软脂-(羧基-14C)酸 | 765-07-1

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 中文名称: 软脂-(羧基-14C)酸
• 英文名称: 1-(14)C-palmitic acid
• 英文别名: [14C]-Palmitic acid；<1-14C>hexadecanoic acid；[1-¹⁴C]-palmitic acid；palmitic acid (1-¹⁴C)；1-C¹⁴-palmitic acid；[1-(14)C]palmitic acid；Hexadecanoic-1-14C acid；(114C)hexadecanoic acid
• CAS: 765-07-1
• 化学式: C₁₆H₃₂O₂
• 分子量: 258.418
• InChiKey: IPCSVZSSVZVIGE-VPMSBSONSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.4
• 重原子数：
  18
• 可旋转键数：
  14
• 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

安全信息

• 危险品标志：
  F,Xi
• 安全说明：
  S16,S26,S36
• 危险类别码：
  R36/37/38
• 危险品运输编号：
  UN 2910

反应信息

• 作为反应物：
  描述：

  软脂-(羧基-14C)酸 在 D-葡萄糖-6-磷酸 、 human recombinant cytochrome 1A₂ 、 rat NADPH-P₄₅₀ reductase 、 yeast glucose 6-phosphate dehydrogenase 、 烟酰胺腺嘌呤双核苷酸磷酸盐 、 1,2-二十二酰基-sn-glycero-3-胆碱磷酸 作用下， 反应 0.33h， 生成
  参考文献：
  名称：

  Elucidation of Functions of Human Cytochrome P450 Enzymes: Identification of Endogenous Substrates in Tissue Extracts Using Metabolomic and Isotopic Labeling Approaches

  摘要：

  后基因组时代生物化学的核心问题之一是在底物未知的情况下阐明蛋白质（包括 "孤儿 "人类细胞色素 P450（P450s））的功能。本文介绍了利用代谢组学和同位素标记方法鉴定组织提取物中 P450s 内源底物的一般策略，包括四个主要步骤：(1) 在 18O2/16O2 混合物（1:1）条件下，将 P450 酶系统与辅助因子和组织提取物进行体外培养。(2) 对反应混合物的有机提取物进行液相色谱/质谱（LC/MS）分析。(3) 使用 DoGEX 程序（Sanchez-Ponce, R. 和 Guengerich, F. P. Anal. Chem. 2007, 79, 3355-3362）可直接识别以 M/M + 2 双重形式出现的同位素标记产物。(4) 对潜在候选者进行表征。以人类 P450 7A1 为初始模型，在肝脏提取物中鉴定其已知产物 7α- 羟基胆固醇，对该策略进行了验证。然后将该策略应用于人类 P450 1A2、2C8 和 2C9，利用人类肝脏提取物进行非靶向底物搜索。共鉴定并验证了七种脂肪酸是这三种肝脏 P450 的底物。随后，通过气相色谱/质谱（GC/MS）分析，确定了这些产物为脂肪酸的羟化和环氧化衍生物。最后，还进行了动力学研究，证实脂肪酸是由 P450s 1A2、2C8 和 2C9 氧化的。因此，这种策略已被证明有助于确定组织提取物中与人类孤儿 P450s 发生的反应。

  DOI：

  10.1021/ac900021a
• 作为产物：
  描述：

  溴代十五烷 在 盐酸 、 水 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 14.0h， 生成 软脂-(羧基-14C)酸
  参考文献：
  名称：

  10th international symposium on the synthesis and applications of isotopes and isotopically labelled compounds-synthesis of compounds labelled with long-lived isotopes Session 1: Monday, June 15, 2009

  摘要：

  摘要：本次会议概述了用于合成带有碳-13、碳-14或氚标记中间体的方法。其他论文描述了在合成标记化合物中利用碳-14和氚中间体的情况，这些标记化合物用于开发医药和农业制剂。版权所有 © 2010 John Wiley & Sons, Ltd.

