penicillic acid | 17397-87-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氢呋喃
• 英文名称: penicillic acid
• 英文别名: 5-hydroxy-4-methoxy-5-(prop-1-en-2-yl)-furan-2(5H)-one；5-hydroxy-5-isopropenyl-4-methoxy-5H-furan-2-one；2-Hydroxy-3-methoxy-5-oxo-2-isopropenyl-2,5-dihydro-furan；5-Hydroxy-5-isopropenyl-4-methoxy-5H-furan-2-on；4-methoxy-5-hydroxy-5-(1-methyl-ethenyl)-2(5H)-furanone；5-Hydroxy-4-methoxy-5-(1-methylethenyl)-2-furanone；5-hydroxy-4-methoxy-5-prop-1-en-2-ylfuran-2-one
• CAS: 17397-87-4
• 化学式: C₈H₁₀O₄
• mdl: MFCD00078152
• 分子量: 170.165
• InChiKey: YCOFRPYSZKIPBQ-UHFFFAOYSA-N

物化性质

• 熔点：
  79-80 °C
• 沸点：
  366.7±42.0 °C(Predicted)
• 密度：
  1.22±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.375
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  penicillic acid 在 碘 、 碳酸氢钠 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 以80%的产率得到
  参考文献：
  名称：

  青霉酸的分离和转化为 6-iodo-α-pyran-2,5-dione：合成果胶内酯 F 的关键中间体

  摘要：

  摘要 从核盘曲霉中分离出青霉酸，并通过碘内酯化作用将其转化为 6-iodo-α-pyran-2,5-diones，这是合成果胶内酯 F 的关键中间体。 使用 NMR 确认了青霉酸及其碘内酯化产物的结构实验。图形概要

  DOI：

  10.1080/00397911.2016.1164864
• 作为产物：
  描述：

  alkaline earth salt of/the/ methylsulfuric acid 在 水 、 magnesium oxide 作用下， 生成 penicillic acid
  参考文献：
  名称：

  Detecting nurse‐perceived patient treatment difficulty of psychiatric patients in hospital: an evaluation of a patient assessment sheet

  摘要：

  Many changes have occurred in hospital psychiatric care, including decreased length of hospital stay and increased patient acuity. These changes highlight the need for nurses to adequately assess and formally document patient treatment difficulties. The purposes of this study were to determine the ability of the Patient Assessment Sheet (PAS) to predict patient ‘problems’ that psychiatric nurses perceived as associated with patient treatment difficulty, and to identify the patient problems missing from the PAS. These purposes were accomplished by comparing the PAS to the Hospital Treatment Rating Scales (HTRS). A correlational design and multiple linear regression technique were used. Eight psychiatric registered nurses assessed a total of 110 patients, admitted consecutively to one inpatient psychiatric unit. The HTRS and the PAS were used independently for each patient. Four PAS items (active affect, passive affect, aggression toward self, and patient confusion) significantly predicted 38% of the variance from the HTRS; and three HTRS items (isolation and withdrawal from relationships, noninvolvement in treatment, and wide variability in mood) significantly predicted 22% of the residual variance from the HTRS. The identified PAS and HTRS items help to make visible patient problems associated with nurse‐perceived patient treatment difficulty. This identification is potentially important for both clinical and political purposes.

  DOI：

  10.1046/j.1365-2850.2000.00285.x

文献信息

• The addition of L-cysteine to unsaturated lactones and related compounds
  作者：D. K. Black

  DOI：10.1039/j39660001123

  日期：——

  The thiol group of cysteine adds to the double bond of unsaturated lactones and related compounds to give thio amino-acids. In certain cases, cyclisation and dehydration leads to the formation of stable, unsaturated, 8-membered cyclic lactams.

  半胱氨酸的硫醇基团加成不饱和内酯和相关化合物的双键，得到硫代氨基酸。在某些情况下，环化和脱水会导致形成稳定的，不饱和的8元环状内酰胺。
• Antimicrobial Polyketide Metabolites from Penicillium bissettii and P. glabrum
  作者：Melissa M. Cadelis、Natasha S. L. Nipper、Alex Grey、Soeren Geese、Shara J. van de Pas、Bevan S. Weir、Brent R. Copp、Siouxsie Wiles

