3-OH-β-apo-13-carotenone | 1191889-26-5

• 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: 3-OH-β-apo-13-carotenone
• 英文别名: (3E,5E,7E)-8-(4-hydroxy-2,6,6-trimethylcyclohexen-1-yl)-6-methylocta-3,5,7-trien-2-one
• CAS: 1191889-26-5
• 化学式: C₁₈H₂₆O₂
• 分子量: 274.403
• InChiKey: JLNMEHQAHDSEEE-HYPKMOEDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  (2E,4E,6E,8E,10E,12E,14E)-15-(4-hydroxy-2,6,6-trimethylcyclohex-1-en-1-yl)-4,9,13-trimethylpentadeca-2,4,6,8,10,12,14-heptaenal 在 Mycobacterium tuberculosis carotenoid cleavage oxygenase 作用下， 生成 3-OH-β-apo-13-carotenone 、 (3RS,all-E)-hydroxyretinal
  参考文献：
  名称：

  结核分枝杆菌ORF Rv0654编码类胡萝卜素加氧酶，介导常规和芳香类胡萝卜素的中央和偏心裂解

  摘要：

  结核分枝杆菌是结核的病原体，被认为缺乏类胡萝卜素，类胡萝卜素是广泛存在的色素，具有重要的功能，可作为自由基清除剂和类胡萝卜素的来源。在哺乳动物中，包括视黄酸在内的类胡萝卜素的合成是由β-胡萝卜素裂解加氧酶I和II分别催化β-胡萝卜素的中心裂解或偏心裂解引起的。在结核分枝杆菌ORF Rv0654编码推定的类胡萝卜素氧保守在其它分枝杆菌。在本研究中，我们研究了相应的酶，在这里称为结核分枝杆菌类胡萝卜素裂解加氧酶（MtCCO）。使用异源表达和纯化的蛋白质，我们表明MtCCO在体外可转化几种类胡萝卜素和类胡萝卜素。此外，产品鉴定表明，与其他类胡萝卜素加氧酶不同，MtCCO裂解中央C15-C15'和C13-C14位置的偏心双键，从而导致视网膜（C 20），β-​​载脂蛋白14 '-胡萝卜素（C 22）和β-载脂蛋白13-胡萝卜素（C 18）和β-胡萝卜素的相应羟基化产物，以及玉米黄质和叶黄素的相应羟基化产物。此外，该酶还切割3

  DOI：

  10.1111/j.1742-4658.2010.07873.x

文献信息

• Process for Synthesis of (3R,3'R,6'R)-Lutein and its Stereoisomers
  申请人：Khachik Frederick

  公开号：US20090264681A1

  公开（公告）日：2009-10-22

  (3R,3′R,6′R)-Lutein and (3R,3′R)-zeaxanthin are two dietary carotenoids that are present in most fruits and vegetables commonly consumed in the US. These carotenoids accumulate in the human plasma, major organs, and ocular tissues. In the past decade, numerous epidemiological and experimental studies have shown that lutein and zeaxanthin play an important role in the prevention of age-related macular degeneration (AMD) that is the leading cause of blindness in the U.S. and Western World. The invention provides a process for the synthesis of (3R,3′R,6′R)-lutein and its stereoisomers from commercially available (rac)-α-ionone by a C 15 +C 10 +C 15 coupling strategy. In addition, the present invention also provides access to the precursors of optically active carotenoids with 3-hydroxy-ε-end group that are otherwise difficult to synthesize. The process developed for the synthesis of lutein and its stereoisomers is straightforward and has potential for commercialization.

  (3R,3′R,6′R)-叶黄素和(3R,3′R)-玉米黄质是两种膳食类胡萝卜素，广泛存在于美国常见的大多数水果和蔬菜中。这些类胡萝卜素在人类血浆、主要器官和眼部组织中积累。在过去的十年里，许多流行病学和实验研究表明，叶黄素和玉米黄质在预防年龄相关性黄斑变性（AMD）中起着重要作用，这是美国和西方世界导致失明的主要原因。本发明提供了一种从商业可获得的（rac）-α-离子酮通过C15+C10+C15偶联策略合成(3R,3′R,6′R)-叶黄素及其立体异构体的方法。此外，本发明还提供了一种获得具有3-羟基-ε-末端基团的光学活性类胡萝卜素前体的方法，否则这些类胡萝卜素前体很难合成。用于合成叶黄素及其立体异构体的方法是简单明了的，并具有商业化潜力。
• Plant growth promoters and methods of using them
  申请人：KING ABDULLAH UNIVERSITY OF SCIENCE AND TECHNOLOGY

  公开号：US10888090B2

  公开（公告）日：2021-01-12

  New plant growth regulators, including compounds and compositions, and methods of use including for promoting root growth. The compounds are carotenoid oxidation products, and a preferred example is 3-OH-β-apo-13-Carotenone. A method comprising promoting the growth of at least one plant with use of an effective amount of at least one composition comprising an effective amount of at least one compound which is represented by A-B-C, wherein B is a bivalent polyene moiety, A is a monovalent moiety linked to B by a six-membered carbon ring, wherein the ring has at least one substituent linked to the ring by an oxygen atom, and C is a monovalent moiety linked to B by a carbonyl group. Synergistic effects can be used with combinations of compounds.

