Aspyrone | 84276-21-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃
• 英文名称: Aspyrone
• 英文别名: 2H-Pyran-2-one, 5,6-dihydro-5-hydroxy-6-methyl-3-(3-methyloxiranyl)-；3-hydroxy-2-methyl-5-(3-methyloxiran-2-yl)-2,3-dihydropyran-6-one
• CAS: 84276-21-1
• 化学式: C₉H₁₂O₄
• 分子量: 184.192
• InChiKey: RCAULRNMJFUWRP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.1
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  59.1
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  Aspyrone 在 sodium hydroxide 、 臭氧 作用下， 生成 3-methyloxirane-2-carboxylic acid
  参考文献：
  名称：

  阿斯匹龙的生物合成，阿斯匹龙菌的一种代谢产物。与14 C和3 H标记的乙酸盐和丙二酸酯的掺入研究

  摘要：

  与14个C标记的乙酸盐和丙二酸酯的掺入研究确定了阿斯泰隆（1）的聚酮化合物来源，并确定了链起始剂单元。五个碳原子来自乙酸甲酯的甲基，其余四个碳原子来自羧基。从[ 2-3 H]乙酸盐掺入tri的方式与由胶束类型的芳香族前体进行的生物合成不一致。没有掺入可能含有2-甲基色酮核的高级前体。有证据表明，芳香族前体不参与阿斯匹隆的生物合成，并且碳骨架（如共代谢型琥珀酸内酯（6）的骨架）是通过线性五元酮中间体的脱羧和重排而生成的。

  DOI：

  10.1039/p19840001013

文献信息

• Studies on fungal metabolites. Part 2. Carbon-13 nuclear magnetic resonance biosynthetic studies on pentaketide metabolites of Aspergillus melleus: 3-(1,2-epoxypropyl)-5,6-dihydro-5-hydroxy-6-methylpyran-2-one and mellein
  作者：John S. E. Holker、Thomas J. Simpson

  DOI：10.1039/p19810001397

  日期：——

  The 13C n.m.r. spectra and incorporations of 13C-labelled precursors into pyrone and dihydroisocoumarin pentaketide metabolites from the culture liquors of Aspergillus melleus are reported. Detection of a two-bond 13C–13C coupling in a metabolite enriched from [1,2-13C2]acetate provides proof for an intramolecular rearrangement occurring during biosynthesis.

  的13个的C NMR谱和掺入13 C标记的前体引入吡喃酮和二氢异香豆素pentaketide代谢物从培养液蜂蜜曲霉报告。在富含[1,2- 13 C 2 ]乙酸的代谢物中检测到双键13 C – 13 C偶联为生物合成过程中发生分子内重排提供了证据。
• Means and methods for controlling commensales
  申请人：B.R.A.I.N. Biotechnology Research and Information Network AG

  公开号：EP2090292A1

  公开（公告）日：2009-08-19

  This invention relates to a cosmetic composition comprising or consisting of one or more compounds selected from the compounds of formulae (A) and (B) wherein ---- represents a single bond or double bond; R1 in formula (A) and R1 in formula (B) are selected from H, linear or branched C1 to C4 alkyl, linear or branched C1 to C4 alkenyl, linear or branched C1 to C4 alkinyl, and linear or branched C1 to C4 alkanoyl; R3 in formula (A) and R3 in formula (B) are selected from H, linear or branched C1 to C4 alkyl, linear or branched C1 to C4 alkenyl, and linear or branched C1 to C4 alkinyl; R2 and R4 in formula (A) are independently selected from H, OH and halogen, or R2 and R4 together are O to form an epoxid, wherein ---- represents a single bond in case R2 and R4 together are O; and R2 and R4 in formula (B) are defined as R2 and R4 in formula (A), respectively.

