C14 二氢神经酰胺 | 61389-70-6

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 鞘脂
• 中文名称: C14 二氢神经酰胺
• 中文别名: C14二氢神经酰胺
• 英文名称: (2S,3R)-2-tetradecanoylaminooctadecane-1,3-diol
• 英文别名: (2S,3R)-2-(N-tetradecanoylamino)-1,3-octadecanediol；N-myristoyl-D-erythro-sphinganine；N-((1S,2R)-2-hydroxy-1-hydroxymethyl-heptadecyl)-myristamide；N-((1S,2R)-2-Hydroxy-1-hydroxymethyl-heptadecyl)-myristamid；D-erythro-2-Myristoylamino-octadecan-1,3-diol；(2S,3R)-2-tetradecanoylaminooctadecan-1,3-diol；N-(tetradecanoyl)-sphinganine；N-[(2S,3R)-1,3-dihydroxyoctadecan-2-yl]tetradecanamide
• CAS: 61389-70-6
• 化学式: C₃₂H₆₅NO₃
• 分子量: 511.873
• InChiKey: UDTSZXVRDXQARY-IOWSJCHKSA-N

物化性质

• 熔点：
  96-100°C
• 沸点：
  656.1±45.0 °C(Predicted)
• 密度：
  0.916±0.06 g/cm3(Predicted)
• 溶解度：
  可溶于氯仿（少许）、甲醇（少许）
• 物理描述：
  Solid

计算性质

• 辛醇/水分配系数(LogP)：
  12.3
• 重原子数：
  36
• 可旋转键数：
  29
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.97
• 拓扑面积：
  69.6
• 氢给体数：
  3
• 氢受体数：
  3

安全信息

• WGK Germany：
  3
• 储存条件：
  -20°C

反应信息

• 作为反应物：
  描述：

  C14 二氢神经酰胺 在 palladium on barium sulfate 氢气 、 silver perchlorate 、 tin(ll) chloride 作用下， 以 四氢呋喃 为溶剂， 生成 (2S,3R)-1-(β-L-arabinopyranosyloxy)-2-tetradecanoylamino-3-octadecanol
  参考文献：
  名称：

  Immunostimulatory and Antitumor Activities of Monoglycosylceramides Having Various Sugar Moieties.

  摘要：

  合成了十种单糖基神经酰胺（MonoCers），它们具有相同的神经酰胺部分和不同的糖基部分，并研究了它们的免疫刺激和抗肿瘤活性。糖与神经酰胺的结合方式已被证明会影响MonoCers的免疫刺激及其相应的抗肿瘤活性的表现。对于含有D-糖的D-MonoCers，α-D-MonoCers（糖以α-构型与神经酰胺结合）显示出比β-D-MonoCers更强的活性。此外，糖的形式，不是呋喃糖形式而是吡喃糖形式，以及吡喃糖形式的糖的2''和4''-羟基，似乎在α-D-MonoCers的活性表现中起着重要作用。

  DOI：

  10.1248/bpb.18.1487
• 作为产物：
  描述：

  溴代十四烷 在 palladium on activated charcoal 吡啶 、 正丁基锂 、 甲酸 、 sodium azide 、 三正丁胺 、 2-氯-1-甲基吡啶碘化物 、 氢气 作用下， 以 四氢呋喃 、 丙醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 82.0h， 生成 C14 二氢神经酰胺
  参考文献：
  名称：

  Structure-Activity Relationship of .alpha.-Galactosylceramides against B16-Bearing Mice

  摘要：

  Agelasphin-9b, (2S,3S,4R)-1-O-(alpha-D-galactopyranosyl)-16-methyl-2-[N-((R)-2-hydroxytetracosanoyl)-amino]-1,3,4-heptadecanetriol, is a potent antitumor agent isolated from the marine sponge Agelas mauritianus. Various analogues of agelasphin-9b (a lead compound) were synthesized, and the relationship between their structures and biological activities was examined using several assay systems. From the results, KRN7000, (2S,3S;4R)-1-O-(alpha-D-galactopyranosyl)2-(N-hexacosanoylamino)-1,3,4-octadecanetriol, was selected as a candidate for clinical application.

  DOI：

  10.1021/jm00012a018

文献信息

• Protection of <i>C. elegans</i> from Anoxia by HYL-2 Ceramide Synthase
  作者：Vincent Menuz、Kate S. Howell、Sébastien Gentina、Sharon Epstein、Isabelle Riezman、Monique Fornallaz-Mulhauser、Michael O. Hengartner、Marie Gomez、Howard Riezman、Jean-Claude Martinou

  DOI：10.1126/science.1168532

  日期：2009.4.17

  Oxygen deprivation is rapidly deleterious for most organisms. However, Caenorhabditis elegans has developed the ability to survive anoxia for at least 48 hours. Mutations in the DAF-2/DAF-16 insulin-like signaling pathway promote such survival. We describe a pathway involving the HYL-2 ceramide synthase that acts independently of DAF-2. Loss of the ceramide synthase gene hyl-2 results in increased sensitivity of C. elegans to anoxia. C. elegans has two ceramide synthases, hyl-1 and hyl-2 , that participate in ceramide biogenesis and affect its ability to survive anoxic conditions. In contrast to hyl-2(lf) mutants, hyl-1(lf) mutants are more resistant to anoxia than normal animals. HYL-1 and HYL-2 have complementary specificities for fatty acyl chains. These data indicate that specific ceramides produced by HYL-2 confer resistance to anoxia.