  新型植物生长调节剂，包括用于促进根系生长的化合物和组合物以及使用方法。这些化合物是类胡萝卜素的氧化产物，一个优选的例子是 3-OH-β-apo-13-Carotenone 。一种方法，包括使用有效量的至少一种组合物促进至少一种植物的生长，该组合物包含有效量的至少一种化合物，该化合物由 A-B-C 表示，其中 B 是二价多烯分子，A 是通过六元碳环与 B 连接的一价分子，其中该环具有至少一个通过氧原子与该环连接的取代基，C 是通过羰基与 B 连接的一价分子。化合物组合可产生协同效应。
• PLANT GROWTH PROMOTERS AND METHODS OF USING THEM
  申请人：KING ABDULLAH UNIVERSITY OF SCIENCE AND TECHNOLOGY

  公开号：US20180184651A1

  公开（公告）日：2018-07-05

  New plant growth regulators, including compounds and compositions, and methods of use including for promoting root growth. The compounds are carotenoid oxidation products, and a preferred example is 3-OH-β-apo-13-Carotenone. A method comprising promoting the growth of at least one plant with use of an effective amount of at least one composition comprising an effective amount of at least one compound which is represented by A-B-C, wherein B is a bivalent polyene moiety, A is a monovalent moiety linked to B by a six-membered carbon ring, wherein the ring has at least one substituent linked to the ring by an oxygen atom, and C is a monovalent moiety linked to B by a carbonyl group. Synergistic effects can be used with combinations of compounds.
• [EN] PLANT GROWTH PROMOTERS AND METHODS OF USING THEM<br/>[FR] PROMOTEURS DE CROISSANCE VÉGÉTALE ET LEURS PROCÉDÉS D'UTILISATION
  申请人：UNIV KING ABDULLAH SCI & TECH

  公开号：WO2017001927A1

  公开（公告）日：2017-01-05

  New plant growth regulators, including compounds and compositions, and methods of use including for promoting root growth. The compounds are carotenoid oxidation products, and a preferred example is 3-OH--β-apo-13-Carotenone. A method comprising promoting the growth of at least one plant with use of an effective amount of at least one composition comprising an effective amount of at least one compound which is represented by A-B-C, wherein B is a bivalent polyene moiety, A is a monovalent moiety linked to B by a six-membered carbon ring, wherein the ring has at least one substituent linked to the ring by an oxygen atom, and C is a monovalent moiety linked to B by a carbonyl group. Synergistic effects can be used with combinations of compounds.
• The Mycobacterium tuberculosis ORF Rv0654 encodes a carotenoid oxygenase mediating central and excentric cleavage of conventional and aromatic carotenoids
  作者：Daniel Scherzinger、Erdmann Scheffer、Cornelia Bär、Hansgeorg Ernst、Salim Al-Babili

  DOI：10.1111/j.1742-4658.2010.07873.x

  日期：2010.11

  acid, is initiated by the β‐carotene cleavage oxygenases I and II catalyzing either a central or an excentric cleavage of β‐carotene, respectively. The M. tuberculosis ORF Rv0654 codes for a putative carotenoid oxygenase conserved in other mycobacteria. In the present study, we investigated the corresponding enzyme, here named M. tuberculosis carotenoid cleavage oxygenase (MtCCO). Using heterologously

  结核分枝杆菌是结核的病原体，被认为缺乏类胡萝卜素，类胡萝卜素是广泛存在的色素，具有重要的功能，可作为自由基清除剂和类胡萝卜素的来源。在哺乳动物中，包括视黄酸在内的类胡萝卜素的合成是由β-胡萝卜素裂解加氧酶I和II分别催化β-胡萝卜素的中心裂解或偏心裂解引起的。在结核分枝杆菌ORF Rv0654编码推定的类胡萝卜素氧保守在其它分枝杆菌。在本研究中，我们研究了相应的酶，在这里称为结核分枝杆菌类胡萝卜素裂解加氧酶（MtCCO）。使用异源表达和纯化的蛋白质，我们表明MtCCO在体外可转化几种类胡萝卜素和类胡萝卜素。此外，产品鉴定表明，与其他类胡萝卜素加氧酶不同，MtCCO裂解中央C15-C15'和C13-C14位置的偏心双键，从而导致视网膜（C 20），β-​​载脂蛋白14 '-胡萝卜素（C 22）和β-载脂蛋白13-胡萝卜素（C 18）和β-胡萝卜素的相应羟基化产物，以及玉米黄质和叶黄素的相应羟基化产物。此外，该酶还切割3