(+/-)-7-(3,4-dihydroxybutyloxy)-2H-1-benzopyran-2-one | 403498-44-2

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 香豆素及其衍生物
• 英文名称: (+/-)-7-(3,4-dihydroxybutyloxy)-2H-1-benzopyran-2-one
• 英文别名: 7-(3,4-dihydroxybutyloxy)-2H-1-benzopyran-2-one；4-[(2-Oxo-2h-1-benzopyran-7-yl)oxy]butane-1,2-diol；7-(3,4-dihydroxybutoxy)chromen-2-one
• CAS: 403498-44-2
• 化学式: C₁₃H₁₄O₅
• 分子量: 250.251
• InChiKey: GCIJRNRDXGAGHR-UHFFFAOYSA-N

物化性质

• 熔点：
  98 °C
• 沸点：
  503.2±50.0 °C(Predicted)
• 密度：
  1.345±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  76
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (+/-)-7-(3,4-dihydroxybutyloxy)-2H-1-benzopyran-2-one 在 bovine serum albumin sodium periodate 、 borate buffer 作用下， 生成 7-羟基香豆素
  参考文献：
  名称：

  Badalassi, Fabrizio; Wahler, Denis; Klein, Gerald, Angewandte Chemie - International Edition, 2000, vol. 39, # 22, p. 4067 - 4070

  摘要：

  DOI：
• 作为产物：
  描述：

  7-[2-(3,3-dimethyl-1,2-dioxolan-4-yl)ethoxy]-2H-1-benzopyran-2-one 在 盐酸 作用下， 以 甲醇 、 水 为溶剂， 反应 17.0h， 以66%的产率得到(+/-)-7-(3,4-dihydroxybutyloxy)-2H-1-benzopyran-2-one
  参考文献：
  名称：

  脂肪酶和酯酶的灵敏且选择性的高通量筛选荧光分析

  摘要：

  7-（3,4-二羟基丁氧基）-2 H -1-苯并吡喃-2-酮（6）的长链脂肪酸酯，例如辛酸酯2a，被证明是对脂肪酶和酯酶异常敏感和选择性的荧光底物。在存在牛血清白蛋白和高碘酸钠的情况下，在2a中酯官能团水解后会释放伞形酮（8）。这些底物对脂酶的敏感性比市售荧光底物4-甲基伞形基庚酸庚酸酯高至少一个数量级。此外，它们在广泛的pH诱导和热水解条件下都稳定，并且不与非催化蛋白（如牛血清白蛋白（BSA））反应。

  DOI：

  10.1002/hlca.200390240

文献信息

• Fluorogenic Cyanohydrin Esters as Chiral Probes for Esterase and Lipase Activity
  作者：Emmanuel Leroy、Nicolas Bensel、Jean-Louis Reymond

  DOI：10.1002/adsc.200303005

  日期：2003.6

  Fluorogenic cyanohydrin esters were prepared that release the fluorescent product umbelliferone by secondary decomposition of the primary cyanohydrin reaction product by cyanide elimination to the aldehyde and subsequent β-elimination. Whereas butyrate 1b and octanoate 1d show the highest reaction rates with enzymes, the highest relative rates above the non-catalyzed background reaction are achieved

  制备了荧光氰醇酯，其通过氰化物消除成醛并随后进行β-消除作用而使初级氰醇反应产物进行二次分解，从而释放出荧光产物伞形酮。丁酸1b和辛酸1d与酶的反应速率最高，而新戊酸酯1c和苯甲酸酯1e的相对速率最高，高于非催化本底反应。当转化率稳定在最大荧光释放量的50％时，检测到对映选择性反应，并通过未反应的氰醇酯底物的手性HPLC分析确认对映选择性。
• Method for releasing a product comprising chemical oxidation, method for detecting said product and uses thereof
  申请人：Reymond Jean-Louis

  公开号：US20070099257A1

  公开（公告）日：2007-05-03

  This invention has as its object a method for releasing a product by subjecting a compound of Formula (II′): R′ 7 R′ 8 (HX)C 1 -C 2 (YH)R′ 9 R′ 10 to a chemical oxidation that cleaves the bond C 1 -C 2 to obtain the product. In the compound of Formula (II′): R′ 7 to R′ 10 , which are identical or different, correspond to a hydrogen atom, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted functional group; X and Y, which are identical or different, are an oxygen atom, a sulfur atom, or an amine of Formula —NR 11 R 12 , wherein R 11 is a hydrogen atom, an alkyl group, or a substituted or unsubstituted aryl group, and R 12 is not a hydrogen atom. The invention also has as its object a method for releasing a product that comprises, before the chemical oxidation stage, a first step for preparing the compound of Formula (II′). The released product can be a volatile molecule or an active substance or else a specific product. The invention also relates to a method for detecting the released product as well as its applications, in particular for detecting catalytic or enzymatic activities.

