{{Chembox <!-- Images --> | Name = Juniperonic acid | ImageFile = Juniperonic acid.png | ImageSize = 250px | ImageAlt = <!-- Names --> | IUPACName = (5''Z'',11''Z'',14''Z'',17''Z'')-icosa-5,11,14,17-tetraenoic acid | OtherNames = | Section1 = {{Chembox Identifiers | CASNo = | CASNo_Ref = {{Cascite|changed|CAS}} | ChemSpiderID = 4471968 | DTXSID = | EC_number = | ChEBI = 82835 | ChEMBL = | KEGG = | UNII = | PubChem = 5312543 | InChI = 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- | InChIKey = JDKIKEYFSJUYJZ-OUJQXAOTSA-N | SMILES = CC/C=C\C/C=C\C/C=C\CCCC/C=C\CCCC(=O)O }} | Section2 = {{Chembox Properties | H=32|O=2|C=20 | MolarMass = | Appearance = | Density = | MeltingPtC = | BoilingPtC = | BoilingPt_ref = | Solubility = }} | Section3 = {{Chembox Hazards | GHSPictograms = | GHSSignalWord = | GHS_ref = | HPhrases = | PPhrases = | MainHazards = | FlashPt = | AutoignitionPt = }} }} '''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.<ref>{{cite web |title=Juniperonic acid {{!}} CAS 18016-45-0 {{!}} SCBT - Santa Cruz Biotechnology |url=https://www.scbt.com/p/juniperonic-acid-18016-45-0?srsltid=AfmBOorEChH6NIyOPRBFmMvTFhYezOpsAd537nqxacD79x180OIhU3Bn |publisher=scbt.com |access-date=31 May 2025 |language=en}}</ref><ref>{{cite book |last1=Gunstone |first1=Frank |title=The Chemistry of Oils and Fats: Sources, Composition, Properties and Uses |date=12 February 2009 |publisher=John Wiley & Sons |isbn=978-1-4051-5002-6 |page=58 |url=https://books.google.com/books?id=KYFU7heynbwC&dq=juniperonic+acid&pg=PA285 |access-date=31 May 2025 |language=en}}</ref><ref>{{cite book |last1=Alasalvar |first1=Cesarettin |last2=Shahidi |first2=Fereidoon |title=Tree Nuts: Composition, Phytochemicals, and Health Effects |date=17 December 2008 |publisher=CRC Press |isbn=978-1-4200-1939-1 |page=287 |url=https://books.google.com/books?id=Uu4nzKx74noC&dq=juniperonic+acid&pg=PA287 |access-date=31 May 2025 |language=en}}</ref>
It is an isomer of eicosatetraenoic acid like the better known omega-6 fatty acid, arachidonic acid.<ref>{{cite book |last1=Gunstone |first1=F. D. |last2=Herslof |first2=B. G. |title=Lipid Glossary 2 |date=12 May 2000 |publisher=Elsevier |isbn=978-0-85709-797-2 |page=70 |url=https://books.google.com/books?id=4ZejAgAAQBAJ&dq=juniperonic+acid&pg=PA70 |access-date=31 May 2025 |language=en}}</ref>
==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.<ref>{{cite journal |last1=Gellerman |first1=Joanne L. |last2=Schlenk |first2=H. |title=A group of fatty acids with 'tetramethylene interruption' in the double bond system |journal=Experientia |date=1 October 1963 |volume=19 |issue=10 |pages=522–523 |doi=10.1007/BF02150889 |pmid=14094055 |url=https://link.springer.com/article/10.1007/BF02150889 |access-date=31 May 2025 |language=en |issn=0014-4754|url-access=subscription }}</ref> 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 gerardiana'' (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.<ref>{{cite book |title=The Etymology of Chemical Names: Tradition and Convenience vs. Rationality in Chemical Nomenclature |date=8 October 2019 |publisher=Walter de Gruyter GmbH & Co KG |isbn=978-3-11-061124-3 |url=https://books.google.com/books?id=M6zWDwAAQBAJ&dq=juniperonic+acid&pg=PT362 |access-date=31 May 2025 |language=en}}</ref> It was first synthesized in 2010 by A. Vik and co-workers.<ref>{{cite journal |last1=Vik |first1=Anders |last2=Hansen |first2=Trond Vidar |last3=Holmeide |first3=Anne Kristin |last4=Skattebøl |first4=Lars |title=Synthesis of juniperonic acid |journal=Tetrahedron Letters |date=26 May 2010 |volume=51 |issue=21 |pages=2852–2854 |doi=10.1016/j.tetlet.2010.03.085 |url=https://www.sciencedirect.com/science/article/abs/pii/S0040403910005162 |access-date=31 May 2025 |issn=0040-4039|url-access=subscription }}</ref>
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.<ref>{{cite journal |last1=Pédrono |first1=Frédérique |last2=Boulier-Monthéan |first2=Nathalie |last3=Boissel |first3=Françoise |last4=Ossemond |first4=Jordane |last5=Viel |first5=Roselyne |last6=Fautrel |first6=Alain |last7=Marchix |first7=Justine |last8=Dupont |first8=Didier |title=Sciadonic acid derived from pine nuts as a food component to reduce plasma triglycerides by inhibiting the rat hepatic Δ9-desaturase |journal=Scientific Reports |date=10 April 2020 |volume=10 |issue=1 |pages=6223 |doi=10.1038/s41598-020-63301-3 |url=https://www.nature.com/articles/s41598-020-63301-3 |access-date=19 May 2025 |language=en |issn=2045-2322|pmc=7148351 }}</ref>
==Uses== Thuja seeds are used in traditional Chinese medicine.<ref>{{cite book |last1=Rai |first1=Mahendra |last2=Acharya |first2=Deepak |last3=Rios |first3=Jose Luis |title=Ethnomedicinal Plants: Revitalizing of Traditional Knowledge of Herbs |date=1 February 2011 |publisher=CRC Press |isbn=978-1-4398-5362-7 |page=145 |url=https://books.google.com/books?id=UoDRBQAAQBAJ&dq=juniperonic+acid&pg=PA145 |access-date=31 May 2025 |language=en}}</ref> This acid exhibits interesting biological activity and becomes ''α''-linolenic acid in animal models.
== References == <references/>
Category:Alkenoic acids Category:Fatty acids