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Polymorphism and Phase Transition Behaviors of Lipids and Related Long-chain Compounds Containing Unsaturated Acyl Chains

Research Project

Project/Area Number 63470010
Research Category

Grant-in-Aid for General Scientific Research (B)

Allocation TypeSingle-year Grants
Research Field 構造化学
Research InstitutionOSAKA UNIVERSITY

Principal Investigator

KOBAYASHI Masamichi  Osaka University, Faculty of Science, Professor, 理学部, 教授 (40028147)

Co-Investigator(Kenkyū-buntansha) KANEKO Fumitoshi  Osaka University, Faculty of Science, Research Associate, 理学部, 助手 (70214468)
TASHIRO Kohji  Osaka University, Faculty of Science, Research Associate, 理学部, 助手 (60171691)
Project Period (FY) 1988 – 1989
Project Status Completed (Fiscal Year 1989)
Budget Amount *help
¥5,100,000 (Direct Cost: ¥5,100,000)
Fiscal Year 1989: ¥700,000 (Direct Cost: ¥700,000)
Fiscal Year 1988: ¥4,400,000 (Direct Cost: ¥4,400,000)
Keywordsunsaturated fatty acids / unsaturated glycerides / polymorphism / polytypism / phase transition / molecular motion / vibrational spectroscopy / X-ray structural analysis
Research Abstract

Phospholipids and glycerides are important materials as main constituents of the cell membranes, bearing the biological functional activities. Naturally occurring lipid compounds consist of long acyl chains joined to a polar group and nearly half of the acyl chains are occupied by unsaturated ones which give the membranes fluidity and promote the biological activity.
The aim of this research project is to elucidate the molecular mechanism of the characteristic function of the unsaturated acyl chains. Polymorphic structures in relation to the thermodynamic stability and the behavior of solid-state phase transition for a series of cis-monounsaturated fatty acids as well as cis-unsaturated triglycerides were investigated by means of IR and Raman spectroscopy, X-ray analysis, DSC, etc.
Unsaturated fatty acids exhibit very complicated polymorphism. The crystal structures of the gamma and gamma_1 phases of erucic acid and the low-melting and high-melting phases of petroselinic acid were fully determined. The molecular and crystal structures of the alpha and alpha_1 phases of erucic acid were also studied. Conformation of the olefine group, subcell structure of the polymethylene chain segments, polytypic structure of the bimolecular layers, and chain mobility have been clarified as the keynote for understanding the physicochemical properties and the phase transition behaviors of the unsaturated lipid compounds. The order-disorder type thermoreversible gamma <double arrow>alpha and gamma_1<double arrow>alpha_1 transitions occurring in cis-monounsaturated fatty acids were recognized as a partial melting process of the methylsided alkyl chains constituting the lamellar interface. The polymorphism of triblycerides whose 2-position is occupied by an oleoyl chain have been investigated. It has been revealed that a large molecular displacement takes place in a coherent fashion during solid-state transitions in saturated fatty acids.

Report

(3 results)
  • 1989 Annual Research Report   Final Research Report Summary
  • 1988 Annual Research Report
  • Research Products

    (66 results)

All Other

All Publications (66 results)

