5-hydroxymethylfuran-3-carboxylic acid | 246178-75-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 呋喃
• 英文名称: 5-hydroxymethylfuran-3-carboxylic acid
• 英文别名: flufuran；5-(Hydroxymethyl)furan-3-carboxylic acid
• CAS: 246178-75-6
• 化学式: C₆H₆O₄
• 分子量: 142.111
• InChiKey: ZEACFIAQNKKVPN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.3
• 重原子数：
  10
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  70.7
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5-hydroxymethylfuran-3-carboxylic acid 在 氯化亚砜 作用下， 以 苯 为溶剂， 反应 5.0h， 生成 N,N-diethyl-2-(chloromethyl)-4-furancarboxamide
  参考文献：
  名称：

  Pevzner; Ignat'ev; Ionin, Russian Journal of General Chemistry, 1999, vol. 69, # 4, p. 551 - 556

  摘要：

  DOI：

文献信息

• The Issue of Misidentification of Kojic Acid with Flufuran in Aspergillus flavus
  作者：Marina DellaGreca、Gaetano De Tommaso、Maria Michela Salvatore、Rosario Nicoletti、Andrea Becchimanzi、Mauro Iuliano、Anna Andolfi

  DOI：10.3390/molecules24091709

  日期：——

  profile of this strain showed kojic acid to be the dominant product in cultures on Czapek-Dox broth. However, an accurate review of papers documenting secondary metabolite production in A. flavus also showed that an isomer of kojic acid, identified as 5-(hydroxymethyl)-furan-3-carboxylic acid and named flufuran is reported from this species. The spectroscopic data of kojic acid were almost identical to

  在研究蜜蜂衰退的复杂现象的过程中，从工蜂的血腔中分离出了黄曲霉。对该菌株代谢组学特征的观察表明，曲酸是 Czapek-Dox 肉汤培养物中的主要产物。然而，对记录黄曲霉次生代谢物产生的论文的准确回顾也表明，该物种报告了一种曲酸异构体，被鉴定为 5-(羟甲基)-呋喃-3-羧酸，并命名为氟呋喃。曲酸的光谱数据与文献报道的氟呋喃的光谱数据几乎相同。这激发了对商业曲酸和 5-(羟甲基)-呋喃-3-羧酸的比较研究，突出了一些差异，例如两种化合物的 13C-NMR 和 UV 光谱，表明曲酸被错误地识别为5-(羟甲基)-呋喃-3-羧酸过去曾出现过。
• Flufuran, an Antifungal 3,5-Disubstituted Furan Produced by<i>Aspergillus flavus</i>Link
  作者：Antonio Evidente、Gennaro Cristinzio、Biancavaleria Punzo、Anna Andolfi、Antonino Testa、Dominique Melck

  DOI：10.1002/cbdv.200800292

  日期：2009.3

  A 3,5-disubstituted furan, named flufuran, was isolated from a culture filtrate of a strain of Aspergillus flavus obtained from a chestnut compost created in the same orchard. Flufuran was identified by spectroscopic methods, and its structure was confirmed through the preparation of some key derivatives, also used to test the antifungal activity. At a concentration of 0.2 mg/ml, assayed against three

  从由在同一果园中产生的栗子堆肥获得的黄曲霉菌株的培养滤液中分离出3，5-二取代的呋喃，称为氟呋喃。通过光谱学方法鉴定了氟呋喃，并通过制备一些关键衍生物确认了其结构，并用于测试其抗真菌活性。对三种疫霉菌进行检定，浓度为0.2 mg / ml，对某些森林和农业植物致病，氟呋喃，尤其是其乙酰基衍生物显示出显着的抗真菌活性。尽管氟呋喃似乎与以前从某些猪Poly属分离的真菌代谢产物相同，但其有趣的抗真菌活性从未见过报道。
• A Diels–Alder probe for discovery of natural products containing furan moieties
  作者：Alyssa S Eggly、Namuunzul Otgontseren、Carson B Roberts、Amir Y Alwali、Haylie E Hennigan、Elizabeth I Parkinson

  DOI：10.3762/bjoc.20.88

  日期：——

  chromatography–mass spectrometry (LC–MS). The molecular probe, which undergoes this reaction with a variety of furans, was designed with both a UV-tag and a mass tag to enable easy identification. The probe has been tested with a variety of purified furans, including natural products, methylenomycin furan (MMF) hormones, and MMF derivatives. Moreover, the molecular probe has been tested in crude supernatants

  抽象的 天然产物 (NP) 是新型药物的绝佳灵感来源，通常针对感兴趣的靶标表现出独特的生物活性。具体来说，含有呋喃部分的纳米粒子显示出对抗多种疾病的活性，包括真菌感染和癌症。然而，从细胞上清液中发现和分离这些小分子具有挑战性。本文描述的工作展示了一种分子探针的开发，该探针可以通过 [4 + 2] Diels-Alder 环加成共价修饰呋喃部分，使它们可以通过液相色谱-质谱 (LC-MS) 轻松识别。该分子探针与多种呋喃发生反应，设计有紫外线标签和质量标签，以便于识别。该探针已使用多种纯化呋喃进行了测试，包括天然产物、亚甲霉素呋喃 (MMF) 激素和 MMF 衍生物。此外，该分子探针已在各种链霉菌菌株的粗上清液中进行了测试，并且能够鉴定 MMF。 Beilstein J. Org. Chem. 2024, 20, 1001–1010. doi:10.3762/bjoc.20.88
• Cryptoporic and isocryptoporic acids from the fungal cultures of Polyporus arcularius and P. ciliatus
  作者：G Cabrera

  DOI：10.1016/s0031-9422(02)00221-2

  日期：2002.9

  In a chemical study of several fungal cultures of Polyporus, a methyl ester of cryptoporic H was isolated from P. ciliatus, together with cryptoporic acid H and 5-hydroxymethylfuran-3-carboxylic acid. Furthermore, two additional compounds, named isocryptoporic acids H and I, were isolated from P. arcularius. These isocryptoporic acids are isomers of the cryptoporic acids with drimenol instead of albicanol as the terpenoid fragment; their structural elucidation was determined by application of spectroscopic methods. (C) 2002 Elsevier Science Ltd. All rights reserved.
• Anti-Inflammatory and Anti-Allergy Extracts from Nettle
  申请人：Alberte Randall S.

  公开号：US20100009927A1

  公开（公告）日：2010-01-14

  The present invention relates in part to nettle extracts that are useful for treating or preventing seasonal allergies, allergic rhinitis, and other inflammatory conditions.