N-月桂酰-D-鞘胺醇 | 74713-60-3

• 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-月桂酰-D-鞘胺醇
• 中文别名: C12-D-赤式-鞘氨醇
• 英文名称: N-lauroylceramide
• 英文别名: C12 ceramide；Laurylsphingosine；N-[(E,2S,3R)-1,3-dihydroxyoctadec-4-en-2-yl]dodecanamide
• CAS: 74713-60-3
• 化学式: C₃₀H₅₉NO₃
• 分子量: 481.803
• InChiKey: HXFPPRPLRSPNIB-VARSQMIESA-N

物化性质

• 熔点：
  70 - 72°C
• 沸点：
  579.38°C (rough estimate)
• 密度：
  0.9777 (rough estimate)
• 溶解度：
  可溶于氯仿（轻微）、DMSO（轻微）、乙酸乙酯（轻微、加热）
• 物理描述：
  Solid
• 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)：
  10.7
• 重原子数：
  34
• 可旋转键数：
  26
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  69.6
• 氢给体数：
  3
• 氢受体数：
  3

安全信息

• 海关编码：
  2924199090
• 安全说明：
  S24/25
• WGK Germany：
  3
• 储存条件：
  存放在-20°C的阴凉干燥处。

SDS

Name:	N-Lauroyl-D-Erythro-Sphingosine Synthetical 99+% Material Safety Data Sheet
Synonym:	Ceramide C12
CAS:	74713-60-3

Section 1 - Chemical Product MSDS Name:N-Lauroyl-D-Erythro-Sphingosine Synthetical 99+% Material Safety Data Sheet
Synonym:Ceramide C12

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
74713-60-3	N-Lauroyl-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# 74713-60-3: 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: C30H59NO3
Molecular Weight: 481.80

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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# 74713-60-3 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
N-Lauroyl-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# 74713-60-3: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 74713-60-3 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 74713-60-3 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

制备方法与用途

C12神经酰胺（N-月桂酰-D-红鞘氨醇），一种天然存在的神经酰胺，由C12鞘磷脂水解形成。研究发现，C12神经酰胺能够增强阿霉素对MDA-MB-231细胞的毒性作用。此外，C12神经酰胺还可用于诊断A型和B型尼曼-匹克病。

反应信息

• 作为反应物：
  描述：

  水 、 N-月桂酰-D-鞘胺醇 生成 laurate anion 、 Sphingosine(1+)
  参考文献：
  名称：

  Identification of a novel amidase motif in neutral ceramidase

  摘要：

  中性CD酶（神经酰胺酶）是新发现的酶，在细胞调控中具有重要作用，但人们对其催化机理知之甚少。本研究克隆了全长的人中性 CD 酶，并将其表达在酵母双基因敲除菌株 Δypc1Δydc1 中，该菌株缺乏酵母 CD 酶 YPC1p 和 YDC1p。人类中性 CD 酶的生化特性表明，该酶表现出经典的 Michaelis-Menten 动力学，在 pH 值为 7.5 时具有最佳活性。Na+ 和 Ca2+ 可增强其活性。Mg2+ 和 Mn2+ 有一定的刺激作用，但 Zn2+、Cu2+ 和 Fe2+ 会抑制该酶。二硫苏糖醇和 2-巯基乙醇对中性 CD 酶有剂量依赖性抑制作用。为了确定哪些氨基酸参与了中性 CD 酶的催化作用，对纯化的酶进行了化学修饰。结果表明，丝氨酸残基修饰剂二异丙基氟磷酸酯（di-isopropyl fluorophosphate）对活性有依赖性抑制作用，这说明丝氨酸残基参与了催化作用。通过对不同物种中性 CD 酶的序列进行比对，选择了所有保守的丝氨酸残基进行定点突变。在被突变为丙氨酸的六个对齐的丝氨酸残基中，只有 S354A 突变体完全丧失了活性。Ser354 位于一个高度保守的六肽序列 GDVSPN 中，而该序列本身又位于一个更大的保守序列（即 NXGDVSPNXXGP/XXC）的中间。此外，将共识序列中的 Asp352 和 Cys362 突变为丙氨酸会导致中性 CD 酶失去活性。因此，本研究发现了一种新的酰胺酶序列，其中含有一个关键的丝氨酸残基，该残基可能在水解神经酰胺中的酰胺键时起亲核作用。

  DOI：

  10.1042/bj20050682
• 作为产物：
  描述：

  月桂酰氯 、 D-鞘氨醇 在 吡啶 、 N-甲基吡咯烷酮 、 p-OH-m-NO₂-C₆H₃-C(O)-resin 作用下， 以 四氢呋喃 为溶剂， 生成 N-月桂酰-D-鞘胺醇
  参考文献：
  名称：

  Inhibitory activity of a ceramide library on interleukin-4 production from activated T cells

  摘要：

  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.

