16-iodohexadecanoic acid | 2536-36-9

• 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: 16-iodohexadecanoic acid
• CAS: 2536-36-9
• 化学式: C₁₆H₃₁IO₂
• 分子量: 382.325
• InChiKey: RNTWMPKPEATMJA-UHFFFAOYSA-N

物化性质

• 熔点：
  76 °C
• 沸点：
  438.4±18.0 °C(Predicted)
• 密度：
  1.249±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  7.1
• 重原子数：
  19
• 可旋转键数：
  15
• 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：

  16-iodohexadecanoic acid 在 六甲基磷酰三胺 、 硫酸 、 水 、 chloroamine-T 、 sodium iodide 、 儿萘酚硼烷 作用下， 反应 37.5h， 生成 (E)-18-Iodo-octadec-17-enoic acid methyl ester
  参考文献：
  名称：

  Synthesis and evaluation of radioiodinated (E)-18-iodo-17-octadecenoic acid as a model iodoalkenyl fatty acid for myocardial imaging

  摘要：

  125I-labeled (E)-18-iodo-17-octadecenoic acid (13) has been prepared and evaluated in rats to determine the myocardial uptake and retention and degree of in vivo deiodination of this model iodovinyl-substituted fatty acid, which contains no structural perturbation to inhibit metabolism. This new agent was prepared by NaI-chloramine-T treatment of (17-carbomethoxyheptadec-1-en-1-yl)boronic acid (11) prepared by catecholborane treatment of methyl 17-octadecynoate (10), followed by basic hydrolysis to the free acid (13). The pivotal substrate, 17-octadecynoic acid (9), was prepared by two new routes. The 125I-labeled acid 13 showed high myocardial uptake (1 h, 1.90-2.28% dose/g) with 45% washout after 2 h but lower heart/blood ratios in comparison to analogues containing the tellurium heteroatom. Deiodination was low for the first 2 h after injection (2 h, 61% dose/g). Excellent myocardial images were obtained in a dog with the 123I-labeled agent.

  DOI：

  10.1021/jm00367a021
• 作为产物：
  描述：

  8-溴辛酸 在 platinum(IV) oxide lithium amide 、 氢气 、 ferric nitrate 、 sodium iodide 作用下， 以 四氢呋喃 、 吡啶 、 乙醚 、 氨 、 丙酮 为溶剂， 反应 22.0h， 生成 16-iodohexadecanoic acid
  参考文献：
  名称：

  Riche, Francoise; Mathieu, Jean-Paul; Vincens, Maurice, Bulletin de la Societe Chimique de France, 1984, vol. 2, # 1-2, p. 49 - 55

  摘要：

  DOI：

文献信息

• Identification of very long chain unsaturated fatty acids from Ximenia oil by atmospheric pressure chemical ionization liquid chromatography–mass spectroscopy
  作者：Tomáš Řezanka、Karel Sigler

  DOI：10.1016/j.phytochem.2006.11.034

  日期：2007.3

  A method is described for the enrichment of very long chain unsaturated fatty acids from total fatty acids of Ximenia oil and their identification as picolinyl esters by means of liquid chromatography-mass spectrometry with atmospheric pressure chemical ionization (LC-MS/APCI). The method is based on the use of preparative reversed phase HPLC and their subsequent identification by microbore LC-MS/APCI

  描述了一种从西梅尼亚油总脂肪酸中富集极长链不饱和脂肪酸的方法，并通过液相色谱-质谱联用常压化学电离 (LC-MS/APCI) 将其鉴定为吡啶甲基酯。该方法基于使用制备型反相 HPLC 及其随后通过微孔 LC-MS/APCI 进行的鉴定。这两种技术的组合被用来识别不寻常的不饱和 VLCFAs，最高可达 tetracontenoic 酸。还合成了四十三碳烯酸的所有四种位置异构体以明确确认它们的结构。
• Synthesis and evaluation of radioiodinated terminal-substituted 5-iodo-(2-thienyl) fatty acids as new myocardial imaging agents
  作者：Mark M. Goodman、Gilbert Kirsch、Furn F. Knapp

  DOI：10.1002/jhet.5570210602

  日期：1984.11

  order to evaluate the stability of radioiodide attached to the 5 position of thiophenes substituted at the 2-position with tissue-specific groups as new radiopharmaceuticals, two [125I]iodothienyl-substituted long-chain fatty acids have been prepared and evaluated in rats. Radioiodide was introduced into the 5 position of 17-(2-thienyi)heptadecanoic acid and 13-(2-thienyl)tridecanoic acid by K-125I

