N-丁酰-D-红鞘氨醇 | 74713-58-9

• 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-丁酰-D-红鞘氨醇
• 中文别名: C4酰胺
• 英文名称: Cer(d18:1/4:0)
• 英文别名: Ceramide 4；N-[(E,2S,3R)-1,3-dihydroxyoctadec-4-en-2-yl]butanamide
• CAS: 74713-58-9
• 化学式: C₂₂H₄₃NO₃
• 分子量: 369.588
• InChiKey: UCBLGIBMIAFISC-CQLAPORSSA-N

物化性质

• 熔点：
  64-67°C
• 沸点：
  499.67°C (rough estimate)
• 密度：
  1.0181 (rough estimate)
• 溶解度：
  DMF：20mg/mL；二甲基亚砜：20mg/mL；乙醇：30mg/mL； PBS (pH 7.2)：< 50 μg/ml
• 稳定性/保质期：
  遵照规定使用和储存，则不会分解。

计算性质

• 辛醇/水分配系数(LogP)：
  6.4
• 重原子数：
  26
• 可旋转键数：
  18
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.86
• 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

SDS

Name:	N-Butanoyl-D-Erythro-Sphingosine Synthetical 99+% Material Safety Data Sheet
Synonym:	Ceramide C4
CAS:	74713-58-9

Section 1 - Chemical Product MSDS Name:N-Butanoyl-D-Erythro-Sphingosine Synthetical 99+% Material Safety Data Sheet
Synonym:Ceramide C4

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
74713-58-9	N-Butanoyl-D-Erythro-Sphingosine	99+%	unlisted

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

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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.

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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.

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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.

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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.

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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).

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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# 74713-58-9: 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.

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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: C22H43NO3
Molecular Weight: 369.588

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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.

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Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 74713-58-9 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
N-Butanoyl-D-Erythro-Sphingosine - Not listed by ACGIH, IARC, or NTP.

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Section 12 - ECOLOGICAL INFORMATION

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

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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.

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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# 74713-58-9: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 74713-58-9 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 74713-58-9 is not listed on the TSCA inventory.
It is for research and development use only.

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SECTION 16 - ADDITIONAL INFORMATION
N/A

反应信息

• 作为反应物：
  描述：

  N-丁酰-D-红鞘氨醇 在 吡啶 、 三氟化硼乙醚 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 甲苯 为溶剂， 反应 54.33h， 生成 (2S,3S,E)-2-butyramido-3-(benzoyloxy)octadec-4-en-1-yl 2,3,4-tri-O-acetyl-6-azido-6-deoxy-β-D-glucopyranoside
  参考文献：
  名称：

  用于活细胞标记的合成糖鞘脂。

  摘要：

  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。

  DOI：

  10.1021/acs.bioconjchem.6b00177
• 作为产物：
  描述：

  D-鞘氨醇 、 丁酰氯 在 吡啶 作用下， 以 N-甲基吡咯烷酮 、 四氢呋喃 为溶剂， 生成 N-丁酰-D-红鞘氨醇
  参考文献：
  名称：

  The Synthesis and Biological Characterization of a Ceramide Library

  摘要：

  A facile synthesis of a combinatorial ceramide library and their activities in the NF-kappaB pathway and in apoptosis induction/prevention were demonstrated. A novel NF-kappaB activating molecule was discovered among ceramide containing beta-galactose, and the structural requirements of ceramides for apoptosis induction was elucidated.

  DOI：

  10.1021/ja017576o

文献信息

• 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。
• The Synthesis and Biological Characterization of a Ceramide Library
  作者：Young-Tae Chang、Jaehwa Choi、Sheng Ding、Eva E. Prieschl、Thomas Baumruker、Jae-Mok Lee、Sung-Kee Chung、Peter G. Schultz

  DOI：10.1021/ja017576o

  日期：2002.3.1

  A facile synthesis of a combinatorial ceramide library and their activities in the NF-kappaB pathway and in apoptosis induction/prevention were demonstrated. A novel NF-kappaB activating molecule was discovered among ceramide containing beta-galactose, and the structural requirements of ceramides for apoptosis induction was elucidated.
• Compositions and methods for detection of lysosomal storage disease
  申请人：GENZYME CORPORATION

  公开号：EP2535050B1

  公开（公告）日：2017-07-05
• US8431335B2
  申请人：——

  公开号：US8431335B2

  公开（公告）日：2013-04-30
• Inhibitory activity of a ceramide library on interleukin-4 production from activated T cells
  作者：Jin Park、Qian Li、Young-Tae Chang、Tae Sung Kim

  DOI：10.1016/j.bmc.2005.01.027

  日期：2005.4

  Allergic diseases are hypersensitivity disorders associated with the production of specific immunoglobulin E (IgE) to environmental allergens. Interleukin (IL)-4, produced primarily by CD4(+) T cells, is an important stimulus for the switch of the antibody isotype to IgE in both mice and humans. In this study we investigated the inhibitory activity of IL-4 production in activated T cells by screening ceramide derivatives prepared by solid phase combinatorial chemistry. Many ceramide derivatives significantly inhibited IL-4 production in T cells. In particular, ceramide derivatives with a lauroyl group showed strong inhibitory activities on IL-4 production in both phorbol 12-myristate 13-acetate (PMA)-activated EL4 T cells and antigen-primed cells, suggesting that they can be used as compounds for the development of anti-allergic agents. (c) 2005 Elsevier Ltd. All rights reserved.