16-aminohexadecanoic acid | 17437-22-8

• 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-aminohexadecanoic acid
• CAS: 17437-22-8
• 化学式: C₁₆H₃₃NO₂
• 分子量: 271.444
• InChiKey: QJGFZBNNVXTCLL-UHFFFAOYSA-N

物化性质

• 沸点：
  407.0±18.0 °C(Predicted)
• 密度：
  0.932±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 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：
  63.3
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  16-aminohexadecanoic acid 在 亚磷酸 、 三氯化磷 、 水 作用下， 以 甲烷磺酸 为溶剂， 反应 48.0h， 以78%的产率得到(16-amino-1-hydroxyhexadecylidene)bisphosphonic acid
  参考文献：
  名称：

  Systematic Study of the Physicochemical Properties of a Homologous Series of Aminobisphosphonates

  摘要：

  氨基双膦酸盐，例如阿仑膦酸和尼瑞膦酸，是一类广为人知的分子，作为各种骨病的药物使用。尽管这些分子已存在数十年，但对它们在可比条件下最重要的物理化学特性的详细理解仍然缺乏。在这项研究中，合成了十种氨基双膦酸盐，H2N(CH2)nC(OH)[P(O)(OH)2]2，其中n=2-5、7-11和15。测定了它们在不同温度和pH下的水溶性、酸解离常数(pKa值)、热稳定性、红外吸收以及液态（1H、13C、31P-NMR）和固态（13C、15N和31P-CPMAS NMR）的核磁共振光谱数据。

  DOI：

  10.3390/molecules170910928
• 作为产物：
  描述：

  cyclohexadecanone oxime 在 吡啶 、 盐酸 、 potassium carbonate 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 、 水 为溶剂， 反应 20.0h， 生成 16-aminohexadecanoic acid
  参考文献：
  名称：

  Dansyl-labeled anionic amphiphile with a hexadecanoic carbon chain: Synthesis and detection for shape transitions in organized molecular assemblies

  摘要：

  The probing properties of a new fluorophore-labeled anionic surfactant, sodium 16-(N-dansyl)aminocetylate (16-DAN-ACA) were investigated systematically in molecular assemblies, especially in the transitions between micelles and vesicles. 16-DAN-ACA can efficiently differentiate the two different aggregate types in mixed cationic and anionic surfactant systems. The fluorescence anisotropy of 16-DAN-ACA was found to be sensitive for directly detecting the micellar growth in micelles containing oppositely charged surfactants; both cationic cetyltrimethylammonium bromide (CTAB) systems and anionic sodium dodecyl sulfate (SDS) systems were studied. The results indicated that the 16-DAN-ACA is a good fluorescent probe for differentiating the different aggregates, and even more can be used to detect the micellar growth. (C) 2014 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.saa.2014.11.113

文献信息

• METHOD FOR THE SYNTHESIS OF AN OMEGA-AMINO ACID OR ESTER STARTING FROM A MONOUNSATURATED FATTY ACID OR ESTER
  申请人：Dubois Jean-Luc

  公开号：US20110224454A1

  公开（公告）日：2011-09-15

  The invention relates to a method for the synthesis of ω-amino alkanoic acids or esters thereof starting from unsaturated natural fatty acids passing through an ω-unsaturated nitrile intermediate compound.

  该发明涉及一种从非饱和天然脂肪酸开始，通过一种ω-非饱和腈中间化合物来合成ω-氨基烷酸或其酯的方法。
• METHOD FOR SYNTHESIZING AN OMEGA-AMINO ACID OR ESTER FROM A MONOUNSATURATED FATTY ACID OR ESTER
  申请人：Couturier Jean-Luc

  公开号：US20140187808A1

  公开（公告）日：2014-07-03

  A method for synthesizing ω-amino-alkanoic acids or the esters thereof from natural unsaturated fatty acids passing through an intermediate ω-unsaturated nitrile compound. The method is simple to implement and, relative to known methods, avoids the environmental constraints and economic disadvantages resulting from the reaction by-products. The method includes synthesizing an ω-amino acid (ester) of formula R3OOC—(CH2) q —CH2NH2, in which R3 is H or an n-butyl radical and q is an integral index of between 2 and 13, from a monounsaturated fatty acid (ester) of formula (R1-CH═CH—(CH2)p-COO) xR2, in which x represents 1, 2 or 3, R1 is H or a hydrocarbon radical comprising from 4 to 11 carbon atoms and, where appropriate, a hydroxyl function, R2 is H or an alkyl radical comprising from 2 to 4 carbon atoms, and may contain one or more heteroatoms, and p is an integral index of between 2 and 11, including a reaction step of ammoniation.