  • [Publications] Kiyotaka Sato: "Stability,Occurrence and Step Morphology of Polymorphs and Polytypes of Stearic Acid I.Stability and Occurrence" J.Cryst.Growth. 87. 236-242 (1988)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1989 Final Research Report Summary
  • [Publications] Kimio Inaoka: "Stability,Occurrence and Morphology of Polymorphs and Polytypes of Stearic Acid II.Mono-lamellar Step Morphology and Composite Polymorphic/Prlytypic Transformation" J.Cryst.Growth. 87. 243-250 (1988)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1989 Final Research Report Summary
  • [Publications] Masamichi Kobayashi: "Molecular Motions of n-Alkane Chains in Urea Adducts Studied by Raman Band Profiles" Rept.Progr.Polym.Phys.Jpn.31. 477-480 (1988)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1989 Final Research Report Summary
  • [Publications] Masao Suzuki: "Polymorphic Behavior of Erucic Acid" J.Am.Oil Chem.Soc.65. 1942-1947 (1988)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1989 Final Research Report Summary
  • [Publications] 小林雅通: "高分子・長鎖分子結晶における分子運動" 化学. 43. 342-343 (1988)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1989 Final Research Report Summary
  • [Publications] Masamichi Kobayashi: "Molecular and Crystal Structures of Lipids and Related Compounds" J.Dispersion Sci.Tech.10. 319-350 (1989)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1989 Final Research Report Summary
  • [Publications] Fumitoshi Kaneko: "Polymorphic Structure and Phase Transitions of Mono-unsaturated Fatty Acids" Proc.ISF-JOCS World Congress. 1. 531-535 (1988)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1989 Final Research Report Summary
  • [Publications] Fumitoshi Kaneko: "Structure and Phase Transition Behavior of Stearic Acid E-Forme" Proc.ISF-JOCS World Congress. 1. 536-541 (1988)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1989 Final Research Report Summary
  • [Publications] Masamichi Kobayashi: "Molecular Motionsof n-Alkane Chains in Urea Adducts:Potential Barrier Heights and Lattice Vibrations of Host Channels" Rept.Progr.Polym.Phys.Jpn.32. 419-422 (1989)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1989 Final Research Report Summary
  • [Publications] Kiyotaka Sato: "Structure and Transformation in Polymorphism of Petroselinic Acid(cis-omega12-octadecenoic acid)" J.Phys.Chem.inpress (1989)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1989 Final Research Report Summary
  • [Publications] 小林雅通: "長鎖状分子および高分子の構造、転移、物性" 海外高分子研究. 36. 42-46 (1990)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1989 Final Research Report Summary
  • [Publications] Fumitoshi Kameko: "Crystal Structure of Stearic Acid E-Form" Acta Crystallogr.C(in press). (1989)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1989 Final Research Report Summary
  • [Publications] Fumitoshi Kaneko: "Vibrational Spectroscopic Study on gamma→alpha phase Transition of cis-monounsaturated Fatty Acids:Palmitoleic and Erucic Acids" J.Phys.Chim,(to be published). (1990)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1989 Final Research Report Summary
  • [Publications] Fumitoshi Kamako: "Crystal Structure of petroselinic acid Low-melting Phase" Acta Crytallogr.c(to be published). (1990)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1989 Final Research Report Summary
  • [Publications] Fumitoshi Kaneko: "Crystal Structure of Petroselinic Acid High-melting Phase" Acta Crystallogr.(to be published). (1990)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1989 Final Research Report Summary
  • [Publications] Kohji Tashiro: "Structural Study on Phase Transition in Ferroelectric Liquid Crystal:Temperature Dependence of Infrared and Raman Spectra" Rept.Progr.Polym.Phys.Jpn.32. 415-418 (1989)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1989 Final Research Report Summary
  • [Publications] Kohji Tashiro: "X-ray Structure Analyses and Vibrational Spectral Measurements of teh Mode Compounds of the Liquid-Crystqlline Arylate Polymers〔1〕 Finding out the Raman Bands Characteristic of the Twisted Biphenyl Structure in Association with the Solid-to-Liquid Crystalline Phase Transition" J.Am.Chem.Soc.(to be published). (1990)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1989 Final Research Report Summary
  • [Publications] Kohji Tashiro: "Structural Study of Phase Transition in Ferroelectric Liquid Crystal〔II〕The Structural Changes Revealed by X-ray Diffraction Measurements" Rept.Progr.Polym.Phys.Jpn.(to be published). (1990)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1989 Final Research Report Summary
  • [Publications] Masamichi Kobayashi: "Vibrational Spectroscopic Aspects of Polymorphism and Phase Transition of Fats and Fatty Acids in "Crystallization and Polymorphism of Fats and Fstty Acids"(Eds.N.Garti&K.Sato)" Marcel Dekker,New York, 140-187 (1988)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1989 Final Research Report Summary
  • [Publications] Masamichi Kobayashi: "Application of Raman Microprobe Technique to the Study of Organic Polymers and Long-chain Compounds in "Vibrational Spectra and Structures Vol.17B"(Eds.H.D.Bist,J.R.Durig,and J.F.Sullivan)" Elsevier,Amsterdam, 369-397 (1989)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1989 Final Research Report Summary
  • [Publications] 小林雅通: "いのちと暮らしのケミ・スト-リ-、第11章" 化学同人, 173-192 (1989)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1989 Final Research Report Summary
  • [Publications] K. Sato, M. Kobayashi, and H. Morishita: "Stability, Occurrence and Step Morphology of Polymorphs and Polytypes of Stearic Acid I. Stability and Occurrence" J. Cryst. Growth, 87, 236-242 (1988).

