1D-MYO-INOSITOL-1,3,4,5,6-PENTAKISPHOSPHATE, (NA+ SALT) | 20298-94-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1D-MYO-INOSITOL-1,3,4,5,6-PENTAKISPHOSPHATE, (NA+ SALT)
• 英文别名: Ins(1,2,3,4,6)P5；1D-myo-inositol 1,2,4,5,6-pentakisphosphate；Ins(1,2,3,4,5)P5；(2-hydroxy-3,4,5,6-tetraphosphonooxycyclohexyl) dihydrogen phosphate；Ins(1,2,4,5,6)P5；(+/-)-myo-Inosit-1,2,3,4,5-pentakis-dihydrogenphosphat；D-myo-inositol 1,2,3,4,5-pentakisphosphate；D-myo-inositol(1,2,3,5,6)pentakisphosphate；myo-inositol 1,2,3,5,6-pentaphosphate；myo-inositol pentakis(dihydrogen phosphate)
• CAS: 20298-94-6；20298-95-7；20298-96-8；20298-97-9；23393-17-1；23486-93-3；25663-09-6；26326-85-2；26326-86-3；31662-65-4；40322-16-5；40322-17-6；114418-96-1；134176-37-7
• 化学式: C₆H₁₇O₂₁P₅
• 分子量: 580.057
• InChiKey: CTPQAXVNYGZUAJ-UOTPTPDRSA-N

物化性质

• 沸点：
  1106.1±75.0 °C(Predicted)
• 密度：
  2.37±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -3.25
• 重原子数：
  32.0
• 可旋转键数：
  10.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  354.03
• 氢给体数：
  11.0
• 氢受体数：
  11.0

反应信息

• 作为反应物：
  描述：

  1D-MYO-INOSITOL-1,3,4,5,6-PENTAKISPHOSPHATE, (NA+ SALT) 在 sodium acetate buffer 、 faba bean 、 phytase from seeds of Vicia faba var. Alameda 作用下， 生成 (+/-)-myo-Inositol-1-phosphate 、 肌醇 1,2,6-三磷酸酯 、 D-myo-inositol 1,2-bisphosphate 、 D-myo-inositol(1,2,5,6)tetrakisphosphate
  参考文献：
  名称：

  Pathway of Dephosphorylation of myo-Inositol Hexakisphosphate by Phytases of Legume Seeds

  摘要：

  Using a combination of high-performance ion chromatography analysis and kinetic studies, the pathway of dephosphorylation of myo-inositol hexakisphosphate by the phytases purified from faba bean and lupine seeds, respectively, was established. The data demonstrate that the legume seed phytases under investigation dephosphorylate myo-inositol hexakisphosphate in a stereospecific way. The phytase from faba bean seeds and the phytase LP2 from lupine seeds degrade phytate by sequential removal of phosphate groups via D-Ins(1,2,3,5,6)P-5, D-Ins(1,2,5,6)P-4, D-Ins(1,2,6)P-3, and D-Ins(1,2)P-2 to finally Ins(2)P, whereas the phytases LP11 and LP12 from lupine seeds generate the final degradation product Ins(2)P via D-Ins(1,2,4,5,6)P-5, D-Ins(1,2,5,6)P-4, D-Ihs(1,2,6)P-3, and D-Ins(1,2)P-2.

  DOI：

  10.1021/jf025620t
• 作为产物：
  描述：

  sodium inositol hexaphosphate 在 acetate buffer 作用下， 反应 0.5h， 生成 1D-MYO-INOSITOL-1,3,4,5,6-PENTAKISPHOSPHATE, (NA+ SALT)
  参考文献：
  名称：

  Pathway of Dephosphorylation of myo-Inositol Hexakisphosphate by Phytases of Legume Seeds

  摘要：

  Using a combination of high-performance ion chromatography analysis and kinetic studies, the pathway of dephosphorylation of myo-inositol hexakisphosphate by the phytases purified from faba bean and lupine seeds, respectively, was established. The data demonstrate that the legume seed phytases under investigation dephosphorylate myo-inositol hexakisphosphate in a stereospecific way. The phytase from faba bean seeds and the phytase LP2 from lupine seeds degrade phytate by sequential removal of phosphate groups via D-Ins(1,2,3,5,6)P-5, D-Ins(1,2,5,6)P-4, D-Ins(1,2,6)P-3, and D-Ins(1,2)P-2 to finally Ins(2)P, whereas the phytases LP11 and LP12 from lupine seeds generate the final degradation product Ins(2)P via D-Ins(1,2,4,5,6)P-5, D-Ins(1,2,5,6)P-4, D-Ihs(1,2,6)P-3, and D-Ins(1,2)P-2.

