2-(2,3-二氢-4-吡喃基)乙酸 | 39115-30-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃
• 中文名称: 2-(2,3-二氢-4-吡喃基)乙酸
• 英文名称: desoxypatulinic acid
• 英文别名: (4-oxo-5,6-dihydro-4H-pyran-3-yl)-acetic acid；Deoxypatulinic acid；2-(4-oxo-2,3-dihydropyran-5-yl)acetic acid
• CAS: 39115-30-5
• 化学式: C₇H₈O₄
• 分子量: 156.138
• InChiKey: NDEBBGKFXQDNLC-UHFFFAOYSA-N

物化性质

• 沸点：
  321.6±21.0 °C(Predicted)
• 密度：
  1.329±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.6
• 重原子数：
  11
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  63.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-(2,3-二氢-4-吡喃基)乙酸 在 甲醇 、 氯仿 、 potassium acetate 、 氯 作用下， 生成 5,6-dihydro-7aH-furo[2,3-b]pyran-2,4-dione
  参考文献：
  名称：

  AlloPATULIN

  摘要：

  DOI：

  10.1021/ja01167a549
• 作为产物：
  描述：

  棒曲霉素 反应 72.0h， 生成 2-(2,3-二氢-4-吡喃基)乙酸
  参考文献：
  名称：

  Conversion of the Mycotoxin Patulin to the Less Toxic Desoxypatulinic Acid by the Biocontrol Yeast Rhodosporidium kratochvilovae Strain LS11

  摘要：

  The infection of stored apples by the fungus Penicillium e., pansum Causes the contamination of fruits and fruit-derived products with the mycotoxin patulin, which is a major issue in food safety Fungal attack can be prevented by beneficial microorganisms, so-called biocontrol agents Previous time-course thin layer chromatography analyses showed that the aerobic incubation of patulin with the biocontrol yeast Rhodosporidium kratochvilovae strain LS11 leads to the disappearance of the mycotoxin spot and the parallel emergence of two new spots, one of which disappears over time In this work, we analyzed the biodegradation of patulin effected by LS11 through HPLC The more stable of the two compounds was purified and characterized by nuclear magnetic resonance as desoxypatulinic acid, whose formation was also quantitated in patulin degradation experiments After R. kratochvilovae LS11 had been incubated m the presence of C-13-labeled patulin, label was traced to desoxypatulinic acid, thus proving that this compound derives from the metabolization of patulin by the yeast Desoxypatulinic acid was much less toxic than patulin to human lymphocytes and, in contrast to patulin, did not react in vitro with the thiol-bearing tripeptide glutathione The lower toxicity of desoxypatulinic acid is proposed to be a consequence of the hydrolysis of the lactone ring and the loss of functional, groups that react with thiol groups The formation of desoxypatulinic acid from patulin represents a novel biodegradation pathway that is also a detoxification process

  DOI：

  10.1021/jf203098v

文献信息

• Welkstoffe und Antibiotika. 12 Mitteilung. Über die Konstitution des Patulins
  作者：B. G. Engel、W. Brzeski、Pl. A. Plattner

  DOI：10.1002/hlca.19490320402

  日期：——

  Das Patulin besitzt nicht die allgemein angenommene Struktur eines Oxymethylen-tetrahydrocomansäure-Lactons I, sein Skelett muss vielmehr demjenigen der Tetrahydro-γ-pyronyl-(3)-essigsäure (VIII) entsprechen, so dass die Formeln II oder (nach Woodward) III wahrscheinlich erscheinen.

  达斯棒曲霉素besitzt nicht模具allgemein angenommene Struktur EINES Oxymethylen-tetrahydrocomansäure-Lactons I，盛Skelett搞乱vielmehr demjenigen DER四氢γ-pyronyl-（3）-essigsäure（VIII）entsprechen，所以DASS死Formeln II奥德（NACH伍德沃德）III wahrscheinlich埃舍宁。
• Structure of Chlorodesoxypatulinic Acid
  作者：R. B. WOODWARD、GURBAKHSH SINGH

  DOI：10.1038/165928b0

  日期：1950.6

  al.1 found that the product of the action of ethanolic hydrogen chloride on patulin gave on hydrolysis a crystalline chloro-acid, C7H7O4Cl, now called Chlorodesoxypatulinic acid. Afterwards, Plattner et al.2 observed that the same acid was readily produced by the action of hydrogen chloride on patulin in moist ethereal solution. The expression (I) was originally deduced1 for Chlorodesoxypatulinic acid