  本发明涉及一种化妆品组合物，该组合物由一种或多种选自式 (A) 和 (B) 化合物的化合物组成。 其中 ---- 代表单键或双键；式 (A) 中的 R1 和式 (B) 中的 R1 选自 H、直链或支链 C1 至 C4 烷基、直链或支链 C1 至 C4 烯基、直链或支链 C1 至 C4 烷基和直链或支链 C1 至 C4 烷酰基；式 (A) 中的 R3 和式 (B) 中的 R3 选自 H、直链或支链 C1 至 C4 烷基、直链或支链 C1 至 C4 烯基和直链或支链 C1 至 C4 烷基；式（A）中的 R2 和 R4 独立选自 H、OH 和卤素，或 R2 和 R4 同为 O 以形成环氧化合物，其中 ---- 在 R2 和 R4 同为 O 的情况下代表单键；式（B）中的 R2 和 R4 分别定义为式（A）中的 R2 和 R4。
• Effect of fungal metabolites and some derivatives against<i>Tribolium castaneum</i>(Herbst) and<i>Nezara viridula</i>(L.)
  作者：Mercè Balcells、Ramon Canela、Josep Coll、Vicent Sanchís、Mercè Torres

  DOI：10.1002/ps.2780450405

  日期：1995.12

  AbstractTwo fungal metabolites, aspyrone (3‐(1,2‐epoxypropyl)‐5‐hydroxy‐6‐methyl‐5,6‐dihydropyran‐2‐one) and asperlactone (3‐(1,2‐epoxypropyl)‐5‐(1‐hydroxyethyl)‐5‐furan‐2‐one) were isolated from an Aspergillus ochraceus Wilhelm strain showing IGR activity against Tribolium castaneum (Herbst). Synthetic derivatives of aspyrone were produced using published methods. These derivatives together with aspyrone and asperlactone were tested for insect growth‐regulating activity against T. castaneum, and for ovicidal activity against Nezara viridula L. Of the compounds tested asperlactone appeared to be the most active.
• [EN] MEANS AND METHODS FOR CONTROLLING COMMENSALES<br/>[FR] MOYENS ET PROCÉDÉS DE LUTTE CONTRE LES COMMENSAUX
  申请人：B R A I N

  公开号：WO2009103501A1

  公开（公告）日：2009-08-27

  This invention relates to a cosmetic composition comprising or consisting of one or more compounds selected from the compounds of formulae (A) and (B) wherein ---- represents a single bond or double bond; R1 in formula (A) and R1 in formula (B) are selected from H, linear or branched C1 to C4 alkyl, linear or branched C1 to C4 alkenyl, linear or branched C1 to C4 alkinyl, and linear or branched C1 to C4 alkanoyl; R3 in formula (A) and R3 in formula (B) are selected from H, linear or branched C1 to C4 alkyl, linear or branched C1 to C4 alkenyl, and linear or branched C1 to C4 alkinyl; R2 and R4 in formula (A) are independently selected from H, OH and halogen, or R2 and R4 together are O to form an epoxid, wherein ---- represents a single bond in case R2 and R4 together are O; and R2 and R4 in formula (B) are defined as R2 and R4 in formula (A), respectively. Preferably, said cosmetic composition is for the cleaning of the skin. Also provided are means and methods for the prevention or reduction of biofilm formation on an intracorporeal device and/or for the removal of biofilm from an intracorporeal device, wherein said biofilm comprises or consists of bacteria of the genus Propionibacterium. Furthermore provided is an intracorporeal device which is coated and/or loaded with one or more compounds as defined above.
• Biosynthesis of aspyrone, a metabolite of Aspergillus malleus. Incorporation studies with 14C- and 3H-labelled acetates and malonate
  作者：R. Jeffrey Copeland、Robert A. Hill、David J. Hinchcliffe、James Staunton

  DOI：10.1039/p19840001013

  日期：——

  Incorporation studies with 14C-labelled acetates and malonate confirm the polyketide origin of aspyrone (1), and identify the chain starter unit. Five carbons are derived from the methyl group of acetate, and the remaining four from the carboxy group. The pattern of incorporation of tritium from [2-3H]acetate is inconsistent with a biosynthesis from aromatic precursors of the mellein type. Possibly

  与14个C标记的乙酸盐和丙二酸酯的掺入研究确定了阿斯泰隆（1）的聚酮化合物来源，并确定了链起始剂单元。五个碳原子来自乙酸甲酯的甲基，其余四个碳原子来自羧基。从[ 2-3 H]乙酸盐掺入tri的方式与由胶束类型的芳香族前体进行的生物合成不一致。没有掺入可能含有2-甲基色酮核的高级前体。有证据表明，芳香族前体不参与阿斯匹隆的生物合成，并且碳骨架（如共代谢型琥珀酸内酯（6）的骨架）是通过线性五元酮中间体的脱羧和重排而生成的。