Synthesis and Identification of Laccol Components from <I>Rhus succedanea</I> Lacquer Sap Synthesis and Identification of Laccol Components from Rhus succedanea Lacquer Sap

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Abstract

Three lacquer saps (<I>Rhus vernicifera, Rhus succedanea</I> and <I>Melanorrhoea usitata</I> lacquer saps) are used for a surface coating in Asia. We previously reported the identification of urushiol components in <I>Rhus vernicifera</I> lacquer sap (Japan, China and Korea). In this study, laccol components in <I>Rhus succedanea</I> lacquer sap (Vietnam and Taiwan) were synthesized by Wittig reaction of ylides derived from alkyl- and alkenylphosphonium iodides with aromatic parts such as 3-(10-oxo-1-decyl)catechol diacetate and 3-(10-oxo-1-decyl)phenol acetate, followed by removal of acetate groups. Identification of natural laccol components from <I>Rhus succedanea</I> lacquer saps was carried out by GC and GC/MS and comparison with synthesized laccol components. Stereostructures and constituent of all laccol components in <I>Rhus succedanea</I> lacquer sap were clarified. By quantitative analysis using GC, the most abundant component was 3-[(10<I>Z</I>, 13<I>E</I>, 15<I>E</I>)-10, 13, 15-heptadecatrienyl]catechol except for red lacquer sap, but the abundance of trienyl components was not higher than that in the Japanese lacquer sap such as <I>Rhus vernicifera</I>. The amount of monoenyl components were higher than in Japanese lacquer sap.<br>

Three lacquer saps (<I>Rhus vernicifera, Rhus succedanea</I> and <I>Melanorrhoea usitata</I> lacquer saps) are used for a surface coating in Asia. We previously reported the identification of urushiol components in <I>Rhus vernicifera</I> lacquer sap (Japan, China and Korea). In this study, laccol components in <I>Rhus succedanea</I> lacquer sap (Vietnam and Taiwan) were synthesized by Wittig reaction of ylides derived from alkyl- and alkenylphosphonium iodides with aromatic parts such as 3-(10-oxo-1-decyl)catechol diacetate and 3-(10-oxo-1-decyl)phenol acetate, followed by removal of acetate groups. Identification of natural laccol components from <I>Rhus succedanea</I> lacquer saps was carried out by GC and GC/MS and comparison with synthesized laccol components. Stereostructures and constituent of all laccol components in <I>Rhus succedanea</I> lacquer sap were clarified. By quantitative analysis using GC, the most abundant component was 3-[(10<I>Z</I>, 13<I>E</I>, 15<I>E</I>)-10, 13, 15-heptadecatrienyl]catechol except for red lacquer sap, but the abundance of trienyl components was not higher than that in the Japanese lacquer sap such as <I>Rhus vernicifera</I>. The amount of monoenyl components were higher than in Japanese lacquer sap.<br>

Journal

  • Journal of Oleo Science

    Journal of Oleo Science 51(7), 473-483, 2002-07-01

    Japan Oil Chemists' Society

References:  10

Codes

  • NII Article ID (NAID)
    10008808131
  • NII NACSIS-CAT ID (NCID)
    AA11503337
  • Text Lang
    ENG
  • Article Type
    ART
  • ISSN
    13473352
  • NDL Article ID
    6263953
  • NDL Source Classification
    ZP25(科学技術--化学・化学工業--油脂類)
  • NDL Call No.
    Z54-J571
  • Data Source
    CJP  NDL  J-STAGE 
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