  BERGEL 等人 1 发现，氯化氢乙醇对棒曲霉素作用的产物在水解时会产生结晶氯酸 C7H7O4Cl，现在称为氯脱氧棒曲霉素。随后，Plattner 等人 2 观察到，氯化氢在潮湿的醚溶液中对棒曲霉素的作用很容易产生相同的酸。表达式 (I) 最初​​是根据氯脱氧棒曲霉素与棒曲霉素的关系推导出来的，因此假定结构 (II) 3。该实验室和 Plattner 的最新发展迫使放弃这些观点，并导致瑞士小组 2 将氯脱氧棒曲霉素制定为 (III)，这与两个新结构 (IV)4 和 (V)2 中的任何一个一致，分别在剑桥和苏黎世提出用于展曲霉素。
• Isotopic Labeling Studies Reveal the Patulin Detoxification Pathway by the Biocontrol Yeast <i>Rhodotorula kratochvilovae</i> LS11
  作者：Cristina Pinedo、Sandra A. I. Wright、Isidro G. Collado、Rebecca J. M. Goss、Raffaello Castoria、Patrizia Hrelia、Francesca Maffei、Rosa Durán-Patrón

  DOI：10.1021/acs.jnatprod.8b00539

  日期：2018.12.28

  Patulin (1) is a mycotoxin contaminant in fruit and vegetable products worldwide. Biocontrol agents, such as the yeast Rhodotorula kratochvilovae strain LS11, can reduce patulin (1) contamination in food. R. kratochvilovae LS11 converts patulin (1) into desoxypatulinic acid (DPA) (5), which is less cytotoxic than the mycotoxin (1) to in vitro human lymphocytes. In the present study, we report our investigations into the pathway of degradation of patulin (1) to DPA (5) by R. kratochvilovae. Isotopic labeling experiments revealed that 5 derives from patulin (1) through the hydrolysis of the gamma-lactone ring and subsequent enzymatic modifications. The ability of patulin (1) and DPA (5) to cause genetic damage was also investigated by the cytokinesis-block micronucleus cytome assay on in vitro human lymphocytes. Patulin (1) was demonstrated to cause much higher chromosomal damage than DPA (5).
• Bioactivity studies of oxysporone and several derivatives
  作者：Anna Andolfi、Lucia Maddau、Benedetto T. Linaldeddu、Bruno Scanu、Alessio Cimmino、Sara Basso、Antonio Evidente

  DOI：10.1016/j.phytol.2014.07.005

  日期：2014.12

  Recently oxysporone, a phytotoxic dihydrofuropyranone, was isolated along with two closely related compounds, afritoxinones A and B, from liquid cultures of Diplodia africana, an invasive fungal pathogen of Phoenicean juniper. In this study, eight derivatives were hemisynthesized and assayed for their phytotoxic and antifungal activities in comparison to the parent compound. Each compound was tested on non-host plants and on four destructive plant pathogens such as Athelia rolfsii, Diplodia corticola, Phytophthora cinnamomi and P. plurivora. The results on the phytotoxic activity showed that the dihydrofuropyranone carbon skeleton and both the double bond the hydroxy group of dihydropyran ring appeared to be structural features important in conferring activity. Although the data concerning the antifungal activity did not allow to extract any structure-activity relationships, it should be underlined that the conversion of oxysporone into the corresponding 4-O-benzoyl derivative led to a compound showing a good antifungal activity towards three out of the four organisms tested. (C) 2014 Phytochemical Society of Europe. Published by Elsevier B.V. All rights reserved.
• Conversion of the Mycotoxin Patulin to the Less Toxic Desoxypatulinic Acid by the Biocontrol Yeast Rhodosporidium kratochvilovae Strain LS11
  作者：Raffaello Castoria、Luisa Mannina、Rosa Durán-Patrón、Francesca Maffei、Anatoly P. Sobolev、Dario V. De Felice、Cristina Pinedo-Rivilla、Alberto Ritieni、Rosalia Ferracane、Sandra A. I. Wright

  DOI：10.1021/jf203098v

  日期：2011.11.9

  The infection of stored apples by the fungus Penicillium e., pansum Causes the contamination of fruits and fruit-derived products with the mycotoxin patulin, which is a major issue in food safety Fungal attack can be prevented by beneficial microorganisms, so-called biocontrol agents Previous time-course thin layer chromatography analyses showed that the aerobic incubation of patulin with the biocontrol yeast Rhodosporidium kratochvilovae strain LS11 leads to the disappearance of the mycotoxin spot and the parallel emergence of two new spots, one of which disappears over time In this work, we analyzed the biodegradation of patulin effected by LS11 through HPLC The more stable of the two compounds was purified and characterized by nuclear magnetic resonance as desoxypatulinic acid, whose formation was also quantitated in patulin degradation experiments After R. kratochvilovae LS11 had been incubated m the presence of C-13-labeled patulin, label was traced to desoxypatulinic acid, thus proving that this compound derives from the metabolization of patulin by the yeast Desoxypatulinic acid was much less toxic than patulin to human lymphocytes and, in contrast to patulin, did not react in vitro with the thiol-bearing tripeptide glutathione The lower toxicity of desoxypatulinic acid is proposed to be a consequence of the hydrolysis of the lactone ring and the loss of functional, groups that react with thiol groups The formation of desoxypatulinic acid from patulin represents a novel biodegradation pathway that is also a detoxification process