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1989 Final Research Report Summary
  • [Publications] K. Inaoka, M. Kobayashi, M. Okada, and K. Sato: "Stability, Occurrence and Step Morphology of Polymorphs and polytypes of Stearic Acid, II. Mono-lamella Step Morphology and Composite Polymorphic/Polytypic Transformation" J. Cryst. Growth, 87, 243-250 (1988).

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1989 Final Research Report Summary
  • [Publications] M. Suzuki, K. Sato, N. Yoshimoto, S. Tanaka, and M. Kobayashi: "Polymorphic Behavior of Erucic Acids" J. Am. Oil Chem. Soc., 65(12), 1942-1947 (1988).

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1989 Final Research Report Summary
  • [Publications] M. Kobayashi, Y. Cho, and H. Koizumi: "Molecular Motion of n-Alkane Chains in Urea Adducts Studied by Raman Band Profiles" Rept. Progr. Polym. Phys. Jpn., 31, 477-480 (1988).

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1989 Final Research Report Summary
  • [Publications] M. Kobayashi: "Vibrational Spectroscopic Aspects of Polymorphism and Phase Transition of Fats and Fatty Acids" Crystallization and Polymorphism of of Fats and Fatty Acids (eds. N. Garti & K. Sato), Marcel Dekker, New York & Basel (1988), pp. 139-189.

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1989 Final Research Report Summary
  • [Publications] M. Kobayashi: "Molecular Motions in Crystals of Polymers and Long-chain Compounds (in japanese)" Kagaku, 43(5), 342-343 (1988).

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1989 Final Research Report Summary
  • [Publications] F. Kaneko, M. Kobayashi, K. Sato, and M. Suzuki: "Polymorphic Structure and Phase Transitions of Monounsaturated Fatty Acids" Proc. ISF-JOCS World Congress, 1, 531-535 (1988).

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1989 Final Research Report Summary
  • [Publications] F. Kaneko, M. Kobayashi, Y. Kitagawa, and Y. Matsuura: "Structure and Phase Transition of Stearic Acid E-Form" Proc. ISF-JOCS World Congress, 1, 536-541 (1988).

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1989 Final Research Report Summary
  • [Publications] M. Kobayashi and F. Kaneko: "Molecular and Crystal Structures of Lipids and Related Compounds" J. Dispersion Sci. Tech., 10, 319-350 (1989).

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1989 Final Research Report Summary
  • [Publications] M. Kobayashi and T. Ishioka: "Application of Raman Microprobe Technique to the Study of Organic Polymers and Long-chain Compounds" Vibrational Spectra and Structures Vol. 17B (eds. H. D. Bist, J. R. During, and J. F. Sullivan) Elsevier, Amsterdam,pp. 369-397 (1989).

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1989 Final Research Report Summary
  • [Publications] K. Sato, N. Yoshimoto, M. Suzuki, M. Kobayashi, and F. Kaneko: "Structure and Transformation in Polymorphism of Petroselinic Acid (cis-omega12-Octadecenoic acid)" J. Phys. Chem. (1989).

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1989 Final Research Report Summary
  • [Publications] F. Kaneko, M. Kobayashi, Y. Kitagawa, and Y. Matsuura: "Crystal Structure of Stearic Acid E-Form" Acta Crystallogr. C (1989).

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1989 Final Research Report Summary
  • [Publications] F. Kaneko, M. Kobayashi, K. Sato, and M. Suzuki: "Vibrational Spectroscopic Study on gamma -> alpha Phase Transition of cis-Mono-unsaturated Fatty Acids: Palmitoleic and Erucic Acids" J. Phys. Chem. (1990).

