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.