Geranyl acetate

Description

Geranyl acetate has a pleasant, flowery odor reminiscent of rose lavender. It has a burning taste, initially somewhat bitter and then sweet. It is produced from geraniol by acetylation or by fractional distillation of essential oils in which it is present.

Description

Geranyl acetate is a monoterpene that has been found in C. sativa with diverse biological activities. It reduces compound action potential (CAP) peak amplitude in isolated frog sciatic nerves (IC₅₀ = 0.51 mM). Geranyl acetate inhibits the radial growth of M. gypsum, T. vercossum, and C. tropicalis on solid media. It is sporicidal against B. subtilis when used at a concentration of 1% in an agar diffusion assay. Geranyl acetate inhibits growth of COLO 205 cells (IC₅₀ = 30 μM) via induction of DNA damage, cell cycle arrest at the G₂/M phase, and mitochondrial apoptosis.

Chemical properties

Clear, colorless liquid; odor of lavender. Soluble in alcohol and ether; insoluble in water and glycerol. Combustible.

Chemical properties

Geranyl Acetate occurs in varying amounts in many essential oils: up to 60% in oils from Callitris and Eucalyptus species and up to 14% in palmarosa oil. A smaller amount occurs in, for example, geranium, citronella, petitgrain, and lavender oils. Geranyl acetate is a liquid with a fruity rose note, reminiscent of pear and slightly of lavender. It is used frequently in perfumery not only to create floral, fruity nuances (e.g., rose) but also for citrus and lavender notes. A small amount is added to fruit aromas for shading.

Chemical properties

Geranyl acetate has a pleasant, fowery odor reminiscent of rose lavender It has a burning taste, initially somewhat bitter and then sweet.

Occurrence

Reported found in a large number of essential oils; Ceylon citronella, palmarose, lemongrass, petitgrain, neroi bigarade, geranium, coriander, lavender, carrot, sassafras, in various Callitris species (C verrucosa, C robusta, and others) and Eucalyptus species (E acervula, E urnigera, etc ) A 60% level has been reported in the essential oil of Eucalyptus macar- thuri and up to 50% in the essential oil of Orthodon citraliferum; also identifed in bitter orange essential oil and Cymbopogon citratus oil Also reported found in citrus peel oils and juices, black currants, pineapple, celery seed, cinnamon, ginger, pepper- mint oil, corn mint oil, nutmeg, mace, thymus, hop oil, beer, rum, grape wines, coffee, tea, passion fruit, tomato, almond, muscal grape, cardamom, coriander leaf and seed, tarragon, lovage, Ocimum basilicum, laurel, myrtle leaf and berry, rosemary, clary sage and calabash nutmeg

The Uses of Geranyl acetate

β-Geranyl Acetate is found in essential oils such as Moroccan commercial essential oils which has anti-oxidant, anti-inflammatory and anti-proliferative activities; and in Salvia scabiosifolia from Bulgaria.

The Uses of Geranyl acetate

Perfumery, flavoring

What are the applications of Application

Geranyl acetate is has anti-oxidant, anti-inflammatory and anti-proliferative activities

Definition

ChEBI: A monoterpenoid that is the acetate ester derivative of geraniol.

Preparation

From geraniol by acetylation or by fractional distillation of essential oils in which it is present.

Aroma threshold values

Detection: 9 to 460 ppb.

Taste threshold values

Taste characteristics at 20 ppm: green, foral, fruity with a citrus nuance.

General Description

Clear colorless liquid with an odor of lavender.

Air & Water Reactions

Insoluble in water.

Reactivity Profile

Geranyl acetate should be protected from light. Geranyl acetate reacts with strong oxidizing agents.

Fire Hazard

Geranyl acetate is probably combustible.

Flammability and Explosibility

Non flammable

Safety Profile

Mildly toxic by ingestion. A human skin irritant. Mutation data reported. Combustible liquid. When heated to decomposition it emits acrid smoke and irritating fumes. See also ESTERS.

Purification Methods

Purify the fragrant smelling geranyl acetate by fractional distillation at as high a vacuum as possible. It is very soluble in EtOH but insoluble in H2O. [Beilstein 2 H 140, 2 I 65, 2 II 153, 2 III 299, 2 IV 204.]