4-hydroxybenzoate | 456-23-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 4-hydroxybenzoate
• 英文别名: p-hydroxybenzoate；4-carboxyphenolate
• CAS: 456-23-5
• 化学式: C₇H₅O₃
• 分子量: 137.115
• InChiKey: FJKROLUGYXJWQN-UHFFFAOYSA-M

物化性质

• 碰撞截面：
  119 Ų [M+H-H2O]+ [CCS Type: DT, Method: single field calibrated with Agilent tune mix (Agilent)]

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  10
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  60.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-hydroxybenzoate 以 甲醇 为溶剂， 生成 对羟基苯甲酸
  参考文献：
  名称：

  Ka Values of Weak Organic Acids in Protic Solvents Obtained from Their First Hyperpolarizabilities in Solution

  摘要：

  The first hyperpolarizabilities (beta) of some weak aromatic organic acids have been measured in protic solvents by the hyper-Rayleigh scattering (HRS) technique at low concentrations. The measured hyperpolarizability (beta(m)) varies between the two extreme limits: the hyperpolarizability of the acid form (beta(HA)) at the lower side and that of the basic form (beta(A-)) at the higher side. The degree of dissociation (alpha) of the acid in a solvent is related to the measured hyperpolarizability, beta(m), by the following relationship: beta(m)(2)=(1-alpha)beta(HA)(2)+alpha beta(A-)(2). The calculated beta's including solvent effects in terms of an Onsager field do not reproduce the experimentally measured hyperpolarizabilities. Other solvent-induced effects like hydrogen bonding and van der Waals interactions seem to influence the first hyperpolarizability and, thus, indirectly the extent of dissociation of these weak acids in these protic solvents.

  DOI：

  10.1021/j100051a014
• 作为产物：
  描述：

  对羟基苯甲酸 在 溴棕三甲铵 作用下， 以 水 为溶剂， 生成 4-hydroxybenzoate
  参考文献：
  名称：

  超声吸收法研究阳离子胶束对芳族羧酸水解反应动力学的影响

  摘要：

  在水溶液中存在十四烷基三甲基溴化铵（TTAB）胶束的情况下，通过超声吸收法对羧酸的原位动力学进行了动力学研究。研究的羧酸分为两类，一类能够形成分子内氢键，即水杨酸衍生物（SAD），另一类不能形成该键，即苯甲酸衍生物（BAD）。所述速率常数（γ 2 ķ ˚F，ķ b），表观解离常数（ķ一个），并且将反应（Δ的体积变化V获得）。不同的K a关于分子内氢键的影响讨论了SAD和BAD观察到的速率常数的依赖性。还观察到SAD和BAD的ΔV的p K a依赖性。这些依赖性大于水溶液中的依赖性。该结果归因于胶束溶液和水溶液中水分子在溶质周围的排列方式的变化。

  DOI：

  10.1039/ft9949000869

文献信息

• MATERIAL FOR FORMING ORGANIC FILM, METHOD FOR FORMING ORGANIC FILM, PATTERNING PROCESS, AND COMPOUND
  申请人：SHIN-ETSU CHEMICAL CO., LTD.

  公开号：US20210181637A1

  公开（公告）日：2021-06-17

  The present invention provides a material for forming an organic film, containing a compound shown by the following general formula (1), and an organic solvent, where X represents an organic group having a valency of n1 and 2 to 50 carbon atoms, n1 represents an integer of 1 to 10, and R 1 represents at least one or more of the following general formulae (2) to (4). This aims to provide an organic film material for forming an organic film that has all of high filling property, high planarizing property, and excellent adhesive force to a substrate.

