GRP-retinal | 121974-71-8

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: GRP-retinal
• 英文别名: 1-{[3,7-dimethyl-9t-(2,6,6-trimethyl-cyclohex-1-enyl)-nona-2t,4t,6t,8-tetraenylidenehydrazinocarbonyl]-methyl}-pyridinium; chloride；1-{[3,7-Dimethyl-9t-(2,6,6-trimethyl-cyclohex-1-enyl)-nona-2t,4t,6t,8-tetraenylidencarbazoyl]-methyl}-pyridinium; Chlorid
• CAS: 121974-71-8
• 化学式: C₂₇H₃₆N₃O*Cl
• 分子量: 454.055
• InChiKey: YRABWMAJUXZIJO-HLIAMUNNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.61
• 重原子数：
  32.0
• 可旋转键数：
  8.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  45.34
• 氢给体数：
  1.0
• 氢受体数：
  2.0

反应信息

• 作为产物：
  描述：

  视黄醛 、 N-氯-N-吡啶基乙酰肼 在 乙醇 作用下， 生成 GRP-retinal
  参考文献：
  名称：

  Quaternary ammonium acyl derivatives of vitamin a aldehyde hydrazones

  摘要：

  公开号：

  US02891068A1

文献信息

• Structural Requirements for Efficient Cellular Photoprotection by Carotenoid Derivatives¶†
  作者：Jeffrey R. Kanofsky、Paul D. Sima

  DOI：10.1562/2003-12-02-ra-017.1

  日期：——

  We have synthesized five carotenoid derivatives: (1) Girard's reagent P (GRP)-retinal from GRP and retinal; (2) GRP-carotenal from GRP and beta-apo-8'-carotenal; (3) Girard's reagent T (GRT)-carotenal from GRT and beta-apo-8'-carotenal; (4) (GRP)2-canthaxanthin from 2 mol of GRP and 1 mot of canthaxanthin; and (5) dansyl hydrazine (DH)-carotenal from DH and beta-apo-8'-carotenal. The first three derivatives are cations, whereas the fourth is a dication and the fifth is a weak base. Using K562 cells, we compared the subcellular distribution of the synthetic carotenoid derivatives with two uncharged natural carotenoids, beta-carotene and beta-apo-8'-carotenal. The two natural carotenoids were present mainly within the cell membranes. The synthetic carotenoid derivatives were more broadly distributed among the cell organelles. The positively charged derivatives had relatively high concentrations in mitochondria, whereas DH-carotenal had a relatively high concentration in lysosomes. We also measured the amount of photoprotection provided by the synthetic and natural carotenoids for K562 cells labeled with a photosensitizer (hypericin, protoporphyrin IX or cis-di[4-sulfonatophenyl]diphenylporphine). In this model system, only carotenoid derivatives with a permanent positive charge provided significant photoprotection. Neither the two natural carotenoids nor DH-carotenal were effective photoprotectors.
• Miki; Hara, Chemical and pharmaceutical bulletin, 1962, vol. 10, p. 922,923
  作者：Miki、Hara

  DOI：——

  日期：——