(3R,4S,5R)-3-dihydro-4,5-dihydroxy-3-tetradecylfuran-2(3H)-one | 211050-23-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酯类
• 英文名称: (3R,4S,5R)-3-dihydro-4,5-dihydroxy-3-tetradecylfuran-2(3H)-one
• 英文别名: (2S,3S,4S)-3-hydroxy-4-methyl-2-tetradecyl-4-butanolide；(2R,3S,4S)-3-hydroxy-4-methyl-2-tetradecyl-butanolide；(3R,4S,5S)-4-hydroxy-5-methyl-3-tetradecyloxolan-2-one
• CAS: 211050-23-6
• 化学式: C₁₉H₃₆O₃
• 分子量: 312.493
• InChiKey: BEEKFGLUGMQFSX-RCCFBDPRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.1
• 重原子数：
  22
• 可旋转键数：
  13
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.95
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (3R,4S,5R)-3-dihydro-4,5-dihydroxy-3-tetradecylfuran-2(3H)-one 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 苯 为溶剂， 以41%的产率得到(3S,4S,5S)-3-tetradecyl-4-hydroxy-5-methyldihydro-2(3H)-furanone
  参考文献：
  名称：

  Asymmetric synthesis of (−)-epi-blastmycinone and (2R,3S,4S)-3-hydroxy-4-methyl-2-(1′-n-tetradecyl)-butanolide via a tungsten-mediated cyclization reaction

  摘要：

  Enantiocontrolled syntheses of the natural lactones 1 and 2 were achieved based on a tungsten-mediated cyclization. The whole syntheses comprise of six or seven steps from readily available 1-trimethylsilyl-pent-1-yne; the overall yields are 25 and 28% for 1 and 2, respectively. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(01)00189-7
• 作为产物：
  描述：

  (E)-trimethyl(pent-3-en-1-yn-1-yl)silane 在 palladium on activated charcoal 盐酸 、 AD-mix-α 、 copper(l) iodide 、 cyclopentadienylW(carbonyl)3 、 甲基磺酰胺 、 氢气 、 N,N-二异丙基乙胺 作用下， 以 甲醇 、 二乙胺 、 苯 为溶剂， 生成 (3R,4S,5R)-3-dihydro-4,5-dihydroxy-3-tetradecylfuran-2(3H)-one
  参考文献：
  名称：

  Asymmetric synthesis of (−)-epi-blastmycinone and (2R,3S,4S)-3-hydroxy-4-methyl-2-(1′-n-tetradecyl)-butanolide via a tungsten-mediated cyclization reaction

  摘要：

  Enantiocontrolled syntheses of the natural lactones 1 and 2 were achieved based on a tungsten-mediated cyclization. The whole syntheses comprise of six or seven steps from readily available 1-trimethylsilyl-pent-1-yne; the overall yields are 25 and 28% for 1 and 2, respectively. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(01)00189-7

文献信息

• Marliolide inhibits skin carcinogenesis by activating NRF2/ARE to induce heme oxygenase-1
  作者：June Lee、Karabasappa Mailar、Ok-Kyung Yoo、Won Jun Choi、Young-Sam Keum

  DOI：10.1016/j.ejmech.2018.02.068

  日期：2018.4

  catalyzes the enzymatic degradation of heme to produce three anti-oxidant molecules: carbon monoxide (CO), ferrous ion (Fe2+), and biliverdin. Induction of HO-1 is currently considered as a feasible strategy to treat oxidative stress-related diseases. In the present study, we identified marliolide as a novel inducer of HO-1 in human normal keratinocyte HaCaT cells. Mechanism-based studies demonstrated

