Chemistry:Laballenic acid

From HandWiki
Laballenic acid
Names
Other names
5,6-octadecadienoic acid
Identifiers
3D model (JSmol)
1911935
ChEBI
ChemSpider
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).
Infobox references

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

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

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

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

Plant derivatives with high content of allenic fatty acids have shown cytotoxic, anti-inflammatory, and antiviral activity.[12][13]

References

  1. ↑ Avato, P.; Tava, A. (1 April 2022). "Rare fatty acids and lipids in plant oilseeds: occurrence and bioactivity" (in en). Phytochemistry Reviews 21 (2): 401–428. doi:10.1007/s11101-021-09770-4. ISSN 1572-980X. Bibcode: 2022PChRv..21..401A. 
  2. ↑ Bagby, M. O.; Jr, C. R. Smith; Wolff, I. A. (1 May 2002). "Laballenic Acid. A New Allenic Acid from Leonotis nepetaefolia Seed Oil1" (in EN). ACS Publications 30 (12): 4227–4229. doi:10.1021/jo01023a055. https://pubs.acs.org/doi/pdf/10.1021/jo01023a055. Retrieved 7 April 2025. 
  3. ↑ Leray, Claude (19 September 2012) (in en). Introduction to Lipidomics: From Bacteria to Man. CRC Press. p. 28. ISBN 978-1-4665-5147-3. https://books.google.com/books?id=plXOBQAAQBAJ&dq=laballenic+acid&pg=PA28. Retrieved 7 April 2025. 
  4. ↑ 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" (in en). Journal of the Chemical Society, Perkin Transactions 1: 2197–2201. doi:10.1039/P19720002197. ISSN 1364-5463. https://pubs.rsc.org/en/content/articlelanding/1972/p1/p19720002197. Retrieved 7 April 2025. 
  5. ↑ Tang, Xinjun; Huang, Xin; Cao, Tao; Han, Yulin; Jiang, Xingguo; Lin, Weilong; Tang, Yang; Zhang, Jiasheng et al. (15 May 2015). "CuBr2-catalyzed enantioselective routes to highly functionalized and naturally occurring allenes" (in en). Organic Chemistry Frontiers 2 (6): 688–691. doi:10.1039/C5QO00084J. ISSN 2052-4129. https://pubs.rsc.org/en/content/articlelanding/2015/qo/c5qo00084j. Retrieved 7 April 2025. 
  6. ↑ Ahmad, Moghis U. (21 July 2017) (in en). Fatty Acids: Chemistry, Synthesis, and Applications. Elsevier. p. 48. ISBN 978-0-12-809544-7. https://books.google.com/books?id=QioUDgAAQBAJ&dq=Lamenallenic+acid&pg=PA48. Retrieved 7 April 2025. 
  7. ↑ 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. PMID 36354284. Bibcode: 2022JAChS.14421022X. https://pubs.acs.org/doi/10.1021/jacs.2c10863. Retrieved 7 April 2025. 
  8. ↑ 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. https://www.sciencedirect.com/science/article/abs/pii/S0040403900701122. Retrieved 7 April 2025. 
  9. ↑ (in en) Comprehensive Natural Products II: Chemistry and Biology. Elsevier. 5 March 2010. p. 27. ISBN 978-0-08-045382-8. https://books.google.com/books?id=pkzx2TeYYT8C&dq=laballenic+acid&pg=PA27. Retrieved 7 April 2025. 
  10. ↑ Ahmad, Moghis U. (21 July 2017) (in en). Fatty Acids: Chemistry, Synthesis, and Applications. Elsevier. p. 48. ISBN 978-0-12-809544-7. https://books.google.com/books?id=QioUDgAAQBAJ&dq=laballenic+acid&pg=PA48. Retrieved 7 April 2025. 
  11. ↑ Lundblad, Roger L.; Macdonald, Fiona (14 June 2018) (in en). Handbook of Biochemistry and Molecular Biology. CRC Press. ISBN 978-1-315-31440-2. https://books.google.com/books?id=SmFoDwAAQBAJ&dq=laballenic+acid&pg=PA1786. Retrieved 7 April 2025. 
  12. ↑ Hoffmann-Röder, Anja; Krause, Norbert (2004). "Synthesis and Properties of Allenic Natural Products and Pharmaceuticals" (in en). Angewandte Chemie International Edition 43 (10): 1196–1216. doi:10.1002/anie.200300628. ISSN 1521-3773. PMID 14991780. https://onlinelibrary.wiley.com/doi/10.1002/anie.200300628. Retrieved 7 April 2025. 
  13. ↑ 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". EXCLI Journal 14: 508–516. doi:10.17179/EXCLI2014-667. PMID 26535039. PMC 4616245. https://www.excli.de/vol14/Bhutani_10042015_proof.pdf. Retrieved 7 April 2025. 



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