3-Hydroxyphenylacetate

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 3-Hydroxyphenylacetate
• 英文别名: 2-(3-hydroxyphenyl)acetate
• 化学式: C8H7O3-
• 分子量: 151.14
• InChiKey: FVMDYYGIDFPZAX-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  11
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.12
• 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：

  3-Hydroxyphenylacetate 、 、 原甲酸三甲酯 在 乙醚 、 碳酸氢钠 、 magnesium sulfate 、 silica gel 、 ethyl acetate n-hexane 作用下， 以 甲醇 为溶剂， 反应 5.0h， 生成 3-羟基苯乙酸甲酯
  参考文献：
  名称：

  Phenyl-isoxazol-3-ol derivative

  摘要：

  本发明涉及一种由式（I）表示的化合物，其具有GPR120激动剂作用，因此对治疗糖尿病或高脂血症有用，或其药学上可接受的盐。在该式中，（AA）表示苯基或类似物，它可以用较低的烷氧基或类似物替代; （BB）表示二价基团或类似物，由苯环中去除两个氢原子而来，该苯环可以用卤原子或类似物替代; X表示具有由1-8个碳原子组成的主链的间隔物，其中主链中的1-3个碳原子可以用氧原子或类似物替代; Y表示氢原子或类似物。

  公开号：

  US08367708B2

文献信息

• PPAR-activating compound and pharmaceutical composition comprising the compound
  申请人：Yamazaki Yukiyoshi

  公开号：US20050101636A1

  公开（公告）日：2005-05-12

  A compound represented by the following formula (1): Or a salt thereof; and therapeutic durgs containing the compound. The compound selectively activates PPARα.

  以下是翻译结果： 由以下公式（1）表示的化合物：或其盐；以及含有该化合物的治疗药物。该化合物具有选择性地激活 PPARα。
• Benzopyran and related LTB.sub.4 antagonists
  申请人：Pfizer Inc.

  公开号：US05550152A1

  公开（公告）日：1996-08-27

  The invention relates to benzopyran leukotriene B.sub.4 (LTB.sub.4) antagonists and pharmaceutical compositions containing the compounds. The compounds inhibit the action of LTB.sub.4 and are therefore useful in the treatment of LTB.sub.4 induced illnesses such as inflammatory disorders.

  该发明涉及苯并吡喃白三烯B.sub.4（LTB.sub.4）拮抗剂和含有该化合物的药物组合物。这些化合物抑制LTB.sub.4的作用，因此在治疗LTB.sub.4引起的疾病，如炎症性疾病方面具有用处。
• NOVEL PHENYL-ISOXAZOL-3-OL DERIVATIVE
  申请人：Hashimoto Noriaki

  公开号：US20100130559A1

  公开（公告）日：2010-05-27

  The present invention relates to a compound represented by formula (I), which has a GPR120 agonist action and thus is useful for treatment of diabetes mellitus or hyperlipidemia, or a pharmaceutically acceptable salt thereof. In the formula, (AA) represents a phenyl or the like, which may be substituted with a lower alkoxy group or the like; (BB) represents a divalent group or the like, derived by removal of two hydrogen atoms from a benzene which may be substituted with a halogen atom or the like; X represents a spacer having a main chain composed of 1-8 carbon atoms wherein 1-3 carbon atoms in the main chain may be substituted with an oxygen atom or the like; and Y represents a hydrogen atom or the like.

  本发明涉及一种由式(I)所表示的化合物，该化合物具有GPR120激动剂作用，因此可用于治疗糖尿病或高脂血症，或其药学上可接受的盐。在该式中，(AA)代表苯或类似物，可能被低烷氧基或类似物取代；(BB)代表二价基团或类似物，由苯中去除两个氢原子而来，该苯可能被卤原子或类似物取代；X代表具有由1-8个碳原子组成的主链的间隔物，其中主链中的1-3个碳原子可能被氧原子或类似物取代；而Y代表氢原子或类似物。
• Novel <i>phacB</i> -Encoded Cytochrome P450 Monooxygenase from <i>Aspergillus nidulans</i> with 3-Hydroxyphenylacetate 6-Hydroxylase and 3,4-Dihydroxyphenylacetate 6-Hydroxylase Activities
  作者：Francisco Ferrer-Sevillano、José M. Fernández-Cañón

