(2E)-2,6-dimethyl-6-hydroxy-2,7-octadienoic acid | 121843-29-6

• 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: (2E)-2,6-dimethyl-6-hydroxy-2,7-octadienoic acid
• 英文别名: 6-Hydroxy-2,6-dimethyl-2,7-Octadienoic acid；(2E)-6-hydroxy-2,6-dimethylocta-2,7-dienoic acid
• CAS: 121843-29-6
• 化学式: C₁₀H₁₆O₃
• 分子量: 184.235
• InChiKey: SSKWMOQUUQAJGV-SOFGYWHQSA-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：

  甲醇 、 (2E)-2,6-dimethyl-6-hydroxy-2,7-octadienoic acid 在 silica supported sodium hydrogen sulphate 作用下， 反应 0.07h， 以90%的产率得到(+/-)-(E)-2,6-dimethyl-6-hydroxy-2,7-octadienioc acid methyl ester
  参考文献：
  名称：

  Singh, Ashima; Sharma; Singh, Jasvinder, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2009, vol. 48, # 3, p. 452 - 454

  摘要：

  DOI：
• 作为产物：
  描述：

  芳樟醇 在 吡啶 、 sodium hydroxide 、 lutidine 、 四丁基氟化铵 、 臭氧 、 苯甲酸 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 、 苯 为溶剂， 反应 53.75h， 生成 (2E)-2,6-dimethyl-6-hydroxy-2,7-octadienoic acid
  参考文献：
  名称：

  Synthesis of (±)-(E)-2,6-dimethyl-6-hydroxyocta-2,7-dienoic acid and the corresponding amide (“acacialactam”)

  摘要：

  The total synthesis of the title compounds in racemic form is described. Linalool was used as the starting material and transformed into the target molecules in 6 steps. The synthetic amide displays spectral properties identical to those reported for the natural compound acacialactam, indicating that the structure proposed for the latter compound is not correct.

  DOI：

  10.1016/s0040-4039(00)76907-3

文献信息

• Ubiquinone and related compounds. XXXVIII. Biological oxidation of ubiquinone.
  作者：HIROSHI MORIMOTO、KUNIKO KURIMOTO、ISUKE IMADA

  DOI：10.1248/cpb.33.3182

  日期：——

  Ubiquinone-2 (1) was oxidized to 6-[7-carboxy-3-methyl- (2E, 6E)-2, 6-octadienyl]-2, 3-dimethoxy-5-methyl-1, 4-benzoquinone (2) and 6-[6, 7-dihydroxy-3, 7-dimethyl- (E)-2-octenyl]-2, 3-dimethoxy-5-methyl-1, 4-benzoquinone (3) by the 6000×g supernatant of guinea-pig liver homogenate in the presence of nicotinamide-adenine dinucleotide (NAD)- and dihydronicotinamideadenine dinucleotide phosphate (NADPH)-generating systems.

  辅酶Q-2 (1) 在存在烟酰胺腺嘌呤二核苷酸 (NAD) 和二氢烟酰胺腺嘌呤二核苷酸磷酸 (NADPH) 生成系统的条件下，通过6000×g的豚鼠肝脏匀浆上清液被氧化为6-[7-羧基-3-甲基-(2E, 6E)-2, 6-辛二烯基]-2, 3-二甲氧基-5-甲基-1, 4-苯醌 (2) 和6-[6, 7-二羟基-3, 7-二甲基-(E)-2-辛烯基]-2, 3-二甲氧基-5-甲基-1, 4-苯醌 (3)。
• Triterpene compositions and methods for use thereof
  申请人：Research Development Foundation

  公开号：US20030039705A1

  公开（公告）日：2003-02-27

  The invention provides novel saponin mixtures and compounds which are isolated from the species Acacia victoriae and methods for their use. These compounds may contain a triterpene moiety, such as acacic or oleanolic acid, to which oligosaccharides and monoterpenoid moieties are attached. The mixtures and compounds have properties related to the regulation of apoptosis and cytotoxicity of cells and exhibit potent anti-tumor effects against a variety of tumor cells. The present application is a continuation-in-part of co-pending U.S. Patent Application Ser. No. 60/099,066, filed Sep. 3, 1998, and a continuation-in-part of U.S. patent application Ser. No. 60/085,997, filed May 19, 1998. The entire text of each of the above-referenced disclosures is specifically incorporated by reference herein without disclaimer.

