(4E,8E,12E)-4,9,13,17-Tetramethyloctadeca-4,8,12,16-tetraen-1-ol | 56882-10-1

• 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: (4E,8E,12E)-4,9,13,17-Tetramethyloctadeca-4,8,12,16-tetraen-1-ol
• 英文别名: (4E,8E,12E)-4,9,13,17-tetramethyl-4,8,12,16-octadecatetraen-1-ol；4,9,13,17-tetramethyloctadeca-4(E),8(E),12(E),16-tetraen-1-ol；(4E,8E,12E)-4,9,13,17-tetramethyl-octadeca-4,8,12,16-tetraen-1-ol；4,9,13,17-Tetramethyloctadeca-4,8,12,16-tetraen-1-ol；4,8,12,16-Octadecatetraen-1-ol, 4,9,13,17-tetramethyl-
• CAS: 56882-10-1
• 化学式: C₂₂H₃₈O
• 分子量: 318.543
• InChiKey: NEYOIHGMUHELNR-GDFIKGLMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.4
• 重原子数：
  23
• 可旋转键数：
  12
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.64
• 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：

  (4E,8E,12E)-4,9,13,17-Tetramethyloctadeca-4,8,12,16-tetraen-1-ol 在 吡啶 、 4-二甲氨基吡啶 、 四氧化锇 、 重铬酸吡啶 、 甲基磺酰胺 、 AD-mix-β 、 sodium acetate 、 potassium carbonate 、 三乙胺 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 32.33h， 生成 (20S)-(4E,8E,12E,16E)-20,21-Epoxy-4,8,13,17,21-pentamethyl-4,8,12,16-docosatetraen-1-al
  参考文献：
  名称：

  Asymmetric Synthesis of a Mechanism-Based Inhibitor of Oxidosqualene Cyclase

  摘要：

  DOI：

  10.1021/jo00097a068
• 作为产物：
  描述：

  角鲨烯 在 lithium aluminium tetrahydride 、 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 生成 (4E,8E,12E)-4,9,13,17-Tetramethyloctadeca-4,8,12,16-tetraen-1-ol
  参考文献：
  名称：

  角鲨烯的新环化机制：希望生物合成中五元C环中间体的扩环步骤。

  摘要：

  从突变的F601A酶的温育混合物中分离出具有6/6 / 5-融合的三环和6/6/6 / 5-融合的四环骨架的三个三萜，这些产物与Markovnikov封闭法一致。通过使用具有高度亲核羟基的角鲨烯类似物成功捕获三环阳离子中间体，使我们提出5元C环的扩环过程涉及角鲨烯环化级联反应。

  DOI：

  10.1271/bbb.63.2038

文献信息

• Synthesis of rac-hippospongic acid A and revision of the structure
  作者：Munetaka Tokumasu、Hiroshi Ando、Yoshikazu Hiraga、Satoshi Kojima、Katsuo Ohkata

  DOI：10.1039/a808526i

  日期：——

  rac-Hippospongic acid A of the reported structure 1 and the revised structure 2 were synthesized. The synthetic strategy of these compounds consists of homologation of (2E,6E,10E)-geranylgeraniol and (2E,6E)-farnesol, respectively, Wadsworth–Emmons reaction, and cyclization to form the tetrahydropyran ring bearing an α-methylene group on the carboxylic moiety. Spectral comparisons of the synthetic compounds 1, 2 and the natural product suggested that hippospongic acid A bears the structure of 2.