  DOI：

  10.1016/j.bmc.2005.01.027

文献信息

• ARTIFICIALLY SYNTHESIZED SPHINGOSINE DERIVATIVE LIPOID MONOMER AND USE OF SAME FOR DELIVERING NUCLEIC ACID
  申请人：Institute of Basic Medical Sciences, Chinese Academy of Medical Sciences

  公开号：EP3777891A1

  公开（公告）日：2021-02-17

  Provided are an artificially synthesized sphingosine lipoid monomer and the use of same for delivering a nucleic acid. In particular, provided is the use or a method of using a compound of formula I, a stereoisomer thereof or a pharmaceutically acceptable salt thereof, or a combination comprising the compound of formula I, the stereoisomer thereof or the pharmaceutically acceptable salt thereof to deliver a nucleic acid to a cell or subject, (I)

  本发明提供了一种人工合成的鞘氨醇类脂质单体及其用于递送核酸的用途。特别是，提供了使用式 I 的化合物、其立体异构体或其药学上可接受的盐，或包含式 I 的化合物、其立体异构体或其药学上可接受的盐的组合物向细胞或受试者递送核酸的用途或方法，(I)
• 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.
• II. Synthesis of Long Chain Fatty Acid Amines of Sphingosine and Dihydrosphingosine¹
  作者：Benjamin Weiss、Paula Raizman

  DOI：10.1021/ja01550a061

  日期：1958.9
• Cholesterol glucosylation is catalyzed by transglucosylation reaction of β-glucosidase 1
  作者：Hisako Akiyama、Susumu Kobayashi、Yoshio Hirabayashi、Kimiko Murakami-Murofushi

  DOI：10.1016/j.bbrc.2013.10.145

  日期：2013.11

  Cholesteryl glucoside (beta-ChIGIc), a monoglucosylated derivative of cholesterol, is involved in the regulation of heat shock responses. beta-ChIGIc, which is rapidly induced in response to heat shock, activates heat shock transcription factor 1 (HSF1) leading to the expression of heat shock protein 70 (HSP70) in human fibroblasts. Identification and biochemical characterization of the enzyme responsible for beta-ChIGIc formation is important for a complete understanding of the molecular mechanisms leading to HSP70-induction following heat shock. Recently, we demonstrated that beta-ChIGIc synthesis is not dependent on UDP-Glucose but glucosylceramide (GlcCer) in animal tissue and human fibroblasts. In this study, we examined the possibility of glucocerebrosidase, a GIcCer-degrading glycosidase, acting as beta-ChIGIc-synthesizing enzyme. Overexpression of beta-glucosidase (GBA1, lysosomal acid beta-glucocerebrosidase) led to an increase in cholesterol glucosylation activity in human fibroblasts. Using a cell line generated from type 2 Gaucher disease patients with severe defects in GBA1 activity, we found that cholesterol glucosylation activity was very low in the cells and the overexpression of GBA1 rescued the activity. In addition, purified recombinant GBA1 exhibits conduritol B-epoxide-sensitive cholesterol glucosylation activity. The optimum pH and temperature for cholesterol glucosylation by GBA1 were at about 5.3 and 43 C, respectively. Short chain C8:0-GIcCer was the most effective donor for cholesterol glucosylation activity among GIcCer containing saturated fatty acid (C8:0 to C18:0) tested. GlcCer containing mono-unsaturated fatty acid was more preferred substrate for cholesterol glucosylation when compared with GIcCer containing same chain length of saturated fatty acid. These results demonstrate, for the first time, a novel function of GBA1 as a beta-ChIGIc-synthesizing enzyme. Therefore, our results also reveal a new pathway for glycolipid metabolism in mammals. (C) 2013 Elsevier Inc. All rights reserved.
• Cloning and Characterization of a Mouse Endoplasmic Reticulum Alkaline Ceramidase
  作者：Cungui Mao、Ruijuan Xu、Zdzislaw M. Szulc、Jacek Bielawski、Kevin P. Becker、Alicja Bielawska、Sehamuddin H. Galadari、Wei Hu、Lina M. Obeid

  DOI：10.1074/jbc.m303875200

  日期：2003.8

  Ceramidases deacylate ceramides, important intermediates in the metabolic pathway of sphingolipids. In this study, we report the cloning and characterization of a novel mouse alkaline ceramidase (maCER1) with a highly restricted substrate specificity. maCER1 consists of 287 amino acids, and it has a 28 and 32% identity to the Saccharomyces alkaline ceramidases (YPC1p and YDC1p) and the human alkaline phytoceramidase, respectively. Reverse transcriptase-PCR analysis demonstrated that maCER1 was predominantly expressed in skin. maCER1 was localized to the endoplasmic reticulum as revealed by immunocytochemistry. In vitro biochemical characterization determined that maCER1 hydrolyzed D-erythro-ceramide exclusively but not D-erythro-dihydroceramide or D-ribo-phytoceramide. Similar to other alkaline ceramidases, maCER1 had an alkaline pH optimum of 8.0, and it was activated by Ca2+ but inhibited by Zn2+, Cu2+, and Mn2+. maCER1 was also inhibited by sphingosine, one of its products. Metabolic labeling studies showed that overexpression of maCER1 caused a decrease in the incorporation of radiolabeled dihydrosphingosine into ceramide and complex sphingolipids but led to a concomitant increase in sphingosine-1-P (S1P) in HeLa cells. Mass measurement showed that overexpression of maCER1 selectively lowered the cellular levels of D-erythro-C-24:1-ceramide, but not other ceramide species and caused an increase in the levels of S1P. Taken together, these data suggest that maCER1 is a novel alkaline ceramidase with a stringent substrate specificity and that maCER1 is selectively expressed in skin and may have a role in regulating the levels of bioactive lipids ceramide and S1P, as well as complex sphingolipids.