13,15-di-cis-β-carotene

• 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: 13,15-di-cis-β-carotene
• 英文别名: 1,3,3-trimethyl-2-[(1E,3E,5E,7E,9E,11E,13Z,15Z,17E)-3,7,12,16-tetramethyl-18-(2,6,6-trimethylcyclohexen-1-yl)octadeca-1,3,5,7,9,11,13,15,17-nonaenyl]cyclohexene
• 化学式: C₄₀H₅₆
• 分子量: 536.885
• InChiKey: OENHQHLEOONYIE-LXAKRSFRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  13.5
• 重原子数：
  40
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为产物：
  描述：

  5,14-bis(benzenesulfonyl)-6,13-dibromo-3,7,12,16-tetramethyl-1,18-bis(2,6,6-trimethyl-1-cyclohexenyl)octadeca-1,3,9,15,17-pentaene 在 potassium methanolate 作用下， 以 环己烷 为溶剂， 反应 8.5h， 生成 β-胡萝卜素 、 13,15-di-cis-β-carotene
  参考文献：
  名称：

  [EN] ClO DIALDEHYDE, SYNTHETIC METHOD THEREOF, AND SYNTHETIC METHOD OF BETA-CAROTENE USING THE SAME
  [FR] DIALDEHYDE C10, PROCEDE DE SYNTHESE ASSOCIE, ET PROCEDE DE SYNTHESE DE BETA-CAROTENE ASSOCIE

  摘要：

  揭示了一种新型中间化合物，可在基于磺酮化学的合成中高效利用，以及该化合物的制备方法和利用上述新型化合物制备β-胡萝卜素的实际合成过程。β-胡萝卜素的合成特点是通过含有苯磺酰基和X基团（卤素或醚）的C40化合物的双消除反应来实现，该C40化合物可通过新型C10二醛与两当量的C15烯基磺酮的偶联反应制备，随后通过将得到的C40二醇的官能团转化为相应的卤化物或醚，从而产生完全共轭的聚烯烃链。

  公开号：

  WO2006038764A1

文献信息

• Kinetic model for studying the isomerization of .alpha.- and .beta.-carotene during heating and illumination
  作者：B. H. Chen、T. M. Chen、J. T. Chien

  DOI：10.1021/jf00047a006

  日期：1994.11

  The thermoisomerization and iodine-catalyzed photoisomerization of all-trans-alpha- and all-trans-beta-carotene were kinetically studied using regression models. Carotene samples were heated at varied temperatures or exposed to a 20 W light for varied lengths of time. Isomerization and degradation reactions were monitored using HPLC with diode array detection. Four cis isomers of beta-carotene and three cis isomers of alpha-carotene were separated and detected. The degradations of both carotenes under heating at 150 degrees C or iodine/light treatment may fit the reversible first-order model. 9-cis and 13-cis were the major beta-carotene isomers formed during heating, while 13,15-di-cis was favored during iodine-catalyzed photoisomerization. The formation of 9-cis and 13-cis from all-trans-alpha-carotene was dependent upon the extent of heat or iodine/light treatment, and the latter was formed in greater amount under either treatment.
• [EN] ClO DIALDEHYDE, SYNTHETIC METHOD THEREOF, AND SYNTHETIC METHOD OF BETA-CAROTENE USING THE SAME<br/>[FR] DIALDEHYDE C10, PROCEDE DE SYNTHESE ASSOCIE, ET PROCEDE DE SYNTHESE DE BETA-CAROTENE ASSOCIE
  申请人：KOO SANGHO

  公开号：WO2006038764A1

  公开（公告）日：2006-04-13

  The novel intermediate compound which can be efficiently utilized in the synthesis of carotenoid compounds based on the sulfone chemistry, the preparation method of the same, and the practical synthetic process for preparing β-carotene by the use of the above novel compound are disclosed. The synthesis of β-carotene is characterized by the double elimination reactions of the C40 compound containing both the benzenesulfonyl group and the group X (either halogen or ether), which can be prepared by the coupling reaction of the novel C10 dialdehyde with two equivalents of the C15 allylic sulfone, followed by the functional group transformation of the resulting C40 diol either to the corresponding halide or to the ether, to produce the fully conjugated polyene chain.

  揭示了一种新型中间化合物，可在基于磺酮化学的合成中高效利用，以及该化合物的制备方法和利用上述新型化合物制备β-胡萝卜素的实际合成过程。β-胡萝卜素的合成特点是通过含有苯磺酰基和X基团（卤素或醚）的C40化合物的双消除反应来实现，该C40化合物可通过新型C10二醛与两当量的C15烯基磺酮的偶联反应制备，随后通过将得到的C40二醇的官能团转化为相应的卤化物或醚，从而产生完全共轭的聚烯烃链。