14-Acetylandrographolide

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

*Corresponding author for this work

Research output: Contribution to journalArticle

Abstract

The title compound, 3-{2-[decahydro-6-hydroxy-5-(hydroxymethyl)-5,8a- dimethyl-2-methylene-1-napthalenyl]ethylidene}dihydro-4-acetoxy-2(3H)-furanone, C 22H 32O 6, 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 P2 12 12 1. While the stereochemical relation between rings is slightly changed from the starting material, acetylation of the hydroxyfuranone moiety completely abolishes O - H⋯O hydrogen bonding there, leaving a C - H⋯O interaction. The hydrogen-bonded chains at the opposite end of the andrographolide molecule persist but reverse direction.

Original languageEnglish
Pages (from-to)93-97
Number of pages5
JournalJournal of Chemical Crystallography
Volume36
Issue number2
Early online date21 Jan 2006
DOIs
Publication statusPublished - Feb 2006

Keywords

  • Acetylation
  • Andrographolide
  • Crystal structure
  • Hydrogen bonding

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  • Cite this

    Rao Jada, S., McMillan, K., Hamzah, A. S., Saad, M. S., Lajis, N. H., Stevens, M. F. G., Schwalbe, C. H., & Stanslas, J. (2006). 14-Acetylandrographolide. Journal of Chemical Crystallography, 36(2), 93-97. https://doi.org/10.1007/s10870-005-9004-1