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1989 Final Research Report Summary
  • [Publications] K. Tashiro, J. Hou, and M. Kobayashi: "Structural Study on Phase Transition in Ferroelectric Liquid Crystal: Temperature Dependence of Infrared and Raman Spectra" Rept. Progr. Polym. Phys. Jpn., 32, 415-418 (1989).

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1989 Final Research Report Summary
  • [Publications] F. Kaneko, M. Kobayashi, Y. Kitagawa, Y. Matsuura, K. Sato, and M. Suzuki: "Crystal Structure of Petroselinic Acid Low-Melting Phase" Acta Crystallogr. (1990).

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1989 Final Research Report Summary
  • [Publications] F. Kaneko, M. Kobayashi, Y. Kitagawa, Y. Matsuura, K. Sato, and M. Suzuki: "Crystal Structure of Petroselinic Acid High-Melting Phase" Acta Crystallogr. C (1990).

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1989 Final Research Report Summary
  • [Publications] Kiyotaka SATO: "Stability,Occurrence and Step Morphology of Polymorphs and Polytypes of Stearic Acid I.Stability and Occurrence" J.Cryst.Growth. 87. 236-242 (1988)

    • Related Report
      1989 Annual Research Report
  • [Publications] Kimio INAOKA: "Stability,Occurrence and Step Morphology of Polymorphs and Polytypes of Stearic Acid II.Mono-1amellar Step Morphology and Composite Polymorphic/Polytypic Transformation" J.Cryst.Growth. 87. 243-250 (1988)

    • Related Report
      1989 Annual Research Report
  • [Publications] Masamichi KOBAYASHI: "Molecular Motions of n-Alkane Chains in Urea Adducts Studied by Raman Band Profiles" Rept.Progr.Polym.Phys.Jpn.31. 477-480 (1988)

    • Related Report
      1989 Annual Research Report
  • [Publications] Masao SUZUKI: "Polymorphic Behavior of Erucic Acid" J.Am.Oil Chem.Soc.65. 1942-1947 (1988)

    • Related Report
      1989 Annual Research Report
  • [Publications] 小林雅通: "高分子・長鎖分子結晶における分子運動" 化学. 43. 342-343 (1988)

    • Related Report
      1989 Annual Research Report
  • [Publications] Masamichi KOBAYASHI: "Molecular and Crystal Structures of Lipids and Related Compounds" J.Dispersion Sci.Tech.10. 319-350 (1989)

    • Related Report
      1989 Annual Research Report
  • [Publications] Fumitoshi KANEKO: "Polymorphic Structure and Phase Transitions of Mono-unsaturated Fatty Acids" Proc.ISF-JOCS World Congress. 1. 531-535 (1988)

    • Related Report
      1989 Annual Research Report
  • [Publications] Fumitoshi KANEKO: "Structure and Phase Transition Behavior of Stearic Acid E-Form" Proc.ISF-JOCS World Congress. 1. 536-541 (1988)

    • Related Report
      1989 Annual Research Report
  • [Publications] Masamichi KOBAYASHI: "Molecular Motions of n-Alkane Chains in Urea Adducts:Potential Barrier Heights and Lattice Vibrations of Host Channels" Rept.Progr.Polym.Phys.Jpn.32. 419-422 (1989)

    • Related Report
      1989 Annual Research Report
  • [Publications] Kiyotaka SATO: "Structure and Transformation in Polymorphism of Petroselinic Acid(cis-ω12-octadecenoic acid)" J.Phys.Chem.(1989)

    • Related Report
      1989 Annual Research Report
  • [Publications] 小林雅通: "長鎖状分子および高分子の構造、転移、物性" 海外高分子研究. 36. 42-46 (1990)

    • Related Report
      1989 Annual Research Report
  • [Publications] Fumitoshi KANEKO: "Crystal Structure of Stearic Acid E-Form" Acta Crystallogr.C. (1989)

    • Related Report
      1989 Annual Research Report
  • [Publications] Fumitoshi KANEKO: "Vibrational Spectroscopic Study on γ→α Phase Transition of cis-monounsaturated Fatty Acids:Palmitoleic and Erucic Acids" J.Phys.Chem.(1990)