  DOI：10.3390/molecules27010240

  日期：——

  penicillic acid (1), citromycetin (2), penialdin A (3), penialdin F (4), and myxotrichin B (5). Semi-synthetic derivatization of 1 led to the discovery of a novel dihydro (1a) derivative that provided evidence for the existence of the much-speculated open-chained form of 1. Upon investigation of the antimicrobial activities of the natural products and derivatives, both penicillic acid (1) and penialdin

  对新西兰国际植物微生物保藏中心的几种真菌进行筛选，鉴定出两种青霉菌株：比塞蒂青霉和光斑青霉，它们对大肠杆菌、肺炎克雷伯菌和金黄色葡萄球菌表现出抗菌活性。通过提取和分馏对真菌的天然产物进行进一步研究，分离出五种已知的聚酮化合物代谢物：青霉酸 (1)、柠檬霉素 (2)、青霉素 A (3)、青霉素 F (4) 和粘菌素乙（5）。 1 的半合成衍生化导致了一种新型二氢 (1a) 衍生物的发现，该衍生物为人们猜测的开链形式 1 的存在提供了证据。在对天然产物和衍生物的抗菌活性进行研究后，发现青霉素酸 (1) 和青霉素 F (4) 被发现可抑制耐甲氧西林金黄色葡萄球菌的生长。还发现 Penialdin F (4) 与柠檬霉素 (2) 一起对脓肿分枝杆菌和海分枝杆菌具有一定的抑制活性。
• The Reactivity of the Fungal Toxin Papyracillic Acid 1
  作者：Rudong Shan、Marc Stadler、Heidrun Anke、Olov Sterner

  DOI：10.1016/s0040-4020(97)00277-9

  日期：1997.4

  Papyracillic acid (1), an antibiotic isolated from the ascomycete Lachnum papyraceum, owes its bioactivities to its reactivity towards nucleophiles. When reacted with cysteine and cysteine methyl ester, it exclusively added the thiol groups to the exomethylene double bond. Both papyracillic acid (1) and its analogue penicillic acid (2) react with pyridine to indolizine derivatives during acetylation

  药草酸（Papyracillic acid）（1）是一种从子囊菌Lachnum papyraceum中分离出来的抗生素，其生物活性归因于其对亲核试剂的反应性。当与半胱氨酸和半胱氨酸甲酯反应时，它仅将硫醇基团添加到外亚甲基双键上。在乙酰化条件下，草吡咯酸（1）及其类似青霉酸（2）均与吡啶反应生成吲哚嗪衍生物。©1997爱思唯尔科学有限公司。
• Cytotoxic and Other Metabolites of <i>Aspergillus </i>Inhabiting the Rhizosphere of Sonoran Desert Plants
  作者：Jian He、E. M. Kithsiri Wijeratne、Bharat P. Bashyal、Jixun Zhan、Christopher J. Seliga、Manping X. Liu、Elizabeth E. Pierson、Leland S. Pierson、Hans D. VanEtten、A. A. Leslie Gunatilaka

  DOI：10.1021/np040139d

  日期：2004.12.1

  In a study to discover potential anticancer agents from rhizosphere fungi of Sonoran desert plants cytotoxic EtOAc extracts of four Aspergillus strains have been investigated. Two new metabolites, terrequinone A (1) and terrefuranone (2), along with Na-acetyl aszonalemin (LL-S490beta) (3) were isolated from As. terreus occurring in the rhizosphere of Ambrosia ambrosoides, whereas As. terreus inhabiting

  在一项旨在从Sonoran沙漠植物的根际真菌中发现潜在抗癌剂的研究中，对四种曲霉菌株的细胞毒性EtOAc提取物进行了研究。从As中分离出两个新的代谢物，terrequinone A（1）和terrefurananone（2），以及Na-乙酰基Aszonalemin（LL-S490beta）（3）。土生于Ambrosia ambrosoides的根际，而As。栖息于不明Brickellia sp。的根际的土。得到脱氢曲维林（4），11-甲氧基曲维林（5）和11-羟基曲维林（6）。作为。从菊苣根际分离的宫颈含有两种新化合物，即4R *，5S *-二羟基-3-甲氧基-5-甲基环己-2-烯酮（7）和6-甲氧基-5（6）-二氢青霉素（8） ，除青霉素（9）。青霉素酸也从As中分离出来。丝虫发生在Larrea tridentata的根际。通过光谱方法和化学衍生化阐明了1-9的结构。2的乙酰化得到14-
• 40. Polarographic studies. Part II. Mould metabolites and related quinones
  作者：James E. Page、F. Arnold Robinson

  DOI：10.1039/jr9430000133

  日期：——