N-油酰基-D-赤型-鞘氨醇 | 34227-83-3

• 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: N-油酰基-D-赤型-鞘氨醇
• 英文名称: dihydroceramide d18:0/18:1(9Z)
• 英文别名: dihydroceramide (d18:0/18:1)；Cer(d18:0/18:1(9Z))；N-((1S,2R)-2-hydroxy-1-hydroxymethyl-heptadecyl)-oleamide；N-((1S,2R)-2-Hydroxy-1-hydroxymethyl-heptadecyl)-oleamid；D-erythro-2-Oleoylamino-octadecan-1,3-diol；(2S,3R)-2-oleoylaminooctadecane-1,3-diol；N-(9Z-octadecenoyl)-sphinganine；(Z)-N-[(2S,3R)-1,3-dihydroxyoctadecan-2-yl]octadec-9-enamide
• CAS: 34227-83-3
• 化学式: C₃₆H₇₁NO₃
• 分子量: 565.965
• InChiKey: MJQIARGPQMNBGT-WWUCIAQXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  13.5
• 重原子数：
  40
• 可旋转键数：
  32
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  69.6
• 氢给体数：
  3
• 氢受体数：
  3

安全信息

• 储存条件：
  -20°C

反应信息

• 作为反应物：
  描述：

  水 、 N-油酰基-D-赤型-鞘氨醇 生成 oleate 、 Sphinganine(1+)
  参考文献：
  名称：

  Alkaline Ceramidase 3 (ACER3) Hydrolyzes Unsaturated Long-chain Ceramides, and Its Down-regulation Inhibits Both Cell Proliferation and Apoptosis

  摘要：

  Ceramides with different fatty acyl chains may vary in their physiological or pathological roles; however, it remains unclear how cellular levels of individual ceramide species are regulated. Here, we demonstrate that our previously cloned human alkaline ceramidase 3 (ACER3) specifically controls the hydrolysis of ceramides carrying unsaturated long acyl chains, unsaturated long-chain (ULC) ceramides. In vitro, ACER3 only hydrolyzed C-18:1-, C-20:1-, C-20:4-ceramides, dihydroceramides, and phytoceramides. In cells, ACER3 overexpression decreased C-18:1- and C-20:1-ceramides and dihydroceramides, whereas ACER3 knockdown by RNA interference had the opposite effect, suggesting that ACER3 controls the catabolism of ULC ceramides and dihydroceramides. ACER3 knockdown inhibited cell proliferation and up-regulated the cyclin-dependent kinase inhibitor p21(CIP1/WAF1). Blocking p21(CIP1/WAF1) up-regulation attenuated the inhibitory effect of ACER3 knockdown on cell proliferation, suggesting that ACER3 knockdown inhibits cell proliferation because of p21(CIP1/WAF1) up-regulation. ACER3 knockdown inhibited cell apoptosis in response to serum deprivation. ACER3 knockdown up-regulated the expression of the alkaline ceramidase 2 (ACER2), and the ACER2 up-regulation decreased non-ULC ceramide species while increasing both sphingosine and its phosphate. Collectively, these data suggest that ACER3 catalyzes the hydrolysis of ULC ceramides and dihydroceramides and that ACER3 coordinates with ACER2 to regulate cell proliferation and survival.

  DOI：

  10.1074/jbc.m109.063586
• 作为产物：
  描述：

  生成 N-油酰基-D-赤型-鞘氨醇
  参考文献：
  名称：

  Journal of the American Chemical Society 2002, 124, 1856-1857

  摘要：

  DOI：

文献信息

• PROCESS FOR PREPARING SPHINGOLIPIDS
  申请人：Evonik Degussa GmbH

  公开号：US20190300917A1

  公开（公告）日：2019-10-03

  The invention provides a process for preparing sphingolipids, compositions comprising sphingolipids and further components, and for the use of the compositions.

  这项发明提供了一种制备鞘脂类物质的过程，包括鞘脂类物质和其他成分的组合物，并用于这些组合物的用途。
• 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。
• Humectant Composition
  申请人：Takasago International Corporation

  公开号：EP1946743A2

  公开（公告）日：2008-07-23

  The present invention relates to a humectant composition containing, as component (A), at least one member selected from a menthol derivative represented by the following formula (1) and p-menthane-3,8-diol: in which R is an alkylene group having 2 to 5 carbon atoms which may be substituted with at least one member selected from the group consisting of a methyl group and a hydroxyl group, and n is an integer of 1 to 3. The humectant composition of the present invention provides an excellent moisture-retention effect.

  本发明涉及一种保湿剂组合物，其中含有至少一种选自下式（1）所代表的薄荷醇衍生物和对薄荷-3,8-二醇的成分（A）： 本发明的保湿剂组合物具有优异的保湿效果。
• Lipid composition and skin care formulation containing the same
  申请人：Ishida Kenya

  公开号：US20060210522A1

  公开（公告）日：2006-09-21

  Bioavailability of a ceramide, which is a minimally soluble material of a skin care composition exhibiting an excellent effect is enhanced by combining at least one component selected from ceramides represented by Formula (1): and at least one component selected from aliphatic alcohol having 12 to 30 carbon atoms.

  将至少一种选自由式（1）表示的神经酰胺的成分与至少一种选自具有 12 至 30 个碳原子的脂肪醇的成分结合，可提高神经酰胺的生物利用率，神经酰胺是护肤组合物中具有优异功效的微溶性材料： 和至少一种选自具有 12 至 30 个碳原子的脂肪醇的成分。