{{chembox | Name = Juniperol | Verifiedfields = | Watchedfields = | verifiedrevid = | ImageFile = Longiborneol_structure.png | ImageSize = 200px | ImageName = | ImageFile1 = | ImageSize1 = 250px | ImageName1 = | IUPACName = (1''R'',3''aR'',4''S'',8''aS'',9''S'')-1,5,5,8''a''-tetramethyldecahydro-1,4-methanoazulen-9-ol | SystematicName= | OtherNames= {{ubl|Macrocarpol|Longiborneol|(+)-Juniperol|(+)-Longiborneol}} |Section1={{Chembox Identifiers | CASNo_Ref = {{Cascite|correct|CAS}} | CASNo=465-24-7 | Beilstein = | ChEMBL = | ChemSpiderID = | PubChem= 11447401 | UNII = 6Y2Y2D5L4D | SMILES=C[C@@]12[C@]3(C)[C@@H](O)[C@@]([C@]1(CC3)[H])([C@](C)(C)CCC2)[H] | StdInChI_Ref = {{stdinchicite|changed|chemspider}} | StdInChI = InChI=1S/C15H26O/c1-13(2)7-5-8-14(3)10-6-9-15(14,4)12(16)11(10)13/h10-12,16H,5-9H2,1-4H3/t10-,11-,12+,14+,15+/m1/s1 | StdInChIKey_Ref = | StdInChIKey = MNNFKQAYXGEKFA-MUGBGTHKSA-N | ChEBI = 172936 }} |Section2={{Chembox Properties | C=15 | H=26 | O=1 | Appearance=pale yellow crystals | Density=1.04 g/cm<sup>3</sup> | MeltingPt=110 °C | BoilingPt=130.00 to 150.00 °C | Solubility=insoluble }} |Section3={{Chembox Hazards | MainHazards= | FlashPt=248.00 °F | AutoignitionPt = }} }} '''Juniperol''' is a tricyclic terpenoid alcohol with the chemical formula {{chem2|C15H26O}}.<ref>{{cite web |title=1,4-Methanoazulen-9-ol, decahydro-1,5,5,8a-tetramethyl-, [1R-(1α,3aβ,4α,8aβ,9S*)]- |url=https://webbook.nist.gov/cgi/inchi/InChI%3D1S/C15H26O/c1-13(2)7-5-8-14(3)10-6-9-15(14%2C4)12(16)11(10)13/h10-12%2C16H%2C5-9H2%2C1-4H3/t10%3F%2C11%3F%2C12-%2C14%3F%2C15%3F/m1/s1 |publisher=NIST |access-date=2 February 2026 |language=en}}</ref> This is one of the primary aromatic and flavor-defining constituents of the essential oil of common juniper (''Juniperus communis'') berries, which are used as the key botanical in gin production.<ref>{{cite journal |last1=Akiyoshi |first1=S. |last2=Erdtman |first2=H. |last3=Kubota |first3=T. |title=Chemistry of the natural order cupressales—XXVI: The identity of junipene, kuromatsuene and longifolene and of juniperol, kuromatsuol, macrocarpol and longiborneol |journal=Tetrahedron |date=1 January 1960 |volume=9 |issue=3 |pages=237–239 |doi=10.1016/0040-4020(60)80012-9 |url=https://www.sciencedirect.com/science/article/abs/pii/0040402060800129 |access-date=2 February 2026 |issn=0040-4020|url-access=subscription }}</ref><ref>{{cite book |title=Fortschritte Der Chemie Organischer Naturstoffe / Progress in the Chemistry of Organic Natural Products / Progrès Dans La Chimie Des Substances Organiques Naturelles |date=6 December 2012 |publisher=Springer Science & Business Media |isbn=978-3-7091-8143-0 |page=230 |url=https://www.google.ru/books/edition/Fortschritte_Der_Chemie_Organischer_Natu/Ugj8CAAAQBAJ?hl=en&gbpv=1&dq=Juniperol&pg=PA230&printsec=frontcover |access-date=2 February 2026 |language=en}}</ref> Juniperol was initially isolated by Mattson in 1913.<ref>{{cite book |title=Acta Chemica Scandinavica |date=1961 |publisher=Munksgaard |page=1003 |url=https://www.google.ru/books/edition/Acta_Chemica_Scandinavica/nD2OwnIJ_i0C?hl=en&gbpv=1&bsq=Juniperol&dq=Juniperol&printsec=frontcover |access-date=2 February 2026 |language=en}}</ref>
==Structure== Juniperol is based on a tricyclic cadinane skeleton. It is classified as a sesquiterpenoid, meaning it is built from three isoprene units ({{chem2|C15}}). Its characteristic aroma is highly dependent on its specific stereochemistry at several chiral centers (the spatial arrangement of atoms). The compound is known as a key contributor to the characteristic "piney," "woody," and "fresh" notes associated with juniper and, by extension, gin.
