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Identification of Petroselinic Acid (Cis-6-octadecenoic Acid) in the Seed Oils of Some of the Family Umbelliferae (Panax schinseng, Aralia continentalis and Acanthopanax sessiliflorus) by GC-MS, IR, 1H-and 13C-NMR Spectroscopic Techniques

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한국응용과학기술학회지 (The Korean Society of Applied Science and Technology)
한국응용과학기술학회(구 한국유화학회) (The Korean Society of Applied Science and Technology (KSAST))
초록

Fatty acid compositions of the seed oils of P. schinseng, A. continentalis and A. sessiliflorus, were analyzed by gas chromatography (GC) equipped with a capillary column. A large unusual peak was observed just before the peak corresponding to oleic acid (cis-9-C18:1). This unknown fatty acid was isolated by silver ion chromatography and then derivatized into the picolinyl ester. The mass spectrum of the picolinyl ester showed molecular ion at m/z=373 with other diagnostic ions such as m/z=178, 218, 232, 246, 274, 288, 302 and 344. Characteristic absorption peaks at 720 cm-1, 1640 cm-1 and 3010 cm-1 in IR spectrum indicated the presence of cis-configurational double bond in the molecule. The 1H-NMR spectrum of this acid gave two quintets centered at δ1.638 (2H, C-3) and δ1.377 (2H, C-4), and two multiplets centered at δ2.022~2.047 (2H, C-5) and δ2.000~2.022 (2H, C-8), and multiplet signals of olefinic protons centered at δ5.3015~5.3426 (C-6, J=9.5 Hz) and δ 5.3465~5.3877 (C-7, J=9.5 Hz). The 13C-NMR spectrum showed 18 carbon resonance signals including an overlapped signal at δ29.7002 for C-12 and δ29.6520 for C-13 (or they can be reversed), and other highly resolved signals at δ33.950, δ24.558, δ26.773 and δ27.205 due to C-2, C-3, C-5 and C-8 of a δ6-octadecenoic acid, respectively. From analysis results this unknown fatty acid could be identified as cis-6-octadecenoic acid. The seed oils of P. schinseng and A. sessiliflorus contained petroselinic acid (59.7%, 56.0%), oleic acid (18.3%, 6.1%) and linoleic acid (16.2%, 30.4%) with small amount of palmitic acid (3.0%, 3.1%) while the seed oil of A. continentalis comprised mainly oleic acid (30.2%), petroselinic acid (29.0%), linoleic acid (24.1%) and palmitic acid (13.1%).

저자
  • Seong-Jin Kim