoloides
  作者：Yoshihito Okada、Shoji Shibata、Tetsuro Ikekawa、Ana M.J. Javellana、Osamu Kamo

  DOI：10.1016/s0031-9422(00)83592-x

  日期：1987.1
• Diastereoisomeric saponins from Albizia julibrissin
  作者：Kun Zou、Wen-yong Tong、Hong Liang、Jing-rong Cui、Guang-zhong Tu、Yu-ying Zhao、Ru-yi Zhang

  DOI：10.1016/j.carres.2004.10.027

  日期：2005.5

  The structures of four new diastereoisomeric triterpenoidal saponins Julibroside J(5), J(8), J(12) and J(13) (1-4) isolated from Albizia julibrissin Durazz. (Leguminosae) have been determined on the basis of comprehensive spectroscopic analysis and chemical degradation. Julibroside, J(8) and J(13) showed marked cytotoxic activities against Bel-7402 cancer cell line at 100 mu g/mL. (c) 2005 Elsevier Ltd. All rights reserved.