12-bromostearic acid | 116971-44-9

• 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: 12-bromostearic acid
• 英文别名: 12-Bromo-octadecanoic acid；12-bromooctadecanoic acid
• CAS: 116971-44-9
• 化学式: C₁₈H₃₅BrO₂
• 分子量: 363.379
• InChiKey: OOXDKNSCVLIEIN-UHFFFAOYSA-N

物化性质

• 沸点：
  444.8±18.0 °C(Predicted)
• 密度：
  1.088±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  8
• 重原子数：
  21
• 可旋转键数：
  16
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.94
• 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：

  12-bromostearic acid 在 tetrabutylammonium (2-pyrrolidonide) 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 以77%的产率得到12-羟基硬脂酸内酯
  参考文献：
  名称：

  Electroorganic chemistry. 91. A novel base useful for synthesis of esters and macrolides

  摘要：

  DOI：

  10.1021/jo00354a030
• 作为产物：
  描述：

  12-羟基硬脂酸 在 咪唑 、 四溴化碳 、 三苯基膦 作用下， 以 二氯甲烷 为溶剂， 反应 21.0h， 以71%的产率得到12-bromostearic acid
  参考文献：
  名称：

  通过扫描 X 射线荧光显微镜对细胞内脂肪酸进行成像

  摘要：

  脂肪酸被细胞吸收并结合到复杂的脂质中，例如中性脂质和甘油磷脂。甘油磷脂是细胞膜的主要成分。超过 1000 种甘油磷脂分子的极性头基和脂肪酸组成各不相同。它们与细胞功能和疾病有关，并已通过质谱法进行了很好的分析。然而，由于使用传统方法的分辨率不足，脂肪酸和甘油磷脂的细胞内成像并未成功。在这里，我们开发了一种用溴 (Br) 标记脂肪酸的方法，并应用扫描 X 射线荧光显微镜 (SXFM) 获得亚微米分辨率的细胞内 Br 映射数据。质谱表明，细胞吸收 Br 标记的脂肪酸并将其主要代谢为 CHO 细胞中的甘油磷脂。SXFM 观察到的大多数 Br 信号位于核周区域。更高的分辨率揭示了 Br 在细胞质中的点状分布。目前的方法使细胞内溴标记脂肪酸的成功可视化。单元素标记结合 SXFM 技术促进了脂肪酸的细胞内成像，这为在单细胞水平上确定脂肪酸及其衍生物的动态变化提供了一种新工具。 -A., Kita, Y

  DOI：

  10.1096/fj.201600569r

文献信息

• Synthesis of novel disulfide containing macrocyclic diacylglycerols
  作者：Sangita Ghosh、Kalpathy R.K Easwaran、Santanu Bhattacharya

  DOI：10.1016/0040-4039(96)01181-1

  日期：1996.8

  New diacylglycerols (2–4) containing intramolecular disulfide linkagas between pendant acyl chains were synthesized. Due to the differences in the location of disulfide units, the present method allows synthesis of macrocyles that vary in sizes.

  合成了新的在酰基侧链之间包含分子内二硫键的二酰基甘油（2-4）。由于二硫键单元位置的不同，本方法允许合成大小变化的大环。
• Synthesis of Macrocyclic Diacyl/Dialkyl Glycerols Containing Disulfide Tether and Studies of Their Effects upon Incorporation in DPPC Membranes. Implications in the Design of Phospholipase A₂ Modulators
  作者：Santanu Bhattacharya、Sangita Ghosh、Kalpathy R. K. Easwaran

  DOI：10.1021/jo980866b

  日期：1998.12.1

  A general method for the preparation of novel disulfide-tethered macrocyclic diacylglycerols (DAGs) has been described. Overall synthesis involved stepwise protection, acylation, and deprotection to yield the bis(omega-bromoacyl) glycerols. In the crucial macrocyclization step, a unique reagent, benzyltriethylammonium tetrathiomolybdate (BTAT), has been used to convert individual bis(omega-bromoacyl) glycerols to their respective macrocyclic disulfides. DAG 6, which had ether linkages between hydrocarbon chains and the glycerol backbone, was also synthesized from an appropriate precursor using a similar protocol. One of the DAGs (DAG 5) had a carbon-carbon tether instead of a disulfide one and was synthesized using modified Glaser coupling. Preparation of alpha-disulfide-tethered DAG (DAG 4) required an alternative method, as treatment of the bisbromo precursor with BTAT gave a mixture of several compounds from which separation of the target molecule was cumbersome. To avoid this problem, the bisbromide was converted to its corresponding dithiocyanate, which on further treatment with BTAT yielded the desired DAG (DAG 4) in good yield. Upon treatment with the reducing agent dithiothreitol (DTT), the DAGs that contain a disulfide tether could be quantitatively converted to their "open-chain" thiol analogues. These macrocyclic DAGs and their reduced "open-chain" analogues have been incorporated in DPPC vesicles to study their effect on model membranes. Upon incorporation of DAG 1 in DPPC vesicles, formation of new isotropic phases was observed by P-31 NMR, These isotropic phases disappeared completely on opening the macrocyclic ring by a reducing agent. The thermotropic properties of DPPC bilayers having DAGs (1-6) incorporated at various concentrations were studied by differential scanning calorimetry. Incorporation of DAGs in general reduced the cooperativity unit (CU) of the vesicles. Similar experiments with reduced "open-chain" DAGs incorporated in a DPPC bilayer indicated a recovery of CU with respect to their macrocyclic "disulfide" counterparts. The effect of inclusion of these DAGs on the activity of phospholipase A(2) (PLA(2)) was studied in vitro. Incorporation of DAC 1 in DPPC membranes potentiated both bee venom and cobra venom PLA(2) activities.
• Granata, Alessandro; Sauriol, Francoise; Perlin, Arthur S., Canadian Journal of Chemistry, 1994, vol. 72, # 7, p. 1684 - 1690
  作者：Granata, Alessandro、Sauriol, Francoise、Perlin, Arthur S.

  DOI：——

  日期：——
• Granata Alessandro, Sauriol Francoise, Perlin Arthur S., Can. J. Chem, 72 (1994) N 7, S 1684-1690
  作者：Granata Alessandro, Sauriol Francoise, Perlin Arthur S.

  DOI：——

  日期：——
• COMPOSITIONS AND RELATED METHODS FOR AGRICULTURE
  申请人：Flagship Pioneering Innovations V, Inc.

  公开号：US20210289794A1

  公开（公告）日：2021-09-23

  The invention comprises methods for decreasing colonization by a bacterium of a gut of a stink bug, the method comprising providing a composition comprising vanillin or an analog thereof; and delivering said composition to an egg from which the stink bug will hatch, whereby colonization by the bacterium within the gut of the stink bug hatched from the egg treated with the composition is decreased relative to a stink bug hatched from an untreated egg. In some embodiments, the decrease in colonization by the bacterium decreases the fitness of the stink bug, e.g., decreases reproductive ability, survival, rate of development, number of eggs, number of hatched eggs, adult emergence rate, body length, body width, body mass, or cuticle thickness. In some embodiments of the methods herein, the bacterial colonization-disrupting agent is an inhibitor of bacterial metabolism. In some embodiments, the bacterial colonization-disrupting agent is a polyhydroxyalkanoate (PHA) synthesis inhibitor.