Juniperonic acid is a polyunsaturated fatty acid featuring a 20-carbon chain with four ''cis''-configured

double bond In chemistry, a double bond is a covalent bond between two atoms involving four bonding electrons as opposed to two in a single bond. Double bonds occur most commonly between two carbon atoms, for example in alkenes. Many double bonds exist betw ...

s at positions 5, 11, 14, and 17. These structural traits categorize the compound as an

omega-3 fatty acid Omega−3 fatty acids, also called omega−3 oils, ω−3 fatty acids or ''n''−3 fatty acids, are polyunsaturated fatty acids (PUFAs) characterized by the presence of a double bond three atoms away from the terminal methyl group in their ...

, and it has drawn significant scientific attention due to its influence on regulating lipid membrane function and cell signaling processes. It is an isomer of

eicosatetraenoic acid Eicosatetraenoic acid (ETA) designates any straight chain tetra-unsaturated 20-carbon fatty acid. These compound are classified as polyunsaturated fatty acids (PUFA). The pure compounds, which are encountered rarely, are colorless oils. Two isomer ...

like the better known

omega-6 fatty acid Omega−6 fatty acids (also referred to as ω−6 fatty acids or ''n''−6 fatty acids) are a family of polyunsaturated fatty acids (PUFA) that share a final carbon-carbon double bond in the ''n''−6 position, that is, the sixth bond, counti ...

arachidonic acid Arachidonic acid (AA, sometimes ARA) is a polyunsaturated omega−6 fatty acid 20:4(ω−6), or 20:4(5,8,11,14). It is a precursor in the formation of leukotrienes, prostaglandins, and thromboxanes. Together with omega−3 fatty acids an ...

History and natural occurrence

The acid was isolated for the first time in 1963 on the leaves and fruits of ''

Ginkgo biloba ''Ginkgo biloba'', commonly known as ginkgo or gingko ( ), also known as the maidenhair tree, is a species of gymnosperm tree native to East Asia. It is the last living species in the order Ginkgoales, which first appeared over 290 million year ...

'' by JL Gellerman and H. Schlenk. It was then identified in the oils of other plants, especially

conifers Conifers () are a group of cone-bearing seed plants, a subset of gymnosperms. Scientifically, they make up the division Pinophyta (), also known as Coniferophyta () or Coniferae. The division contains a single extant class, Pinopsida. All e ...

: ''

Taxodium distichum ''Taxodium distichum'' (baldcypress, bald-cypress, bald cypress, swamp cypress; ; ''cipre'' in Louisiana) is a deciduous conifer in the family Cupressaceae. It is native to the southeastern United States. Hardy and tough, this tree adapts to a ...

'' (14.25%), ''

Cupressus funebris ''Cupressus funebris'', the Chinese weeping cypress, is a species of cypress native to southwestern and central China. It may also occur naturally in Vietnam. Description ''Cupressus funebris'' is a medium-sized coniferous tree growing to 20–3 ...

'' (10.27%), Platycladus orientalis (9%), ''

Taxus cuspidata ''Taxus cuspidata'', the Japanese yew or spreading yew, is a member of the genus ''Taxus'', native to Japan, Korea, northeast China and the extreme southeast of Russia. Names In Japan, the tree is known as ''ichi'i'' (一位), meaning "first ...

'' (6.8%), etc.; in other flowering plants: ''Ephedra gerardianaii'' (19.2%), ''Caltha sp.'' (9.4%), ''

Ephedra nevadensis ''Ephedra nevadensis'', commonly known as Nevada ephedra, gray ephedra, Mormon tea and Nevada jointfir, is a species of gymnosperm native to dry areas of western North America. Its range extends west to California, east to Colorado, north to O ...

'' (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 ''Juniperus communis'', the common juniper, is a species of small tree or shrub in the cypress family Cupressaceae. An evergreen conifer, it has the largest geographical range of any woody plant, with a circumpolar distribution throughout the coo ...

'' (18%), which is why the acid is called juniperonic. It was first synthesized in 2010 by A. Vik and co-workers. Oftentimes, it is found in conifers together with other fatty acids ( taxoleic, pinolenic, taxoleic,

sciadonic acid Sciadonic acid, also known as eicosatrienoic acid, is a polyunsaturated fatty acid. In regard to its structure, sciadonic acid has 3 double bonds in the 5, 11, and 14 positions all of which are in the ''cis'' configuration. It is further classifi ...

) that have a double bond in the position 5, separated by more than one

methylene group A methylene group is any part of a molecule that consists of two hydrogen atoms bound to a carbon Carbon () is a chemical element; it has chemical symbol, symbol C and atomic number 6. It is nonmetallic and tetravalence, tetravalent—m ...

from the next double bond.

Uses

Thuja ''Thuja'' ( ) is a genus of coniferous tree or shrub in the Cupressaceae (cypress family). There are five species in the genus, two native to North America and three native to eastern Asia. The genus is monophyletic and sister to ''Thujopsis''. M ...

seeds are used in

traditional Chinese medicine Traditional Chinese medicine (TCM) is an alternative medicine, alternative medical practice drawn from traditional medicine in China. A large share of its claims are pseudoscientific, with the majority of treatments having no robust evidence ...

.{{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 The CRC Press, LLC is an American publishing group that specializes in producing technical books. Many of their books relate to engineering, science and mathematics. Their scope also includes books on business, forensics and information technol ...

, 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 This acid exhibits interesting biological activity and becomes

α-linolenic acid α-Linolenic acid, also known as ''alpha''-linolenic acid (ALA) (from Greek ''alpha'' denoting "first" and ''linon'' meaning flax), is an ''n''−3, or omega-3, essential fatty acid. ALA is found in many seeds and oils, including flaxseed, ...

in animal models.

References

Alkenoic acids Fatty acids