  本发明提供了一种用于形成有机薄膜的材料，包含以下通用式（1）所示的化合物和有机溶剂，其中X代表具有n1价的有机基团，具有2至50个碳原子，n1代表1至10的整数，R1代表至少一个或更多以下通用式（2）至（4）中的一种。这旨在提供一种用于形成具有高填充性、高平整性和对基底具有优异粘附力的有机薄膜的有机薄膜材料。
• Selective Enzymatic Transformation to Aldehydes<i>in vivo</i>by Fungal Carboxylate Reductase from<i>Neurospora crassa</i>
  作者：Daniel Schwendenwein、Giuseppe Fiume、Hansjörg Weber、Florian Rudroff、Margit Winkler

  DOI：10.1002/adsc.201600914

  日期：2016.11.3

  with only a handful of biocatalysts available to this end. We have increased the spectrum of carboxylate-reducing enzymes (CARs) with the sequence of a fungal CAR from Neurospora crassa OR74A (NcCAR). NcCAR was efficiently expressed in E. coli using an autoinduction protocol at low temperature. It was purified and characterized in vitro, revealing a broad substrate acceptance, a pH optimum at pH 5.5-6

  羧酸的酶促还原还处于初期，只有少数几种生物催化剂可用于此目的。我们已经利用来自神经孢霉OR74A（NcCAR）的真菌CAR的序列增加了羧酸盐还原酶（CARs）的谱图。NcCAR在低温下使用自动诱导方案在大肠杆菌中有效表达。对其进行了纯化和体外表征，显示了广泛的底物接受性，最适pH值为5.5-6.0，Tm为45°C和副产物焦磷酸盐的抑制作用（可通过添加焦磷酸酶来缓解）。NcCAR的合成效用已在使用大肠杆菌K-12 MG1655 RARE菌株进行全细胞生物转化中得到证实，目的是抑制过度还原为不想要的酒精。由戊酸（30 mM）以克规模制备芳香化合物胡椒醛，分离出的产率为92％，纯度> 98％。这对应于1.5g / L / h的生产率。
• Two UGT84 Family Glycosyltransferases Catalyze a Critical Reaction of Hydrolyzable Tannin Biosynthesis in Pomegranate (Punica granatum)
  作者：Nadia N. Ono、Xiaoqiong Qin、Alexander E. Wilson、Gang Li、Li Tian

  DOI：10.1371/journal.pone.0156319

  日期：——

  Hydrolyzable tannins (HTs) play important roles in plant herbivore deterrence and promotion of human health. A critical step in HT production is the formation of 1-O-galloyl-β-D-glucopyranoside (β-glucogallin, ester-linked gallic acid and glucose) by a UDP-glucosyltransferase (UGT) activity. We cloned and biochemically characterized four candidate UGTs from pomegranate (Punica granatum), of which only UGT84A23 and UGT84A24 exhibited β-glucogallin forming activities in enzyme assays. Although overexpression and single RNAi knockdown pomegranate hairy root lines of UGT84A23 or UGT84A24 did not lead to obvious alterations in punicalagin (the prevalent HT in pomegranate) accumulation, double knockdown lines of the two UGTs resulted in largely reduced levels of punicalagins and bis-hexahydroxydiphenyl glucose isomers. An unexpected accumulation of galloyl glucosides (ether-linked gallic acid and glucose) was also detected in the double knockdown lines, suggesting that gallic acid was utilized by an unidentified UGT activity for glucoside formation. Transient expression in Nicotiana benthamiana leaves and immunogold labeling in roots of pomegranate seedlings collectively indicated cytosolic localization of UGT84A23 and UGT84A24. Overall, functional characterization and localization of UGT84A23 and UGT84A24 open up opportunities for further understanding the regulatory control of HT metabolism in plants and its coordination with other biochemical pathways in the metabolic network.

