N-硬脂酰神经鞘氨醇 | 2304-81-6

• 物质功能分类: 化学试剂 - 有机试剂 - 脂肪醇
• 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-硬脂酰神经鞘氨醇
• 中文别名: (2R,3R,4E)-硬脂酰鞘氨醇
• 英文名称: (2S,3R,4E)-2-(N-stearoylamino)-4-octadecene-1,3-diol
• 英文别名: N-stearoyl-D-erythro-sphingosine；N-((2S,3R,E)-1,3-dihydroxyoctadec-4-en-2-yl)stearamide；C₁₈ceramide；cer(d18:1/18:0)；ceramide C18:0；N-[(E,2S,3R)-1,3-dihydroxyoctadec-4-en-2-yl]octadecanamide
• CAS: 2304-81-6
• 化学式: C₃₆H₇₁NO₃
• 分子量: 565.965
• InChiKey: VODZWWMEJITOND-NXCSZAMKSA-N

物化性质

• 熔点：
  99-101 °C
• 比旋光度：
  [α]D20 -2～-5゜ (c=0.5, CHCl3)
• 沸点：
  630.97°C (rough estimate)
• 密度：
  0.9512 (rough estimate)
• 溶解度：
  氯仿（微溶、加热、超声处理）、甲醇（微溶）
• 物理描述：
  Solid
• 碰撞截面：
  256.4 Ų [M+Na]+ [CCS Type: DT, Method: single field calibrated with Agilent tune mix (Agilent)]
• 稳定性/保质期：
  在常温常压下保持稳定。

计算性质

• 辛醇/水分配系数(LogP)：
  13.9
• 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

• 安全说明：
  S24/25
• WGK Germany：
  3
• 海关编码：
  29225000
• 储存条件：
  冷藏应储存在阴凉、干燥的地方，并存放在密闭容器中。建议在-20°C下保存。

SDS

Name:	N-Stearoyl-D-erythro-spinghosine synthetical 99+% Material Safety Data Sheet
Synonym:	Ceramide C1
CAS:	2304-81-6

Section 1 - Chemical Product MSDS Name:N-Stearoyl-D-erythro-spinghosine synthetical 99+% Material Safety Data Sheet
Synonym:Ceramide C1

---

Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
2304-81-6	N-Stearoyl-D-erythro-spinghosine, synt	99+%	unlisted

Hazard Symbols: None Listed.
Risk Phrases: None Listed.

---

Section 3 - HAZARDS IDENTIFICATION
EMERGENCY OVERVIEW
Not available.
Potential Health Effects
Eye:
May cause eye irritation.
Skin:
May cause skin irritation.
Ingestion:
May cause irritation of the digestive tract. The toxicological properties of this substance have not been fully investigated.
Inhalation:
May cause respiratory tract irritation.
Chronic:
Not available.

---

Section 4 - FIRST AID MEASURES
Eyes: Flush eyes with plenty of water for at least 15 minutes, occasionally lifting the upper and lower eyelids. Get medical aid.
Skin:
Get medical aid. Flush skin with plenty of water for at least 15 minutes while removing contaminated clothing and shoes.
Ingestion:
Get medical aid. Wash mouth out with water.
Inhalation:
Remove from exposure and move to fresh air immediately. If not breathing, give artificial respiration. If breathing is difficult, give oxygen. Get medical aid.
Notes to Physician:

---

Section 5 - FIRE FIGHTING MEASURES
General Information:
As in any fire, wear a self-contained breathing apparatus in pressure-demand, MSHA/NIOSH (approved or equivalent), and full protective gear.
Extinguishing Media:
Use extinguishing media most appropriate for the surrounding fire.

---

Section 6 - ACCIDENTAL RELEASE MEASURES
General Information: Use proper personal protective equipment as indicated in Section 8.
Spills/Leaks:
Vacuum or sweep up material and place into a suitable disposal container.

