(all-E)-12'-Apo-ψ-caroten-12'-al

• 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: (all-E)-12'-Apo-ψ-caroten-12'-al
• 英文别名: (all-E)-12'-Apo-ψ-carotin-12'-al；12'-Apo-Ψ-carotin-12'-al；(2E,4E,6E,8E,10E,12E,14E)-2,7,11,15,19-pentamethylicosa-2,4,6,8,10,12,14,18-octaenal；apo-12′-lycopenal；(all-E)-2,7,11,15,19-pentamethyl-eicosa-2,4,6,8,10,12,14,18-octaenal；12'-apo-ψ-caroten-12'-al；apo-12'-lycopenal；apo-Lycopenal
• 化学式: C₂₅H₃₄O
• 分子量: 350.544
• InChiKey: CTKROHWZDNWNMY-MSWJQUEKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.5
• 重原子数：
  26
• 可旋转键数：
  10
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

上下游信息

• 上游原料

  中文名称	英文名称	CAS号	化学式	分子量
  ——	γ-retinal	1070-48-0	C20H28O	284.442
  番茄红素	lycopene	502-65-8	C40H56	536.885
  ——	(all-E)-15-Apo-ψ-carotin-15-saeure-methylester	103834-54-4	C21H30O2	314.468
  (E)-ψ-紫罗兰酮	pseudoionone	3548-78-5	C13H20O	192.301

• 下游产品

  中文名称	英文名称	CAS号	化学式	分子量
  ——	(5Z)-lycopene	101468-86-4	C40H56	536.885
  ——	(7Z,9Z)-Lycopene	145678-42-8	C40H56	536.885
  (6E,8E,10Z,12E,14Z,16E,18Z,20E,22E,26E)-2,6,10,14,19,23,27,31-八甲基三十二碳-2,6,8,10,12,14,16,18,20,22,26,30-十二烯	all-trans-neurosporene	502-64-7	C40H58	538.901
  ——	(9Z)-Neurosporin	——	C40H58	538.901
  ——	(5Z)-Neurosporin	——	C40H58	538.901

反应信息

• 作为反应物：
  描述：

  (all-E)-12'-Apo-ψ-caroten-12'-al 在 Lindlar's catalyst 喹啉 、 正丁基锂 、 氢气 作用下， 以 正己烷 、 二氯甲烷 为溶剂， -78.0~25.0 ℃ 、100.0 kPa 条件下， 反应 0.83h， 生成 (7Z,9Z)-Lycopene
  参考文献：
  名称：

  番茄红素的十四个（Z）-异构体以及一些乙炔二氢和四氢氢化番茄红素的合成，分离和NMR光谱表征

  摘要：

  番茄红素的八个（Z）异构体是通过立体控制合成方法制备的，并通过1 H-NMR，13 C-NMR，质谱和UV / VIS光谱进行了全面表征：（5 Z）-，（7 Z）-，（15 Z）-，（5 Z，5'Z）-，（7 Z，7'Z）-，（7 Z，9 Z）-，（9 Z，9'Z）-和（7 Z，9 Z， 7' ž，9' ž）-lycopene。六个额外的（Z）异构体，即（9 Z）-，（13 Z）-，（5ž，9' Ž） - ，（9 Ž，13' Ž） - ，（5 Ž，9 Ž，5' Ž） - ，和（5 Ž，13 Ž，5' Ž）-lycopene，在小分离半制备可得自异构体混合物的量。HPLC并通过1 H-NMR光谱鉴定。

  DOI：

  10.1002/hlca.19920750611
• 作为产物：
  描述：

  γ-retinal 在 manganese(IV) oxide 、 氢氧化钾 、 二异丁基氢化铝 作用下， 以 四氢呋喃 为溶剂， 反应 1.75h， 生成 (all-E)-12'-Apo-ψ-caroten-12'-al
  参考文献：
  名称：

  合成胡萝卜素-端基和（Z）-修饰末端的多巴宾登根

  摘要：

  末端共轭双键具有ψ-端基和（Z）-构型的胡萝卜素的合成

  DOI：

  10.1002/hlca.19850680604

文献信息

• Carotenoids and related compounds. Part XV. The structure and synthesis of phytoene, phytofluene, ζ-carotene, and neurosporene
  作者：J. B. Davis、L. M. Jackman、P. T. Siddons、B. C. L. Weedon

  DOI：10.1039/j39660002154

  日期：——

  Structures have been established for the polyenes, phytoene, phytofluene, ζ-carotene and neurosporene by spectral studies and synthesis. The stereochemistry of these polyenes is discussed.

