Skip to main content
Journal of Wood Science

Official Journal of the Japan Wood Research Society

Download PDF
  • Note
  • Published:

Facile synthesis of rubiadin by microwave heating

Journal of Wood Science volume 52, pages 90–92 (2006)Cite this article

Abstract

Rubiadin (4) (1,3-dihydroxy-2-methylanthraquinone), which is one of the natural dyes from the roots of Rubiaceae, was synthesized from phthalic anhydride (1) and 2,6-dihydroxytoluene (3) by two reaction steps, that is, a Friedel-Crafts reaction with AlCl3 and a cyclization with H2SO4/HBO2. Microwave heating resulted in remarkable acceleration of the reaction rate in the first reaction, and had an effect in reducing the reaction time and increasing the yield of rubiadin (4) in the second reaction.

References

  1. Lee HH (1969) Coloring matters from Prismatomeris malayana. Phytochemistry 8:501–503

    Article  CAS  Google Scholar 

  2. Jasril, Lajis NH, Abdullah MA, Ismail NH, Ali AM, Marziah M, Ariff AB, Kitajima M, Takayama H, Alimi N (2000) Anthraquinones from cell suspension culture of Morinda elliptica. Nat Prod Sci 6:40–43

    CAS  Google Scholar 

  3. Ali AM, Ismail NH, Mackeen MM, Yazan LS, Mohamed SM, Ho ASH, Lajis NH (2000) Antiviral cyototoxic and antimicrobial activities of anthraquinones isolated from the root of Morinda elliptica. Pharm, Biol 38:298–301

    Article  CAS  Google Scholar 

  4. Hirose Y (1960) Syntheses of damnacanthal, damnacanthol, norjuzunal and norjuzunol, the coloring matters of Damnacanthus spp. Chem Pharm Bull 8:417–426

    CAS  Google Scholar 

  5. Chari VM, Neelakantan S, Seshadri TR (1966) A convenient synthesis of rubiadin. Indian J Chem 4:330–331

    CAS  Google Scholar 

  6. Courchesne M, Brassard P (1993) Identification and characterization of naturally occurring rubiadins. J Nat Prod 56:722–730

    Article  CAS  Google Scholar 

  7. Boisvert L, Brassard P (1989) Naturally occurring rubiadins. Chem Lett 1055-1058

  8. Zhao H, Biehl E (1995) Preparation of naturally occurring anthraquinones using the aryne reaction. J Nat Prod 58:1970–1974

    Article  CAS  Google Scholar 

  9. Lidstrom P, Tierney J, Wathey B, Westman J (2001) Microwave assisted organic synthesis — a review. Tetrahedron 57:9225–9283

    Article  CAS  Google Scholar 

  10. Nakahara H (1976) Boric acid (in Japanese). In: The Chemical Society of Japan (ed) Shi-Jikkenkagaku Koza 8-I. Maruzen, Tokyo, p 364

Download references

Author information

Authors and Affiliations

  1. Division of Forest and Biomaterials Science, Graduate School of Agriculture, Kyoto University, Sakyo-ku, Kyoto, 606-8502, Japan

    Toshiyuki Takano, Tomomi Kondo & Fumiaki Nakatsubo

Authors
  1. Toshiyuki Takano
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Tomomi Kondo
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Fumiaki Nakatsubo
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Toshiyuki Takano.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Takano, T., Kondo, T. & Nakatsubo, F. Facile synthesis of rubiadin by microwave heating. J Wood Sci 52, 90–92 (2006). https://doi.org/10.1007/s10086-005-0727-6

Download citation

  • Received:

  • Accepted:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10086-005-0727-6

Key words