• Title/Summary/Keyword: petroselinic acid

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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

  • Kim, Seong-Jin
    • Journal of the Korean Applied Science and Technology
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    • v.22 no.4
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    • pp.323-331
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    • 2005
  • 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 $(cis-9-C_{18:1})$. 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 ${\delta}1.638$ (2H, C-3) and ${\delta}1.377$ (2H, C-4), and two multiplets centered at ${\delta}2.022{\sim}2.047$ (2H, C-5) and ${\delta}2.000{\sim}2.022$ (2H, C-8), and multiplet signals of olefinic protons centered at ${\delta}5.3015{\sim}5.3426$ (C-6, J=9.5 Hz) and ${\delta}\;5.3465{\sim}5.3877$ (C-7, J=9.5 Hz). The $^13C-NMR$ spectrum showed 18 carbon resonance signals including an overlapped signal at ${\delta}29.7002$ for C-12 and ${\delta}29.6520$ for C-13 (or they can be reversed), and other highly resolved signals at ${\delta}33.950$, ${\delta}24.558$, ${\delta}26.773$ and ${\delta}27.205$ due to C-2, C-3, C-5 and C-8 of a ${\Delta}^6-octadecenoic$ 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%).

Resolution of Molecular Species of the Triacylglycerol Containing Petroselinic Acid $(cis-C_{18:1{\omega}12)$ by Silver Ion-HPLC

  • Joh, Yong-Goe;Kim, Seong-Jin
    • Journal of the Korean Applied Science and Technology
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    • v.22 no.4
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    • pp.339-348
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    • 2005
  • On the analysis of triacylglycerol (TG) from the kernels of Acanthopanax sessiliflorus by reversed phase-HPLC, it was separated into three main fractions of PN 44, 46 and 48, according to partition number (PN). On the contrary, it could be clearly classified into seven fractions of SMM, MMM, SMD, MMD, SDD, MDD and MDT by silver ion-HPLC by the number of double bond in the acyl chains of TG species. But resolution of so-called critical pairs of TG molecular species such as molecular pairs of $P_eLL$ $[C_{18:1{\omega}12}/(C_{18:2{\omega}6)2}]$ and OLL $[C_{18:1{\omega}9}/(C_{18:2{\omega}6)2}]$ and OOL $[(C_{18:1{\omega}9)2}/C_{18:2{\omega}6]$, and $P_eP_eL$ $[(C_{18:2{\omega}12)2}/C_{18:1{\omega}6]$ was not achieved $(P_e;$ petroselinic acid, L; linoleic acid, O; oleic acid). On the other hand, TG extracted from Aralia continentalis kernels were also fractionated into seven groups of SSM, SMM, MMM, SMD, MMD, SDD and MDD (S; saturated acid, M; monoenoic acid, D; dienoic acid) by silver ion-HPLC, although it's were classified into three groups of PN 44, 46 and 48 by reversed phase-HPLC. The fractions of SMM, MMM, MMD and MDD were divided into two subfractions, respectively; the fractions of SMM, MMM, MMD and MDD were resolved into the subfraction of $PP_e/P_e$ and POO (critical pairs from each other), that of $P_e/P_e/P_e$ and OOO, that of $P_e/P_e/L$ and OOL, and that of $P_e/L/L$ and OLL.

Unambiguous Evidence for Phase Transitions of Oleic Acid in Pure Liquid State by Near-Infrared Spectroscopy and Pricipan Comaonent Analysis

  • Nobuya Yokochi;Makio Iwahashi;Masao Suzuki;Yukihiro Ozaki
    • Near Infrared Analysis
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    • v.1 no.2
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    • pp.21-27
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    • 2000
  • Temperature-dependent changes in near-infrared (NIR) spectra have been measured for oleic acid, and nonanoic acid in the pure liquid state. Particular attention has been paid to the 5400-4800 cm$\^$-1/ region where a number of combination bands appear. The NIR spectra of oleic acid show that a band at 5303 cm$\^$-1/ increases with temperature while that at 5270 cm/sup-1/ decreases. It ha been found from their second derivative spectra that these spectral changes take place stepwisely with two break points at 30 and 53$\^{C}$, which correspond to the phase transition temperatures oleic acid reported previously. Principle component analysis (PCA) has been carried out for the NIR spectra of oleic acid in the 5400-4800 cm$\^$-1/ region measured over a temperature range of 15-80$\^{C}$. core plots of the first and second principal components (PCs) show that the NIR spectra are classified into three groups; the spectra measured in the temperature range of 15-30$\^{C}$, those in the range of 31-53$\^{C}$, and those in the range of 54-80$\^{C}$. These temperature ranges correspond to those for quasi-smectic liquid crystal, disordered liquid crystal, and isotropic liquid of oleic acid in the pure liquid state. In other words, PCA provides unambiguous evidence for the phase transitions. similar studies have been carried out for petroselinic acid and nonanoic acid in the pure liquid states, but they do not show any evidence for phase transitions.