Juniperonic acid

Last updated
Juniperonic acid
Juniperonic acid.png
Names
IUPAC name
(5Z,11Z,14Z,17Z)-icosa-5,11,14,17-tetraenoic acid
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
PubChem CID
  • InChI=1S/C20H32O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20(21)22/h3-4,6-7,9-10,15-16H,2,5,8,11-14,17-19H2,1H3,(H,21,22)/b4-3-,7-6-,10-9-,16-15-
    Key: JDKIKEYFSJUYJZ-OUJQXAOTSA-N
  • CC/C=C\C/C=C\C/C=C\CCCC/C=C\CCCC(=O)O
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]

Contents

It is an isomer of eicosatetraenoic acid like the better known omega-6 fatty acid, arachidonic acid. [4]

History and natural occurrence

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

Thuja seeds are used in traditional Chinese medicine. [9] This acid exhibits interesting biological activity and becomes α-linolenic acid in animal models.

References

  1. ↑ "Juniperonic acid | CAS 18016-45-0 | SCBT - Santa Cruz Biotechnology". scbt.com . Retrieved 31 May 2025.
  2. ↑ 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.
  3. ↑ 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.
  4. ↑ 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.
  5. ↑ 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.
  6. ↑ 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.
  7. ↑ 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.
  8. ↑ 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.
  9. ↑ 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.
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.