N-辛酰基-D-神经鞘氨醇 | 74713-59-0

• 物质功能分类: 有机原料 - 氨基化合物 - 酰胺类化合物
• 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-辛酰基-D-神经鞘氨醇
• 英文名称: N-octanoylsphingosine
• 英文别名: C8-ceramide；N-octanoyl-D-erythro-sphingosine；N-[(E,2S,3R)-1,3-dihydroxyoctadec-4-en-2-yl]octanamide
• CAS: 74713-59-0
• 化学式: C₂₆H₅₁NO₃
• 分子量: 425.696
• InChiKey: APDLCSPGWPLYEQ-WRBRXSDHSA-N

物化性质

• 熔点：
  68-70°C
• 沸点：
  541.37°C (rough estimate)
• 密度：
  0.9974 (rough estimate)
• 溶解度：
  可溶于DMSO或乙醇：可溶
• 稳定性/保质期：

  遵照规定使用和储存，则不会发生分解。

计算性质

• 辛醇/水分配系数(LogP)：
  8.5
• 重原子数：
  30
• 可旋转键数：
  22
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  69.6
• 氢给体数：
  3
• 氢受体数：
  3

安全信息

• WGK Germany：
  3
• 海关编码：
  2924199090
• 安全说明：
  S24/25

SDS

Name:	N-Octanoyl-D-Erythro-Sphingosine Synthetical 99+% Material Safety Data Sheet
Synonym:	Ceramide C8
CAS:	74713-59-0

Section 1 - Chemical Product MSDS Name:N-Octanoyl-D-Erythro-Sphingosine Synthetical 99+% Material Safety Data Sheet
Synonym:Ceramide C8

---

Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
74713-59-0	N-Octanoyl-D-Erythro-Sphingosine	99+%	unlisted

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

---

Section 3 - HAZARDS IDENTIFICATION
EMERGENCY OVERVIEW
The toxicological properties of this material have not been fully investigated.
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. The toxicological properties of this substance have not been fully investigated.
Chronic:
No information found.

---

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. Wash clothing before reuse.
Ingestion:
Never give anything by mouth to an unconscious person. Get medical aid. Do NOT induce vomiting. If conscious and alert, rinse mouth and drink 2-4 cupfuls of milk or water. 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:
Treat symptomatically and supportively.

---

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. During a fire, irritating and highly toxic gases may be generated by thermal decomposition or combustion.
Extinguishing Media:
Use water spray, dry chemical, carbon dioxide, or chemical foam.

---

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. Clean up spills immediately, observing precautions in the Protective Equipment section. Avoid generating dusty conditions.
Provide ventilation.

---

Section 7 - HANDLING and STORAGE
Handling:
Wash thoroughly after handling. Use with adequate ventilation.
Minimize dust generation and accumulation. Avoid breathing dust, vapor, mist, or gas. Avoid contact with eyes, skin, and clothing.
Keep container tightly closed. Avoid ingestion and inhalation.
Storage:
Store in a tightly closed container. Store in a dry area. Deep freeze (below -20C).

---

Section 8 - EXPOSURE CONTROLS, PERSONAL PROTECTION
Engineering Controls:
Facilities storing or utilizing this material should be equipped with an eyewash facility and a safety shower. Use adequate ventilation to keep airborne concentrations low.
Exposure Limits CAS# 74713-59-0: Personal Protective Equipment Eyes: Wear appropriate protective eyeglasses or chemical safety goggles as described by OSHA's eye and face protection regulations in 29 CFR 1910.133 or European Standard EN166.
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 to off-white
Odor: Not available.
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: Not available.
Freezing/Melting Point: Not available.
Autoignition Temperature: Not available.
Flash Point: Not available.
Explosion Limits, lower: Not available.
Explosion Limits, upper: Not available.
Decomposition Temperature:
Solubility in water:
Specific Gravity/Density:
Molecular Formula: C26H51NO3
Molecular Weight: 425.69

---

Section 10 - STABILITY AND REACTIVITY
Chemical Stability:
Stable.
Conditions to Avoid:
Incompatible materials, dust generation.
Incompatibilities with Other Materials:
Oxidizing agents.
Hazardous Decomposition Products:
Nitrogen oxides, carbon monoxide, carbon dioxide.
Hazardous Polymerization: Will not occur.

