5-二十一烷基间苯二酚 | 70110-59-7

• 物质功能分类: 分析化学 - 标准品 - 食品和饮料标准品
• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 中文名称: 5-二十一烷基间苯二酚
• 英文名称: 5-n-heneicosylresorcinol
• 英文别名: 5-heneicosylresorcinol；5-Henicosylbenzene-1,3-diol
• CAS: 70110-59-7
• 化学式: C₂₇H₄₈O₂
• 分子量: 404.677
• InChiKey: BLHLKJLSYHEOGY-UHFFFAOYSA-N

物化性质

• 熔点：
  99 °C(Solv: cyclohexane (110-82-7))
• 沸点：
  526.7±20.0 °C(Predicted)
• 密度：
  0.935±0.06 g/cm3(Predicted)
• 溶解度：
  丙酮：可溶；氯仿：可溶； DMSO：可溶；乙酸乙酯：可溶
• 物理描述：
  Solid

计算性质

• 辛醇/水分配系数(LogP)：
  12.3
• 重原子数：
  29
• 可旋转键数：
  20
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  40.5
• 氢给体数：
  2
• 氢受体数：
  2

安全信息

• 危险品标志：
  Xi
• 安全说明：
  S26
• 危险类别码：
  R36
• WGK Germany：
  3

反应信息

• 作为反应物：
  描述：

  5-二十一烷基间苯二酚 在 diclazuril 作用下， 生成 [2,4,6-2H3]-5-heneicosylresorcinol
  参考文献：
  名称：

  Synthesis of deuterated 5-n-alkylresorcinols

  摘要：

  本研究探讨了制备氘多标记 5-正烷基间苯二酚的四种替代方法。通过酸性 H/D 交换合成的环状标记 2H3- 烷基间苯二酚在电喷雾电离质谱条件下是稳定的，但在电子轰击电离质谱条件下会出现扰乱。通过两种不同的全合成方法制备的侧链标记 2H4-衍生物在 D2 气体氘代化过程中由于 H/D 的重新分布和交换而受到氘标记数量不同的同位素的污染。带有 ω-2H3 标记的衍生物在定量工作中遇到的所有相关分析条件下都是同位素纯的，而且完全稳定。Copyright © 2008 John Wiley & Sons, Ltd. All Rights Reserved.

  DOI：

  10.1002/jlcr.1463
• 作为产物：
  描述：

  3,5-二甲氧基苄醇 在 dilithium tetrachlorocuprate 、 三溴化硼 、 三溴化磷 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 生成 5-二十一烷基间苯二酚
  参考文献：
  名称：

  Properties of mixed monolayers and bilayers of long-chain 5-n-alkylresorcinols and dipalmitoylphosphatidylcholine

  摘要：

  5-n-Alkylresorcinols with different chain length are known to occur in different plants and procaryonts, for example in the cysts of the Azotobacter genus. To study the monolayer and bilayer behaviour of these amphiphilic compounds, we synthesized three analogues with different chain length, namely 5-n-octadecylresorcinol (18AR), 5-n-nonadecylresorcinol(19AR) and 5-n-heneicosylresorcinol (21AR). The pure alkylresorcinols form stable monolayers, 18AR and 19AR, show a phase transition from a liquid-condensed to a liquid-expanded state at temperatures between 20 and 40 degrees C and at lateral pressures below 15 dyn/cm. In mixtures with dipalmitoylphosphatidylcholine (DPPC), monolayer isobars at higher lateral pressures (20-30 dyn/cm) show an increase in the transition temperature to values greater than 50 degrees C for the liquid-condensed to liquid-expanded state of DPPC when the alkylresorcinol content is increased. Particularly in the liquid-expanded state, alkylresorcinols show a strong condensing effect on DPPC monolayers. 18AR/DPPC monolayers at a pressure of 5 dyn/cm show indications of an azeotropic behaviour. A similar increase in transition temperature is observed by differential scanning calorimetry (DSC) and differential scanning densitometry (DSD) in DPPC/alkylresorcinol bilayers. The transition enthalpy decreases with increasing alkylresorcinol content. All alkylresorcinols seem to be completely miscible with DPPC up to at least 50 mol%. The DSD data indicate a slight condensing effect of the alkylresorcinols on the liquid-crystalline phase of DPPC.

