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Pure Appl. Chem., Vol. 72, No. 8, pp. 1493-1523, 2000.

 

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 (IUPAC Recommendations 2000)

G.P. Moss

Department of Chemistry, Queen Mary and Westfield College, Mile End Road, London, E1 4NS, UK

World Wide Web version prepared by G. P. Moss

Abstract: Lignans and neolignans are a large group of natural products characterized 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 carbonÝcarbon 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 carbonÝcarbon 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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World Wide Web version prepared by G. P. Moss

<http://www.chem.qmw.ac.uk/iupac/lignan/>

 

 

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