β-Carotin | 6811-73-0

• 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: β-Carotin
• CAS: 6811-73-0
• 化学式: C₄₀H₅₆
• 分子量: 536.885
• InChiKey: OENHQHLEOONYIE-VSUJAWCVSA-N

物化性质

• 熔点：
  166 °C
• 沸点：
  654.7±22.0 °C(Predicted)
• 密度：
  0.941±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  12.61
• 重原子数：
  40.0
• 可旋转键数：
  10.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  0.0
• 氢给体数：
  0.0
• 氢受体数：
  0.0

安全信息

• 海关编码：
  2915900090

反应信息

• 作为反应物：
  描述：

  β-Carotin 以 氘代苯 为溶剂， 生成 β-胡萝卜素
  参考文献：
  名称：

  Doering, W. Von E.; Sotiriou-Leventis, Chariklia; Roth, Journal of the American Chemical Society, 1995, vol. 117, # 10, p. 2747 - 2757

  摘要：

  DOI：
• 作为产物：
  描述：

  β-胡萝卜素 以 氘代苯 为溶剂， 生成 β-Carotin
  参考文献：
  名称：

  Doering, W. Von E.; Sotiriou-Leventis, Chariklia; Roth, Journal of the American Chemical Society, 1995, vol. 117, # 10, p. 2747 - 2757

  摘要：

  DOI：

文献信息

• Unique properties of the 11-cis and 11,11′-di-cis isomers of β-carotene as revealed by electronic absorption, resonance Raman and 1H and 13C NMR spectroscopy and by HPLC analysis of their thermal isomerization
  作者：Ying Hu、Hideki Hashimoto、Gérard Moine、Urs Hengartner、Yasushi Koyama

  DOI：10.1039/a703763e

  日期：——

  of other isomers. (2) The frequencies of the CC stretching Raman lines of these isomers are the same as that of the all-trans isomer, and do not follow the general trend of high-frequency shifts found in other mono-cis and di-cis isomers. The Raman lines due to the out-of-plane C–H wagging and methyl rocking modes appear in the 11,11′-di-cis isomer. (3) The 1H chemical shifts of these isomers indicate

  与β-胡萝卜素的全反式和其他顺式异构体相比，11-顺式和11,11'-二顺式异构体表现出以下独特的性质。（1）B的波长ü + â†甲克-（0-0）这两种异构体的吸收是类似于清一色的反式异构体，并且不按它的蓝移的一般规则在发现其他单顺和二顺式异构体。它们的消光系数明显低于其他异构体。（2）这些异构体的C C拉伸拉曼线的频率与全反式的频率相同异构体，而没有按照高频率偏移的其他单中发现大势顺和二顺式异构体。由于11：11'-顺式异构体出现面外CH摆动和甲基摇摆模式而产生的拉曼线。（3）这些异构体的1 H化学位移表明甲基和烯属1 H原子在11-顺式弯曲的凹面之间存在严重的空间相互作用，而它们的13 C化学位移表明顺式C11 C12发生扭曲和极化键。（4）这些异构体的热异构化速率远高于15-顺式异构体，即先前已知的最不稳定的异构体。
• Henry; Catignani; Schwartz, Journal of the American Oil Chemists' Society, 1998, vol. 75, # 7, p. 823 - 829
  作者：Henry、Catignani、Schwartz

  DOI：——

  日期：——
• Chlorophyll a-sensitized trans-cis photoisomerization of all-trans-.beta.-carotene
  作者：Niels Henrik Jensen、Anne B. Nielsen、Robert Wilbrandt

  DOI：10.1021/ja00386a048

  日期：1982.11
• Triplet-sensitized and thermal isomerization of all-trans, 7-cis, 9-cis, 13-cis and 15-cis isomers of .beta.-carotene: configurational dependence of the quantum yield of isomerization via the T1 state
  作者：Michitaka Kuki、Yasushi Koyama、Hiroyoshi Nagae

  DOI：10.1021/j100172a016

  日期：1991.9

  The products of triplet-sensitized photoisomerization (excitation at 337 nm of the sensitizer, anthracene) and thermal isomerization of beta-carotene in n-hexane, starting from the all-trans, 7-cis, 9-cis, 13-cis, and 15-cis isomers, were analyzed by HPLC. Direct photoisomerization (excitation at 488 and 337 nm) was also examined for comparison. Three different isomerization patterns were found in both triplet-sensitized and thermal isomerization: pattern A, cis to trans isomerization around each cis bond; pattern B, trans to cis isomerization in the central part of the conjugated chain; and pattern C, cis to another cis isomerization. In the T1 state, the pattern A isomerization was predominant even for the peripheral-cis (7-cis and 9-cis) isomers and its efficiency was extremely high for the central-cis (13-cis and 15-cis) isomers. In the S0 state, the pattern B isomerization, instead, was predominant for the peripheral-cis isomers, and the pattern A isomerization was predominant only for the central-cis isomers. The quantum yields of triplet-sensitized isomerization (decrease of the starting isomer per triplet species generated) were determined to be as follows: all-trans, 0.04; 7-cis, 0.12; 9-cis, 0.15; 13-cis, 0.87; and 15-cis, 0.98. In direct photoisomerization, the quantum yield of isomerization at 488-nm (337 nm) excitation was 4 (3) orders of magnitude lower than the above values, the relative values among the isomers being similar to the above. Further, the overall isomerization patterns of direct photoexcitation were similar to those of triplet-sensitized isomerization, supporting the idea that isomerization takes place via the T1 state even in the case of direct photoexcitation. Carbon-carbon pi-bond orders of model polyenes in the T1 and S0 states were calculated by using the Pariser-Parr-Pople CI theory; bond lengths were optimized by using a bond order-bond length relationship. Isomerization characteristics in the T1 and S0 states observed were discussed based on the results of the calculations.