apo-8,12'-carotendial

• 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: apo-8,12'-carotendial
• 英文别名: 10',10-diapocarotene-10',10-dial；diapo-8',12-lycopendial；12',8-Diapocarotene-12',8-dial；(2E,4E,6E,8E,10E)-2,6,11-trimethyldodeca-2,4,6,8,10-pentaenedial
• 化学式: C₁₅H₁₈O₂
• 分子量: 230.307
• InChiKey: SMBNPLHCLLYLPU-LWDLGRCGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  17
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  34.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  apo-8,12'-carotendial 在 potassium methanolate 、 二甲基亚砜 作用下， 以 甲醇 为溶剂， 生成
  参考文献：
  名称：

  Electron uptake by classical electron donators: astaxanthin and carotenoid aldehydes

  摘要：

  Carotenoids are prime examples for antioxidants: they donate electrons to noxious radicals. Density functional calculations anticipate the possibility of electron uptake by carotenoids. This prediction has been confirmed experimentally: carbonyl carotenoids, including the super-antioxidant astaxanthin, easily take up electrons and react as antireductants. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2012.06.029
• 作为产物：
  描述：

  2,7-二甲基-2,4,6-辛三烯二醛 在 对甲苯磺酸 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 0.83h， 生成 apo-8,12'-carotendial
  参考文献：
  名称：

  Electron uptake by classical electron donators: astaxanthin and carotenoid aldehydes

  摘要：

  Carotenoids are prime examples for antioxidants: they donate electrons to noxious radicals. Density functional calculations anticipate the possibility of electron uptake by carotenoids. This prediction has been confirmed experimentally: carbonyl carotenoids, including the super-antioxidant astaxanthin, easily take up electrons and react as antireductants. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2012.06.029

文献信息

• Cleavage Products of Lycopene Produced by in Vitro Oxidations:  Characterization and Mechanisms of Formation
  作者：Catherine Caris-Veyrat、Antje Schmid、Michel Carail、Volker Böhm

  DOI：10.1021/jf034735+

  日期：2003.12.1

  The aim of this study was to produce in vitro oxidation products of lycopene, which could be possible in vivo metabolites. An oxidation of lycopene with potassium permanganate gave a range of lycopene degradation compounds resulting from the oxidative cleavage of one or two carbon-carbon double bonds. Eleven apo-lycopenals/ones and six apo-carotendials were obtained and tentatively characterized by

  这项研究的目的是生产番茄红素的体外氧化产物，这可能是体内代谢产物。番茄红素用高锰酸钾的氧化产生了一系列番茄红素降解化合物，这些化合物是由一个或两个碳-碳双键的氧化裂解产生的。获得了十一种载脂蛋白低碳脂蛋白/单糖和六种载脂蛋白-胡萝卜素，并通过HPLC-DAD-MS进行了初步鉴定。首次分离了载脂蛋白-11-冰醛和载脂蛋白8,6'-胡萝卜素，并通过（1）H NMR进行了表征。番茄红素受到金属卟啉催化的大气氧氧化，该金属卟啉是细胞色素P450酶活性中心的模型系统。形成（E）-番茄红素的（Z）-异构体，一氧化物和裂解化合物。我们提出了该系统氧化番茄红素的机理。
• [EN] REGULATING PLANT GROWTH USING A DIAPOCAROTENOID<br/>[FR] RÉGULATION DE LA CROISSANCE DE PLANTES AU MOYEN D'UN DIAPOCAROTÉNOÏDE
  申请人：UNIV KING ABDULLAH SCI & TECH

  公开号：WO2019180638A1

  公开（公告）日：2019-09-26

  Embodiments of the present disclosure describe diapocarotenoid plant growth regulators represented by formula (I): R-A-R (I) or a precursor, salt, solvate, stereoisomer or polymorph thereof; wherein R is a monovalent carbonyl moiety selected from the group consisting of aldehydes, ethers, diethers, carboxylic acids, alcohols, and ester carboxylates and A is a bivalent polyene represented by the bivalent moiety -(CRa=CRb)x- wherein x is the number of double bonds in polyene moiety A, and Ra and Rb are, independently, hydrogen, a hydrocarbon, or an alkoxy group, and composition of the diapocarotenoid plant growth regulators in an agronomically acceptable carrier. Methods of regulating plant growth including promoting root development, increasing nutrient uptake, enhancing resistance to abiotic stress factors, invigorating plant growth, increasing plant yield, and increasing plant biomass by applying at least one diapocarotenoid plant growth regulator to a seed, plant propagation material, plant or plant growth medium are also described.

