Laballenic acid
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| Other names
5,6-octadecadienoic acid
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| Identifiers | |
3D model (JSmol)
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| ChEBI | |
| ChemSpider | |
PubChem CID
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| Properties | |
| C18H32O2 | |
| Molar mass | 280.452 g·mol−1 |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Laballenic acid is a linear fatty acid composed of 18 carbon atoms, with two consecutive double bonds (allene) in position 5=6=7. It has the structural formula CH3-(CH2)10-CH=C=CH-(CH2)3-COOH.
The acid is one of the rare allenic fatty acids found in nature.[1]
Discovery
[edit]The acid was initially isolated in 1964 from the seed oil of Leonotis nepetifolia, a plant of the family Lamiaceae by M.O. Bagby, C.R. Smith Jr., and I.A. Wolff, and identified by the same authors a year later.[2][3]
Laballenic acid has also been found in Phlomoides tuberosa.
Synthesis
[edit]Several methods of synthesis have been published.[4] An efficient and enantioselective synthesis dates back to the year 2022. A further enantioselective synthesis is based on copper(II) bromide catalysis and the use of diphenylprolinol as a chiral auxiliary.[5]
It has also been reported that lamenallenic acid is probably biosynthesized from laballenic acid.[6]
Physical properties
[edit]Laballenic acid has axial chirality and is therefore optically active.[7][8] The absolute configuration of laballenic acid was determined by stereoselective synthesis.[9]
There exist two configurations: the (R)-form and the (S)-form of laballenic acid.[10] The naturally occurring acid has the R-configuration: it is an isomer of linoleic acid related with the similar phlomic acid.[11]
Use
[edit]Plant derivatives with high content of allenic fatty acids have shown cytotoxic, anti-inflammatory, and antiviral activity.[12][13]
References
[edit]- ^ Avato, P.; Tava, A. (1 April 2022). "Rare fatty acids and lipids in plant oilseeds: occurrence and bioactivity". Phytochemistry Reviews. 21 (2): 401–428. doi:10.1007/s11101-021-09770-4. ISSN 1572-980X. Retrieved 7 April 2025.
- ^ Bagby, M. O.; Jr, C. R. Smith; Wolff, I. A. (1 May 2002). "Laballenic Acid. A New Allenic Acid from Leonotis nepetaefolia Seed Oil1". ACS Publications. doi:10.1021/jo01023a055. Retrieved 7 April 2025.
- ^ Leray, Claude (19 September 2012). Introduction to Lipidomics: From Bacteria to Man. CRC Press. p. 28. ISBN 978-1-4665-5147-3. Retrieved 7 April 2025.
- ^ Cowie, J. S.; Landor, Phyllis D.; Landor, S. R.; Punja, N. (1 January 1972). "Allenes. Part XXII. The synthesis and absolute configuration of laballenic and lamenallenic acids". Journal of the Chemical Society, Perkin Transactions 1 (0): 2197–2201. doi:10.1039/P19720002197. ISSN 1364-5463. Retrieved 7 April 2025.
- ^ Tang, Xinjun; Huang, Xin; Cao, Tao; Han, Yulin; Jiang, Xingguo; Lin, Weilong; Tang, Yang; Zhang, Jiasheng; Yu, Qiong; Fu, Chunling; Ma, Shengming (15 May 2015). "CuBr2-catalyzed enantioselective routes to highly functionalized and naturally occurring allenes". Organic Chemistry Frontiers. 2 (6): 688–691. doi:10.1039/C5QO00084J. ISSN 2052-4129. Retrieved 7 April 2025.
- ^ Ahmad, Moghis U. (21 July 2017). Fatty Acids: Chemistry, Synthesis, and Applications. Elsevier. p. 48. ISBN 978-0-12-809544-7. Retrieved 7 April 2025.
- ^ Xu, Xianghong; Wang, Mingxu; Peng, Lingzi; Guo, Chang (23 November 2022). "Nickel-Catalyzed Asymmetric Propargylation for the Synthesis of Axially Chiral 1,3-Disubstituted Allenes". Journal of the American Chemical Society. 144 (46): 21022–21029. doi:10.1021/jacs.2c10863. ISSN 0002-7863. Retrieved 7 April 2025.
- ^ Landor, S. R.; Punja, N. (1 January 1966). "The synthesis and absolute configuration of laballenic acid". Tetrahedron Letters. 7 (40): 4905–4907. doi:10.1016/S0040-4039(00)70112-2. ISSN 0040-4039. Retrieved 7 April 2025.
- ^ Comprehensive Natural Products II: Chemistry and Biology. Elsevier. 5 March 2010. p. 27. ISBN 978-0-08-045382-8. Retrieved 7 April 2025.
- ^ Ahmad, Moghis U. (21 July 2017). Fatty Acids: Chemistry, Synthesis, and Applications. Elsevier. p. 48. ISBN 978-0-12-809544-7. Retrieved 7 April 2025.
- ^ Lundblad, Roger L.; Macdonald, Fiona (14 June 2018). Handbook of Biochemistry and Molecular Biology. CRC Press. ISBN 978-1-315-31440-2. Retrieved 7 April 2025.
- ^ Hoffmann-Röder, Anja; Krause, Norbert (2004). "Synthesis and Properties of Allenic Natural Products and Pharmaceuticals". Angewandte Chemie International Edition. 43 (10): 1196–1216. doi:10.1002/anie.200300628. ISSN 1521-3773. Retrieved 7 April 2025.
- ^ Patel, Neeraj K.; Khan, Mohd. Shahid; Bhutani, Kamlesh K. (2015). "Investigations on Leucas cephalotes (Roth.) Spreng. for inhibition of LPS-induced pro-inflammatory mediators in murine macrophages and in rat model" (PDF). EXCLI Journal; 14:Doc508; ISSN 1611-2156. doi:10.17179/EXCLI2014-667. Retrieved 7 April 2025.