Phlomic acid

Phlomic acid

Names
Other names Eicosa-7,8-dienoic acid
Identifiers
3D model (JSmol)	Interactive image
PubChem CID	102066359
InChI InChI=1S/C20H36O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20(21)22/h12,14H,2-11,15-19H2,1H3,(H,21,22) Key: IDIFLXHHWAEGTC-UHFFFAOYSA-N
SMILES CCCCCCCCCCCC=C=CCCCCCC(=O)O
Properties
Chemical formula	C20H36O2
Molar mass	308.506 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

Phlomic acid is an unsaturated fatty acid with an allene group, which gives it axial chirality and makes it optically active. Phlomic is related to laballenic acid but has a shorter chain length. ^[1]

Phlomic acid is composed of 20 carbon atoms, with two consecutive double bonds (allene) in the position 7=8=9. The acid has the structural formula CH₃-(CH₂)₁₀-CH=C=CH-(CH₂)₅-COOH. This is one of the rare allenic fatty acids found in nature, probably biosynthesized by elongation of laballenic acid. ^[2]

Natural occurrence

Phlomisic acid is found in some plant species of the Lamiaceae family. For example, it is present at 2.9% in the seed oil of Phlomoides tuberosa . ^[2] Other species of the genera Phlomis , such as deadnettle, hedgenettle, and Leonurus also contain the compound. ^[3] Out many species of the genus Leucas examined, 11 species contained small amounts of phlomisic acid. Only in two species was the content above 1%, and the highest measured content was 1.86%. ^[4]

Synthesis

Starting from hex-5-yn-1-ol, phlomic acid can be synthesized by a copper(II) bromide-catalyzed reaction with (S)-dimethylprolinol as a chiral auxiliary. ^[5]

Discovery

The common name of the acid comes from the genus Phlomis . ^[6] Phlomic acid was initially isolated in 1997 by K. Aitzetmüller, N. and K. Tsevegsüren Vosmann in the seed oil of various Lamiaceae . ^[2] Further analysis have found that phlomic acid almost always occurs in association with laballenic acid and gadoleic acid.

Uses

Plant derivatives with high content of allenic fatty acids have shown cytotoxic, anti-inflammatory, and antiviral activity. ^[7]

References

1. 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.
2. 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.
3. Sokovic, M. D.; Dokovic, D.; Tesevic, V.; Vajs, V.; Marin, P. D. (1 July 2009). "Fatty acid composition of seed oil of Phlomis fruticosa growing in Montenegro". Chemistry of Natural Compounds . 45 (4): 528–529. doi:10.1007/s10600-009-9390-2. ISSN   1573-8388 . Retrieved 7 April 2025.
4. Choudhary, Ashish Kumar; Sunojkumar, P.; Mishra, Girish (1 November 2017). "Fatty acid profiling and multivariate analysis in the genus Leucas reveals its nutritional, pharmaceutical and chemotaxonomic significance". Phytochemistry . 143: 72–80. doi:10.1016/j.phytochem.2017.07.007. ISSN   0031-9422 . Retrieved 7 April 2025.
5. Ma, Dengke; Duan, Xinyu; Fu, Chunling; Huang, Xin; Ma, Shengming (July 2018). "Dimethylprolinol Versus Diphenylprolinol in CuBr2-Catalyzed Enantioselective Allenylation of Terminal Alkynols". Synthesis . 50 (13): 2533–2545. doi:10.1055/s-0036-1592007. ISSN   0039-7881 . Retrieved 7 April 2025.
6. The Etymology of Chemical Names: Tradition and Convenience vs. Rationality in Chemical Nomenclature. Walter de Gruyter GmbH & Co KG. 8 October 2019. p. 280. ISBN   978-3-11-061271-4 . Retrieved 7 April 2025.
7. 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.