  本发明的目的是通过将式（II'）的化合物暴露于化学氧化作用下，断裂C1-C2键获得产品的方法。在式（II'）的化合物中，R'7到R'10是相同或不同的氢原子、取代或未取代的烷基或取代或未取代的功能基团；X和Y是相同或不同的氧原子、硫原子或式—NR11R12的胺，其中R11是氢原子、烷基或取代或未取代的芳基，而R12不是氢原子。本发明还涉及在化学氧化阶段之前，制备式（II'）化合物的第一步骤的释放产品的方法。释放的产品可以是挥发性分子、活性物质或特定产品。本发明还涉及检测释放产品的方法及其应用，特别是用于检测催化或酶活性。
• Non-hydrolytic microbial probes
  申请人：Biosynth AG

  公开号：EP2184367A1

  公开（公告）日：2010-05-12

  A method of detecting the presence of selected living cells in a sample, comprises the steps of contacting the sample with a substrate compound and monitoring for a signal caused by a metabolic activity of said selected living cells resulting in a release of a signalogenic moiety from the substrate compound. The substrate compound has the formula wherein X is O or NH, A is H or a first enzymatically hydrolyzable group, B is R3 or CH-Y-D, wherein Y is O or NH and D is H or a second enzymatically hydrolyzable group, R1, R2 and R3 are independently selected inert groups, and Sig-O is a signalogenic moiety that upon release thereof converts to said signalophore.

  一种检测样品中是否存在选定活细胞的方法，包括以下步骤：将样品与一种底物化合物接触，并监测由所述选定活细胞的代谢活动导致底物化合物释放信号分子而产生的信号。底物化合物的分子式为 其中 X 是 O 或 NH，A 是 H 或第一可酶水解基团，B 是 R3 或 CH-Y-D，其中 Y 是 O 或 NH，D 是 H 或第二可酶水解基团，R1、R2 和 R3 是独立选择的惰性基团，Sig-O 是信号原分子，释放后转化为所述信号团。
• Enzyme Fingerprints of Activity, and Stereo- and Enantioselectivity from Fluorogenic and Chromogenic Substrate Arrays
  作者：Denis Wahler、Fabrizio Badalassi、Paolo Crotti、Jean-Louis Reymond

  DOI：10.1002/1521-3765(20020715)8:14<3211::aid-chem3211>3.0.co;2-g

  日期：2002.7.15

  A series of stereochemically and structurally diverse fluorogenic and chromogenic substrates for hydrolytic enzymes has been synthesized and used to characterize enzyme activity profiles of esterases, lipases, proteases, peptidases, phosphatases, and epoxide hydrolases. The substrates used are particularly resilient to nonspecific reactions due to their mechanism of activation. The activities recorded with the individual substrates are therefore remarkably reproducible, and enable us to use the overall pattern of activity as a specific fingerprint for the enzyme sample. Fingerprints of activity, and enantio- and stereoselectivity are displayed as arrays of color-scale squares that are easily analyzed visually. Such fingerprints might be useful for quality control, enzyme discovery, and possibly for addressing the issue of functional convergence in enzymes.
• Esterase screening using whole cells of Brazilian soil microorganisms
  作者：Simone M. Mantovani、Luciana G. de Oliveira、Anita J. Marsaioli

  DOI：10.1590/s0103-50532010000800011

  日期：——

  A miniaturized enzymatic assay using fluorescent probes to reveal esterase producing microorganisms was optimized and applied to screen 64 soil bacterial strains. The best results were validated using traditional non-fluorogenic assays with acetyl and propanoyl phenylethanol to confirm the miniaturized results. The most active microorganisms belong to the genus Bacillus showing esterase activity and good enantiomeric ratios for the resolution of phenylethanol derivatives (E > 30). Part of the microorganisms are kept in our laboratory in glycerol or freeze-dried and the best microorganisms will be deposited in the CBMAI/CPQBA/Unicamp culture collection.