Laballenic acid

Last updated
Laballenic acid
Laballenic acid.png
Names
Other names
5,6-octadecadienoic acid
Identifiers
3D model (JSmol)
1911935
ChEBI
ChemSpider
PubChem CID
  • InChI=1S/C18H32O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18(19)20/h12,14H,2-11,15-17H2,1H3,(H,19,20)
    Key: YXJXBVWHSBEPDQ-UHFFFAOYSA-N
  • CCCCCCCCCCCC=C=CCCCC(=O)O
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).

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.

Contents

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". Phytochemistry Reviews. 21 (2): 401–428. Bibcode:2022PChRv..21..401A. doi: 10.1007/s11101-021-09770-4 . ISSN   1572-980X.
  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" . ACS Publications . 30 (12): 4227–4229. doi:10.1021/jo01023a055 . Retrieved 7 April 2025.
  3. ↑ 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.
  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" . Journal of the Chemical Society, Perkin Transactions 1 : 2197–2201. doi:10.1039/P19720002197. ISSN   1364-5463 . Retrieved 7 April 2025.
  5. ↑ 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.
  6. ↑ 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.
  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. Bibcode:2022JAChS.14421022X. doi:10.1021/jacs.2c10863. ISSN   0002-7863. PMID   36354284 . 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 . Retrieved 7 April 2025.
  9. ↑ Comprehensive Natural Products II: Chemistry and Biology. Elsevier. 5 March 2010. p. 27. ISBN   978-0-08-045382-8 . Retrieved 7 April 2025.
  10. ↑ 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.
  11. ↑ 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.
  12. ↑ 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. PMID   14991780 . 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" (PDF). EXCLI Journal. 14: 508–516. doi:10.17179/EXCLI2014-667. PMC   4616245 . PMID   26535039 . Retrieved 7 April 2025.
This page is based on this Wikipedia article
Text is available under the CC BY-SA 4.0 license; additional terms may apply.
Images, videos and audio are available under their respective licenses.