  DOI：

  10.1021/jf025620t

文献信息

• [EN] SYNTHESIS OF CYCLOHEXANE DERIVATIVES USEFUL AS SENSATES IN CONSUMER PRODUCTS<br/>[FR] SYNTHÈSE DE DÉRIVÉS DE CYCLOHEXANE UTILES COMME AGENTS SENSORIELS DANS DES PRODUITS DE CONSOMMATION
  申请人：PROCTER & GAMBLE

  公开号：WO2010019730A1

  公开（公告）日：2010-02-18

  The present invention provides synthetic routes for preparing various isomers of cyclohexane-based coolants, such as menthyl esters and menthanecarboxamide derivatives, in particular those substituted at the amide nitrogen, for example with an aromatic ring or aryl moiety. Such structures have high cooling potency and long lasting sensory effect, which make them useful in a wide variety of consumer products. One synthetic route involves a copper catalyzed coupling of a primary menthanecarboxamide with an aryl halide, such reaction working best in the presence of potassium phosphate and water. Using this synthetic route, specific isomers can be prepared including the menthanecarboxamide isomer having the same configuration as l-menthol and new isomers such as a neoisomer having opposite stereochemistry at the carboxamide (C-1) position. The neoisomer unexpectedly has potent and long lasting cooling effect. Preparation schemes for neoisomers of other menthyl derivatives which are useful as coolants, including esters, ethers, carboxy esters and other N-substituted carboxamides are also provided.

  本发明提供了合成路径，用于制备基于环己烷的各种异构体冷却剂，例如薄荷酯和薄荷烷甲酰衍生物，特别是那些在酰胺氮上取代的，例如带有芳香环或芳基的。这些结构具有高冷却效能和持久的感官效果，使它们在各种消费品中有用。一种合成路径涉及使用铜催化剂将一种初级薄荷烷甲酰胺与芳香卤代烃偶联，这种反应在存在磷酸钾和水的情况下效果最佳。利用这种合成路径，可以制备特定的异构体，包括具有与l-薄荷醇相同构型的薄荷烷甲酰胺异构体以及具有在羧酰胺（C-1）位置上相反立体化学的新异构体，该新异构体意外地具有强效和持久的冷却效果。还提供了其他薄荷衍生物的新异构体的制备方案，这些衍生物包括酯类、醚类、羧酯类和其他N-取代羧酰胺，它们也可用作冷却剂。
• The Pathway of Dephosphorylation of<i>myo</i>-Inositol Hexakisphosphate by Phytases from Wheat Bran of<i>Triticum aestivum</i>L. cv. Nourin #61
  作者：Tadao NAKANO、Toshio JOH、Kazumasa NARITA、Toshiro HAYAKAWA

  DOI：10.1271/bbb.64.995

  日期：2000.1

  Phytases are the primary enzymes responsible for the hydrolysis of phytic acid, myo-inositol-1, 2, 3, 4, 5, 6-hexakisphosphate (InsP6). The pathway of hydrolysis of InsP6 by phytase from wheat bran of Triticum aestivum L. cv. Nourin #61 is proved in this study. Structures of the intermediates were established by a variety of nuclear magnetic resonance techniques (1H-, two-dimensional 1H-1H coupling-correlation

  植酸酶是负责水解植酸，肌醇-1、2、3、4、5、6-六磷酸（InsP6）的主要酶。植酸酶从普通小麦小麦麸皮中水解InsP6的途径。这项研究证明了Nourin＃61。中间体的结构通过各种核磁共振技术（1H-，二维1H-1H耦合相关光谱和二维31P-1H相关光谱），气相色谱法和生物测定法建立。根据确定的结构，磷酸酯的初始水解发生在InsP6的D / L-4位置，从而生成D / L-Ins（1、2、3、5、6）P5。脱磷酸作用后，脱磷酸途径分为两条途径。主路线通过D / L-Ins（1、2、5、6）P4，D / L-Ins（1、2、6）P3和D / L-Ins（1、2）P2进行，而次要路线则通过D / L-Ins（1、2、3、6）P4，Ins（1、2、3）P3和D / L-Ins（1、2）P2进行。D / L-Ins（1、2）在D / L-1或2位水解P2，最后产生肌醇。
• Flexible Stereo- and Regioselective Synthesis ofmyo-Inositol Phosphates(Part 2): Via Nonsymmetrical Conduritol B Derivatives
  作者：Michael A. L. Podeschwa、Oliver Plettenburg、Hans-Josef Altenbach

