8'-apo-β-carotenol pentynoate | 1374137-41-3

• 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: 8'-apo-β-carotenol pentynoate
• 英文别名: 8'-β-apocarotenol pent-4-ynoate；[(2E,4E,6E,8E,10E,12E,14E,16E)-2,6,11,15-tetramethyl-17-(2,6,6-trimethylcyclohexen-1-yl)heptadeca-2,4,6,8,10,12,14,16-octaenyl] pent-4-ynoate
• CAS: 1374137-41-3
• 化学式: C₃₅H₄₆O₂
• 分子量: 498.749
• InChiKey: DCHAPXWBVNABQD-PULBWXAFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.6
• 重原子数：
  37
• 可旋转键数：
  13
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  D-glucopyranosyl azide 、 8'-apo-β-carotenol pentynoate 在 bis-triphenylphosphano-copper(I) butyrate 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 以72%的产率得到8'-(1-(β-D-glucopyranosyl)-1,2,3-triazol-4-yl)propanoyloxy-8'-apo-β-carotene
  参考文献：
  名称：

  Synthesis of carotenoid-monosaccharide conjugates via azide–alkyne click-reaction

  摘要：

  Carotenoid pentynoates were coupled to protected and unprotected sugar azides via an azide-alkyne click-reaction using bis-triphenylphosphano-copper(I)-butyrate (C3H7COOCu(PPh3)(2)) complex. Protected sugars delivered the conjugates with excellent yields, whereas with unprotected ones amphipathic carotenoid-sugar derivatives were obtained in good or moderate yields in a simple way. (C )2016 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2016.12.035
• 作为产物：
  描述：

  β-阿朴胡萝卜素醛 在 4-二甲氨基吡啶 、 sodium tetrahydroborate 、 N,N'-二环己基碳二亚胺 作用下， 以 乙醇 、 二氯甲烷 、 甲苯 为溶剂， 反应 13.0h， 生成 8'-apo-β-carotenol pentynoate
  参考文献：
  名称：

  Synthesis of carotenoid-monosaccharide conjugates via azide–alkyne click-reaction

  摘要：

  Carotenoid pentynoates were coupled to protected and unprotected sugar azides via an azide-alkyne click-reaction using bis-triphenylphosphano-copper(I)-butyrate (C3H7COOCu(PPh3)(2)) complex. Protected sugars delivered the conjugates with excellent yields, whereas with unprotected ones amphipathic carotenoid-sugar derivatives were obtained in good or moderate yields in a simple way. (C )2016 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2016.12.035

文献信息

• Study on the Synthesis, Antioxidant Properties, and Self-Assembly of Carotenoid–Flavonoid Conjugates
  作者：Ildikó Línzembold、Dalma Czett、Katalin Böddi、Tibor Kurtán、Sándor Balázs Király、Gergely Gulyás-Fekete、Anikó Takátsy、Tamás Lóránd、József Deli、Attila Agócs、Veronika Nagy

  DOI：10.3390/molecules25030636

  日期：——

  capsanthin afforded carotenoid–flavonoid conjugates. The trolox-equivalent antioxidant capacity against ABTS•+ radical cation and self-assembly of the final products were examined. The 1:1 flavonoid–carotenoid hybrids generally showed higher antioxidant activity than their parent flavonoids but lower than that of the corresponding carotenoids. The diflavonoid hybrids of zeaxanthin and capsanthin, however

  类黄酮和类胡萝卜素具有有益的生理作用，例如高抗氧化能力、抗癌、免疫调节和抗炎特性，以及对紫外线的保护作用。实现了疏水性类胡萝卜素与亲水性黄酮类化合物（例如大豆黄酮和白杨素）的共价偶联，产生了新的两亲结构。黄豆苷元和白杨素的 7-叠氮己基醚通过五个步骤制备，并且它们的叠氮-炔[4+2]环加成与 8'-apo-β-胡萝卜素、玉米黄质和辣椒红的戊烯酸盐发生类胡萝卜素-类黄酮缀合物。对ABTS•+自由基阳离子的抗氧化能力和最终产品的自组装进行了检测。 1:1 类黄酮-类胡萝卜素杂合体通常表现出比其母体类黄酮更高的抗氧化活性，但低于相应的类胡萝卜素。然而，人们发现玉米黄质和辣椒红的二黄酮混合物在抗氧化能力方面表现出协同增强作用。玉米黄质-类黄酮缀合物的 ECD（电子圆二色性）和 UV-vis 分析表明，根据所用非质子极性溶剂的溶剂比例和类型，它们在丙酮/水和四氢呋喃/水混合物中形成不同的光学活性 J
• Introduction of click chemistry to carotenoids
  作者：Magdolna Háda、Veronika Nagy、Anikó Takátsy、József Deli、Jan Hait、Attila Agócs

  DOI：10.1016/j.tetlet.2012.03.027

  日期：2012.5

  We describe the synthesis of carotenoid derivatives via the azide-alkyne click reaction and optimize the conditions for these sensitive molecules. After finding the mildest conditions possible for the reaction we were able to use the click reaction for the synthesis of PEG-carotenoid conjugates starting from carotenoid pentynoates and PEG azides. (C) 2012 Elsevier Ltd. All rights reserved.