甘氨酸正辛酯.盐酸盐 | 39540-30-2

• 物质功能分类: 有机原料 - 氨基化合物 - 无环单胺、多胺及其衍生物和盐
• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 中文名称: 甘氨酸正辛酯.盐酸盐
• 中文别名: 甘氨酸n-辛酯盐酸盐；氨基乙酸正辛酯盐酸盐；甘氨酸正辛酯
• 英文名称: glycine octyl ester hydrochloride
• 英文别名: (2-Octoxy-2-oxoethyl)azanium;chloride；(2-octoxy-2-oxoethyl)azanium;chloride
• CAS: 39540-30-2
• 化学式: C₁₀H₂₁NO₂*ClH
• 分子量: 223.743
• InChiKey: OORFEZYGSYLFCL-UHFFFAOYSA-N

物化性质

• 熔点：
  66-72°C
• 稳定性/保质期：
  常规情况下不会分解，也没有危险反应。

计算性质

• 辛醇/水分配系数(LogP)：
  2.27
• 重原子数：
  14
• 可旋转键数：
  9
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  52.3
• 氢给体数：
  2
• 氢受体数：
  3

安全信息

• 安全说明：
  S26,S36/37/39
• 危险类别码：
  R36/37/38
• 海关编码：
  2922499990
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335
• 储存条件：
  密封、阴凉、干燥处保存。

制备方法与用途

应用

氨基乙酸正辛酯盐酸盐可用作医药中间体，在实验室研发和化工医药合成过程中有广泛应用。

制备

将100克工业氨基乙酸、400毫升正辛醇及11克对甲基苯磺酸加入三口烧瓶中，连接分水器、冷凝管和搅拌器。加热并梯度升温，待没食子酸完全溶解后，在105℃下反应直至无水生成（约需4小时）。之后进行中和处理、洗涤、低温冷却结晶、真空抽滤，得到白色针状的氨基乙酸正辛酯粗品；再经过精制、重结晶和真空干燥，最终获得81.2克含量为99.3%的氨基乙酸正辛酯成品。最后通过加入盐酸，即可得到所需的氨基乙酸正辛酯盐酸盐。

反应信息

• 作为反应物：
  描述：

  甘氨酸正辛酯.盐酸盐 、 足球烯 在 sodium nitrite 作用下， 以 甲苯 为溶剂， 反应 48.0h， 以51%的产率得到
  参考文献：
  名称：

  Are the pyrazolines formed from the reaction of [60]fullerene with alkyl diazoacetates unstable?

  摘要：

  [60]Fullerene-fused pyrazolines I were prepared by the reaction Of C-60 with alky diazoacetates under the solid-state high-speed vibration milling conditions as well as in toluene solution. Pyrazolines 1 were stable in refluxing toluene and its thermolysis process in 1,2-dichlorobenzeiie was investigated, the decomposition rates and activation energies of pyrazolines I were obtained. The current work demonstrated that the liquid-phase reaction of C-60 with alkyl diazoacetates undergoes via 1,3-dipolar cycloaddition pathway at room temperature, or proceeds via carbene mechanism at a temperature of refluxing toluene, thus clarifies the previous ambiguity of its reaction mechanism. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2004.02.074
• 作为产物：
  描述：

  glycine octyl ester 在 盐酸 作用下， 反应 1.0h， 以80%的产率得到甘氨酸正辛酯.盐酸盐
  参考文献：
  名称：

  氨基酸酯盐酸盐及其制备方法与应用

  摘要：

  本发明公开氨基酸酯盐酸盐及其制备方法与应用，将氨基酸、醇、对甲苯磺酸加入到甲苯中，130～140℃回流反应4h，反应液用质量百分比浓度为5%的NaOH溶液萃取3次，有机层使用无水硫酸钠干燥过夜，蒸去溶剂，以石油醚:异丙醇体积比为5～6:1混合的混合液为洗脱剂进行柱层析，得无色液体氨基酸酯；在氨基酸酯中通入干燥的氯化氢气体1～1.5h，得到氨基酸酯盐酸盐；氨基酸酯盐酸盐作为促渗剂在经皮给药系统使用效果好，氨基酸酯盐酸盐促进药物的透皮吸收，使角质细胞的流动性增强，有效增加药物的透皮量，本发明药物经皮促渗剂可有效改善药物的溶解性，提高药物吸收率，并提高治疗效果，具有广阔的应用前景。