  为了评估附着在2位被组织特异性基团取代的噻吩5位上的放射性碘的稳定性，作为新的放射性药物，已经制备了两种[ 125 I]碘代噻吩基取代的长链脂肪酸，并在大鼠中进行了评估。 。通过对其相应的5- [双-（三氟乙酰氧基）] th衍生物进行K- 125I处理，将放射性碘化物引入17-（2-噻吩基）十七烷酸和13-（2-噻吩基）十三烷酸的5位。用17- [5- [ 125 I]碘（2-噻吩基）]十七烷酸在大鼠中进行的组织分布研究显示，心脏摄取明显增加，滞留时间延长，并伴有体内除碘和中度血液水平。将心脏对17种碳脂肪酸的摄取与13种碳类似物13- [5- [5- [ 135 I]碘（2-噻吩基）]十三烷酸的摄入量进行比较，表明心肌对17种碳脂肪酸的摄取比13碳类似物。这些结果表明，在长链脂肪酸的末端位置取代的5-碘噻吩基部分不干扰心肌摄取，并且这种化合物可能作为一类新的心肌显像剂有价值。
• Regio- and Chemoselective One-Step 3-O-Alkylenation of Unprotected Ascorbic Acid Using ω-Iodoalkanols
  作者：Bang Luu、Thierry Muller、Paul Heuschling

  DOI：10.1055/s-0028-1087662

  日期：——

  A regio- and chemoselective alkylenation employing unprotected ascorbic acid and a series of unprotected iodoalkanols in the presence of sodium hydrogen carbonate in dimethyl sulfoxide is described. This atom economic high yielding procedure delivers the corresponding 3-O-alkylene ethers in a single step without prior protection. Specific 3-O-etherification was also observed with ­unprotected 16-iodohexadecanoic acid and with 2-(10-iododecyl)isoindole-1,3-dione. Furthermore, an 2-O-alkylene derivative was obtained when 3-O-benzyl ascorbic acid was reacted with unprotected 10-iododecanol under slightly modified conditions. Finally, the antioxidative activity of all compounds was determined and compared to vitamin C and E.

  描述了一种使用未保护的抗坏血酸和一系列未保护的碘烷醇，在碳酸氢钠存在下于二甲基亚砜中进行的区域和化学选择性烷基化。这种原子经济、高产率的程序在无需事先保护的情况下，单步合成了相应的3-O-烷基醚。同时，未保护的16-碘十六酸和2-(10-碘十烷基)异吲哚-1,3-二酮也观察到了特定的3-O-醚化。此外，当3-O-苄基抗坏血酸与未保护的10-碘癸醇在稍微修改的条件下反应时，获得了一个2-O-烷基衍生物。最后，所有化合物的抗氧化活性被测定并与维生素C和E进行了比较。
• [EN] CT CONTRAST AGENT FOR DETECTION OF CACHEXIA<br/>[FR] AGENT DE CONTRASTE CT POUR LA DÉTECTION DE LA CACHEXIE
  申请人：UNIV GENEVE

  公开号：WO2020165349A1

  公开（公告）日：2020-08-20

  The invention relates to an iodinated CT contrast agent for non-invasive diagnosis of cachexia. This is possible by superior resolution of CT combined with CT contrast agent specific for the brown and/or beige adipose tissue (BAT).

  该发明涉及一种碘化的CT造影剂，用于无创诊断消瘦症。这是通过CT的优越分辨率结合专门用于棕色和/或米色脂肪组织（BAT）的CT造影剂实现的。
• [EN] NANOEMULSION OF IODINATED FATTY ACIDS FOR CT IMAGING<br/>[FR] NANOÉMULSION D'ACIDES GRAS IODÉS POUR IMAGERIE PAR TOMOGRAPHIE ASSISTÉE PAR ORDINATEUR (CT)
  申请人：UNIV GENEVE

  公开号：WO2019030024A1

  公开（公告）日：2019-02-14

  The invention relates to an iodinated CT contrast agent made of fatty acid derivatives for noninvasive visualisation and quantification of the brown and/or beige adipose tissue (BAT) or for imaging the heart and/or liver of a subject. Advantageously, this contrast agent is to be taken orally which is a breakthrough in CT imaging. Image resolution by CT is significantly enhanced compared to PET.

  该发明涉及一种由脂肪酸衍生物制成的碘化物CT造影剂，用于无创可视化和量化褐色和/或米色脂肪组织（BAT），或者用于成像受试者的心脏和/或肝脏。优点是，这种造影剂可口服摄入，这是CT成像的一项突破。与PET相比，CT的图像分辨率显著提高。