hexadecenoic acid

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: hexadecenoic acid
• 英文别名: hexadec-6-enoic acid；6-Hexadecenoic acid
• 化学式: C₁₆H₃₀O₂
• 分子量: 254.413
• InChiKey: NNNVXFKZMRGJPM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.2
• 重原子数：
  18
• 可旋转键数：
  13
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.81
• 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：

  hexadecenoic acid 在 盐酸 、 4-二甲氨基吡啶 、 四氧化锇 、 N-甲基吗啉氧化物 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 二氯甲烷 、 水 、 丙酮 、 乙腈 为溶剂， 反应 16.0h， 生成
  参考文献：
  名称：

  Collimonins A–D, Unstable Polyynes with Antifungal or Pigmentation Activities from the Fungus-Feeding Bacterium Collimonas fungivorans Ter331

  摘要：

  The isolation and structure elucidation of collimonins A D (1-4) from the fungus-feeding bacterium Collimonas fungivorans Ter331 are reported. Collimonins are new derivatives of polyoxygenated hexadecanoic acid, including an ene-triyne moiety. Their absolute configurations were fully determined by combining spectroscopic, chemical, and crystalline sponge methods. Collimonins showed antifungal or pigmentation activities against the fungus Aspergillus niger ATCC 9029.

  DOI：

  10.1021/acs.orglett.8b01311
• 作为产物：
  描述：

  癸醛 、 (5-羧基戊基)三苯基溴化磷 在 sodium hexamethyldisilazane 作用下， 以 四氢呋喃 为溶剂， 反应 13.0h， 以22%的产率得到hexadecenoic acid
  参考文献：
  名称：

  Collimonins A–D, Unstable Polyynes with Antifungal or Pigmentation Activities from the Fungus-Feeding Bacterium Collimonas fungivorans Ter331

  摘要：

  The isolation and structure elucidation of collimonins A D (1-4) from the fungus-feeding bacterium Collimonas fungivorans Ter331 are reported. Collimonins are new derivatives of polyoxygenated hexadecanoic acid, including an ene-triyne moiety. Their absolute configurations were fully determined by combining spectroscopic, chemical, and crystalline sponge methods. Collimonins showed antifungal or pigmentation activities against the fungus Aspergillus niger ATCC 9029.

  DOI：

  10.1021/acs.orglett.8b01311

文献信息

• Efficient <i>N</i>-Acyldopamine Synthesis
  作者：Yotaro Matsumoto、Akihiro Ito、Motonari Uesugi、Atsushi Kittaka

  DOI：10.1248/cpb.c16-00162

  日期：——

  N-Acyldopamines are endogenous analogs of capsaicin that exhibit cannabinoid-like activities and were identified from brain extracts. Among them, N-arachidonoyldopamine (AADA) and N-oleoyldopamine (ODA) were characterized as transient receptor potential vanilloid type V1 channel (TRPV1) ligands. Recently, it was shown that N-acyldopamines may possess diverse physiological roles in addition to their ligand activities. To study the multiple functions and action mechanisms of endogenous N-acyldopamines, a simple and efficient method of N-acyldopamine synthesis was investigated. The eighteen potentially endogenous N-acyldopamines and two deuterated ones, N-palmitoyl dopamine-d5 and N-stearoyl dopamine-d5, were efficiently synthesized without protective groups in CH2Cl2 under optimized conditions using propylphosphoric acid cyclic anhydride (PPACA) as a condensation agent.

  N-Acyldopamines 是辣椒素的内源性类似物，具有类似大麻素的活性，是从脑提取物中鉴定出来的。其中，N-丙烯酰多巴胺（AADA）和 N-油酰多巴胺（ODA）被鉴定为瞬时受体电位香草素 V1 型通道（TRPV1）配体。最近的研究表明，N-乙酰多巴胺除了配体活性外，还可能具有多种生理作用。为了研究内源性 N-acyldopamines 的多种功能和作用机制，我们研究了一种简单高效的 N-acyldopamine 合成方法。在优化的条件下，以丙基磷酸环酐（PPACA）为缩合剂，在CH2Cl2中高效合成了18种潜在的内源性N-acyldopamine和两种氚化的N-棕榈酰多巴胺-d5和N-硬脂酰多巴胺-d5。
• Photobiocatalytic Decarboxylation for the Synthesis of Fatty Epoxides from Renewable Fatty Acids
  作者：Ran Ge、Pengpeng Zhang、Xuetian Dong、Yuanying Li、Zhoutong Sun、Yongyi Zeng、Bishuang Chen、Wuyuan Zhang

  DOI：10.1002/cssc.202201275

  日期：2022.10.21

  Photobiocatalysis: The synthesis of fatty epoxides from renewable fatty acids is achieved by using the photodecarboxylase from Chlorella variabilis NC64A (CvFAP) and four homologues. This work expands the known substrate specificity of the newly discovered photodecarboxylases for valorization of fatty acids in synthetic chemistry, offering a new catalytic methodology.

  光生物催化：从可再生脂肪酸合成脂肪环氧化物是通过使用来自小球藻NC64A ( Cv FAP) 的光脱羧酶和四种同系物来实现的。这项工作扩展了新发现的光脱羧酶的已知底物特异性，用于合成化学中脂肪酸的价值化，提供了一种新的催化方法。
• Collimonins A–D, Unstable Polyynes with Antifungal or Pigmentation Activities from the Fungus-Feeding Bacterium <i>Collimonas fungivorans</i> Ter331
  作者：Kenji Kai、Mai Sogame、Fumie Sakurai、Norihiro Nasu、Makoto Fujita

  DOI：10.1021/acs.orglett.8b01311

  日期：2018.6.15

  The isolation and structure elucidation of collimonins A D (1-4) from the fungus-feeding bacterium Collimonas fungivorans Ter331 are reported. Collimonins are new derivatives of polyoxygenated hexadecanoic acid, including an ene-triyne moiety. Their absolute configurations were fully determined by combining spectroscopic, chemical, and crystalline sponge methods. Collimonins showed antifungal or pigmentation activities against the fungus Aspergillus niger ATCC 9029.