  本公开的实施例描述了由公式（I）表示的二缩醛类胡萝卜素植物生长调节剂：R-A-R（I）或其前体，盐，溶剂，立体异构体或多形体；其中R是单价羰基基团，所选自醛，醚，二醚，羧酸，醇和酯羧酸酯的群体，而A是由双价多烯表示的双价基团，该双价基团由-(CRa=CRb)x-表示，其中x是多烯基团A中双键的数量，而Ra和Rb是独立的氢，烃基或烷氧基。将二缩醛类胡萝卜素植物生长调节剂与农学上可接受的载体混合的组合物也被描述。还描述了通过将至少一种二缩醛类胡萝卜素植物生长调节剂施用于种子，植物繁殖材料，植物或植物生长介质来调节植物生长的方法，包括促进根系发育，增加养分吸收，增强对非生物胁迫因素的抵抗力，激发植物生长，增加植物产量和增加植物生物质。
• Regulating plant growth using a diapocarotenoid
  申请人：King Abdullah University of Science and Technology

  公开号：US11523610B2

  公开（公告）日：2022-12-13

  Embodiments of the present disclosure describe diapocarotenoid plant growth regulators represented by formula (I): R-A-R (I) or a precursor, salt, solvate, stereoisomer or polymorph thereof; wherein R is a monovalent carbonyl moiety selected from the group consisting of aldehydes, ethers, diethers, carboxylic acids, alcohols, and ester carboxylates and A is a bivalent polyene represented by the bivalent moiety —(CR a ═CR b ) x —, wherein x is the number of double bonds in polyene moiety A, and R a and R b are, independently, hydrogen, a hydrocarbon, or an alkoxy group, and composition of the diapocarotenoid plant growth regulators in an agronomically acceptable carrier. Methods of regulating plant growth including promoting root development, increasing nutrient uptake, enhancing resistance to abiotic stress factors, invigorating plant growth, increasing plant yield, and increasing plant biomass by applying at least one diapocarotenoid plant growth regulator to a seed, plant propagation material, plant or plant growth medium are also described.

  本公开的实施方案描述了由式（I）代表的二羰基类植物生长调节剂：R-A-R (I)或其前体、盐、溶液剂、立体异构体或多晶型；其中 R 是选自由醛、醚、二醚、羧酸、醇和酯羧酸盐组成的组的一价羰基，A 是二价多烯，由二价分子-(CR a ═CR b ) x -，其中 x 是多烯分子 A 中双键的数目，R a 和 R b 分别为氢、烃或烷氧基，以及二碳糖苷类植物生长调节剂在农艺学上可接受的载体中的组合物。还描述了调节植物生长的方法，包括通过向种子、植物繁殖材料、植物或植物生长介质施用至少一种二碳类黄酮植物生长调节剂来促进根系发育、增加养分吸收、增强对非生物性胁迫因子的抵抗力、促进植物生长、增加植物产量和增加植物生物量。
• CAROTENOID OXIDATION PRODUCTS AS CHEMOPREVENTIVE AND CHEMOTHERAPEUTIC AGENTS
  申请人：Sharoni Yoav

  公开号：US20090069417A1

  公开（公告）日：2009-03-12

  The present invention relates to a method for the chemoprevention and treatment of cancer, by administering a pharmaceutical composition comprising a carotenoid derivative, such as a derivative of lycopene, a- and b-carotene, phytoene, phytofluene, lutein, zeaxanthin, α- and β-cryptoxanthin, canthaxanthin, astaxanthin, or other carotenoid. The carotenoid derivative is a carotenoid oxidation product, and is preferably an aldehyde derivative, a dialdehyde derivative or a ketone derivative. The carotenoid derivative can be a derivative of any naturally occurring carotenoid, such as those found in tomatoes and other fruits and vegetables.
• REGULATING PLANT GROWTH USING A DIAPOCAROTENOID
  申请人：King Abdullah University of Science and Technology

  公开号：US20210000108A1

  公开（公告）日：2021-01-07

  Embodiments of the present disclosure describe diapocarotenoid plant growth regulators represented by formula (I): R-A-R (I) or a precursor, salt, solvate, stereoisomer or polymorph thereof; wherein R is a monovalent carbonyl moiety selected from the group consisting of aldehydes, ethers, diethers, carboxylic acids, alcohols, and ester carboxylates and A is a bivalent polyene represented by the bivalent moiety —(CR a ═CR b ) x —, wherein x is the number of double bonds in polyene moiety A, and R a and R b are, independently, hydrogen, a hydrocarbon, or an alkoxy group, and composition of the diapocarotenoid plant growth regulators in an agronomically acceptable carrier. Methods of regulating plant growth including promoting root development, increasing nutrient uptake, enhancing resistance to abiotic stress factors, invigorating plant growth, increasing plant yield, and increasing plant biomass by applying at least one diapocarotenoid plant growth regulator to a seed, plant propagation material, plant or plant growth medium are also described.