  缺氧对大多数生物来说是迅速有害的。然而，秀丽隐杆线虫已经发展出至少48小时的无氧生存能力。DAF-2 / DAF-16胰岛素样信号通路的突变促进了这种生存。我们描述了涉及独立于DAF-2的HYL-2鞘磷脂合成酶的一条途径。鞘磷脂合成酶基因hyl-2的缺失导致秀丽隐杆线虫对缺氧的敏感性增加。秀丽隐杆线虫有两种鞘磷脂合成酶hyl-1和hyl-2，它们参与鞘磷脂的生物合成并影响其在无氧条件下的生存能力。与hyl-2（lf）突变体相比，hyl-1（lf）突变体比正常动物更能抵抗缺氧。HYL-1和HYL-2对脂肪酸基团具有互补的特异性。这些数据表明，由HYL-2产生的特定鞘磷脂使其对缺氧具有抗性。
• Mammalian Lass6 and its related family members regulate synthesis of specific ceramides
  作者：Yukiko Mizutani、Akio Kihara、Yasuyuki Igarashi

  DOI：10.1042/bj20050291

  日期：2005.8.15

  The Lass (longevity-assurance homologue) family members, which are highly conserved among eukaryotes, function in ceramide synthesis. In the mouse, there are at least five Lass family members, Lass1, Lass2, Lass4, Lass5 and the hitherto uncharacterized Lass6. To investigate specific roles for each Lass member in ceramide synthesis, we cloned these five mouse proteins. Overproduction of any Lass protein in cultured cells resulted in an increase in cellular ceramide, but the ceramide species produced varied. Overproduction of Lass1 increased C18:0-ceramide levels preferentially, and overproduction of Lass2 and Lass4 increased levels of longer ceramides such as C22:0- and C24:0-ceramides. Lass5 and Lass6 produced shorter ceramide species (C14:0- and C16:0-ceramides); however, their substrate preferences towards saturated/unsaturated fatty acyl-CoA differed. In addition to differences in substrate preferences, we also demonstrated by Northern blotting that Lass family members are differentially expressed among tissues. Additionally, we found that Lass proteins differ with regard to glycosylation. Of the five members, only Lass2, Lass5 and Lass6 were N-glycosylated, each at their N-terminal Asn residue. The occurrence of N-glycosylation of some Lass proteins provides topological insight, indicating that the N-termini of Lass family members probably face the luminal side of the endoplasmic reticulum membrane. Furthermore, based on a proteinase K digestion assay, we demonstrated that the C-terminus of Lass6 faces the cytosolic side of the membrane. From these data we propose topology for the conserved Lag1 motif in Lass family members, namely that the N-terminal region faces the luminal side and the C-terminal region the cytosolic side of the endoplasmic reticulum membrane.

  Lass（长寿保证同源物）家族成员在真核生物中高度保守，在神经酰胺合成中发挥作用。在小鼠体内，至少有五个 Lass 家族成员，即 Lass1、Lass2、Lass4、Lass5 和迄今尚未定性的 Lass6。为了研究每个 Lass 成员在神经酰胺合成中的特定作用，我们克隆了这五种小鼠蛋白。在培养细胞中过度生产任何一种 Lass 蛋白都会导致细胞神经酰胺的增加，但产生的神经酰胺种类各不相同。过量生产 Lass1 会优先增加 C18:0 神经酰胺的含量，而过量生产 Lass2 和 Lass4 则会增加较长神经酰胺的含量，如 C22:0 和 C24:0 神经酰胺。Lass5 和 Lass6 产生较短的神经酰胺种类（C14:0- 和 C16:0-神经酰胺）；但是，它们对饱和/不饱和脂肪酰基-CoA 的底物偏好不同。除了底物偏好的差异，我们还通过 Northern 印迹技术证明了 Lass 家族成员在不同组织中的表达差异。此外，我们还发现 Lass 蛋白在糖基化方面存在差异。在五个成员中，只有 Lass2、Lass5 和 Lass6 在其 N 端 Asn 残基上进行了 N-糖基化。一些 Lass 蛋白发生 N-糖基化提供了拓扑学上的启示，表明 Lass 家族成员的 N 端可能面向内质网膜的腔侧。此外，基于蛋白酶 K 消化试验，我们证明 Lass6 的 C 端面向膜的细胞质一侧。根据这些数据，我们提出了 Lass 家族成员中保守的 Lag1 基序的拓扑结构，即 N 端区域面向内质网膜的腔侧，C 端区域面向内质网膜的细胞质侧。
• Clear aqueous ceramide composition
  申请人：Takasago International Corporation

