lipid nomenclature (original) (raw)

IUPAC-IUB Commission on Biochemical Nomenclature (CBN)

Nomenclature of Lipids

Recommendations, 1976

https://iupac.qmul.ac.uk/lipid/

World Wide Web version Prepared by G. P. Moss

School of Physical and Chemical Sciences, Queen Mary University of London,
Mile End Road, London, E1 4NS, UK
g.p.moss@qmul.ac.uk

These Rules are as close as possible to the published version prepared by the Working Group on Lipid Nomenclature: H. Hirschmann (U.S.A.), P. Karlson (Federal Republic of Germany; convenor), W. Stoffel (Federal Republic of Germany), F. Snyder (U.S.A.), S. Veibel (Denmark), F. Vögtle (Federal Republic of Germany) and the Working Group on Glycolipid Nomenclature: S. Basu (U.S.A.), R. O. Brady (U.S.A.), R. M. Burton (U.S.A.), R. Caputto (Argentina), S. Gatt (Israel), S. I. Hakomori (U.S.A.), M. Philippart (U.S.A.), L. Svennerholm (Sweden), D. Shapiro (Israel), C. C. Sweeley (U.S.A.), H. Wiegandt (Federal Republic of Germany; convenor) [see _Biochem. J.,_ 1978, **171**, 21-35; _Chem. Phys. Lipids,_ 1978, **21**, 159-173; _Eur. J. Biochem.,_ 1977, **79**, 11-21; _Hoppe-Seyler's Z. Physiol. Chem.,_ 1977, **358**, 617-631; _J. Lipid Res.,_ 1978, **19**, 114-128; _Lipids,_ 1977, **12**, 455-468; _Mol. Cell. Biochem.,_ 1977, **17**, 157-171; Biochemical Nomenclature and Related Documents, 2nd edition, Portland Press, 1992, pages 180-190. Copyright IUPAC and IUBMB; reproduced with the permission of IUPAC and IUBMB]. If you need to cite these rules please quote these references as their source.

Any comments should be sent to any member of the Committee.

CONTENTS * I. Fatty acids, neutral fats, long-chain alcohols and long-chain bases
* A. Generic terms (Lip-1.1 to Lip-1.5)
* B. Individual compounds
* 1. Fatty acids and alcohols (Lip-1.6 to Lip-1.7)
* 2. Sphinganine and derivatives (Lip-1.8 to Lip-1.11)
* 3. Glycerol derivatives (Lip-1.12 to Lip-1.13)
* C. Symbols and abbreviations (Lip-1.14 to Lip-1.18) * II. Phospholipids
* A. Generic terms (Lip-2.1 to Lip-2.10)
* B. Individual compounds (Lip-2.11 to Lip-2.12) * III. Glycolipids
* A. General considerations
* B. Generic terms (Lip-3.1 to Lip-3.5)
* C. Individual compounds (Lip-3.6 to Lip-3.12)
* D. Symbols and abbreviations (Lip-3.13 to Lip-3.14) * IV. Neuraminic acid (Lip-4.1 to Lip-4.3) * References * Appendix A: names of and symbols for higher fatty acids * Appendix B: symbols recommended for various constituents of lipids * Appendix C: abbreviated representation of gangliosides * Supplement: derivatives of phosphatidic acid * Lip-1.10 - no longer recommended.
Introduction
In 1967, a 'Document for Discussion' on lipid nomenclature [1] was issued by CBN. It included a special system for the designation of configuration in glycerol derivatives that deviated considerably from standard stereochemical nomenclature. This system is based upon a fixed numbering ('stereospecific numbering') for glycerol, regardless of substituents. It was hoped [1] that 'discussion will lead shortly to the formulation' of recommendations acceptable to chemists in the field of lipids.
In subsequent years, there has been little discussion about this principle of stereospecific numbering; it has been well-accepted within the field of glycerol derivatives, for which it has been especially useful and is widely used. However, during this same period, many new and complex lipids and gIycolipids have been isolated. Moreover, the Commissions on the Nomenclature of Organic Chemistry (CNOC) and Inorganic Chemistry (CNIC) issued, in 1973, Nomenclature of Organic Chemistry, Section D [2], which includes a section on the nomenclature of phosphorus-containing organic compounds and necessitates a reconsideration of the earlier nomenclature [1] in this area.
Note. CBN does not wish to imply that the idea of stereospecific numbering should be applied to other groups of compounds. it is the symmetry of glycerol itself, but the asymmetry of its derivatives carrying different substituents at O-1 and O-3, as well as the unique place of these compounds in lipid metabolism, that makes this special treatment desirable.
The present 'Recommendations 1976' are based on reports of working groups on lipids and glycolipids. The main features are:
(a) the system of stereospecific numbering is retained;
(b) semisystematic nomenclature is extended to the plasmalogens;
(c) a semisystematic nomenclature for higher glycosphingolipids, based on trivial names for specific tri- and tetrasaccharides, is proposed.

Partial update
Since the preparation of this report the Nomenclature of Glycolipids, Recommendations 1997, have been published [see Adv. Carbohydr. Chem. Biochem. 1999, 55, in press; Carbohydr. Res., 1998, 312, 167-175; Eur. J. Biochem., 1998, 257, 293-298; Glycoconjugate J., 1999, 16, 1-6; J. Mol. Biol., 1999, 286, 963-970; Pure Appl. Chem., 1997, 69, 2475-2487]. These supercede parts of this document.

References for this section
1. IUPAC-IUB Commission on Biochemical Nomenclature (1967) Eur. J. Biochem. 2, 127-131, also 12, 1 (1970); [see also Biochemistry, 1967, 6, 3287-3292; Biochem. J., 1967, 105, 897-902; J. Biol. Chem., 1967, 242, 4845-4849; Hoppe-Seyler's Z. Physiol. Chem., 1969, 350, 279-285 (on German)].
2. International Union of Pure and Applied Chemistry (1973) Information Bulletin, Appendix 31. [See also Nomenclature of Organic Chemistry, Sections A, B, C, D, E, F, and H, Pergamon Press, 1979. Edited by J Rigaudy and S P Klesney.]

Continued with Lip 1 and Lip 2. Fatty acids, neutral fats, long-chain alcohols and long-chain bases
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