  所报道的化合物1和修订结构2的rac-Hippospongic酸A已被合成。这些化合物的合成策略包括分别对(2E,6E,10E)-香叶香叶醇和(2E,6E)-金合欢醇进行同系化反应，Wadsworth-Emmons反应，以及形成在羧基部分带有α-甲基的二氢吡喃环的环合反应。通过对比合成化合物1、2与天然产物的光谱数据，表明Hippospongic酸A具有结构2。
• VITAMIN C COMPLEXES
  申请人：CENTRE NATIONAL DE LA RECHERCHE SCIENTIFIQUE

  公开号：US20150045426A1

  公开（公告）日：2015-02-12

  A complex formed of at least one molecule of 5-(1,2-dihydroxy-ethyl)-3,4-dihydroxy-5H-furan-2-one or a derivative covalently bonded with at least one hydrocarbon radical with formula (A) as follows: wherein: •-m 1=1, 2, 3, 4, 5 or 6; •-m 2=0, 1, 2, 3, 4, 5 or 6; and represents the site of the bond with the molecule of 5-(1,2-dihydroxy-ethyl)-3,4-dihydroxy-5H-furan-2-one or derivative. Formula (I)

  至少包含一个分子5-(1,2-二羟基乙基)-3,4-二羟基-5H-呋喃-2-酮或其衍生物与至少一个具有以下式(A)的碳氢基团共价结合形成的复合物：其中： •-m1=1, 2, 3, 4, 5或6； •-m2=0, 1, 2, 3, 4, 5或6；并表示与5-(1,2-二羟基乙基)-3,4-二羟基-5H-呋喃-2-酮或其衍生物结合的位置。公式(I)
• An approach to the synthesis of (3R)- and (3S)-2,3-epoxysqualene
  作者：Mohamed A. Abadallah、Jayant N. Shah

  DOI：10.1039/p19750000888

  日期：——

  In an approach to the synthesis of (3R)- and (3S)-2,3-epoxysqualene, 4-[(4R)-2,2,5,5-tetramethyl-1,3-dioxolan-4-yl]butan-2-one and triphenyl-(4,9,13,17-tetramethyloctadeca-4,8,12,16-tetraenyl)phosphonium iodide have been prepared.

  在合成（3 R）-和（3 S）-2,3-环氧角鲨烯的方法中，4-[（（4 R）-2,2,5,5-四甲基-1,3-二氧戊环-4-制备了[基]丁基-2-酮和三苯基-（4,9,13,17-四甲基十八烷基-4,8,12,16-四烯基）碘化phosph。
• Synthesis of Sulfur- and Sulfoxide-Substituted 2,3-Oxidosqualenes and Their Evaluation as Inhibitors of 2,3-Oxidosqualene-Lanosterol Cyclase
  作者：Yi Feng Zheng、Allan C. Oehlschlager、Nafsika H. Georgopapadakou、Peter G. Hartman、Petra Scheliga

  DOI：10.1021/ja00107a011

  日期：1995.1

  2,3-Oxidosqualene (23-OS) analogs that contain thioether (52-55) and sulfoxide (56-60) at positions normally occupied by carbons considered to be cationic during 2,3-oxidosqualene-lanosterol cyclase (OSC) cyclization (C-6, C-10, C-14, and C-19) were synthesized and tested as substrate mimic inhibitors of fungal and mammalian OSC. The analogs were found to be potent inhibitors of cyclase in cell-free extracts of Candida albicans and rat liver. Thioether analogs were more potent than the corresponding sulfoxides. In both series, those 2,3-OS analogs containing a sulfur at the position normally occupied by C-19 were the most potent. With C. albicans cyclase, the IC50 for thioether 55 was 0.0023 mu M while 60 exhibited an IC50 of 0.065 mu M, which are the lowest values reported for a inhibitor of this enzyme. Similarly, thioether 55 displayed an IC50 of 0.00082 mu M for rat liver cyclase which is the best inhibitor up to date for this enzyme. These results suggest that mimics with modification in the region of C-19 of 2,3-OS have a high affinity for the active site of these enzymes. The same series of analogs (52-60) were also tested for inhibition of cholesterol biosynthesis in intact MDBK (Madin Darbin bovine kidney) cells and for in vitro antifungal activity against C. albicans.
• SEN, STEPHANIE E.;WAWRZENCZYK, CZESLAW;PRESTWICH, GLENN D., J. MED. CHEM., 33,(1990) N, C. 1698-1701
  作者：SEN, STEPHANIE E.、WAWRZENCZYK, CZESLAW、PRESTWICH, GLENN D.

  DOI：——

  日期：——