  DOI：10.1128/ec.00226-06

  日期：2007.3

  Aspergillus nidulans catabolizes phenylacetate (PhAc) and 3-hydroxy-, 4-hydroxy-, and 3,4-dihydroxyphenylacetate (3-OH-PhAc, 4-OH-PhAc, and 3,4-diOH-PhAc, respectively) through the 2,5-dihydroxyphenylacetate (homogentisic acid) catabolic pathway. Using cDNA subtraction techniques, we isolated a gene, denoted phacB , which is strongly induced by PhAc (and its hydroxyderivatives) and encodes a new cytochrome P450 (CYP450). A disrupted phacB strain ( ΔphacB ) does not grow on 3-hydroxy-, 4-hydroxy-, or 3,4-dihydroxy-PhAc. High-performance liquid chromatography and gas chromatography-mass spectrum analyses of in vitro reactions using microsomes from wild-type and several A. nidulans mutant strains confirmed that the phacB -encoded CYP450 catalyzes 3-hydroxyphenylacetate and 3,4-dihydroxyphenylacetate 6-hydroxylations to generate 2,5-dihydroxyphenylacetate and 2,4,5-trihydroxyphenylacetate, respectively. Both of these compounds are used as substrates by homogentisate dioxygenase. This cytochrome P450 protein also uses PhAc as a substrate to generate 2-OH-PhAc with a very low efficiency. The phacB gene is the first member of a new CYP450 subfamily (CYP504B).

  摘要 黑曲霉 通过 2,5-二羟基苯乙酸（同戊酸）分解途径分解苯乙酸（PhAc）和 3-羟基、4-羟基和 3,4-二羟基苯乙酸（分别为 3-OH-PhAc、4-OH-PhAc 和 3,4-diOH-PhAc）。利用 cDNA 减去技术，我们分离出了一个基因，命名为 phacB 该基因受到 PhAc（及其羟基衍生物）的强烈诱导，并编码一种新的细胞色素 P450（CYP450）。中断的 phacB 菌株 ( ΔphacB ）不能在 3-羟基、4-羟基或 3,4-二羟基-PhAc 上生长。使用野生型和几种噬菌体的微粒体对体外反应进行了高效液相色谱和气相色谱-质谱分析。 A. nidulans 突变株的微粒体进行的体外反应的高效液相色谱和气相色谱-质谱分析证实 phacB -编码的 CYP450 催化 3- 羟基苯乙酸酯和 3,4- 二羟基苯乙酸酯的 6- 羟基化反应，分别生成 2,5- 二羟基苯乙酸酯和 2,4,5- 三羟基苯乙酸酯。这两种化合物都被均五酯二氧 化酶用作底物。这种细胞色素 P450 蛋白也以 PhAc 为底物生成 2-OH-PhAc，但效率很低。这种 phacB 基因是新的 CYP450 亚家族（CYP504B）的第一个成员。
• Disruption of phacA, an Aspergillus nidulans Gene Encoding a Novel Cytochrome P450 Monooxygenase Catalyzing Phenylacetate 2-Hydroxylation, Results in Penicillin Overproduction
  作者：José Manuel Mingot、Miguel Angel Peñalva、José Manuel Fernández-Cañón

  DOI：10.1074/jbc.274.21.14545

  日期：1999.5

  Aspergillus nidulans utilizes phenylacetate as a carbon source via homogentisate, which is degraded to fumarate and acetoacetate. Mutational evidence strongly suggested that phenylacetate is converted to homogentisate through two sequential hydroxylating reactions in positions 2 and 5 of the aromatic ring. Using cDNA substraction techniques, we have characterized a gene, denoted phacA, whose transcription is strongly induced by phenylacetate and which putatively encodes a cytochrome P450 protein. A disrupted phacA strain does not grow on phenylacetate but grows on 2-hydroxy- or 2,5-dihydroxyphenylacetate. Microsomal extracts of the disrupted strain are deficient in the NADPH-dependent conversion of phenylacetate to 2-hydroxyphenylacetate. We conclude that PhacA catalyzes the ortho-hydroxylation of phenylacetate, the first step of A. nidulans phenylacetate catabolism, The involvement of a P450 enzyme in the ortho-hydroxylation of a monoaromatic compound has no precedent, In addition, PhacA shows substantial sequence divergence with known cytochromes P450 and defines a new family of these enzymes, suggesting that saprophytic fungi may represent a source of novel cytochromes P450,Phenylacetate is a precursor for benzylpenicillin production, phacA disruption increases penicillin production 3-5-fold, indicating that catabolism competes with antibiotic biosynthesis for phenylacetate and strongly suggesting strategies for Penicillium chrysogenum strain improvement by reverse genetics.