# Juniperonic acid

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{{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
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| Section3       = {{Chembox Hazards
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'''Juniperonic acid''' is a polyunsaturated fatty acid featuring a 20-carbon chain with four ''cis''-configured [double bond](/source/double_bond)s at positions 5, 11, 14, and 17. These structural traits categorize the compound as an [omega-3 fatty acid](/source/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](/source/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](/source/John_Wiley_%26_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](/source/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](/source/eicosatetraenoic_acid) like the better known [omega-6 fatty acid](/source/omega-6_fatty_acid), [arachidonic acid](/source/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](/source/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](/source/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](/source/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](/source/conifers): ''[Taxodium distichum](/source/Taxodium_distichum)'' (14.25%), ''[Cupressus funebris](/source/Cupressus_funebris)'' (10.27%), [Platycladus orientalis](/source/Platycladus_orientalis) (9%), ''[Taxus cuspidata](/source/Taxus_cuspidata)'' (6.8%), etc.; in other flowering plants: ''[Ephedra gerardiana](/source/Ephedra_gerardiana)'' (19.2%), ''[Caltha](/source/Caltha)'' sp. (9.4%), ''[Ephedra nevadensis](/source/Ephedra_nevadensis)'' (9.3%), and ''[Ephedra przewalskii](/source/Ephedra_przewalskii)'' (8.8%), among others; and in some marine animals.

The acid was later discovered in the seed oil of ''[Juniperus communis](/source/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](/source/Walter_de_Gruyter_GmbH_%26_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](/source/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](/source/Taxoleic_acid), [pinolenic](/source/Pinolenic_acid), [taxoleic](/source/Taxoleic_acid), [sciadonic acid](/source/sciadonic_acid)) that have a double bond in the position 5, separated by more than one [methylene group](/source/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](/source/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](/source/Thuja) seeds are used in [traditional Chinese medicine](/source/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](/source/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](/source/%CE%91-Linolenic_acid) in animal models.

== References ==
<references/>

Category:Alkenoic acids
Category:Fatty acids

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Adapted from the Wikipedia article [Juniperonic acid](https://en.wikipedia.org/wiki/Juniperonic_acid) by Wikipedia contributors ([contributor history](https://en.wikipedia.org/wiki/Juniperonic_acid?action=history)). Available under [Creative Commons Attribution-ShareAlike 4.0 International](https://creativecommons.org/licenses/by-sa/4.0/). Changes may have been made.