  DOI：

  10.1016/0009-3084(94)90074-4

文献信息

• An expedient synthesis of 5-<i>n</i>-alkylresorcinols and novel 5-<i>n</i>-alkylresorcinol haptens
  作者：Kirsti Parikka、Kristiina Wähälä

  DOI：10.3762/bjoc.5.22

  日期：——

  The first synthesis of bioactive long alkyl chain 5-n-alkylresorcinols, present in whole grain products, by a novel modification of the Wittig reaction is described. All the main long chain 5-n-alkylresorcinols present in rye and wheat, including C₂₃ and C₂₅ analogues and haptens, which have not been previously prepared, were synthesised. Microwave-promoted reactions of a semi-stabilized ylid and alkanals in water gave good yields in both pressurized and open systems. An alternative microwave-promoted synthesis starting from non-stabilized alkyltriphenylphosphonium salts and 3,5-dimethoxybenzaldehyde worked as well. Aqueous media were suitable for the reactions even if the starting materials were not soluble in water. The 5-n-alkylresorcinols are potential biomarkers of whole grain intake, and the new hapten derivatives of 5-n-alkylresorcinols will open the way for the immunochemical detection techniques of alkylresorcinols.

  描述了通过一种新颖的Wittig反应改进合成生物活性长烷基链5-烷基间苯二酚，这种物质存在于全谷物产品中。合成了黑麦和小麦中所有主要的长链5-烷基间苯二酚，包括C23和C25类似物以及以前未制备的半抗原。在水中，半稳定叶立德和烷醛的微波促进反应在加压和开放系统中均获得良好产率。另一种微波促进合成方法是从非稳定的烷基三苯基膦盐和3,5-二甲氧基苯甲醛出发。即使起始材料在水中不溶解，水介质也适用于这些反应。5-烷基间苯二酚是全谷物摄入的潜在生物标志物，而新的5-烷基间苯二酚半抗原衍生物将为烷基间苯二酚的免疫化学检测技术打开道路。
• Malondialdehyde trapping by food phenolics
  作者：Rosario Zamora、Esmeralda Alcon、Francisco J. Hidalgo

  DOI：10.1016/j.foodchem.2023.135915

  日期：2023.8

  The reactions between malondialdehyde and 2,5-dimethylresorcinol, orcinol, olivetol, and alkylresocinols were studied in an attempt to investigate both if this lipid oxidation product is trapped by phenolics analogously to other reactive carbonyls and to elucidate the chemical structures of the produced adducts. After being formed, malondialdehyde is both partially fractionated to acetaldehyde and

  研究了丙二醛与 2,5-二甲基间苯二酚、orcinol、olivetol 和烷基间苯二酚之间的反应，试图研究这种脂质氧化产物是否像其他反应性羰基一样被酚类物质捕获，并阐明所产生的加合物的化学结构。形成后，丙二醛既部分分馏成乙醛，又低聚成二聚体和三聚体。所有这些化合物都与酚类反应生成三种主要的衍生物：5(或 7)-alkyl-7(或 5)-hydroxy-4-methyl-4 H -chromene-3- carbaldehydes、7-alkyl-9-hydroxy- 6 H -2,6-methanobenzo[ d ][1,3]dioxocine-5-carbaldehydes, and 4-(3-formylphenyl)-7-hydroxy-4 H-色烯-3-甲醛。通过半制备高效液相色谱 (HPLC) 分离出总共 24 种加合物，并通过单维和二维核磁共振 (NMR) 光谱和质谱 (MS)
• Glycan therapeutics and related methods thereof
  申请人：KALEIDO BIOSCIENCES, INC.

  公开号：US10314853B2

  公开（公告）日：2019-06-11

  Preparations of glycan therapeutics, pharmaceutical compositions and medical foods thereof, optionally comprising micronutrients, polyphenols, prebiotics, probiotics, or other agents are provided and methods of making same. Also provided are methods of using said gycan therapeutics, e.g. for the modulation of human gastrointestinal microbiota and to treat dysbioses.

  本发明提供了可选择包含微量营养素、多酚、益生元、益生菌或其他制剂的聚糖疗法制剂、药物组合物及其医用食品，以及制造方法。还提供了使用所述糖治疗剂的方法，例如用于调节人类胃肠道微生物群和治疗菌群失调。
• Processes and host cells for genome, pathway, and biomolecular engineering
  申请人：enEvolv, Inc.

  公开号：US10370654B2

  公开（公告）日：2019-08-06

  The present disclosure provides compositions and methods for genomic engineering.

  本公开提供了基因组工程的组合物和方法。
• Glycan therapeutics and method of treating conditions associated with TMAO
  申请人：Kaleido Biosciences, Inc.

  公开号：US11229660B2

  公开（公告）日：2022-01-25

  Preparations of glycan therapeutics, pharmaceutical compositions and medical foods thereof, optionally comprising micronutrients, polyphenols, prebiotics, probiotics, or other agents are provided and methods of making same. Also provided are methods of using said gycan therapeutics, e.g. for the modulation of human gastrointestinal microbiota and to treat dysbioses.

  本发明提供了可选择包含微量营养素、多酚、益生元、益生菌或其他制剂的聚糖疗法制剂、药物组合物及其医用食品，以及制造方法。还提供了使用所述糖治疗剂的方法，例如用于调节人类胃肠道微生物群和治疗菌群失调。