Juniperol
Chemical compound
From Wikipedia, the free encyclopedia
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]
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| Names | |
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| IUPAC name
(1R,3aR,4S,8aS,9S)-1,5,5,8a-tetramethyldecahydro-1,4-methanoazulen-9-ol | |
Other names
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| Identifiers | |
3D model (JSmol) |
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| ChEBI | |
PubChem CID |
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| UNII | |
CompTox Dashboard (EPA) |
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| Properties | |
| 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 |
| 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).
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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).
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.