  可水解单宁（HTs）在阻止植物食草动物和促进人类健康方面发挥着重要作用。HT 生成的一个关键步骤是通过 UDP-葡萄糖基转移酶（UGT）活性形成 1-O-galloyl-β-D-glucopyranoside（β-glucogallin，酯连接没食子酸和葡萄糖）。我们从石榴（Punica granatum）中克隆了四个候选 UGTs 并对其进行了生物化学鉴定，其中只有 UGT84A23 和 UGT84A24 在酶测定中显示出了β-葡糖苷形成活性。虽然 UGT84A23 或 UGT84A24 的过表达和单 RNAi 敲除石榴毛根品系并不会导致厚朴苷（石榴中最常见的 HT）积累发生明显变化，但这两种 UGT 的双敲除品系会导致厚朴苷和双六羟基二苯葡萄糖异构体的水平大大降低。在双基因敲除品系中还检测到没食子酰葡萄糖苷（醚键没食子酸和葡萄糖）的意外积累，这表明没食子酸被一种未确定的 UGT 活性利用来形成葡萄糖苷。UGT84A23 和 UGT84A24 在烟草叶片中的瞬时表达和在石榴幼苗根部的免疫金标记共同表明了它们在细胞质中的定位。总之，UGT84A23 和 UGT84A24 的功能表征和定位为进一步了解植物 HT 代谢的调控及其与代谢网络中其他生化途径的协调提供了机会。
• Single transition state in the transfer of a neutral phosphoryl group between phenoxide ion nucleophiles in aqueous solution
  作者：Salem A. Ba-Saif、Mark A. Waring、Andrew Williams

  DOI：10.1021/ja00178a040

  日期：1990.10

  reaction of 4-nitrophenolate ion with the 4-nitrophenyl ester is slightly imbalanced whereby bond formation does not keep up with bond fission in the transition states; the transition state, therefore, has some phosphorylium ion character. Transfer of the diethylphosphoryl group between weakly basic oxyanion nucleophiles is probably a concerted process with a transition state with more of the character

  取代酚盐离子与磷酸 4-硝基苯基二苯酯反应的二级速率常数 (k ArO ) 服从 18 个取代基范围内的线性方程。线性图与涉及单个过渡态或两步过程的机制一致，中间体具有非常活泼的中间体，其形成和分解的过渡态几乎相同；指数 (0.53) 的值也与具有离散中间体的常规逐步过程不一致。4-硝基苯酚离子与 4-硝基苯酯的对称反应略微不平衡，因此键的形成跟不上过渡态的键裂变；因此，过渡态具有一些磷离子特征。
• Flavoenzyme‐mediated Regioselective Aromatic Hydroxylation with Coenzyme Biomimetics
  作者：Alice Guarneri、Adrie H. Westphal、Jos Leertouwer、Joy Lunsonga、Maurice C. R. Franssen、Diederik J. Opperman、Frank Hollmann、Willem J. H. Berkel、Caroline E. Paul

  DOI：10.1002/cctc.201902044

  日期：2020.3.6

  selective aromatic hydroxylation with coenzyme biomimetics. The carbamoylmethyl‐substituted biomimetic in particular affords full conversion in less than two hours for the selective hydroxylation of 5 mM 3‐ and 4‐hydroxybenzoates, displaying similar rates as with NADH, achieving a 10 mM/h enzymatic conversion of the medicinal product gentisate. This biomimetic appears to generate less uncoupling of

  区域选择性芳族羟基化对于生产有价值的化合物是合乎需要的。外部含有黄素的单加氧酶通过烟酰胺腺嘌呤二核苷酸辅酶的黄素还原，随后与分子氧反应，活化并选择性地将氧原子掺入酚类化合物中。这项研究提供了辅酶仿生剂黄素酶催化选择性芳香族羟基化反应原理的证明。特别是氨基甲酰基甲基取代的仿生品可在不到两个小时的时间内实现5 mM 3-羟基和4-羟基苯甲酸酯的选择性羟基化的完全转化，显示出与NADH相似的速率，实现了药用产品龙胆酸酯的10 mM / h的酶促转化。这种仿生物似乎产生较少的羟基解偶联，这通常导致不希望的过氧化氢。因此，我们表明这些黄素酶具有与仿生剂结合应用的潜力。

表征谱图