==Natural occurrence== Juniperol is biosynthesized within the glandular tissues of juniper berries and needles via the mevalonate pathway, a common route for terpenoid production.
While most abundant in ''Juniperus communis'', it has also been identified, often in lower concentrations or as different stereoisomers, in the essential oils of other plants within the Cupressaceae family (e.g., certain cypresses and cedars, for example, ''Cedrus deodara'' and ''Cupressus macrocarpa''<ref>{{cite book |last1=Hegnauer |first1=R. |title=Chemotaxonomie der Pflanzen: Eine Übersicht über die Verbreitung und die systematische Bedeutung der Pflanzenstoffe |date=1 December 2013 |publisher=Springer-Verlag |isbn=978-3-0348-9389-3 |page=359 |url=https://www.google.ru/books/edition/Chemotaxonomie_der_Pflanzen/YMsiBgAAQBAJ?hl=en&gbpv=1&dq=juniperol+Cupressus+macrocarpa&pg=PA359&printsec=frontcover |access-date=2 February 2026 |language=de}}</ref>) and in some other aromatic plants like cannabis.
==Physical properties== The compound forms white to pale yellow crystals, insoluble in water.<ref>{{cite book |title=Proceedings of the Pennsylvania Pharmaceutical Association |date=1901 |publisher=Pennsylvania Pharmaceutical Association |url=https://www.google.ru/books/edition/Proceedings_of_the_Pennsylvania_Pharmace/08oyAQAAMAAJ?hl=en&gbpv=1&bsq=Juniperol,+gin&dq=Juniperol,+gin&printsec=frontcover |access-date=2 February 2026 |language=en}}</ref> However, it is lipophilic (soluble in oils and organic solvents).
==Uses== Juniperol is a critical flavor and fragrance molecule, fundamental to the gin's identity.<ref>{{cite web |title=Juniper |url=https://www.theginguild.com/ginopedia/gin-botanicals/juniper/ |publisher=theginguild.com |access-date=2 February 2026}}</ref><ref>{{cite book |title=The American Perfumer and Essential Oil Review |date=1954 |publisher=Moore Publishing Company |page=47 |url=https://www.google.ru/books/edition/The_American_Perfumer_and_Essential_Oil/Cy1GGkoIIVQC?hl=en&gbpv=1&bsq=Juniperol,+gin&dq=Juniperol,+gin&printsec=frontcover |access-date=2 February 2026 |language=en}}</ref> During gin distillation (particularly in the traditional pot still method), juniperol volatilizes and carries over into the distillate, providing the foundational juniper character upon which other botanical notes are layered.<ref>{{cite web |title=Juniperol |url=https://scent.vn/en/pages/compound/juniperol-1145?srsltid=AfmBOooYGXkX6p2oOc-PgtG0ZfIqk-rreC67HifoJzGtWbF4fkVUKoQh |publisher=Scent.vn |access-date=2 February 2026 |language=en}}</ref> The balance of juniperol with other compounds like pinene, myrcene, and terpineol defines the profile of a specific gin.
== See also == * Borneol * Fenchol * Myrtenol
== References == {{reflist}}
{{Terpenoids}}
Category:Diterpenoids Category:Tertiary alcohols Category:Perfume ingredients Category:Food ingredients Category:Sesquiterpenes Category:Gins Category:Juniperus