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Geraniol. noun ge·ra·ni·ol jə-ˈrā-nē-ˌȯl -ˌōl : a fragrant liquid unsaturated alcohol C10H18O used chiefly in perfumes and soap
Introduction:
Geraniol is a monoterpenoid alcohol that occurs naturally and belongs to the monoterpenoid family. This page provides an overview of geraniol, including its chemical properties, natural sources, uses, and potential benefits.
History:
Geraniol was first isolated in pure form in 1871 by German chemist Oscar Jacobsen. He obtained geraniol through distillation from the essential oil derived from geranium grass (Andropogon schoenanthus) found in India. The chemical structure of geraniol was determined by French chemist Albert Verley in 1919.
Chemical Properties:
Geraniol is characterized by its molecular formula C10H18O and consists of ten carbon atoms. It is a colorless oil, although commercial samples can have a yellowish appearance. Geraniol has low solubility in water but is soluble in common organic solvents. Its distinct feature is the hydroxyl group (-OH) attached to a ten-carbon backbone.
Sources:
Geraniol is the primary component of essential oils such as citronella oil, rose oil, and palmarosa oil. It occurs in small quantities in various other essential oils, including geranium, lemon, and more. The fragrance of geraniol resembles that of roses, making it a popular ingredient in perfumes and scented products.
Uses:
Geraniol finds application in perfumery, adding a pleasant floral scent to various fragrances. It is used in the formulation of flavors, contributing to the profiles of peach, raspberry, grapefruit, red apple, plum, lime, orange, lemon, watermelon, pineapple, and blueberry flavors. Geraniol is also employed as an insect repellent, particularly for mosquitoes.
Occurrence in Nature:
In nature, geraniol is produced by the scent glands of honeybees to mark nectar-bearing flowers and locate hive entrances. It plays a role in their communication and foraging behaviors. Furthermore, geraniol occurs naturally in various plant sources, contributing to their unique aromas and flavors.
Role in Biosynthesis:
Geraniol is an important precursor in the biosynthesis pathway of other terpenes, including myrcene and ocimene. It is also involved in the production of many cannabinoids, such as CBGA, which are compounds of interest in the cannabis plant.
Cultivars (strains) with Geraniol Dominance:
Reactions:
Under acidic conditions, geraniol can undergo conversion to α-terpineol, a cyclic terpene. The alcohol group in geraniol can participate in typical reactions observed for alcohols. It can be transformed into the tosylate, a precursor to the chloride. Geranyl chloride can also be obtained through the Appel reaction by treating geraniol with triphenylphosphine and carbon tetrachloride. Geraniol can undergo hydrogenation and oxidation reactions, leading to the formation of other compounds such as geranial, an aldehyde.
Health and Safety:
According to the Workplace Hazardous Materials Information System (WHMIS), geraniol is classified as D2B (Toxic materials causing other effects). It is important to consider safety guidelines when handling geraniol and related products.
Overall, geraniol exhibits a wide range of applications and plays significant roles in nature, from fragrance and flavor enhancement to insect repellency and biosynthesis pathways.
Formula: C10H18O
Molar mass: 154.253 g·mol−1
PubChem CID: 637566
Melting Point: −15 °C (5 °F; 258 K)
Boiling Point: 230 °C (446 °F; 503 K)
Density: 0.889 g/cm3