  公开号：

  CN110305030B

文献信息

• Synthesis and bactericidal activity of amino acid higher ester hydrochlorides
  作者：V. E. Limanov、I. R. Svitova、T. B. Kruchenok、I. M. Tsvirova、L. A. Yaroslavskaya

  DOI：10.1007/bf00773019

  日期：1984.10

  been described by the reaction of cesium salts of amino acids with higher alkyl halides [14]. Instead of hydrogen chloride, it was proposed to use strong cation exchangers [ii], and also chlorosulfonic acid [8] as catalysts. It was found that amino acid higher ester hydrochlorides can also be obtained by treating a suspension of an amino acid in alcohol with thionyl chloride, phosphorus trichloride

  目前工作的目的是在阳离子SAA中寻找有效的微毒杀菌剂。为了研究，我们选择了氨基酸的高级酯的盐酸盐。我们假设这些化合物对温血动物的毒性比其他阳离子 SAA 低，因为合成它们的原料氨基酸比用于制备烷基胺盐和相应季铵化合物的胺毒性小得多。我们已经证明这些化合物具有抗微生物活性，尤其是对于 γ 阳性微生物 [2, 4]。根据[3, 5]的数据，作为杀菌剂，最令人感兴趣的是缬氨酸、β-丙氨酸、B-氨基丁酸和赖氨酸的月桂酸酯的盐酸盐。它们的制备方法非常不完善。已经描述了通过氨基酸盐酸盐与高级醇反应合成氨基酸酯盐酸盐。结果表明，直接酯化只能得到甘氨酸高级酯盐酸盐，并提出通过氨基酸低级酯盐酸盐与高级醇的酯交换反应制备其他氨基酸的衍生物[12]。这些化合物 I 的合成方法已通过氨基酸的铯盐与高级烷基卤化物的反应进行了描述 [14]。建议使用强阳离子交换剂 [ii] 和氯磺酸 [8] 作为催化剂，而不是氯化氢
• [EN] TRANSDERMAL PENETRATION ENHANCERS<br/>[FR] ACTIVATEURS DE PENETRATION TRANSDERMIQUE
  申请人：UNIV KARLOVA

  公开号：WO2004074235A1

  公开（公告）日：2004-09-02

  The invention provides compounds based on ceramide analogues of the general the general formula (I), wherein R1= H or CH2OH; R2 = C8 to C16 alkyl; R3 = C7 to C15 alkyl, cis-heptadec-8­-en-1-yl, CH(R1)NHCOR4, CH=CHCOOR4 or CH(OH)CH(OH)COOR4; R4 = C7 to C16 alkyl. The compounds of the general formula (I) are used as transdermal penetration enhancers. Pharmaceutical and cosmetic compositions, containing ceramide analogues of the general formula (I) in the amount from 0.1 to 5.0 w/w percent, preferably in the amount from 0.1 to 1.0 w/w percent.

  该发明提供了一种基于泛用式(I)的神经酰胺类似物的化合物，其中R1= H或CH2OH；R2 = C8到C16烷基；R3 = C7到C15烷基、顺式-庚十七烯-8-基、CH(R1)NHCOR4、CH=CHCOOR4或CH(OH)CH(OH)COOR4；R4 = C7到C16烷基。泛用式(I)的化合物被用作经皮渗透增强剂。含有泛用式(I)的神经酰胺类似物的药用和化妆品组合物，其含量从0.1%到5.0%重量/重量百分比，最好在0.1%到1.0%重量/重量百分比。
• Novel Reactions of [60]Fullerene with Amino Acid Esters and Carbon Disulfide
  作者：Guan-Wu Wang、Jia-Xing Li、Yu-Jin Li、You-Cheng Liu

  DOI：10.1021/jo052116p

  日期：2006.1.1

  Novel reactions of C60 with amino acid ester hydrochlorides and CS2 in the presence of Et3N affording fullerene derivatives 2 and 3 containing biologically active amino acids, thioamide, and thiourea units have been investigated. The thioamide groups in compounds 2 are sensitive to moisture and can easily be hydrolyzed to amide groups.