  DOI：

  10.1002/jlcr.1762

文献信息

• Relationship between the Anchor Structure of the Galactosyl Ligand for Liposome Modification and Accumulation in the Liver.
  作者：Naokazu MURAHASHI、Atsushi SASAKI、Kunio HIGASHI、Anri MORIKAWA、Harutami YAMADA

  DOI：10.1248/bpb.18.82

  日期：——

  Liposomes which have been modified with (8-hexadecanoylamido-3, 6-dioxaoctyl)-β-D-galactose (Gal-t-pa), a straight chain palmitoyl derivative, and are composed of dipalmitoylphosphatidylcholine (DPPC), cholesterol (CH), and dicetyl phosphate (DCP) at a ratio of 10 : 10 : 1, showed the same accumulation in the liver as the control liposome. Also, liposomes which have been modified with 8-(2-hexadecyloctadecanoylamido)-3, 6-dioxaoctyl}-β-D-galactoside (Gal-t-psa) showed remarkable accumulation in the liver. The accumulation of liposomes modified with galactose derivatives in the rat liver differed markedly according to the anchor structure. To clarify the cause of this finding, we produced [3H] inulin entrapped [14C] Gal-t-pa modified double label liposomes and evaluated changes in their rat plasma concentration, distribution in the organs, and the in vitro interaction with rat plasma. [14C] Gal-t-pa on the liposome surface bound to serum albumin and was released, resulting in no accumulation in the liver. In addition, sialic acid palmitoyl derivatives and glucuronic acid palmitoyl derivatives behaved similarly. As with the galactose derivatives, they also bound to serum albumin, being released from liposomes. These results suggest that adequate attention should be paid to the anchor structure of the ligand, in order to incorporate a recognition element into liposomes for transport to cells.

  脂质体经过（8-十六烷酰基-3,6-二氧代辛基）-β-D-半乳糖（Gal-t-pa）修饰，这是一种直链棕榈酰衍生物，由二棕榈酰磷脂酰胆碱（DPPC）、胆固醇（CH）和二鲸蜡基磷酸酯（DCP）按10:10:1的比例组成，在肝脏中的积累与对照脂质体相同。此外，经过8-(2-十六烷酰基-18烷酰基氨基)-3,6-二氧代辛基}-β-D-半乳糖苷（Gal-t-psa）修饰的脂质体在肝脏中表现出显著的积累。根据锚定结构的不同，经过半乳糖衍生物修饰的脂质体在大鼠肝脏中的积累也明显不同。为了弄清这一发现的原因，我们生产了[3H]菊粉包裹的[14C] Gal-t-pa修饰的双
• Tully, Sarah E.; Cravatt, Benjamin F., Journal of the American Chemical Society, 2010, vol. 132, p. 3264 - 3265
  作者：Tully, Sarah E.、Cravatt, Benjamin F.

  DOI：——

  日期：——
• Dauben, Journal of the American Chemical Society, 1948, vol. 70, p. 1378
  作者：Dauben

  DOI：——

  日期：——
• Fatty acid-binding site environments of serum vitamin D-binding protein and albumin are different
  作者：Narasimha Swamy、Rahul Ray

  DOI：10.1016/j.bioorg.2008.02.002

  日期：2008.6

  Vitamin D-binding protein (DBP) and albumin (ALB) are abundant serum proteins and both possess high-affinity binding for saturated and unsaturated fatty acids. However, certain differences exist. We surmised that in cases where serum albumin level is low, DBP presumably can act as a transporter of fatty acids. To explore this possibility we synthesized several alkylating derivatives of 14 C-palmitic acid to probe the fatty acid-binding pockets of DBP and ALB. We observed that N-ethyl-5-phenylisooxzLzolium-3'-sulfonate-ester (WRX-ester) of C-14-palmitic acid specifically labeled DBP; but p-nitrophenyl- and N-hydroxysuccinimidyl-esters failed to do so. However, p-nitrophenyl ester of C-14-palmitic acid specifically labeled bovine ALB, indicating that the micro-environment of the fatty acid-binding domains of DBP and ALB may be different; and DBP may not replace ALB as a transporter of fatty acids. (C) 2008 Elsevier Inc. All rights reserved.
• A novel catalyst for O-acylation in lipid chemistry
  作者：Elena L. Vodovozova、Julian G. Molotkovsky

  DOI：10.1016/s0040-4039(00)73199-6

  日期：1994.3

  A new route for acylation of lysophosphatidylcholine (lysoPC) by condensation it with fatty acid/dicyclohexycarbodiimide (DCC) under catalysis of 4-hydroxypyridine (4PyOH) is described; as suggested O-acylation proceeds via formation of the activated 4PyOH-ester. This one-pot method does not need fatty acid excess it is especially suitable for the small-scale syntheses of phosphatidylcholines (PC) with precious or labile (e.g. photoaffine) fatty acid residues.