  一种从天然不饱和脂肪酸通过中间体ω-不饱和腈化合物合成ω-氨基-烷酸或其酯的方法。该方法实施简单，与已知方法相比，避免了由反应副产物导致的环境限制和经济劣势。该方法包括从公式为(R1-CH═CH—(CH2)p-COO)xR2的单不饱和脂肪酸(酯)合成公式为R3OOC—(CH2)q—CH2NH2的ω-氨基酸(酯)，其中R3是H或n-丁基基团，q是2到13之间的整数指数，x代表1、2或3，R1是H或含4到11个碳原子的烃基团，适当情况下还含有羟基，R2是H或含2到4个碳原子的烷基基团，可包含一个或多个杂原子，p是2到11之间的整数指数，包括氨化反应步骤。
• [EN] INSULIN-INCRETIN CONJUGATES<br/>[FR] CONJUGUÉS D'INSULINE-INCRÉTINE
  申请人：MERCK SHARP & DOHME

  公开号：WO2017160669A1

  公开（公告）日：2017-09-21

  Insulin-incretin conjugates comprising a peptide having agonist activity at the glucagon-like 1 (GLP-1) receptor, the glucagon (GCG) receptor, and/or the gastric inhibitory protein (GIP) receptor conjugated to an insulin molecule having agonist activity at the insulin receptor and use of the conjugates for treatment of metabolic diseases, for example, Type 2 diabetes, are described.

  胰岛素-胰高血糖素共轭物包括具有在胰高血糖素样1（GLP-1）受体、胰高血糖素（GCG）受体和/或胃抑制性蛋白（GIP）受体上激动剂活性的肽与具有在胰岛素受体上激动剂活性的胰岛素分子结合，以及利用这些共轭物治疗代谢性疾病，例如2型糖尿病。
• [EN] INSULIN DIMER-INCRETIN CONJUGATES<br/>[FR] CONJUGUÉS DIMÈRES D'INSULINE-INCRÉTINE
  申请人：MERCK SHARP & DOHME

  公开号：WO2017189342A1

  公开（公告）日：2017-11-02

  Insulin dimers conjugated to peptides having at least one incretin activity are disclosed.

  已披露将胰岛素二聚体与至少具有一种胰岛素增效活性的肽共轭化。
• Parallel anti-sense two-step cascade for alcohol amination leading to ω-amino fatty acids and α,ω-diamines
  作者：Sihyong Sung、Hyunwoo Jeon、Sharad Sarak、Md Murshidul Ahsan、Mahesh D. Patil、Wolfgang Kroutil、Byung-Gee Kim、Hyungdon Yun

  DOI：10.1039/c8gc02122h

  日期：——

  Running two two-step cascades in parallel anti-sense to transform an alcohol to an amine allowed the conversion of ω-hydroxy fatty acids (ω-HFAs) and α,ω-diols to the corresponding ω-amino fatty acids (ω-AmFAs) and α,ω-diamines, respectively. The network required only two enzymes namely an aldehyde reductase (AHR) and a transaminase (TA). Benzylamine served on the one hand as amine donor and on the

  将两个两步式级联反应平行进行反义以将醇转化为胺，可将ω-羟基脂肪酸（ω-HFA）和α，ω-二醇转化为相应的ω-氨基酸脂肪酸（ω-AmFAs） ）和α，ω-二胺。该网络仅需要两种酶，即醛还原酶（AHR）和转氨酶（TA）。苄胺一方面用作胺供体，另一方面在脱氨基后生成苯甲醛也用作氧化剂。使用纯化的酶以及全细胞系统将所有测试的ω-HFA有效地转化为其相应的ω-AmFA，分别表达两种酶，转化率在80-95％之间。另外，单细胞共表达所有酶均成功产生了ω-AmFA和α，ω-二胺，产率> 90％。