Chemistry:Lamenallenic acid

From HandWiki
Lamenallenic acid
Names
Other names
(E)-5,6,16-octadecatrienoic acid
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
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).
Infobox references

Lamenallenic acid is a linear octadecatrienic fatty acid with the structural formula CH3CH=CH(CH2)8CH=C=CH(CH2)3COOH.[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]

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) (in en). The Lipid Handbook with CD-ROM. CRC Press. p. 7. ISBN 978-1-4200-0967-5. https://books.google.com/books?id=INZa6WmqDA8C&dq=Lamenallenic+acid&pg=PA7. 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. https://plantfadb.org/fatty_acids/10099. 
  3. ↑ 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. 
  4. ↑ Parker, W. (1974) (in en). Aliphatic Chemistry: Volume 2. Royal Society of Chemistry. p. 63. ISBN 978-0-85186-512-6. https://books.google.com/books?id=RnvjTqiYnIsC&dq=Lamenallenic+acid&pg=PA63. Retrieved 7 April 2025. 
  5. ↑ Gunstone, Frank D.; Harwood, John L.; Padley, Fred B. (21 July 1994) (in en). The Lipid Handbook, Second Edition. CRC Press. p. 52. ISBN 978-0-412-43320-7. https://books.google.com/books?id=m9J9pTDZEGEC&dq=Lamenallenic+acid&pg=PA715. 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. PMID 16742552. 
  7. ↑ Aitzetmüller, Kurt; Tsevegsüren, Nanzad; Vosmann, Klaus (1997). "A New Allenic Fatty Acid in Phlomis (Lamiaceae) Seed Oil" (in en). Lipid / Fett 99 (3): 74–78. doi:10.1002/lipi.19970990304. ISSN 1521-4133. https://onlinelibrary.wiley.com/doi/10.1002/lipi.19970990304. 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. https://www.sciencedirect.com/org/science/article/pii/S2052411022018028. Retrieved 7 April 2025. 



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