---

Section 7 - HANDLING and STORAGE
Handling:
Avoid breathing dust, vapor, mist, or gas. Avoid contact with skin and eyes.
Storage:
Store in a tightly closed container. Deep freeze (below -20C). Keep refrigerated. (Store below 4C/39F.)

---

Section 8 - EXPOSURE CONTROLS, PERSONAL PROTECTION
Engineering Controls:
Use adequate ventilation to keep airborne concentrations low.
Exposure Limits CAS# 2304-81-6: Personal Protective Equipment Eyes: Not available.
Skin:
Wear appropriate protective gloves to prevent skin exposure.
Clothing:
Wear appropriate protective clothing to prevent skin exposure.
Respirators:
Follow the OSHA respirator regulations found in 29 CFR 1910.134 or European Standard EN 149. Use a NIOSH/MSHA or European Standard EN 149 approved respirator if exposure limits are exceeded or if irritation or other symptoms are experienced.

---

Section 9 - PHYSICAL AND CHEMICAL PROPERTIES

Physical State: Powder
Color: white
Odor: Not available.
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: Not available.
Freezing/Melting Point: 99 - 101 deg C
Autoignition Temperature: Not available.
Flash Point: Not available.
Explosion Limits, lower: Not available.
Explosion Limits, upper: Not available.
Decomposition Temperature:
Solubility in water: insoluble
Specific Gravity/Density:
Molecular Formula:
Molecular Weight: 565.96

---

Section 10 - STABILITY AND REACTIVITY
Chemical Stability:
Not available.
Conditions to Avoid:
Incompatible materials.
Incompatibilities with Other Materials:
Strong oxidizing agents.
Hazardous Decomposition Products:
Carbon monoxide, oxides of nitrogen, carbon dioxide.
Hazardous Polymerization: Has not been reported

---

Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 2304-81-6 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
N-Stearoyl-D-erythro-spinghosine, synthetical - Not listed by ACGIH, IARC, or NTP.

---

Section 12 - ECOLOGICAL INFORMATION

---

Section 13 - DISPOSAL CONSIDERATIONS
Dispose of in a manner consistent with federal, state, and local regulations.

---

Section 14 - TRANSPORT INFORMATION

IATA
Shipping Name: Not regulated.
Hazard Class:
UN Number:
Packing Group:
IMO
Shipping Name: Not regulated.
Hazard Class:
UN Number:
Packing Group:
RID/ADR
Shipping Name: Not regulated.
Hazard Class:
UN Number:
Packing group:

---

Section 15 - REGULATORY INFORMATION

European/International Regulations
European Labeling in Accordance with EC Directives
Hazard Symbols: Not available.
Risk Phrases:
Safety Phrases:
S 24/25 Avoid contact with skin and eyes.
WGK (Water Danger/Protection)
CAS# 2304-81-6: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 2304-81-6 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 2304-81-6 is not listed on the TSCA inventory.
It is for research and development use only.

---

SECTION 16 - ADDITIONAL INFORMATION
N/A

制备方法与用途

C18-鞘氨醇可以促进受损神经元的谷氨酸释放。此外，它还能够诱导神经胶质瘤细胞的死亡。鞘氨醇（Ceramide）参与多种细胞功能，包括分化、细胞周期调控、细胞间黏附、衰老以及细胞凋亡。

反应信息

• 作为反应物：
  描述：

  N-硬脂酰神经鞘氨醇 在 吡啶 、 2,6-二甲基吡啶 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 19.67h， 生成 (2S,3R,4E)-3-(tert-butyldimethylsilyloxy)-2-(octadecanoylamino)-4-octadecene-1-ol
  参考文献：
  名称：

