74713-59-0

• 常用中文名：N-辛酰基-D-神经鞘氨醇
• 常用英文名：C8-Ceramide
• CAS号：74713-59-0
• 分子式：C₂₆H₅₁NO₃
• 分子量：425.688
• 相关类别： 信号通路 细胞凋亡 细胞凋亡
• 发布时间：2018-03-11 08:00:00
• 更新时间：2024-01-03 19:55:24
• C8-Ceramide (N-Octanoyl-D-erythro-sphingosine) 是一种细胞渗透性的内源性神经酰胺类似物。C8-Ceramide 具有具有抗增殖特性,能作为化疗试剂。C8-Ceramide 能刺激树突状细胞促进 T 细胞对病毒感染的反应。C8-Ceramide 在体外能轻微地诱导 PKC 活化。

名称

• 中文名: N-辛酰基-D-神经鞘氨醇
• 英文名: c8 ceramide
• 英文别名: 08:0 CERAMIDE; C8-D-ERYTHRO-CERAMIDE; N-[(2S,3R,4E)-1,3-Dihydroxy-4-octadecen-2-yl]octanamide; CERAMIDE C8; N-Octanoyl-C18-sphingosine; MFCD00236496; Octanamide, N-[(1S,2R,3E)-2-hydroxy-1-(hydroxymethyl)-3-heptadecen-1-yl]-; C8 CERAMINE,D-ERYTHRO; N-OCTANOYL-D-SPHINGOSINE; N-Octanoyl-D-erythro-sp; N-OCTANOYLSPHINGOSINE; N-Octanoyl-D-erythr; N-octanoyl-D-erythro-sphingosine

物化性质

• 密度: 0.9±0.1 g/cm3
• 沸点: 595.5±50.0 °C at 760 mmHg
• 熔点: 68-70°C
• 分子式: C₂₆H₅₁NO₃
• 分子量: 425.688
• 闪点: 313.9±30.1 °C
• 精确质量: 425.386902
• PSA: 69.56000
• LogP: 9.09
• 外观性状: waxy solid
• 蒸汽压: 0.0±3.8 mmHg at 25°C
• 折射率: 1.482
• 储存条件:

  密闭于-20 ºC阴凉干燥环境中

• 稳定性:

  遵照规定使用和储存则不会分解。

• 水溶解性: DMSO or ethanol: soluble
• 分子结构:

  1、 摩尔折射率：129.17

  2、 摩尔体积（m³/mol）：453.0

  3、 等张比容（90.2K）：1115.0

  4、 表面张力（dyne/cm）：36.6

  5、 极化率（10 ^-24cm ³）：51.20

• 更多:

  1. 性状：无可用

  2. 密度（g/mL,25/4℃）：无可用

  3. 相对蒸汽密度（g/mL,空气=1）：无可用

  4. 熔点（ºC）：68-70

  5. 沸点（ºC,常压）：无可用

  6. 沸点（ºC,5.2kPa）：无可用

  7. 折射率：无可用

  8. 闪点（ºC）：无可用

  9. 比旋光度（º）：无可用

  10. 自燃点或引燃温度（ºC）：无可用

  11. 蒸气压（kPa,25ºC）：无可用

  12. 饱和蒸气压（kPa,60ºC）：无可用

  13. 燃烧热（KJ/mol）：无可用

  14. 临界温度（ºC）：无可用

  15. 临界压力（KPa）：无可用

  16. 油水（辛醇/水）分配系数的对数值：无可用

  17. 爆炸上限（%,V/V）：无可用

  18. 爆炸下限（%,V/V）：无可用

  19. 溶解性：无可用

生物活性

• 描述: C8-Ceramide (N-Octanoyl-D-erythro-sphingosine) 是一种细胞渗透性的内源性神经酰胺类似物。C8-Ceramide 具有具有抗增殖特性,能作为化疗试剂。C8-Ceramide 能刺激树突状细胞促进 T 细胞对病毒感染的反应。C8-Ceramide 在体外能轻微地诱导 PKC 活化。
• 相关类别:
  信号通路 >> 细胞凋亡 >> 细胞凋亡
  信号通路 >> 表观遗传学 >> PKC
  研究领域 >> 癌症
  信号通路 >> 自噬 >> 自噬
  研究领域 >> 炎症/免疫
  信号通路 >> TGF-beta/Smad 信号通路 >> PKC
• 靶点:

  PKC

  apoptosis

  autophagy

• 体外研究: C8神经酰胺(3μ米；48小时)不可逆地减少肿瘤细胞增殖并诱导形态学改变[1]。C8神经酰胺可诱导人宫颈肿瘤细胞坏死样细胞死亡,但不诱导凋亡生化标志物PARP的caspase依赖性裂解[1]。C8神经酰胺可增加内源性ROS水平(10-30)µ米；24小时)通过调节SOD1和SOD2的开关,引起抗增殖(10-50µ米；24小时),从而触发细胞凋亡(10-50µ米；48小时)的NSCLC H1299细胞[2]。细胞活力测定[1]细胞系：CALO细胞、INBL细胞、HeLa细胞浓度：3μM孵育时间：48h结果：肿瘤细胞数明显减少。细胞增殖试验[2]细胞系：H1299细胞浓度：10µM、 20个µM、 30个µM、 40个µM、 50个µ结果：细胞增殖率呈剂量依赖性下降,IC50为22.9µM。细胞周期分析[2]细胞系：H1299细胞浓度：10µM、 20个µM、 30个µM、 40个µM、 50个µ结果：引起G1期阻滞。凋亡分析[2]细胞系：H1299细胞浓度：10µM、 20个µM、 30个µM孵育时间：24小时、48小时结果：提高了半胱氨酸天冬氨酸蛋白酶-3的水平。
• 体内研究: C8神经酰胺(0.1mg/kg；鼻内给药)诱导病毒感染小鼠对病毒感染产生更强烈的CD8+和CD4+T细胞反应[3]。动物模型：C57BL/6小鼠,感染淋巴细胞性脉络丛脑膜炎病毒[2]剂量：0.1mg/kg给药：鼻腔给药结果：增加肺CD8+T细胞对流感的反应。
• 参考文献:

  [1]. Rebeca López-Marure , et al. Ceramide promotes the death of human cervical tumor cells in the absence of biochemical and morphological markers of apoptosis. Biochem Biophys Res Commun. 2002 May 10;293(3):1028-36.

  [2]. Yuli C. Chang, et al. Exogenous C8-Ceramide Induces Apoptosis by Overproduction of ROS and the Switch of Superoxide Dismutases SOD1 to SOD2 in Human Lung Cancer Cells. Int J Mol Sci. 2018 Oct; 19(10): 3010.

  [3]. Curtis J. Pritzl, et al. A ceramide analogue stimulates dendritic cells to promote T cell responses upon virus infections. J Immunol. 2015 May 1; 194(9): 4339–4349.

  [4]. H W Huang, et al. Ceramides modulate protein kinase C activity and perturb the structure of Phosphatidylcholine/Phosphatidylserine bilayers. Biophys J. 1999 Sep; 77(3): 1489–1497.

  [5]. Lan Weiss, et al. Ceramide contributes to pathogenesis and may be targeted for therapy in VCP inclusion body myopathy. Hum Mol Genet. 2021 Jan 7;ddaa248.

MSDS

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

毒性和生态

生态学数据: 该物质对环境可能有危害，对水体应给予特别注意。

安全

• 安全声明 (欧洲): S24/25
• WGK德国: 3
• 海关编码: 2924199090

合成路线

123-78-4 111-64-8 ~% 74713-59-0

文献：Journal of the American Chemical Society, , vol. 124, # 9 p. 1856 - 1857

123-78-4 1956-10-1 ~% 74713-59-0

文献：Journal of Organic Chemistry, , vol. 59, # 21 p. 6495 - 6498

上下游产品

上游产品  3
123-78-4 111-64-8 1956-10-1
下游产品  0

海关

海关编码	2924199090
中文概述	2924199090. 其他无环酰胺（包括无环氨基甲酸酯)(包括其衍生物及盐）. 增值税率:17.0%. 退税率:13.0%. 监管条件:无. 最惠国关税:6.5%. 普通关税:30.0%
申报要素	品名, 成分含量, 用途, 包装
Summary	2924199090. other acyclic amides (including acyclic carbamates) and their derivatives; salts thereof. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:30.0%