    • Related Report
      1989 Annual Research Report
  • [Publications] Fumitoshi KANEKO: "Crystal Structure of petroselinic acid Low-melting Phase" Acta Crystallogr.C. (1990)

    • Related Report
      1989 Annual Research Report
  • [Publications] Fumitoshi KANEKO: "Crystal Structure of Petroselinic Acid High-melting Phase" Acta Crystallogr.(1990)

    • Related Report
      1989 Annual Research Report
  • [Publications] Kohji TASHIRO: "Structural Study on Phase Transition in Ferroelectric Liquid Crystal:Temperature Dependence of Infrared and Raman Spectra" Rept.Progr.Polym.Phys.Jpn.32. 415-418 (1989)

    • Related Report
      1989 Annual Research Report
  • [Publications] Kohji TASHIRO: "X-ray Structure Analyses and Vibrational Spectral Measurements of the Model Compounds of the Liquid-Crystalline Arylate Polymers[1]Finding out the Raman Bands Characteristic of the Twisted Biphenyl Structure in Association with the Solid-to-Liquid Crystalline Phase Transition" J.Am.Chem.Soc.(1990)

    • Related Report
      1989 Annual Research Report
  • [Publications] Kohji TASHIRO: "Structural Study on Phase Transition in Ferroelectric Liquid Crystal[II]The Structural Changes Revealed by X-ray Diffraction Measurements" Rept.Progr.Polym.Phys.Jpn.(1990)

    • Related Report
      1989 Annual Research Report
  • [Publications] Masamichi KOBAYASHI: "Vibrational Spectroscopic Aspects of Polymorphism and Phase Transition of Fats and Fatty Acids in“Crystallization and Polymorphism of Fats and Fatty Acids"(Eds.N.Garti & K.Sato)" Marcel Dekker,New York, 140-187 (1988)

    • Related Report
      1989 Annual Research Report
  • [Publications] Masamichi KOBAYASHI: "Application of Raman Microprobe Technique to the Study of Organic Polymers and Long-chain Compounds in“Vibrational Spectra and Structures Vol.17B"(Eds.H.D.Bist,J.R.Durig,and J.F.Sullivan)." Elsevier,Amsterdam, 369-397 (1989)

    • Related Report
      1989 Annual Research Report
  • [Publications] 小林雅通: "いのちと暮しのケミ・スト-リ-、第11章" 化学同人, 173-192 (1989)

    • Related Report
      1989 Annual Research Report
  • [Publications] Kiyotaka SATO: J.Cryst.Growth. 87. 236-242 (1988)

    • Related Report
      1988 Annual Research Report
  • [Publications] Kimio INAOKA: J.Cryst.Growth. 87. 243-250 (1988)

    • Related Report
      1988 Annual Research Report
  • [Publications] Masamichi KOBAYASHI: Rep.Progr.Polym.Phys.Jpn.31. 477-480 (1988)

    • Related Report
      1988 Annual Research Report
  • [Publications] Masao SUZUKI: J.Am.Oil Chem.Soc.65. 1942-1947 (1988)

    • Related Report
      1988 Annual Research Report
  • [Publications] 小林雅通: 化学. 43. 342-343 (1988)

    • Related Report
      1988 Annual Research Report
  • [Publications] Masamichi KOBAYASHI: J.Dispersion Sci.Tech.(1989)

    • Related Report
      1988 Annual Research Report
  • [Publications] Masamichi KOBAYASHI: "Vibrational Spectroscopic Aspects of Polymorphism and Phase Transition of Fats and Fatty(Acids in"Crystallization and Polymorphism of Fats and Fatty Acids"" Marcel Dekker, 140-187 (1988)

    • Related Report
      1988 Annual Research Report
  • [Publications] Masamichi KOBAYASHI: "Application of Raman Microprobe Technique to the Study of Organic Polymers and Long-chain Compounds in"Vibrational spectra and Structures Vol.17B"" Elsevier, 369-397 (1989)

    • Related Report
      1988 Annual Research Report

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Published: 1988-04-01   Modified: 2016-04-21  

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