Lamenallenic acid

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Lamenallenic acid
Lamenallenic acid.png
Names
Other names
(E)-5,6,16-octadecatrienoic acid
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
PubChem CID
  • InChI=1S/C18H30O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18(19)20/h2-3,12,14H,4-11,15-17H2,1H3,(H,19,20)/b3-2+
    Key: IHBRXZJPXHXMCN-NSCUHMNNSA-N
  • C/C=C/CCCCCCCCC=C=CCCCC(=O)O
Properties
C18H30O2
Molar mass 278.436 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Lamenallenic acid is a linear octadecatrienic fatty acid with the structural formula CH3-CH=CH-(CH2)8-CH=C=CH-(CH2)3-COOH. [1] The delta notation is 18:3-delta-5,6allene,16t. [2] This is one of the rare allenic fatty acids found in nature, probably biosynthesized from laballenic acid. [3]

Contents

Physical properties

Some authors have attributed the cis-configuration to the double bond in the position 16=17.

The allene group is responsible for the marked optical activity of the acid. Lamenallenic acid is levorotatory with (R)-configuration. [4]

Discovery

The acid was initially isolated in 1967 by Mikolajczak, Rogers, Smith, and Wolff in the seed oil of Lamium purpureum (10-16%), a plant of the Lamiaceae family. [5] [6] The compound is also found in the seed oil of other Lamiaceae: Lamium maculatum (~8%), Lamium album (~5%), Lamium amplexicaule (~5%). [7]

Synthesis

The acid can be obtained by a highly enantioselective synthesis, utilizing the recently developed EATA (enantioselective allenylation of terminal alkynes) reaction and aerobic oxidation reaction. [8]

References

  1. ↑ Gunstone, Frank D.; Harwood, John L. (13 March 2007). The Lipid Handbook with CD-ROM. CRC Press. p. 7. ISBN   978-1-4200-0967-5 . Retrieved 7 April 2025.
  2. ↑ "PlantFAdb: 18:3-delta-5,6allene,16t; Lamenallenic acid; 5,6,16-Octadecatrienoic acid; 5,6,16-Octadecatrienoic acid, (E)-(-)-; 5,6,16-Octadecatrienoic acid, [R-(E)]-; (-)-Octadeca-5,6-trans-16-trienoic acid; Lamenallenic acid". plantfadb.org. Retrieved 8 April 2025.
  3. ↑ 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.
  4. ↑ Parker, W. (1974). Aliphatic Chemistry: Volume 2. Royal Society of Chemistry. p. 63. ISBN   978-0-85186-512-6 . Retrieved 7 April 2025.
  5. ↑ Gunstone, Frank D.; Harwood, John L.; Padley, Fred B. (21 July 1994). The Lipid Handbook, Second Edition. CRC Press. p. 52. ISBN   978-0-412-43320-7 . Retrieved 7 April 2025.
  6. ↑ Mikolajczak, K. L.; Rogers, M. F.; Smith, C. R.; Wolff, I. A. (December 1967). "An octadecatrienoic acid from Lamium purpureum L. seed oil containing 5,6-allenic and trans-16-olefinic unsaturation". The Biochemical Journal . 105 (3): 1245–1249. doi:10.1042/bj1051245. ISSN   0264-6021. PMC   1198447 . PMID   16742552.
  7. ↑ Aitzetmüller, Kurt; Tsevegsüren, Nanzad; Vosmann, Klaus (1997). "A New Allenic Fatty Acid in Phlomis (Lamiaceae) Seed Oil" . Lipid / Fett. 99 (3): 74–78. doi:10.1002/lipi.19970990304. ISSN   1521-4133 . Retrieved 7 April 2025.
  8. ↑ Jiang, Xingguo; Xue, Yufeng; Ma, Shengming (1 January 2017). "Aerobic oxidation and EATA-based highly enantioselective synthesis of lamenallenic acid". Organic Chemistry Frontiers. 4 (6): 951–957. doi:10.1039/c6qo00785f. ISSN   2052-4129 . Retrieved 7 April 2025.
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