  鞘磷脂-胆固醇结合物的设计，合成及其有序膜的形成

  摘要：

  脂质筏是漂浮在脂质双层海洋中的富含胆固醇（Chol）的微区。尽管人们认为Chol优先与鞘磷脂（如鞘磷脂（SM））相互作用，而不是与甘油磷脂相互作用，但主要由于脂质分子的高迁移率和分子间相互作用较弱，因此尚未确定特异性相互作用的起源。在这项研究中，我们合成了具有功能设计的连接子部分的SM–Chol共轭物，以抑制Chol的迁移，并通过去污剂不溶性测定，荧光各向异性实验和荧光猝灭测定检查了它们的有序膜的形成。在所有测试中，由结合物制备的膜均显示出与SM–Chol（1：1）膜相当的有序结构域特性。为了深入了解由共轭物组成的双层结构，我们用64个分子的共轭物进行了分子动力学模拟，这表明共轭物通过在连接子部分弯曲而形成稳定的双层结构，并且大多数情况下会重现氢键之间的氢键。 SM和Chol部分。这些结果暗示在SM和Chol之间在有序域中的分子识别本质上是由共轭分子再现的，因此证明这些共轭分子可以潜在地用

  DOI：

  10.1002/chem.201100849
• 作为产物：
  描述：

  正十四烷基三苯基溴化膦 在 吡啶 、 sodium tetrahydroborate 、 sodium azide 、 溶剂黄146 、 苯基锂 、 N,N'-二环己基碳二亚胺 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 、 环己烷 、 水 、 N,N-二甲基甲酰胺 、 异丙醇 为溶剂， 反应 56.33h， 生成 N-硬脂酰神经鞘氨醇
  参考文献：
  名称：

  从单-O-异亚丙基-d-木糖或-d-半乳糖制备d-赤型-鞘氨醇及其相关化合物的新途径

  摘要：

  摘要描述了由d-木糖或d-半乳糖有效合成d-赤型-鞘氨醇和-神经酰胺的方法。2,4-O-异亚丙基-d-苏糖及其甲酸酯的混合物是一步合成的，该混合物可从3,5-O-异亚丙基-d-木呋喃糖或4,6-O-异亚丙基-d-吡喃半乳糖中得到。用三苯基膦基四-和-十六-癸基进行Wittig链化。通过在C-2处引入叠氮基并将叠氮化物选择性还原，分别将所得的1,3- O-异丙基亚甲基化的C 18和C 20烯烃转化为相应的1,3- O-保护的鞘氨醇具有2（S），3（R）-d-赤型构型，通过与硬脂酰基或木质素酰基的N-酰化序列，并水解除去异亚丙基，从中制备了多种神经酰胺。

  DOI：

  10.1016/0008-6215(86)84009-5

文献信息

• Enantioselective Synthesis ofD-erythro-Sphingosine and of Ceramide
  作者：Radomir Julina、Thomas Herzig、Bruno Bernet、Andrea Vasella

  DOI：10.1002/hlca.19860690216

  日期：1986.3.19

  The enynol 2 was transformed into D-erythro-sphingosine 11 (7 steps, 46%) and into ceramide 1 (8 steps, 41% overall yield). The key steps were the mono-epoxidation of the enynol 5 (Ti(t-BuO)4, (−)-D-diethyl tartrate, t-BuOOH) to 6 (86%, ≥ 98% ee), the regioselective intramolecular opening of the oxirane 6via the benzylurethane 7, and the reductive tranformation of the acetylene 9 into the oxazolidinone

  烯醇2被转化为双-赤-鞘氨醇11（7步，46％）和神经酰胺1（8步，总产率41％）。关键步骤是烯醇5（Ti（t -BuO）4，（-）-D-酒石酸二乙酯，t -BuOOH）的单环氧化为6（86％，≥98％ee）的区域选择性分子内开放的环氧乙烷6经由所述benzylurethane 7，和乙炔的还原穿越- 9到恶唑烷酮10（栗，EtNH 2，88％）。
• Synthesis of UDP-glucose: N-acylsphingosine glucosyltransferase inhibitors
  申请人：Genzyme Corporation

  公开号：US20030050299A1

  公开（公告）日：2003-03-13

  Disclosed is a novel enantiomeric synthesis cermamide-like inhibitors of UDP-glucose: N-acylsphingosine glucosyltransferase. Also disclosed are novel intermediates formed during the synthesis.

