INTERNATIONAL UNION OF PURE AND APPLIED CHEMISTRY
and
INTERNATIONAL UNION OF BIOCHEMISTRY AND MOLECULAR BIOLOGY

IUPAC-IUB Joint Commission on Biochemical Nomenclature (JCBN)

Nomenclature of Lignans and Neolignans

(Recommendations 2000)

http://www.chem.qmul.ac.uk/iupac/lignan/

World Wide Web version prepared by G. P. Moss

Department of Chemistry, Queen Mary University of London,
Mile End Road, London, E1 4NS, UK
e-mail g.p.moss@qmul.ac.uk

These Rules are as close as possible to the published version [see Pure Appl. Chem., 2000, 72, 1493-1523; reproduced with the permission of IUPAC and IUBMB]. If you need to cite these rules please quote this references as their source.

A PDF of these recommendations is available.

German translation see Angew. Chem., 2005, 117, 2339-2351.

Any comments should be sent to any member of the Committee

This document was prepared by G. P. Moss in collaboration with P. K. Agrawal (India), D. C. Ayres (UK), E. Brown (France), J. R. Bull (South Africa), J. R. Cole (USA), P. M. Dewick (UK), J. M. Fang (Taipei), S. F. Fonseca (Brazil), O. R. Gottlieb (Brazil), Y. Kato (Japan), L. H. Klemm (USA), J. Mann (UK), A. Pelter (UK), R. Stevenson (USA), J. Van der Eycken (Belgium) and D. A Whiting (UK).

Abstract: Lignans and neolignans are a large group of natural products characterised by the coupling of two C6C3 units. For nomenclature purposes the C6C3 unit is treated as propylbenzene and numbered from 1 to 6 in the ring, starting from the propyl group, and with the propyl group numbered from 7 to 9, starting from the benzene ring. With the second C6C3 unit the numbers are primed. When the two C6C3 units are linked by a bond between positions 8 and 8' the compound is referred to and named as a lignan. In the absence of the C-8 to C-8' bond, and where the two C6C3 units are linked by a carbon-carbon bond it is referred to and named as a neolignan. The linkage with neolignans may include C-8 or C-8'. Where there are no direct carbon-carbon bonds between the C6C3 units and they are linked by an ether oxygen atom the compound is named as an oxyneolignan. The nomenclature provides for the naming of additional rings and other modifications following standard organic nomenclature procedures for naming natural products. Provision is included to name the higher homologues. The sesquineolignans have three C6C3 units and dineolignans have four C6C3 units.

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