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N-Octanoyl-3-O-tetrahydropyranyl-D-erythro-sphingosine | 158983-56-3

中文名称
——
中文别名
——
英文名称
N-Octanoyl-3-O-tetrahydropyranyl-D-erythro-sphingosine
英文别名
3-O-tetrahydropyranyl-C8-ceramide;N-[(E,2S,3R)-1-hydroxy-3-(oxan-2-yloxy)octadec-4-en-2-yl]octanamide
N-Octanoyl-3-O-tetrahydropyranyl-D-erythro-sphingosine化学式
CAS
158983-56-3
化学式
C31H59NO4
mdl
——
分子量
509.814
InChiKey
VSVOCMYZCMUFJA-RBSMHDDWSA-N
BEILSTEIN
——
EINECS
——
  • 物化性质
  • 计算性质
  • ADMET
  • 安全信息
  • SDS
  • 制备方法与用途
  • 上下游信息
  • 反应信息
  • 文献信息
  • 表征谱图
  • 同类化合物
  • 相关功能分类
  • 相关结构分类

物化性质

  • 沸点:
    656.3±55.0 °C(predicted)
  • 密度:
    0.97±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

  • 辛醇/水分配系数(LogP):
    9.9
  • 重原子数:
    36
  • 可旋转键数:
    24
  • 环数:
    1.0
  • sp3杂化的碳原子比例:
    0.9
  • 拓扑面积:
    67.8
  • 氢给体数:
    2
  • 氢受体数:
    4

上下游信息

  • 上游原料
    中文名称 英文名称 CAS号 化学式 分子量
  • 下游产品
    中文名称 英文名称 CAS号 化学式 分子量

反应信息

  • 作为反应物:
    描述:
    N-Octanoyl-3-O-tetrahydropyranyl-D-erythro-sphingosine四氮唑对甲苯磺酸叔丁胺 作用下, 以 甲醇二氯甲烷乙腈 为溶剂, 反应 5.0h, 生成 C8-ceramide-1-(2-cyanoethyl)phosphate
    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:
    参考文献:
    名称:
    Synthesis of Sphingomyelin and Ceramide 1-Phosphate from Ceramide without Protection of the Allylic Hydroxyl Group
    摘要:
    DOI:
    10.1021/jo00100a069
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文献信息

  • Synthesis of Sphingomyelin and Ceramide 1-Phosphate from Ceramide without Protection of the Allylic Hydroxyl Group
    作者:Hoe-Sup Byun、Ravi Kumar Erukulla、Robert Bittman
    DOI:10.1021/jo00100a069
    日期:1994.10
  • Ceramide 1-(2-cyanoethyl) phosphate enhances store-operated Ca2+ entry in thyroid FRTL-5 cells
    作者:Kid Törnquist、Cia Ramström、Britt Rudnäs、Karel D Klika、Benoit Dugué、Jeffrey Adams、Robert Zipkin、Kalevi Pihlaja、Michael Pasternack
    DOI:10.1016/s0014-2999(02)02362-2
    日期:2002.10
    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.
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