Synthesis of Small Libraries of Natural Products: Part II: Identification of a New Natural Product from the Essential Oil of Pleurospermum austriacum (L.) Hoffm. (Apiaceae)

Molecules. 2023 Jun 6;28(12):4574. doi: 10.3390/molecules28124574.

Abstract

Herein, comprehensive data of NMR, MS, IR, and gas chromatography (RI) obtained by GC-MS on commonly used capillary columns of different polarity (non-polar DB-5MS and polar HP-Innowax) of a series of esters of all constitutional isomers of hexanoic acid with a homologous series of ω-phenylalkan-1-ols (phenylmethanol, 2-phenylethanol, 3-phenylpropan-1-ol, 4-phenylbutan-1-ol, and 5-phenylpentan-1-ol) and phenol, in total 48 chemical entities, were collected. The created synthetic library allowed the identification of a new constituent of the P. austriacum essential oil (3-phenylpropyl 2-methylpentanoate). The accumulated spectral and chromatographical data, as well as the established correlation between RI values and structures of regioisomeric hexanoates, provide (phyto)chemists with a tool that will make future identification of related natural compounds a straightforward task.

Keywords: GC-MS; NMR; Pleurospermum austriacum; esters; structure elucidation; synthetic library.

MeSH terms

  • Apiaceae* / chemistry
  • Biological Products*
  • Chromatography, Gas / methods
  • Gas Chromatography-Mass Spectrometry / methods
  • Oils, Volatile* / chemistry

Substances

  • Oils, Volatile
  • Biological Products

Grants and funding

This work was funded by the Ministry of Science, Technological Development and Innovations of Serbia [No. contract 451-03-47/2023-01/200124].