  已经研究了在Et 3 N存在下C 60与氨基酸酯盐酸盐和CS 2的新反应，得到了具有生物活性氨基酸，硫酰胺和硫脲单元的富勒烯衍生物2和3。化合物2中的硫酰胺​​基对湿气敏感并且可以容易地水解为酰胺基。
• Novel skin permeation enhancers based on amino acid ester ionic liquid: Design and permeation mechanism
  作者：Luyao Zheng、Zhiyuan Zhao、Ye Yang、Yaming Li、Chengxiao Wang

  DOI：10.1016/j.ijpharm.2020.119031

  日期：2020.2

  based on amino acids. We first screened 15 methyl amino acid ester hydrochlorides ([AAC1]Cl) for their skin permeation enhancements using 5-Fluorouracil (5-Fu) and Hydrocortisone (HC) as model drugs. Glycine methyl ester hydrochloride ([GlyC1]Cl), L-proline methyl ester hydrochloride ([L-ProC1]Cl), and L-leucine methyl ester hydrochloride ([L-LeuC1]Cl) were selected, and their ester sites were modified

  这项研究开发了基于氨基酸的新型离子液体（ILs）。我们首先使用5-氟尿嘧啶（5-Fu）和氢化可的松（HC）作为模型药物，筛选了15种甲基氨基酸酯盐酸盐（[AAC1] Cl）的皮肤渗透增强作用。选择甘氨酸甲酯盐酸盐（[GlyC1] Cl），L-脯氨酸甲酯盐酸盐（[L-ProC1] Cl）和L-亮氨酸甲酯盐酸盐（[L-LeuC1] Cl），并对它们的酯位进行修饰具有不同的碳链（C8和C12）。所得的IL显示出对两种药物的改善的渗透。TEWL和CLSM分析显示修饰的IL对皮肤屏障功能的调节作用，而L-脯氨酸十二烷基酯盐酸盐（[ProC12] Cl）和L-亮氨酸十二烷基酯盐酸盐（[L-LeuC12] Cl）表现出最强的活性。通过ATR-FTIR，固体NMR，SEM和TEM分析进一步研究了渗透机理。结果表明，[L-ProC12] Cl和[L-LeuC12] Cl结合了氨基酸酯和IL溶剂的优势，并通过
• Synthetic ceramide analogues as skin permeation enhancers: structure–Activity relationships
  作者：Kateřina Vávrová、Alexandr Hrabálek、Pavel Doležal、Lucie Šámalová、Karel Palát、Jarmila Zbytovská、Tomáš Holas、Jana Klimentová

  DOI：10.1016/j.bmc.2003.09.034

  日期：2003.12

  The study presents new information about the structure-activity relationships of the skin permeation enhancers. A series of ceramide analogues including eight different polar head groups and six different chain lengths was synthesised. The compounds were evaluated as permeation enhancers in vitro using porcine skin. The physico-chemical parameters of the tested compounds obtained by computer modelling were used to evaluate, by multiple linear regression, the enhancement ratios (ERs) of the compounds. The regression analysis suggests that the hydrogen bonding ability of the compounds is inversely related to the ER values and that the molecular size and lipophilicity must be well balanced. In the studied enhancers having the same chain length, the enhancement activity is dependent only on their permeability coefficients. This finding confirms the Warner's hypothesis that the polar head of an enhancer is responsible for the permeation and anchoring of the molecule into the stratum corneum lipids and that it does not influence the mechanism of action. For the specific action of enhancers, that is disordering of the intercellular lipid packing, the length of the hydrophobic chain(s) and not the lipophilicity is important. Furthermore, the examination of the FTIR spectra indicated that the most active substances possess the most ordered chains. The described relationships could bring more rational approaches in designing new potent enhancers for transdermal formulations. (C) 2003 Elsevier Ltd. All rights reserved.