棕榈酸-13C16 | 56599-85-0

• 物质功能分类: 分析化学 - 食品安全 - 脂肪酸、脂肪酸甲酯
• 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: 棕榈酸-13C16
• 中文别名: 棕榈酸13C16
• 英文名称: [U-¹³C]palmitic acid
• 英文别名: ¹³C16-palmitic acid；palmitic-¹³C₁₆ acid；palmitic acid-¹³C₁₆；palmitic acid；(13)C-palmitic acid；Palmitic acid-13C16；(1,2,3,4,5,6,7,8,9,10,11,12,13,14,15,16-13C16)hexadecanoic acid
• CAS: 56599-85-0
• 化学式: C₁₆H₃₂O₂
• 分子量: 272.253
• InChiKey: IPCSVZSSVZVIGE-BZDICNBSSA-N

物化性质

• 熔点：
  61-64 °C
• 沸点：
  271.5 °C/100 mmHg(lit.)
• 密度：
  0.904 g/mL at 25 °C
• 闪点：
  206℃
• 溶解度：
  可溶于氯仿（少许）、乙酸乙酯（少许）、甲醇（少许）

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：
  Xi
• 安全说明：
  S26,S37/39
• 危险类别码：
  R36,R36/37/38
• WGK Germany：
  3
• 危险标志：
  GHS07
• 危险性描述：
  H319
• 危险性防范说明：
  P305 + P351 + P338

反应信息

• 作为反应物：
  描述：

  棕榈酸-13C16 在 4-二甲氨基吡啶 、 lithium hydroxide monohydrate 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 为溶剂， 反应 60.0h， 生成 16:1/¹³C₁₆-PAHSA/16:0-TG
  参考文献：
  名称：

  Discovery of FAHFA-Containing Triacylglycerols and Their Metabolic Regulation

  摘要：

  FAHFAs are a class of bioactive lipids, which show great promise for treating diabetes and inflammatory diseases. Deciphering the metabolic pathways that regulate endogenous FAHFA levels is critical for developing diagnostic and therapeutic strategies. However, it remains unclear how FAHFAs are metabolized in cells or tissues. Here, we investigate whether FAHFAs can be incorporated into other lipid classes and identify a novel class of endogenous lipids, FAHFA-containing triacylglycerols (FAHFA-TGs), which contain a FAHFA group esterified to the glycerol backbone. Isotope-labeled FAHFAs are incorporated into FAHFA-TGs when added to differentiated adipocytes, which implies the existence of enzymes and metabolic pathways capable of synthesizing these lipids. Induction of lipolysis (i.e., triacylglycerol hydrolysis) in adipocytes is associated with marked increases in nonesterified FAHFA levels, demonstrating that FAHFA-TGs breakdown is a regulator of cellular FAHFA levels. To quantify FAHFA levels in FAHFA-TGs and determine their regioisomeric distributions, we developed a mild alkaline hydrolysis method that liberates FAHFAs from triacylglycerols for easier detection. FAHFA-TG concentrations are greater than 100-fold than that of nonesterified FAHFAs, indicating that FAHFA-TGs are a major reservoir of FAHFAs in cells and tissues. The discovery of FAHFA-TGs reveals a new branch of TG and FAHFA metabolism with potential roles in metabolic health and regulation of inflammation.

  DOI：

  10.1021/jacs.9b00045
• 作为产物：
  描述：

  [1,2-¹³C]acetyl-CoA 、 [(13)C4]malonyl-CoA 在 乙二胺四乙酸 、 recombinant rat fatty acid synthase 、 还原型辅酶Ⅰ 、 1,4-二巯基-2,3-丁二醇 作用下， 生成 棕榈酸-13C16
  参考文献：
  名称：

  Mammalian fatty acid synthase activity from crude tissue lysates tracing 13C-labeled substrates using gas chromatography–mass spectrometry