---

Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 74713-59-0 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
N-Octanoyl-D-Erythro-Sphingosine - 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
Not regulated as a hazardous material.
IMO
Not regulated as a hazardous material.
RID/ADR
Not regulated as a hazardous material.

---

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# 74713-59-0: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 74713-59-0 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 74713-59-0 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

生物活性

C8-神经酰胺（N-十八碳基-D-反式鞘氨醇）是一种细胞渗透性的内源性神经酰胺类似物。它具有抗增殖特性，可用作化疗试剂，并能刺激树突状细胞促进T细胞对病毒感染的反应。在体外实验中，C8-神经酰胺轻微诱导PKC活化。

靶点

靶点	效应
PKC
凋亡
自噬

体外研究

C8-神经酰胺（3 μM；48小时）不可逆地降低肿瘤细胞增殖并诱导形态变化。

C8-神经酰胺可引起类似坏死的细胞死亡，但在人宫颈癌细胞中不诱导依赖caspase的PARP裂解。

C8-神经酰胺可能通过调节SOD1和SOD2开关增加内源性ROS水平（10-30 μM；24小时），导致抗增殖（10-50 μM；24小时）并最终诱导NSCLC H1299细胞的凋亡（10-50 μM；48小时）。

细胞活力测定

项目	数据
细胞系	CALO、INBL和HeLa细胞
浓度	3 μM
孵育时间	48小时
结果	显著减少肿瘤细胞数量

细胞增殖测定

项目	数据
细胞系	H1299细胞
浓度	10、20、30、40和50 μM
孵育时间	24小时
结果	剂量依赖性地减少细胞增殖，半数抑制浓度为22.9 μM

细胞周期分析

项目	数据
细胞系	H1299细胞
浓度	10、20、30、40和50 μM
孵育时间	24小时
结果	导致G1期阻滞

凋亡分析

项目	数据
细胞系	H1299细胞
浓度	10、20和30 μM
孵育时间	24小时和48小时
结果	增加cleaved caspase-3的水平

体内研究

C8-神经酰胺（0.1 mg/kg；鼻内给药）在病毒感染的小鼠中更强烈地诱导CD8+和CD4+T细胞对病毒感染的反应。

动物模型

项目	数据
动物模型	C57BL/6小鼠，带淋巴细胞性脑膜炎病毒感染
剂量	0.1 mg/kg
给药方式	鼻内给药
结果	增加肺部对流感的CD8+T细胞反应

反应信息

• 作为反应物：
  描述：

  N-辛酰基-D-神经鞘氨醇 在 咪唑 、 四氮唑 、 四丁基氟化铵 、 4-甲基苯磺酸吡啶 、 对甲苯磺酸 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 2.0h， 生成 1-O-(bis(2-cyanoethyl)phosphoro)-C8-ceramide
  参考文献：
  名称：

  Ceramide 1-(2-cyanoethyl) phosphate enhances store-operated Ca2+ entry in thyroid FRTL-5 cells