  公开号：EP1153595A2

  公开（公告）日：2001-11-14

  Provided is a clear aqueous ceramide composition comprising 1.0 to 5.0% by weight, based on the total composition, of a ceramide represented by formula (I): wherein R1 represents a hydrocarbon group having 9 to 17 carbon atoms; and R2 represents an acyl group having 2 to 30 carbon atoms which can contain a hydroxyl group, a long-chain fatty acid having 12 to 24 carbon atoms, a nonionic surface active agent, and water. The clear aqueous composition is useful as cosmetics, bath agents, hair-careproducts, external preparations for the skin, skin protective preparations, particularly medical external preparations for the treatment or protection of the skin, or a component making up these preparations.

  本发明提供了一种透明的含水神经酰胺组合物，该组合物含有按重量计为 1.0 至 5.0%的由式(I)代表的神经酰胺： 其中 R1 代表具有 9 至 17 个碳原子的烃基；R2 代表具有 2 至 30 个碳原子的酰基，该酰基可含有羟基、 具有 12 至 24 个碳原子的长链脂肪酸、非离子表面活性剂和水。这种透明的水性组合物可用作化妆品、沐浴剂、护发产品、皮肤外用制剂、皮肤保护制剂，特别是用于治疗或保护皮肤的医用外用制剂，或这些制剂的组成部分。
• Lipid composition containing a liquid crystal structure
  申请人：Takasago International Corporation

  公开号：EP1166769A1

  公开（公告）日：2002-01-02

  This invention relates to a novel lipid composition for use in cosmetics capable of increasing moisture-keeping ability or barrier function of the stratum corneum, protecting the skin and improving dry or rough skin, and to products which use the same, such as cosmetics and medicaments. Particularly, it relates to a lipid composition which comprises at least one component (A) selected from the group consisting of a 2-acylaminoalkane-1,3-diol and optically active compounds thereof, at least one component (B) selected from the group consisting of a 2-acylaminoalkane-1,3-diol in which at least one of the α-position and β-position of the acyl group is substituted with hydroxyl group and optically active compounds thereof and at least one component (C) selected from sterols, wherein the components (A), (B) and (C) are mixed at a ratio that constructs a liquid crystal structure, and to products which contain the lipid composition, such as cosmetics and medicaments.

  本发明涉及一种用于化妆品的新型脂质组合物，该组合物能够提高角质层的保湿能力或屏障功能，保护皮肤，改善干燥或粗糙的皮肤，还涉及使用该组合物的产品，如化妆品和药品。特别是，本发明涉及一种脂质组合物，它包括至少一种选自 2-酰氨基烷-1,3-二醇及其光学活性化合物组的组分（A）、至少一种选自 2-酰氨基烷-1、其中至少一个酰基的 α 位和β 位被羟基取代的 2-酰氨基烷-1,3-二醇及其光学活性化合物，以及至少一种选自甾醇的组分（C），其中组分（A）、（B）和（C）按一定比例混合可形成液晶结构。
• Fragrance retaining composition and use
  申请人：Takasago International Corporation

  公开号：EP1254651A1

  公开（公告）日：2002-11-06

  There is provided a fragrance-retaining composition comprising: an ingredient (A) composed of 2-acylaminoalkan-1,3-diols and/or optically active forms thereof represented by the formula I: in which R1 signifies a straight-chain alkyl group having 9 to 17 carbon atoms, and R2 signifies a straight-chain acyl group having 14 to 24 carbon atoms and of 2-acylaminoalkan-1,3-diols and/or optically active forms thereof represented by the formula II:    in which R1 signifies a straight-chain alkyl group having 9 to 17 carbon atoms, and R3 signifies an acetyl group or a straight-chain acyl group having 2 to 24 carbon atoms with a hydroxy group at α- or β-position; and an ingredient (B) consisting of sterol-based compounds.

  本发明提供了一种留香组合物，该组合物包括：由 2-酰基氨基烷-1,3-二醇和/或其光学活性形式组成的成分（A），由式 I.表示，其中 R1 表示具有 9 至 17 个碳原子的直链烷基，R2 表示具有 14 至 24 个碳原子的直链酰基： 其中 R1 表示具有 9 至 17 个碳原子的直链烷基，R2 表示具有 14 至 24 个碳原子的直链酰基，以及由式 II： 其中 R1 表示具有 9 至 17 个碳原子的直链烷基，R3 表示乙酰基或具有 2 至 24 个碳原子的直链酰基，在 α 或 β 位上带有羟基；以及由甾醇类化合物组成的成分 (B)。