Juniperol

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
CAS Number	465-24-7 ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:172936;
PubChem CID	11447401;
UNII	6Y2Y2D5L4D;
CompTox Dashboard (EPA)	DTXSID001317844 ;
	InChI 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 Key: MNNFKQAYXGEKFA-MUGBGTHKSA-N;
	SMILES C[C@@]12[C@]3(C)[C@@H](O)[C@@]([C@]1(CC3)[H])([C@](C)(C)CCC2)[H];
Properties
Chemical formula	C15H26O
Molar mass	222.372 g·mol−1
Appearance	pale yellow crystals
Density	1.04 g/cm3
Melting point	110 °C
Boiling point	130.00 to 150.00 °C
Solubility in water	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). Infobox references

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]

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 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^[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).^{[citation needed]}

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

↑ "1,4-Methanoazulen-9-ol, decahydro-1,5,5,8a-tetramethyl-, [1R-(1α,3aβ,4α,8aβ,9S*)]-". NIST. Retrieved 2 February 2026.
↑ Akiyoshi, S.; Erdtman, H.; Kubota, T. (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.
↑ "Page 230". in: Erdtman, H.; Norin, T. (1966). "The Chemistry of the Order Cupressales". Fortschritte der Chemie Organischer Naturstoffe / Progress in the Chemistry of Organic Natural Products / Progrès dans la Chimie des Substances Organiques Naturelles. pp. 206–287. doi:10.1007/978-3-7091-8143-0_4. ISBN 978-3-7091-8145-4.
↑ Erdtman, H.; Kubota, T.; Larsen, P. Olesen (1961). "The Chemistry of the Natural Order Cupressales. XXXVII. Monoterpenes from the Bark of Juniperus communis L.". Acta Chemica Scandinavica. 15: 1003–1006. doi:10.3891/acta.chem.scand.15-1003.
↑ "Page 359". in: Hegnauer, R. (1962). "Gymnospermae". Chemotaxonomie der Pflanzen. pp. 293–482. doi:10.1007/978-3-0348-9389-3_19.
↑ Proceedings of the Pennsylvania Pharmaceutical Association. Pennsylvania Pharmaceutical Association. 1901. Retrieved 2 February 2026.^{[verification needed]}^{[full citation needed]}
↑ "Juniper". theginguild.com. Retrieved 2 February 2026.
↑ The American Perfumer and Essential Oil Review. Moore Publishing Company. 1954. p. 47. Retrieved 2 February 2026.
↑ "Juniperol". Scent.vn. Retrieved 2 February 2026.

[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. (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.

[3] "Page 230". in: Erdtman, H.; Norin, T. (1966). "The Chemistry of the Order Cupressales". Fortschritte der Chemie Organischer Naturstoffe / Progress in the Chemistry of Organic Natural Products / Progrès dans la Chimie des Substances Organiques Naturelles. pp. 206–287. doi:10.1007/978-3-7091-8143-0_4. ISBN 978-3-7091-8145-4.

[4] Erdtman, H.; Kubota, T.; Larsen, P. Olesen (1961). "The Chemistry of the Natural Order Cupressales. XXXVII. Monoterpenes from the Bark of Juniperus communis L.". Acta Chemica Scandinavica. 15: 1003–1006. doi:10.3891/acta.chem.scand.15-1003.

[5] "Page 359". in: Hegnauer, R. (1962). "Gymnospermae". Chemotaxonomie der Pflanzen. pp. 293–482. doi:10.1007/978-3-0348-9389-3_19.

[6] Proceedings of the Pennsylvania Pharmaceutical Association. Pennsylvania Pharmaceutical Association. 1901. Retrieved 2 February 2026.^{[verification needed]}^{[full citation needed]}

[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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Structure

Natural occurrence

Physical properties

Uses

See also

References