  摘要：

  Sphingolipid derivatives cause diverse effects towards the regulation of intracellular free Ca2+ concentrations ([Ca2+](i)) in a multitude of nonexcitable cells. In the present investigation, the effect of C-8 ceramide-1-(2-cyanoethyl) phosphate (C1CP) on store-operated Ca2+ (SOC) entry was investigated. C1CP evoked a modest increase in [Ca2+](i) The increase was inhibited by the SOC channel antagonist 1-(beta-[3-(4methoxyphenyl)propoxy]-4-methoxyphenethyl)-1H-imidazole (SKF96365) but not by overnight pretreatment of the cells with pertussis toxin. C1CP did not invoke the production of inositol phosphates. When cells were stimulated with both C1CP and thapsigargin, the thapsigargin-invoked increase in [Ca2+](i) was enhanced in comparison to control cells. When Ca2+ was added to cells treated with both C1CP and thapsigargin in a Ca2+-free buffer, the increase in [Ca2+](i) was enhanced in comparison to control cells. In patch-clamp experiments, C1CP hyperpolarized the membrane potential (E-m) of the cells and attenuated the thapsigargin-invoked depolarization of the E-m. The effects of C1CP came, in part, as a result of a decreased conductance of the cell membrane towards Cl- ions, as C1CP in a Cl--free solution also enhanced Ca2+ entry. Barium 2-cyanoethylphosphate (Ba2Cy), which also contains the 2-cyanoethyl group, did not modulate thapsigargin-invoked changes in [Ca2+](i) nor did it modulate the E-m. In conclusion, C1CP enhances SOC entry, in part, via hyperpolarization of the E-m and attenuation of the thapsigargin-invoked membrane depolarization, thus increasing the electrochemical gradient for Ca2+ ions. Hence, C1CP may be a useful reagent for investigating the cellular effects of ceramide derivatives. (C) 2002 Elsevier Science B.V. All rights reserved.

  DOI：

  10.1016/s0014-2999(02)02362-2
• 作为产物：
  描述：

  D-鞘氨醇 、 辛酰氯 以 二氯甲烷 、 水 为溶剂， 生成 N-辛酰基-D-神经鞘氨醇
  参考文献：
  名称：

  Exploring Leishmania major Inositol Phosphorylceramide Synthase (LmjIPCS): Insights into the ceramide binding domain

  摘要：

  本文描述了一组神经酰胺类似物的合成，这些类似物探讨了酰基链的疏水性、羟基化的程度和性质。它们已被用于检测寄生原生动物酶LmjIPCS。这些研究表明，尽管C-3羟基团对酶的代谢转化不是必需的，但它提供了增强的亲和力。鉴于该酶的膜结合性质，需要一个长（C13）碳氢神经酰胺尾部以实现高亲和力和代谢转化。虽然N-酰基链也对亲和力有所贡献，但缺乏酰胺键连接的类似物在酶和细胞基础测试中作为竞争性抑制剂发挥了作用。针对这一观察结果，我们提出了一个理论模型。

  DOI：

  10.1039/c0ob00871k

文献信息

• Synthetic Glycosphingolipids for Live-Cell Labeling
  作者：Martin Dauner、Ellen Batroff、Verena Bachmann、Christof R. Hauck、Valentin Wittmann

  DOI：10.1021/acs.bioconjchem.6b00177

  日期：2016.7.20

  insight into their localization. However, the attachment of a fluorophore to the glycan part or - more commonly - to the lipid part of glycosphingolipids is known to alter the biophysical properties and can perturb the biological function of the probe. Presented here is the synthesis of novel glycosphingolipid probes with mono and disaccharide head groups and ceramide moieties containing fatty acids of varying

  糖鞘脂是涉及许多生物学过程的细胞膜的重要组成部分。荧光标记的糖鞘脂经常用于深入了解其定位。然而，已知荧光团与糖鞘脂的聚糖部分或更通常地与脂质部分的附着会改变生物物理特性，并且会干扰探针的生物学功能。本文介绍的是具有单糖和二糖首基以及神经酰胺部分的新型糖鞘脂探针的合成，所述神经酰胺部分含有链长不同的脂肪酸（C4至C20）。这些糖鞘脂具有作为化学报告基的叠氮基或炔基，可以通过生物正交连接反应将荧光团连接至其上。可以以灵活的方式选择荧光标签和与其连接的任何接头。我们通过共聚焦显微镜技术选择性观察活细胞的质膜，证明了探针的适用性。具有较短脂肪酸的衍生物可直接应用于HEK 293T细胞，而具有较长脂肪酸的疏水性鞘糖脂可使用融合脂质体递送至细胞。
• The relationship between the structure of the headgroup of sphingolipids and their ability to form complex high axial ratio microstructures
  作者：Alex S Goldstein、Michael H Gelb、Paul Yager