  通过光谱研究和合成，已经建立了多烯，八氢番茄红素，八氢番茄红素，ζ-胡萝卜素和神经孢子烯的结构。讨论了这些多烯的立体化学。
• 10′-Apolycopin-10′-ol und 10′-Apolycopin-10′-säure aus Blüten der Rosenhybride ‘Maréchal Niel’. 6. Mitteilung über Farbstoffe aus Rosen
  作者：Edith Märki-Fischer、Peter Uebelhart、Conrad Hans Eugster

  DOI：10.1002/hlca.19870700804

  日期：1987.12.16

  10′-Apolycopen-10′-ol and 10′-Apolycopen-10′-oic Acid from the Petals of the Rose Hybrid ‘Maréchal Niel’

  玫瑰杂种'MaréchalNiel'的花瓣中的10'-Apolycopen-10'-ol和10'-Apolycopen-10'-oic酸
• Identification and Quantification of Apo-lycopenals in Fruits, Vegetables, and Human Plasma
  作者：Rachel E. Kopec、Ken M. Riedl、Earl H. Harrison、Robert W. Curley、Damian P. Hruszkewycz、Steven K. Clinton、Steven J. Schwartz

  DOI：10.1021/jf100415z

  日期：2010.3.24

  Research has suggested that lycopene may be metabolized by eccentric cleavage, catalyzed by beta-carotene oxygenase 2, resulting in the generation of apo-lycopenals. Apo-6'-lycopenal and apo-8'-lycopenal have been reported previously in raw tomato. We now show that several other apo-lycopenals are also present in raw and processed foods, as well as in human plasma. Apo-lycopenal standards were prepared by in vitro oxidation of lycopene, and a high-performance liquid chromatography-tandem mass spectrometry (HPLC-MS/MS) method using atmospheric pressure chemical ionization in negative mode was developed to separate and detect the apo-6'-, apo-8-, apo-10'-, apo-12'-, apo-14'-, and apo-15'-lycopenal products formed in the reaction. Hexane/acetone extracts of raw tomato, red grapefruit, watermelon, and processed tomato products were analyzed, as well as plasma of individuals who had consumed tomato juice for 8 weeks. Apo-6'-, apo-8'-, apo-10'-, apo-12'-, and apo-14'-lycopenals were detected and quantified in all food products tested, as well as plasma. The sum of apo-lycopenals was 6.5 mu g/100 g Roma tomato, 73.4 mu g/100 g tomato paste, and 1.9 nmol/L plasma. We conclude that several apo-lycopenals, in addition to apo-6'- and -8'-lycopenal, are present in lycopene-containing foods. In addition, the presence of apo-lycopenals in plasma may derive from the absorption of apo-lycopenals directly from food and/or human metabolism.
• 360. Carotenoids and related compounds. Part XI. Syntheses of δ-carotene and ε-carotene
  作者：P. S. Manchand、R. Rüegg、U. Schwieter、P. T. Siddons、B. C. L. Weedon

  DOI：10.1039/jr9650002019

  日期：——
• Fractionation and Characterization of Lycopene-Oxidation Products by LC-MS/MS (ESI)⁺: Elucidation of the Chemopreventative Potency of Oxidized Lycopene in Breast-Cancer Cell Lines
  作者：Bangalore Prabhashankar Arathi、Poorigali Raghavendra-Rao Sowmya、Gini Chempakathinal Kuriakose、Shivaprasad Shilpa、Hulikere Jagdish Shwetha、Sharath Kumar、Marisiddaiah Raju、Vallikannan Baskaran、Rangaswamy Lakshminarayana

  DOI：10.1021/acs.jafc.8b04850

  日期：2018.10.31

  Lycopene (LYC) has been correlated with the reduction of certain cancers and chronic diseases. However, the existence and biofunctionality of degraded, oxidized, and biotransformed LYC products in vivo have not been revealed. Therefore, this study aimed to screen and elucidate the potential bioactive lycopene-derived products in breast-cancer and noncancerous cells. LYC-oxidation or -cleavage products were generated using KMnO4. These oxidation products were separated as fractions I-III by silica column chromatography using gradient solvent systems. Further, LC-MS/MS (ESI)(+) was used to elucidate their possible fragmentation patterns and structures. Fraction II showed higher cytotoxicity (IC50 value of 64.5 mu M), cellular uptake, and apoptosis-inducing activity in MCF-7 cells. This fraction consists of major peak m/z 323, identified as apo-8,6'-carotendial. The cytotoxicity-inducing activity may be due to partial ROS generation with mitochondrial dysfunction. Further, the role of apo-8,6'-carotendial in the induction of apoptosis is demonstrated for the first time. These results illustrated that LYC-oxidation derivatives or metabolites are involved in growth inhibition of cancer cells. Exploration of specific oxidized-carotenoid products will give further insight into the field of nutritional biochemistry.