Journal of Chemical Crystallography

, Volume 36, Issue 2, pp 93–97 | Cite as


  • Srinivasa Rao Jada
  • Katherine McMillan
  • Ahmad S. Hamzah
  • Mohammad S. Saad
  • Nordin H. Lajis
  • Malcolm F.G. Stevens
  • Carl H. Schwalbe
  • Johnson Stanslas

The title compound, 3-{2-[decahydro-6-hydroxy-5-(hydroxymethyl)-5,8a-dimethyl-2-methylene-1-napthalenyl]ethylidene}dihydro-4-acetoxy-2(3H)-furanone, C22H32O6, was synthesised from andrographolide. It crystallizes in the orthorhombic system with a = 7.4219(12), b = 11.8411(10), c = 23.777(4) Å in space group P212121. While the stereochemical relation between rings is slightly changed from the starting material, acetylation of the hydroxyfuranone moiety completely abolishes O--H\( \cdots \)O hydrogen bonding there, leaving a C--H\( \cdots \)O interaction. The hydrogen-bonded chains at the opposite end of the andrographolide molecule persist but reverse direction.


Andrographolide acetylation crystal structure hydrogen bonding 



The Malaysian Ministry of Science, Technology and Innovation (MOSTI) is thanked for funding this project under the Intensification of Research in Priority Areas (IRPA) Programme (Grants: 06-02-04-0088 and 06-02-04-0603-EA001). The European Association for Cancer Research (EACR) is thanked for a travel fellowship (to Jada) to carry out research at The University of Nottingham, United Kingdom.


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Copyright information

© Springer Science+Business Media, Inc. 2005

Authors and Affiliations

  • Srinivasa Rao Jada
    • 1
  • Katherine McMillan
    • 2
  • Ahmad S. Hamzah
    • 3
  • Mohammad S. Saad
    • 4
  • Nordin H. Lajis
    • 5
  • Malcolm F.G. Stevens
    • 6
  • Carl H. Schwalbe
    • 2
  • Johnson Stanslas
    • 5
    • 6
  1. 1.Faculty of Medicine and Health SciencesUniversiti Putra MalaysiaSelangorMalaysia
  2. 2.Aston Pharmacy SchoolAston TriangleBirminghamUK
  3. 3.Faculty of Applied SciencesUniversity Technology MARAShah AlamMalaysia
  4. 4.Faculty of AgricultureUniversiti Putra MalaysiaSelangorMalaysia
  5. 5.Institute of BioscienceUniversiti Putra MalaysiaSelangorMalaysia
  6. 6.School of PharmacyThe University of NottinghamNottinghamUK

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