5-乙酰氨基-2-呋喃酮 | 16275-44-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氢呋喃
• 中文名称: 5-乙酰氨基-2-呋喃酮
• 英文名称: 4-acetamido-4-hydroxy-2-butenoic acid γ-lactone
• 英文别名: 4-acetamido-4-hydroxy-2-butenoic acid r-lactone；4-acetamido-2-buten-4-olide；butenolide；5-acetylamino-5H-furan-2-one；N-(2,5-dihydro-5-oxo-2-furanyl)-acetamide；Acetamide, N-(2,5-dihydro-5-oxo-2-furanyl)-；N-(5-oxo-2H-furan-2-yl)acetamide
• CAS: 16275-44-8
• 化学式: C₆H₇NO₃
• 分子量: 141.126
• InChiKey: HUSDLVGPEKVWAL-UHFFFAOYSA-N

物化性质

• 熔点：
  115 °C
• 沸点：
  471.7±44.0 °C(Predicted)
• 密度：
  1.26±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.3
• 重原子数：
  10
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  55.4
• 氢给体数：
  1
• 氢受体数：
  3

ADMET

毒理性

• 毒性总结

丁内酯导致脂质过氧化，破坏膜脂双层并损害膜蛋白。它还通过损害线粒体呼吸链复合物I–IV的活性，尤其是在肝脏中，诱导活性氧种类的产生，导致氧化应激。此外，丁内酯通过抑制Ca2+/Mg2+-ATPase和Na+/K+-ATPase的活性来破坏阳离子梯度，这可能是脂质过氧化的副作用，或者是通过与这些酶活性位点中的巯基结合。

Butenolide causes lipid peroxidation, disrupting the membrane lipid bilayer and causing damage to membrane protiens. It also induces production of reactive oxygen species by impairing the activities of complexes I–IV of the mitochondrial respiratory chain, especially in the liver, leading to oxidative stress. In addition, butenolide disrupts the cation gradient by inhibiting the activity of Ca2+/Mg2+-ATPase and Na+/K+-ATPase, likely either as a side effect of lipid peroxidation or by binding to the sulfhydryl groups in the active sites of these enzymes. (A3036, A3037)

来源:Toxin and Toxin Target Database (T3DB)

毒理性

• 致癌物分类

未列在IARC目录中。

Not listed by IARC.

来源:Toxin and Toxin Target Database (T3DB)

毒理性

• 健康影响

丁内酯具有心脏毒性和肝脏毒性。镰刀菌毒素与食物中毒性白细胞减少症和食管癌都有关联。食用被镰刀菌毒素污染的食物也被认为是克山病和卡辛-贝克病的可疑病因因素。

Butenolide is cardiotoxic and hepatotoxic. Fusarium mycotoxins has been associated with both alimentary toxic aleukia, and esophageal cancer. Consumption of Fusarium mycotoxins-contaminated foodstuffs has also been considered as a suspected etiological factor for Kashin–Beck disease and Keshan disease. (A3036, A3039)

来源:Toxin and Toxin Target Database (T3DB)

毒理性

• 暴露途径

口服、皮肤、吸入和 parenteral（被污染的药物）。 (A3101)

Oral, dermal, inhalation, and parenteral (contaminated drugs). (A3101)

来源:Toxin and Toxin Target Database (T3DB)

毒理性

• 症状

丁内酯刺激眼睛和皮肤。还可能导致体重减轻和生长迟缓。

Butenolide irritates the eyes and skin. It may also cause weight loss and growth retardation. (A3036, A3038)

来源:Toxin and Toxin Target Database (T3DB)

安全信息

• 海关编码：
  2932209090

制备方法与用途

类别：有毒物质

• 毒性分级：高毒
• 急性毒性：
  • 口服（小鼠）LD50：275毫克/公斤
  • 腹腔（小鼠）LD50：43.6毫克/公斤
• 刺激数据：
  • 皮肤（豚鼠）：0.01毫克/公斤 阳性反应
• 可燃性危险特性：可燃，火场排出辛辣刺激烟雾
• 储运特性：库房低温、通风、干燥；与食品原料分开存放
• 灭火剂：水、二氧化碳、干粉、砂土

反应信息

• 作为产物：
  描述：

  乙酰胺 、 5-羟基呋喃-2(5H)-酮 反应 1.0h， 生成 5-乙酰氨基-2-呋喃酮
  参考文献：
  名称：

  Poskonin, V. V.; Badovskaya, L. A.; Gavrilova, S. P., Journal of Organic Chemistry USSR (English Translation), 1989, vol. 25, # 8.2, p. 1535 - 1539

  摘要：

  DOI：

文献信息

• Acidophilic fusarium oxysporum strains, methods of their production and methods of their use
  申请人：Sustainable Bioproducts, Inc.

  公开号：US10344306B2

  公开（公告）日：2019-07-09

  The present invention provides isolated acidophilic Fusarium oxysporum strains, such as MK7, and their progeny, compositions comprising such strains and their progeny, methods of producing such strains and their progeny, and methods of using such strains and their progeny.

  本发明提供了分离的嗜酸镰孢菌株（如 MK7）及其后代、包含这些菌株及其后代的组合物、生产这些菌株及其后代的方法以及使用这些菌株及其后代的方法。
• Filamentous fungal biomats, methods of their production and methods of their use
  申请人：SUSTAINABLE BIOPRODUCTS, INC.

  公开号：US10577579B2

  公开（公告）日：2020-03-03

  A novel method of growing fungi is disclosed which uses an engineered artificial media and produces high density filamentous fungi biomats that can be harvested with a minimum of processing and from which fungal products such as antibiotics, proteins, and lipids can be isolated, the method resulting in lowered fungus cultivation costs for energy usage, oxygenation, water usage and waste stream production.

  本发明公开了一种新颖的真菌生长方法，该方法使用工程化人工培养基，生产出高密度丝状真菌生物垫，只需进行少量处理即可收获，并可从中分离出抗生素、蛋白质和脂质等真菌产品。
• Valla, Alain; Giraud, Michel; Labia, Roger, Bulletin de la Societe Chimique de France, 1997, vol. 134, # 6, p. 601 - 604
  作者：Valla, Alain、Giraud, Michel、Labia, Roger、Morand, Annick

  DOI：——

  日期：——
• FENG, GUOCHEN;SUN, CHONGYAN;ZHANG, YUGIU, XUASYUEH SHITSZI, 10,(1988) N, S. 331-332
  作者：FENG, GUOCHEN、SUN, CHONGYAN、ZHANG, YUGIU

  DOI：——

  日期：——
• POSKONIN, V. V.;BADOVSKAYA, L. A.;GAVRILOVA, S. P.;KULNEVICH, V. G., ZH. ORGAN. XIMII, 25,(1989) N, S. 1701-1706
  作者：POSKONIN, V. V.、BADOVSKAYA, L. A.、GAVRILOVA, S. P.、KULNEVICH, V. G.

  DOI：——

  日期：——

表征谱图