  披露了一种新型对映合成UDP葡萄糖：N-酰基鞘氨醇葡糖转移酶抑制剂的方法。同时还披露了在合成过程中形成的新型中间体。
• Synthesis ofD-Erythro- andD-Threo-Sphingosine Derivatives FromL-Serine
  作者：Peter Herold

  DOI：10.1002/hlca.19880710208

  日期：1988.3.16

  The protected serine aldehyde 10 was converted to the crystalline N-Boc-protected sphingosines 6–9 by a three-step reaction sequence. Compound 10 was transformed with high diastereoselectivity (95%) either to the erythro- or threo-alkynols, 17 and 18, respectively. The erythro-isomer 17 is formed by the addition to 10 of lithium pentadecyne 16 in THF/HMPT at −78°, whereas the corresponding threo-isomer

  受保护的丝氨酸醛10转化为结晶Ñ -Boc保护的鞘氨醇6 - 9通过3步反应序列。将化合物10以高非对映选择性（95％）转化为分别为赤型或苏型炔烃17和18。的赤式异构体17通过加入形成为10锂pentadecyne的16在THF / HMPT在-78℃，而相应的苏式异构体18在ZnBr的存在下制备2在Et 2 O中。缩醛部分的脱保护得到1，3-二醇19和20。通过在Lindlar催化剂上进行部分加氢，将这些二醇用Red-Al选择性还原为（E）-鞘氨醇6和8或（Z） -异构体7和9。N- Boc基团的裂解和进一步转化为神经酰胺很容易实现，这是通过将6转化为N-十八烷酰基-D-赤型-鞘氨醇5来实现的。
• Stannyl ceramides as efficient acceptors for synthesising β-galactosyl ceramides
  作者：José Antonio Morales-Serna、Yolanda Díaz、M. Isabel Matheu、Sergio Castillón

  DOI：10.1039/b809570a

  日期：——

  β-Galactosyl ceramides have been obtained in excellent yields and stereoselectivities by reacting disarmed glycosyl donors with stannyl ethers. The broad compatibility of stannyl ethers with various leaving group–promoter pairs is demonstrated.

  β-半乳糖苷神经酰胺通过将非活性糖苷供体与锡醚反应获得了优异的产率和立体选择性。证明了锡醚与各种离去基–促进剂配对的广泛相容性。
• One-Pot Syntheses of Immunostimulatory Glycolipids
  作者：Matthew Schombs、Francine E. Park、Wenjun Du、Suvarn S. Kulkarni、Jacquelyn Gervay-Hague

  DOI：10.1021/jo100366v

  日期：2010.8.6

  Glycolipids containing α-linked galactosyl and glucosyl moieties have been shown to possess unique immunostimulatory activity creating a need for access to diverse and anomerically pure sources of these compounds for immunological studies. To meet this demand, glycosyl iodides were enlisted in the synthesis of these biologically relevant glycoconjugates. In the first-generation protocol, per-O-benzyl galactosyl

  含有 α 连接的半乳​​糖基和葡萄糖基部分的糖脂已被证明具有独特的免疫刺激活性，因此需要获得这些化合物的各种异头纯来源以进行免疫学研究。为了满足这一需求，糖基碘化物被用于合成这些生物相关的糖缀合物。在第一代方案中，per- O-苄基半乳糖基碘与活化的鞘氨醇受体有效偶联，但发现完全功能化的神经酰胺没有反应性。为了克服这个障碍，per- O研究了-三甲基甲硅烷基糖基碘化物，并显示其与神经酰胺和甘油酯受体进行高效偶联。与其他供体所观察到的相反，我们检测到葡萄糖基和半乳糖基碘化物的反应性几乎没有差异。三甲基甲硅烷基保护基团在激活供体进行亲核攻击方面发挥双重作用，同时提供瞬时保护：甲硅烷基在甲醇分解时很容易去除。所有反应均以完全的受体区域选择性进行，无需额外的保护基操作，并且仅形成所需的 α-异头异构体。这三步，