Citronellol
Citronellol is an acyclic monoterpenoid alcohol with the molecular formula C₁₀H₂₀O and the IUPAC name 3,7-dimethyloct-6-en-1-ol, existing as two enantiomers: (+)-citronellol and (–)-citronellol, which impart citrus and rose-like scents, respectively.[1][2] It occurs naturally in essential oils from numerous aromatic plants, including roses (Rosa damascena, up to 35% in oil), geraniums (Pelargonium species), citronella grass (Cymbopogon nardus), and eucalyptus (Eucalyptus citriodora), often as a mixture of enantiomers or partial racemate.[1][3][2] The compound is a pale yellow oily liquid with a density of 0.855 g/cm³ at 20°C, a boiling point of 224°C, and low water solubility (200 mg/L at 25°C), making it suitable for volatile applications.[1] Citronellol's primary uses are in perfumery and cosmetics, where it provides fresh, floral notes in fragrances, soaps, shampoos, and detergents; it is also employed as a flavoring agent in foods like citrus, cherry, and strawberry products.[1][2] In addition, it functions as an insect repellent, particularly in citronella oil formulations, and as a miticide in agriculture to attract pests for control.[1][2] Emerging research highlights its biological activities, including anti-inflammatory, antinociceptive, and anticonvulsant effects, potentially via inhibition of nitric oxide and pro-inflammatory cytokines, though it can act as a skin sensitizer.[3]Properties
Chemical structure
Citronellol has the IUPAC name 3,7-dimethyloct-6-en-1-ol.[1][4] Its molecular formula is C₁₀H₂₀O, and the molecular weight is 156.27 g/mol.[1][4] This compound is an acyclic monoterpenoid consisting of an eight-carbon chain with a primary alcohol functional group (-CH₂OH) at position 1.[1] A carbon-carbon double bond is present between carbons 6 and 7, while methyl groups are attached to carbons 3 and 7, giving the structure HOCH₂CH₂CH(CH₃)CH₂CH₂CH=C(CH₃)CH₃.[1][4] The skeletal formula of citronellol is represented below, showing the carbon chain with branches and the double bond:In line notation, citronellol is expressed using the SMILES string CC(CCC=C(C)C)CCO.[1]CH₃ | HO-CH₂-CH₂-CH-CH₂-CH₂-CH=C-CH₃ | CH₃CH₃ | HO-CH₂-CH₂-CH-CH₂-CH₂-CH=C-CH₃ | CH₃
Physical properties
Citronellol is a colorless oily liquid at room temperature.[1] It has a boiling point of 224 °C at standard atmospheric pressure.[1] The melting point is below -20 °C, indicating it remains liquid under typical ambient conditions.[1] The density of citronellol is 0.855 g/cm³ at 20 °C.[1] It exhibits limited solubility in water, approximately 200 mg/L at 25 °C, but is fully miscible with ethanol, diethyl ether, fixed oils, and propylene glycol.[1] The octanol-water partition coefficient (logP) is 3.91, reflecting its lipophilic nature primarily due to the extended nonpolar alkyl chain in its structure.[1] Additional physical characteristics include a vapor pressure of 0.02 mm Hg at 25 °C.[1] The refractive index is 1.456 at 20 °C.[5] Viscosity measures 11.1 mPa·s at 20 °C.[1]| Property | Value | Conditions | Source |
|---|---|---|---|
| Boiling point | 224 °C | 760 mm Hg | PubChem |
| Melting point | < -20 °C | - | PubChem |
| Density | 0.855 g/cm³ | 20 °C | PubChem |
| Water solubility | 200 mg/L | 25 °C | PubChem |
| LogP | 3.91 | - | PubChem |
| Vapor pressure | 0.02 mm Hg | 25 °C | PubChem |
| Refractive index | 1.456 | 20 °C | Sigma-Aldrich |
| Viscosity | 11.1 mPa·s | 20 °C | PubChem |