  DOI：10.1002/ejoc.200400918

  日期：2005.7

  myo-inositol phosphates. Optically pure compounds can be prepared, in both forms, from p-benzoquinone by enzymatic resolution of a diacetoxyconduritol key intermediate. Monosubstituted inositol derivatives can be obtained by breaking the C2 symmetry of conduritol B derivatives. A wide variety of myo-inositol phosphates can be synthesized by combining the previously reported symmetrical approach with

  一种实用的路线的制备描述肌醇肌醇磷酸盐。可以通过对乙酰氨基乙酸二硬脂醇关键中间体的酶促拆分，从对苯醌制备两种形式的光学纯化合物。单取代的肌醇衍生物可通过破坏Conduritol B衍生物的C 2对称性而获得。各种各样的肌肌醇磷酸盐可以通过组合与这个新的非对称的方法先前报道的对称方法来合成。（©Wiley-VCH Verlag GmbH＆Co.KGaA，69451 Weinheim，Germany，2005）
• Quantitative Analysis of Phytate Globoids Isolated from Wheat Bran and Characterization of Their Sequential Dephosphorylation by Wheat Phytase
  作者：Lisbeth Bohn、Lone Josefsen、Anne S. Meyer、Søren K. Rasmussen

  DOI：10.1021/jf071191t

  日期：2007.9.1

  when pure phytic acid was replaced with phytate globoids as substrate. Time course degradation of phytic acid or phytate globoids using purified wheat phytase was followed by HPIC identification of inositol phosphates appearing and disappearing as products. In both cases, enzymatic degradation initiated at both the 3- and 6-positions of phytic acid and end products were inositol and phosphate.

  纯化了小麦植酸酶，以研究该酶对其纯底物（植酸-肌醇六磷酸）和其天然底物（植酸球状）的作用。从麦麸中纯化植酸球蛋白至均质，并通过ICP-MS定量其营养相关参数。球形物质的主要成分是植酸（40％w / w），蛋白质（46％w / w）和几种矿物质，特别是K> Mg> Ca> Fe（按浓度顺序）。酶动力学研究表明，当纯植酸被植酸球体替代时，K（m）和V（max）分别降低29％和37％。使用纯化的小麦肌醇六磷酸酶随时间推移降解肌醇六磷酸或肌醇六磷酸球，然后通过HPIC鉴定肌醇磷酸酯作为产物的出现和消失。在这两种情况下，在植酸的3位和6位上开始的酶促降解以及最终产物是肌醇和磷酸盐。
• Synthesis of Cyclohexane Derivatives Useful as Sensates in Consumer Products
  申请人：Yelm Kenneth Edward

  公开号：US20100076080A1

  公开（公告）日：2010-03-25

  The present invention provides synthetic routes for preparing various isomers of cyclohexane-based coolants, such as menthyl esters and menthanecarboxamide derivatives, in particular those substituted at the amide nitrogen, for example with an aromatic ring or aryl moiety. Such structures have high cooling potency and long lasting sensory effect, which make them useful in a wide variety of consumer products. One synthetic route involves a copper catalyzed coupling of a primary menthanecarboxamide with an aryl halide, such reaction working best in the presence of potassium phosphate and water. Using this synthetic route, specific isomers can be prepared including the menthanecarboxamide isomer having the same configuration as l-menthol and new isomers such as a neoisomer having opposite stereochemistry at the carboxamide (C-1) position. The neoisomer unexpectedly has potent and long lasting cooling effect. Preparation schemes for neoisomers of other menthyl derivatives which are useful as coolants, including esters, ethers, carboxy esters and other N-substituted carboxamides are also provided.

  本发明提供了合成环己基冷却剂的各种异构体的合成路线，例如酯类薄荷醇和酰胺衍生物，特别是那些在酰胺氮上被取代的，例如芳香环或芳基基团。这样的结构具有高冷却效能和持久的感官效应，使它们在各种消费品中有用。一种合成路线涉及一种铜催化的一次性薄荷醇酰胺与芳基卤化物的偶联反应，这种反应在存在磷酸钾和水的情况下效果最好。使用这种合成路线，可以制备特定的异构体，包括具有与l-薄荷醇相同构型的薄荷醇酰胺异构体和新的异构体，例如在羧酰胺（C-1）位置具有相反立体化学的新异构体。这种新异构体出人意料地具有强大而持久的冷却效果。还提供了其他薄荷醇衍生物的新异构体的制备方案，这些衍生物包括酯类、醚类、羧酸酯类和其他N-取代酰胺。