Juniperol

Last updated
Juniperol
Names
IUPAC name
(1R,3aR,4S,8aS,9S)-1,5,5,8a-tetramethyldecahydro-1,4-methanoazulen-9-ol
Other names
  • Macrocarpol
  • Longiborneol
  • (+)-Juniperol
  • (+)-Longiborneol
Identifiers
3D model (JSmol)
ChEBI
PubChem CID
UNII
  • 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 X mark.svgN
    Key: MNNFKQAYXGEKFA-MUGBGTHKSA-N
  • C[C@@]12[C@]3(C)[C@@H](O)[C@@]([C@]1(CC3)[H])([C@](C)(C)CCC2)[H]
Properties
C15H26O
Molar mass 222.372 g·mol−1
Appearancepale yellow crystals
Density 1.04 g/cm3
Melting point 110 °C
Boiling point 130.00 to 150.00 °C
insoluble
Hazards
Flash point 248.00 °F
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Juniperol is a tricyclic terpenoid alcohol with the chemical formula C15H26O. [1] 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. [2] [3] Juniperol was initially isolated by Mattson in 1913. [4]

Contents

Structure

Juniperol is based on a tricyclic cadinane skeleton. It is classified as a sesquiterpenoid, meaning it is built from three isoprene units (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 occurence

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 [5] ) and in some other aromatic plants like cannabis.

Physical properties

The compound forms white to pale yellow crystals, insoluble in water. [6] 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. [7] [8] 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. [9] The balance of juniperol with other compounds like pinene, myrcene, and terpineol defines the profile of a specific gin.

References

  1. ↑ "1,4-Methanoazulen-9-ol, decahydro-1,5,5,8a-tetramethyl-, [1R-(1α,3aβ,4α,8aβ,9S*)]-". NIST . Retrieved 2 February 2026.
  2. ↑ Akiyoshi, S.; Erdtman, H.; Kubota, T. (1 January 1960). "Chemistry of the natural order cupressales—XXVI: The identity of junipene, kuromatsuene and longifolene and of juniperol, kuromatsuol, macrocarpol and longiborneol". Tetrahedron . 9 (3): 237–239. doi:10.1016/0040-4020(60)80012-9. ISSN   0040-4020 . Retrieved 2 February 2026.
  3. ↑ Fortschritte Der Chemie Organischer Naturstoffe / Progress in the Chemistry of Organic Natural Products / Progrès Dans La Chimie Des Substances Organiques Naturelles. Springer Science & Business Media. 6 December 2012. p. 230. ISBN   978-3-7091-8143-0 . Retrieved 2 February 2026.
  4. ↑ Acta Chemica Scandinavica. Munksgaard. 1961. p. 1003. Retrieved 2 February 2026.
  5. ↑ Hegnauer, R. (1 December 2013). Chemotaxonomie der Pflanzen: Eine Übersicht über die Verbreitung und die systematische Bedeutung der Pflanzenstoffe (in German). Springer-Verlag. p. 359. ISBN   978-3-0348-9389-3 . Retrieved 2 February 2026.
  6. ↑ Proceedings of the Pennsylvania Pharmaceutical Association. Pennsylvania Pharmaceutical Association. 1901. Retrieved 2 February 2026.
  7. ↑ "Juniper". theginguild.com. Retrieved 2 February 2026.
  8. ↑ The American Perfumer and Essential Oil Review. Moore Publishing Company. 1954. p. 47. Retrieved 2 February 2026.
  9. ↑ "Juniperol". Scent.vn. Retrieved 2 February 2026.
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