  摘要：

  Fatty acid synthase (FASN or FAS, EC 2.3.1.85) is the sole mammalian enzyme to synthesize fatty acids de novo from acetyl- and malonyl-coenzyme A (CoA) esters: This article describes a new method that directly quantifies uniformly labeled C-13(16)-labeled palmitate ([C-13(16)]palmitate) by tracing [C-13(2)]acetyl-CoA and [C-13(3)]malonyl-CoA using an in vitro FASN assay. This method used gas chromatography-mass spectrometry (GC-MS) to detect [C-13(16)]palmitate carboxylate anions (m/z 271) of pentafluorobenzyl (PFB) derivatives and was highly sensitive at femtomole quantities. Uniformly incorporated [C-13(16)]palmitate was the primary product of both recombinant and crude tissue lysate FASN. Quantification of FASN protein within crude tissue lysates ensured equal FASN amounts, preserved steady-state kinetics, and enabled calculation of FASN-specific activity. FASN activity determined by [C-13(16)]palmitate synthesis was consistent with values obtained from p-nicotinamide adenine dinucleotide 2'-phosphate (NADPH) oxidation assays. Analysis of FASN activity from tissue extracts was not hampered by contaminating enzymes or preexisting fatty acids. Crude mammary gland and liver lysates had significantly different activities at 82 and 65 nmol min(-1) mg(-1), respectively, suggesting that tissue-specific activity levels differ in a manner unrelated to FASN amount. GC-MS quantification of [C-13(16)]palmitate synthesis permits sensitive evaluation of FASN activity from tissues of varied physiological states and of purified FASN activity in the presence of modifying proteins, enzymes, or drugs. (C) 2012 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.ab.2012.06.013

文献信息

• Maternal obesity results in decreased syncytiotrophoblast synthesis of palmitoleic acid, a fatty acid with anti‐inflammatory and insulin‐sensitizing properties
  作者：Véronique Ferchaud‐Roucher、Kelsey Barner、Thomas Jansson、Theresa L. Powell

  DOI：10.1096/fj.201802444r

  日期：2019.5

  Decreased syncytiotrophoblast POA synthesis may contribute to insulin resistance and low‐grade inflammation in the mother, placenta, or fetus (or a combination of the 3) in pregnancies complicated by obesity.—Ferchaud‐Roucher, V., Barner, K., Jansson, T., Powell, T. L. Maternal obesity results in decreased syncytiotrophoblast synthesis of palmitoleic acid, a fatty acid with anti‐inflammatory and insulin‐sensitizing

  胎儿依赖于合体滋养层（人类胎盘的运输上皮细胞）输送脂肪酸（FA）。肥胖孕妇有血脂异常；然而，肥胖是否影响胎盘脂质转运和代谢仍有待完全确定。棕榈油酸 (POA) 是一种具有抗炎和胰岛素增敏特性的 FA，由硬脂酰辅酶 A 去饱和酶 (SCD) 活性催化的棕榈酸 (PA) 合成。我们假设从妊娠合并肥胖症的孕妇中分离出的原代人滋养层细胞 (PHT) 中 FA 的摄取和掺入以及 POA 的合成减少。从 7 名肥胖 [体重指数 (BMI) = 37.5 ± 1.9] 和 12 名正常 (BMI = 23.6 ± 0.6) 母亲的胎盘中分离出绒毛细胞滋养层。使用统一标记的 (U[13C])-PA、油酸 (OA)、亚油酸和二十二碳六烯酸的 FA 混合物评估 FA 的吸收和掺入。通过 GC-MS 对细胞总脂质和脂质类别中的细胞 [13C] FA 进行定量。与正常母亲相比，从肥胖母亲分离的 PHT 中 [13C]
• Synthesis of Lysophosphatidylcholine and Mixed Phosphatidylcholine
  作者：Athanasios Papangelis、Trond Ulven

  DOI：10.1021/acs.joc.2c00335

  日期：2022.6.17

  Lysophosphatidylcholine (LPC) and phosphatidylcholine (PC) are important membrane constituents implicated in signaling and immune regulation. Synthesis of LPCs is challenging due to rapid acyl migration, e.g., induced by chromatography. We here report a highly regioselective synthesis of LPC and mixed PC via an intermediate allowing specific terminal acyl introduction, yielding the pure LPC without

  溶血磷脂酰胆碱 (LPC) 和磷脂酰胆碱 (PC) 是参与信号传导和免疫调节的重要膜成分。由于快速的酰基迁移，例如由色谱法诱导，LPC 的合成具有挑战性。我们在这里报告了 LPC 和混合 PC 的高度区域选择性合成，通过中间体允许特定的末端酰基引入，通过非常温和的 TBS 脱保护产生纯 LPC，无需色谱，使用 1 equiv 的 TFA 在水溶液中。该方法能够合成甘油、酰基和胆碱标记的 LPC。
• US9673030B2
  申请人：——

  公开号：US9673030B2

  公开（公告）日：2017-06-06