Juniperonic acid
 | |
| Names | |
|---|---|
| IUPAC name
(5Z,11Z,14Z,17Z)-icosa-5,11,14,17-tetraenoic acid
| |
| Identifiers | |
3D model (JSmol)
|
|
| ChEBI | |
| ChemSpider | |
PubChem CID
|
|
| |
| |
| Properties | |
| C20H32O2 | |
| Molar mass | 304.474 g·mol−1 |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
| |
Juniperonic acid is a polyunsaturated fatty acid featuring a 20-carbon chain with four cis-configured double bonds at positions 5, 11, 14, and 17. These structural traits categorize the compound as an omega-3 fatty acid, and it has drawn significant scientific attention due to its influence on regulating lipid membrane function and cell signaling processes.[1][2][3]
It is an isomer of eicosatetraenoic acid like the better known omega-6 fatty acid, arachidonic acid.[4]
History and natural occurrence
[edit]The acid was isolated for the first time in 1963 on the leaves and fruits of Ginkgo biloba by JL Gellerman and H. Schlenk.[5] It was then identified in the oils of other plants, especially conifers: Taxodium distichum (14.25%), Cupressus funebris (10.27%), Platycladus orientalis (9%), Taxus cuspidata (6.8%), etc.; in other flowering plants: Ephedra gerardianaii (19.2%), Caltha sp. (9.4%), Ephedra nevadensis (9.3%), and Ephedra przewalskii (8.8%), among others; and in some marine animals.
The acid was later discovered in the seed oil of Juniperus communis (18%), which is why the acid is called juniperonic.[6] It was first synthesized in 2010 by A. Vik and co-workers.[7]
Oftentimes, it is found in conifers together with other fatty acids (taxoleic, pinolenic, taxoleic, sciadonic acid) that have a double bond in the position 5, separated by more than one methylene group from the next double bond.[8]
Uses
[edit]Thuja seeds are used in traditional Chinese medicine.[9] This acid exhibits interesting biological activity and becomes α-linolenic acid in animal models.
References
[edit]- ^ "Juniperonic acid | CAS 18016-45-0 | SCBT - Santa Cruz Biotechnology". scbt.com. Retrieved 31 May 2025.
- ^ Gunstone, Frank (12 February 2009). The Chemistry of Oils and Fats: Sources, Composition, Properties and Uses. John Wiley & Sons. p. 58. ISBN 978-1-4051-5002-6. Retrieved 31 May 2025.
- ^ Alasalvar, Cesarettin; Shahidi, Fereidoon (17 December 2008). Tree Nuts: Composition, Phytochemicals, and Health Effects. CRC Press. p. 287. ISBN 978-1-4200-1939-1. Retrieved 31 May 2025.
- ^ Gunstone, F. D.; Herslof, B. G. (12 May 2000). Lipid Glossary 2. Elsevier. p. 70. ISBN 978-0-85709-797-2. Retrieved 31 May 2025.
- ^ Gellerman, Joanne L.; Schlenk, H. (1 October 1963). "A group of fatty acids with 'tetramethylene interruption' in the double bond system". Experientia. 19 (10): 522–523. doi:10.1007/BF02150889. ISSN 0014-4754. PMID 14094055. Retrieved 31 May 2025.
- ^ The Etymology of Chemical Names: Tradition and Convenience vs. Rationality in Chemical Nomenclature. Walter de Gruyter GmbH & Co KG. 8 October 2019. ISBN 978-3-11-061124-3. Retrieved 31 May 2025.
- ^ Vik, Anders; Hansen, Trond Vidar; Holmeide, Anne Kristin; Skattebøl, Lars (26 May 2010). "Synthesis of juniperonic acid". Tetrahedron Letters. 51 (21): 2852–2854. doi:10.1016/j.tetlet.2010.03.085. ISSN 0040-4039. Retrieved 31 May 2025.
- ^ Pédrono, Frédérique; Boulier-Monthéan, Nathalie; Boissel, Françoise; Ossemond, Jordane; Viel, Roselyne; Fautrel, Alain; Marchix, Justine; Dupont, Didier (10 April 2020). "Sciadonic acid derived from pine nuts as a food component to reduce plasma triglycerides by inhibiting the rat hepatic Δ9-desaturase". Scientific Reports. 10 (1): 6223. doi:10.1038/s41598-020-63301-3. ISSN 2045-2322. Retrieved 19 May 2025.
- ^ Rai, Mahendra; Acharya, Deepak; Rios, Jose Luis (1 February 2011). Ethnomedicinal Plants: Revitalizing of Traditional Knowledge of Herbs. CRC Press. p. 145. ISBN 978-1-4398-5362-7. Retrieved 31 May 2025.