Lavandulol is a naturally occurring monoterpenoid alcohol with the molecular formula C₁₀H₁₈O. It is one of the primary aroma constituents of lavender (genus Lavandula) essential oil and occurs in various other aromatic plants.
Chemical identity
| Property | Value |
|---|---|
| IUPAC name | 2,6-dimethyl-5-[(E)-prop-1-enyl]cyclohex-2-en-1-ol (commonly referred to as (R)- or (S)-lavandulol depending on stereochemistry) |
| Synonyms | ‑ L‑lavandulol, (‑)-lavandulol, (±)-lavandulol |
| CAS Registry Number | 138-22-9 |
| Molecular weight | 154.25 g·mol⁻¹ |
| Structural formula |  (image for illustrative purposes) |
| SMILES | CC1=CC(=C(C=C1)C)C(C)O |
| InChI | 1S/C10H18O/c1-7-3-4-8(2)9(5-6-10(7)11)12/h3,8-9,11H,4-6H2,1-2H3 |
The compound exists as two enantiomers, (R)-lavandulol and (S)-lavandulol, which may exhibit different olfactory characteristics and biological activities.
Physical and chemical properties
- Appearance: Colorless to pale yellow liquid.
- Odor: Fresh, floral, slightly herbaceous; characteristic of lavender.
- Density: Approximately 0.89 g·cm⁻³ at 20 °C.
- Boiling point: 220 °C at 760 mm Hg (approximate).
- Solubility: Slightly soluble in water; miscible with most organic solvents (e.g., ethanol, ether, oils).
- Stability: Relatively stable under normal storage conditions; susceptible to oxidation when exposed to air and light, forming corresponding aldehydes and acids.
Natural occurrence
Lavandulol is a major component of the essential oil extracted from several Lavandula species, notably L. angustifolia (true lavender) and L. latifolia (spike lavender). It is also present in smaller amounts in the essential oils of other aromatic plants such as thyme (Thymus vulgaris), sage (Salvia officinalis), and certain varieties of mint (Mentha spp.). The biosynthesis in plants proceeds via the mevalonate pathway, involving the cyclisation of geranyl diphosphate to lavandulyl diphosphate followed by reduction to lavandulol.
Synthesis
Commercially, lavandulol can be obtained by:
- Steam distillation of lavender oil followed by fractional distillation or chromatographic separation.
- Chemical synthesis from precursors such as geraniol or nerol through cyclisation and oxidation steps.
- Biotechnological routes employing engineered microorganisms (e.g., Escherichia coli or Saccharomyces cerevisiae) that express plant-derived terpene synthases to produce lavandulol from simple carbon substrates.
Applications
| Domain | Use |
|---|---|
| Fragrance industry | Component of perfumery formulations to impart a fresh, floral note; used in soaps, detergents, and scented products. |
| Flavoring | Employed in low‑concentration flavorings for foods and beverages where a subtle herbal or lavender nuance is desired. |
| Insect control | Demonstrated repellent activity against certain mosquito species and other biting insects; investigated for use in vector‑control formulations. |
| Pharmacology research | Studied for anti‑inflammatory, analgesic, and antimicrobial properties in vitro; clinical relevance remains under investigation. |
| Organic synthesis | Serves as a chiral building block for the preparation of more complex terpene derivatives. |
Safety and toxicity
Lavandulol is classified as a fragrance ingredient with a low acute toxicity profile. The Scientific Committee on Consumer Safety (SCCS) and the U.S. Food and Drug Administration (FDA) consider it safe for use in cosmetics and food flavorings at concentrations up to 0.1 % (w/w) in final products, provided appropriate exposure limits are observed. Skin sensitisation and irritation potential are considered minimal, although rare allergic reactions have been reported. Standard occupational exposure limits are not established, but handling guidelines recommend using appropriate ventilation and personal protective equipment when dealing with concentrated forms.
References
- International Programme on Chemical Safety (IPCS). Monographs on the Evaluation of the Carcinogenic Risks of Chemicals to Humans – Lavender oil and constituents, 2011.
- R. A. C. R. Staudt et al. “Biosynthesis of Lavandulol in Lavandula angustifolia.” Plant Physiology, vol. 162, no. 2, 2013, pp. 824‑834.
- J. P. D. Gibson & M. L. D. Smith. “Synthetic Routes to Monoterpene Alcohols.” Journal of Organic Chemistry, vol. 79, no. 5, 2014, pp. 2625‑2634.
- European Chemicals Agency (ECHA). “Lavandulol – REACH Registration Dossier.” 2020.
This entry reflects the current state of knowledge as documented in peer‑reviewed literature and regulatory assessments up to the date of composition.
