7',8'-dihydro-β,ψ-carotene | 514-90-9

• 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: 7',8'-dihydro-β,ψ-carotene
• 英文别名: all-(E)-β,ψ-carotene；trans-β-zeacarotene；β-zeacarotene；all-E-β-zeacarotene；β-Zeacarotin; all-trans-7',8'-Dihydro-γ-carotin；15,15'-cis-7',8'-Dihydro-γ-carotin；beta-Zeacarotene；2-[(1E,3E,5E,7E,9E,11E,13E,15E,19E)-3,7,12,16,20,24-hexamethylpentacosa-1,3,5,7,9,11,13,15,19,23-decaenyl]-1,3,3-trimethylcyclohexene
• CAS: 514-90-9
• 化学式: C₄₀H₅₈
• 分子量: 538.901
• InChiKey: MICBIPJWKDDGNL-FILYMEKXSA-N

物化性质

• 沸点：
  647.5±35.0 °C(Predicted)
• 密度：
  0.907±0.06 g/cm3(Predicted)
• 熔点：
  96-97 °C

计算性质

• 辛醇/水分配系数(LogP)：
  14.5
• 重原子数：
  40
• 可旋转键数：
  14
• 环数：
  1.0
• 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

• 作为反应物：
  描述：

  7',8'-dihydro-β,ψ-carotene 生成 trans-7,8-dihydro-β-carotene
  参考文献：
  名称：

  The Carotenoid 7, 8-Dihydro-psi end Group can be Cyclized by the Lycopene Cyclases from the Bacterium Erwinia Uredovora and the Higher Plant Capsicum Annuum

  摘要：

  The genes for geranylgeranyl diphosphate synthase (crtE) and phytoene synthase (crtB) from the epiphytic bacterium Erwinia uredovora and the phytoene desaturase gene from the photosynthetic bacterium Rhodobacter capsulatus (Rc‐crtI) were introduced into Escherichia coli, which resulted in the accumulation of the acyclic carotenoid, neurosporene. Further introduction of the lycopene cyclase gene from E. uredovora (crtY) or the higher plant Capsicum annuum (Icy) resulted in the production of a bicyclic carotenoid, 7,8‐dihydro‐β‐carotene, via monocyclic β‐zeacarotene. ζ‐Carotene was also found to be cyclized to bicyclic 7,8,7′,8′‐tetrahydro‐β‐carotene by the Erwinia cyclase. These results indicate that both lycopene cyclases can cyclize a 7,8‐dihydro‐ψ end group to a 7,8‐dihydro‐β end group, in addition to the usual cyclization of the ψ end group to the β end group. Furthermore, β‐carotene hydroxylase from Enwnia (CrtZ) was able to add a hydroxyl group to the 7,8‐dihydro‐β end group and the β end group.

  DOI：

  10.1111/j.1432-1033.1996.0291t.x
• 作为产物：
  描述：

  反,反-法呢基溴 在 sodium methylate 作用下， 以 N,N-二甲基甲酰胺 、 苯 为溶剂， 生成 7',8'-dihydro-β,ψ-carotene
  参考文献：
  名称：

  类胡萝卜素中的合成物。18.米特隆。合成von 7'，8'-Dihydro-γ-carotin（β-Zeacarotin）和3'，4'-Dehydro-γ-carotin（Torulin）

  摘要：

  通过15,15'-脱氢-apo-12'-胡萝卜素（C 35）与法呢基三苯基溴化a的WITTIG反应可以完成7'，8'-二氢-γ-胡萝卜素（β-玉米ze烯）的全合成。。

  DOI：

  10.1002/hlca.19610440415

文献信息

• Process for the preparation of zeacarotenes
  申请人：DSM IP Assets B.V.

  公开号：EP2130833A1

  公开（公告）日：2009-12-09

  The present invention relates to process for the preparation of zeacarotenes and to intermediates in the process for the preparation of zeacarotenes.

  本发明涉及一种制备玉米胡萝卜素的方法，以及在制备玉米胡萝卜素过程中的中间体。
• PROCESS FOR THE PREPARATION OF ZEACAROTENES
  申请人：PUHL Andreas

  公开号：US20090312587A1

  公开（公告）日：2009-12-17

  The present invention relates to process for the preparation of zeacarotenes and to intermediates in the process for the preparation of zeacarotenes.

  本发明涉及制备玉米黄素的方法以及制备玉米黄素的中间体的方法。
• Synthesen in der Carotinoid-Reihe. 18. Mitteilung. Synthese von 7′, 8′-Dihydro-γ-carotin (β-Zeacarotin) und 3′,4′-Dehydro-γ-carotin (Torulin)
  作者：R. Rüegg、U. Schwieter、G. Ryser、P. Schudel、O. Isler

  DOI：10.1002/hlca.19610440415

  日期：——

  The total synthesis of 7′,8′-dihydro-γ-carotene (β-zeacarotene) has been accomplished by a WITTIG reaction of 15,15′-dehydro-apo-12′-carotenal(C35) with farnesyltriphenyl-phosphonium bromide.

  通过15,15'-脱氢-apo-12'-胡萝卜素（C 35）与法呢基三苯基溴化a的WITTIG反应可以完成7'，8'-二氢-γ-胡萝卜素（β-玉米ze烯）的全合成。。
• The Carotenoid 7, 8-Dihydro-psi end Group can be Cyclized by the Lycopene Cyclases from the Bacterium Erwinia Uredovora and the Higher Plant Capsicum Annuum
  作者：Shinichi Takaichi、Gerhard Sandmann、Georg Schnurr、Yoshiko Satomi、Akashi Suzuki、Norihiko Misawa

  DOI：10.1111/j.1432-1033.1996.0291t.x

  日期：1996.10

  The genes for geranylgeranyl diphosphate synthase (crtE) and phytoene synthase (crtB) from the epiphytic bacterium Erwinia uredovora and the phytoene desaturase gene from the photosynthetic bacterium Rhodobacter capsulatus (Rc‐crtI) were introduced into Escherichia coli, which resulted in the accumulation of the acyclic carotenoid, neurosporene. Further introduction of the lycopene cyclase gene from E. uredovora (crtY) or the higher plant Capsicum annuum (Icy) resulted in the production of a bicyclic carotenoid, 7,8‐dihydro‐β‐carotene, via monocyclic β‐zeacarotene. ζ‐Carotene was also found to be cyclized to bicyclic 7,8,7′,8′‐tetrahydro‐β‐carotene by the Erwinia cyclase. These results indicate that both lycopene cyclases can cyclize a 7,8‐dihydro‐ψ end group to a 7,8‐dihydro‐β end group, in addition to the usual cyclization of the ψ end group to the β end group. Furthermore, β‐carotene hydroxylase from Enwnia (CrtZ) was able to add a hydroxyl group to the 7,8‐dihydro‐β end group and the β end group.