crocin-4 | 55750-86-2

• 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: crocin-4
• 英文别名: Crocin-4；1-O-methyl 16-O-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl] (2E,4E,6E,8E,10E,12E,14E)-2,6,11,15-tetramethylhexadeca-2,4,6,8,10,12,14-heptaenedioate
• CAS: 55750-86-2
• 化学式: C₂₇H₃₆O₉
• 分子量: 504.577
• InChiKey: ATQIQIBBBWQWOT-OMNKTTJZSA-N

物化性质

• 沸点：
  699.6±55.0 °C(Predicted)
• 密度：
  1.23±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  36
• 可旋转键数：
  12
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  143
• 氢给体数：
  4
• 氢受体数：
  9

制备方法与用途

藏红花中的类胡萝卜素成分藏红花苷-4是一种有效的渗透大脑的抗氧化剂。它能抑制Aβ纤维在大脑中的聚集及其伴随的沉积，并且可应用于阿尔茨海默病的研究。此外，藏红花苷-4还表现出抗肿瘤和抗炎活性[1][2][3]。

反应信息

• 作为反应物：
  描述：

  crocin-4 在 水 、 sodium hydroxide 作用下， 反应 4.0h， 生成 藏红花酸
  参考文献：
  名称：

  Trans-crocin 4 is not hydrolyzed to crocetin following i.p. administration in mice, while it shows penetration through the blood brain barrier

  摘要：

  A novel, fit-for-purpose, highly sensitive, analytical UPLC-PDA methodology was developed and fully validated, according to ICH, FDA and EMA guidelines, for the rapid and accurate quantification of trans-crocin 4 (TC4) and crocetin (CRC) in mice plasma and brain after Lp. administration. A PDA based methodology shows a wider applicability as it is cost effective and can be easily and seamlessly adopted by the pharma industry. The separation of the analytes was performed on a C18 Hypersil Gold column with 2.5 min run time, employing the internal standard (ISTD) methodology. The two methods were successfully applied for the determination of CRC and TC4 in mouse plasma and brain after Lp. administration of TC4 (50 mg/kg) in a time range of 0-240 min. Due to the selection of i.p. administration route, the first-pass metabolism and/or gastric hydrolysis were bypassed, a fact that enhanced the bioavailability of TC4. Furthermore, TC4 was found to be capable of crossing the Blood Brain Barrier (BBB) and build up levels in the mouse brain, regardless of its highly hydrophilic character. CRC was not detected in any plasma or brain sample, although it has been reported that TC4 quickly hydrolyzes to CRC after p.o. administration. Therefore i.p. administration could be used in the case of TC4 for the accurate determination of its biological role. Overall, the developed methodology offers important information about the bioavailability of TC4 in mouse plasma and for the first time, demonstrates the ability of TC4 to penetrate the BBB and localize inside the brain.

  DOI：

  10.1016/j.fitote.2018.06.012