  本发明提供了从维多利亚金合欢(Acacia victoriae)物种中分离出来的新型皂苷混合物和化合物，以及它们的使用方法。这些化合物可能包含三萜基团，如金合欢酸或齐墩果酸，附着有寡糖和单萜基团。这些混合物和化合物具有与细胞凋亡和细胞毒性调节相关的特性，并对多种肿瘤细胞表现出强效的抗肿瘤作用。本申请是待决美国专利申请号60/099,066的续篇，该专利申请于1998年9月3日提交，并且是待决美国专利申请号60/085,997的续篇，该专利申请于1998年5月19日提交。上述所有引用文件的全部内容都被明确地并入本文，不做免责声明。
• THERAPEUTIC USES OF OLIGOMERIC AND POLYMERIC MONOTERPENES
  申请人：Hazan Zadik

  公开号：US20120213727A1

  公开（公告）日：2012-08-23

  The invention relates to therapeutic methods comprising use of oligomeric and polymeric forms of the monoterpene compounds alloocimene, limonene, alpha-pinene, beta-pinene, geranyl acetate, alpha-phellandrene, gamma-terpinene, 3-carene and 2-carene. More particularly, the invention relates to methods of treating degenerative neurological conditions, and treating skin disorders.

  本发明涉及使用单萜化合物alloocimene、limonene、alpha-pinene、beta-pinene、geranyl acetate、alpha-phellandrene、gamma-terpinene、3-carene和2-carene的寡聚体和聚合体形式的治疗方法。更具体地，本发明涉及治疗退行性神经疾病和治疗皮肤疾病的方法。
• Isolation and Structures of Avicins D and G:  In Vitro Tumor-Inhibitory Saponins Derived from <i>Acacia </i><i>v</i><i>ictoriae</i>
  作者：Gamini S. Jayatilake、Delano R. Freeberg、Zhengjie Liu、Steve L. Richheimer、Mary E. Blake、David T. Bailey、Valsala Haridas、Jordan U. Gutterman

  DOI：10.1021/np020400v

  日期：2003.6.1

  Two new saponins named avicins D (1) and G (2) were isolated from the seed pods of the desert legume plant Acacia victoriae. The structures, elucidated by 1D and 2D NMR studies and by chemical means, were characterized as acacic acid-bearing oligosaccharides at C-3 and C-28 with a side chain linked to C-21 comprised of two monoterpene carboxylic acids and a quinovose moiety. Both compounds exhibited

  从沙漠豆科植物金合欢（Acacia victoriae）的种子荚中分离出了两种新的皂素，分别称为avicins D（1）和G（2）。通过1D和2D NMR研究以及化学方法阐明的结构被表征为在C-3和C-28处带有乙酸的寡糖，其侧链连接到由两个单萜烯羧酸和一个喹诺夫糖部分组成的C-21 。两种化合物在体外均表现出针对人T细胞白血病（Jurkat细胞）的有效细胞毒性（凋亡）。
• Isolation of Two Novel Terpenoid Glucose Esters from Riesling Wine
  作者：Bernd Bonnländer、Beate Baderschneider、Monika Messerer、Peter Winterhalter

  DOI：10.1021/jf9706033

  日期：1998.4.1

  A glycosidic isolate of Riesling wine was separated with multilayer coil countercurrent chromatography (MLCCC). After acetylation and subsequent purification by high-performance liquid chromatography (HPLC), the glucose esters of (E)-2,6-dimethyl-6-hydroxyocta-2,7-dienoic acid (1) and (2E,6E)-10,11-dihydroxy-3,7,11-trimethyl-2,6-dodecadienoic acid (2) were identified for the first time as nine constituents. The identification was achieved by mass spectrometry (DCI-MS) as well as nuclear magnetic resonance spectroscopy (H-1 NMR, C-13 NMR, COSY, HMBC). In biomimetic studies carried out with (E)-2,6-dimethyl-6-hydroxyocta-2,7-dienoic acid the potent nine aroma compound 3a,4,5,7a-tetrahydro-3,6-dimethylbenzofuran-2(3H)-one (wine lactone) was formed, thus revealing an important aroma precursor function for glucoconjugate 1.