  DOI：10.1016/s0009-3084(00)00204-8

  日期：2001.1

  examined for their ability to form complex high axial ratio microstructures (CHARMS), potential drug delivery vehicles. In general, if the modified ceramide had either a hydrogen bond donor or acceptor at C-1 and C-3, including hydrophobic or hydrophilic groups attached to C-1 microstructures formed. Tolerated groups include amides, esters, sulfonates, and ethers. If modification at C-3 added significant

  制备了具有化学修饰的极性头基的神经酰胺，并检查了其形成复杂的高轴向比微结构（CHARMS）（潜在的药物递送载体）的能力。通常，如果改性的神经酰胺在C-1和C-3处具有氢键供体或受体，包括与形成的C-1微结构相连的疏水或亲水基团。容许的基团包括酰胺，酯，磺酸盐和醚。如果C-3处的修饰增加了大量的体积（大于4个碳原子，而与亲水性无关），则会形成无定形聚集体。具有通过循环结构桥接的C-1和C-3的神经酰胺也可形成微结构。通过使用具有胺头基的鞘脂，可以在形成后共价修饰CHARM。
• One-step labelling of sphingolipids via a scrambling cross-metathesis reaction
  作者：Peter Nussbaumer、Peter Ettmayer、Carsten Peters、Daniela Rosenbeiger、Klemens Högenauer

  DOI：10.1039/b508132g

  日期：——

  The alkyl chain in the backbone of sphingosine derivatives can be exchanged with functionalised (labelled) side chains in a single step under cross-metathesis reaction conditions.

  在交叉甲基化反应条件下，鞘磷脂衍生物骨架中的烷基链可与功能化（标记）侧链进行一步交换。
• Methods for detection of lysosomal storage disease
  申请人：Zhang Xiaokui K.

  公开号：US20080248513A1

  公开（公告）日：2008-10-09

  The present invention provides compositions for performing assays of enzyme activity associated with lysosomal storage diseases. The invention further provides methods for determining enzyme activity, and methods for the screening for lysosomal storage disease in an individual.

  本发明提供了用于执行与溶酶体贮积病相关的酶活性测定的组合物。该发明还提供了测定酶活性的方法，以及筛选个体的溶酶体贮积病的方法。
• Purification and characterization of human intestinal neutral ceramidase
  作者：Lena Ohlsson、Carina Palmberg、Rui-Dong Duan、Maria Olsson、Tomas Bergman、Åke Nilsson

  DOI：10.1016/j.biochi.2007.03.009

  日期：2007.8

  of known neutral/alkaline ceramidases. The enzyme has neutral pH optimum and catalyses both hydrolysis and formation of ceramide without distinct bile salt dependence. It is inhibited by Cu(2+) and Zn(2+) ions and by low concentrations of cholesterol. The enzyme is a glycoprotein but deglycosylation does not affect its activity. Our study indicates that neutral ceramidase is expressed in human intestine

  鞘脂通过肠中的鞘磷脂酶和神经酰胺酶降解为神经酰胺和鞘氨醇，这可以抑制细胞增殖并诱导细胞凋亡，因此在肠中具有抗肿瘤作用。尽管以前的啮齿动物研究（包括对敲除小鼠的实验）表明中性神经酰胺酶在神经酰胺消化中的作用，但人类酶从未纯化过并以其纯化形式表征。我们在这里报告从人类回肠造口术内容，使用辛酰基-[（14）C]鞘氨醇为底物纯化和表征中性神经酰胺酶。经过四个色谱步骤，获得了具有116kDa的均一蛋白带。MALDI质谱法鉴定了16种类似于先前由El Bawab等人克隆的人神经酰胺酶的肽。[人线粒体神经酰胺酶，J。的分子克隆和表征。生物学 化学 275（2000）21508-21513]和Hwang等。[人中性神经酰胺酶在HEK293细胞中表达的亚细胞定位，Biochem。生物物理学。Res。社区 331（2005）37-42]。通过RT-PCR和5'-RACE方法，从人十二指肠活检样品获得了中性神经