4',5'-didehydro-4,5'-retro-β,β-carotene | 3297-24-3

• 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: 4',5'-didehydro-4,5'-retro-β,β-carotene
• 英文别名: isocarotene；all-trans-retro-dehydrocarotene；all-trans-retro-Dehydrocarotin；All-trans-retrodehydrocarotin；Dehydro-retro-carotin；Dehydro-retrocaroten
• CAS: 3297-24-3；16962-72-4；71629-79-3
• 化学式: C₄₀H₅₄
• 分子量: 534.869
• InChiKey: RRMHVWZOQSOJEK-FXTZBFNASA-N

物化性质

• 熔点：
  180-181 °C (decomp)
• 沸点：
  656.7±22.0 °C(Predicted)
• 密度：
  0.949±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  12.38
• 重原子数：
  40.0
• 可旋转键数：
  9.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  0.0
• 氢给体数：
  0.0
• 氢受体数：
  0.0

反应信息

• 作为反应物：
  描述：

  4',5'-didehydro-4,5'-retro-β,β-carotene 生成 斑蝥黄
  参考文献：
  名称：

  合成含氧类胡萝卜素的新方法。

  摘要：

  AbstractSix keto carotenoids (4, 5, 6, 11, 12, and 22) were synthesized from intermediates which were prepared from the condensation products of mesityl oxide and acetoacetic ester. Compounds 4 and 22 can serve as precursors for zeaxanthin, while 5 can be used as an intermediate for xanthophyll. Echinenone and canthaxanthin were prepared by a new approach from vitamin A. Two new types of keto carotenoids with the keto functions incorporated into the unsaturated chain were prepared.

  DOI：

  10.1002/hlca.19700530513
• 作为产物：
  描述：

  海胆烯酮 在 盐酸 、 sodium tetrahydroborate 作用下， 以 氯仿 为溶剂， 生成 4',5'-didehydro-4,5'-retro-β,β-carotene
  参考文献：
  名称：

  Structure Elucidation of Polyene Systems with Extensive Charge DelocalizationCarbocations from Allylic Carotenols

  摘要：

  The structures of two diastereomeric cations, readily prepared from beta,beta-caroten-4-ol (1) by treatment with trifluoroacetic acid, have been determined by NIR and NMR spectroscopy, resulting in the complete structure elucidation of the most extensively delocalized carbocations so far described. Higher partial charge was observed toward the center of the polyene chain (larger filled red circles). Bond reversion occurs in the central region of the molecule.

  DOI：

  10.1021/ol034987w

文献信息

• The Hydrolytic Cleavage Products of Boron Trifluoride Complexes of β-Carotene, Some Dehydrogenated Carotenes and Anhydrovitamin A₁
  作者：F. J. Petracek、L. Zechmeister

  DOI：10.1021/ja01594a057

  日期：1956.7
• Conversion of Dehydro-β-carotene, via its Boron Trifluoride Complex, into an Isomer of Cryptoxanthin¹
  作者：L. Wallcave、L. Zechmeister

  DOI：10.1021/ja01114a030

  日期：1953.9