  血红素加氧酶-1（HO-1）催化血红素的酶促降解，产生三种抗氧化剂分子：一氧化碳（CO），亚铁离子（Fe 2+）和biliverdin。HO-1的诱导目前被认为是治疗氧化应激相关疾病的可行策略。在本研究中，我们确定了马里利利德是人正常角质形成细胞HaCaT细胞中HO-1的新型诱导剂。基于机理的研究表明，马里内酯对HO-1的诱导是通过马里内利德与KEAP1的直接结合，通过激活NRF2 / ARE来实现的。构效关系揭示了对HO-1的诱导至关重要的马里里利德的化学部分，这为迈克尔反应作为一种潜在的作用机理提供了支持。最后，我们观察到马里立内酯在DMBA / TPA诱导的小鼠皮肤癌变模型中显着抑制了乳头状瘤的形成，并且该事件与体内降低8-OH-G和4-HNE的形成密切相关。在一起，我们的研究提供了第一个证据，证明马里利内酯可能有效治疗与氧化应激相关的皮肤疾病。
• 신규한 마리올라이드 유도체 및 이를 함유하는 만성 염증성 질환의 예방 또는 치료용 조성물
  申请人：Dongguk University Industry-Academic Cooperation Foundation 동국대학교 산학협력단(220060081783) BRN ▼201-82-04468

  公开号：KR101890058B1

  公开（公告）日：2018-08-21

  본 발명의 화학식 1로 표시되는 마리올라이드 유도체 또는 이의 약학적으로 허용가능함 염, 및 이를 유효성분으로 함유하는 만성 염증성 질환의 예방 또는 치료용 조성물에 관한 것이다. 본 발명의 화학식 1로 표시되는 마리올라이드 유도체는 Nrf2의 활성화를 통해 HO-1(heme oxygenase-1)의 발현을 증가시켜 염증성 사이토카인 및 각종 염증 인자의 발현을 억제함으로써, 만성 염증성 질환의 치료제나 건강기능식품 첨가물로서 용이하게 이용될 수 있다.

  这是关于含有化学式1的马里奥莱德衍生物或其在药学上可接受的盐，并将其作为有效成分含有的用于预防或治疗慢性炎症性疾病的组合物的发明。含有化学式1的马里奥莱德衍生物通过激活Nrf2来增加HO-1（血红素氧化酶-1）的表达，从而抑制炎性细胞因子和各种炎症因子的表达，因此可以作为慢性炎症性疾病的治疗药物或保健食品添加剂方便地使用。
• Stereoselective synthesis of (2R,3S,4S)-3-hydroxy-4-methyl-2-tetradecyl-4-butanolide starting from 2,5-anhydro-d-mannitol
  作者：Shunya Takahashi、Narihito Ogawa、Nobuo Sakairi、Tadashi Nakata

  DOI：10.1016/j.tet.2005.04.059

  日期：2005.7

  A novel approach to natural beta-hydroxy-gamma-lactone 2 from 2,5-anhydro-D-mannitol (1) is described. The key reactions in this synthesis include stereoselective methylation of aldehyde 3 with lithium dimethylcuprate, an intramolecular radical cyclization of seleno carbonate 11 and an intermolecular cross-metathes is of 3-allyl-4-hydroxy-gamma-lactone 16 with 1-tridecene. (c) 2005 Elsevier Ltd. All rights reserved.
• Asymmetric synthesis of (−)-epi-blastmycinone and (2R,3S,4S)-3-hydroxy-4-methyl-2-(1′-n-tetradecyl)-butanolide via a tungsten-mediated cyclization reaction
  作者：Bo Liu、Ming-Jung Chen、Ching-Yu Lo、Rai-Shung Liu

  DOI：10.1016/s0040-4039(01)00189-7

  日期：2001.3

  Enantiocontrolled syntheses of the natural lactones 1 and 2 were achieved based on a tungsten-mediated cyclization. The whole syntheses comprise of six or seven steps from readily available 1-trimethylsilyl-pent-1-yne; the overall yields are 25 and 28% for 1 and 2, respectively. (C) 2001 Elsevier Science Ltd. All rights reserved.