Geraniol

Geraniol is a monoterpenoid and an alcohol. It is the primary component of rose oil, palmarosa oil, and citronella oil (Java type). It is a colorless oil, although commercial samples can appear yellow. It has low solubility in water, but it is soluble in common organic solvents. The functional group derived from geraniol (in essence, geraniol lacking the terminal −OH) is called geranyl. Geraniol is a monoterpenoid and an alcohol. It is the primary component of rose oil, palmarosa oil, and citronella oil (Java type). It is a colorless oil, although commercial samples can appear yellow. It has low solubility in water, but it is soluble in common organic solvents. The functional group derived from geraniol (in essence, geraniol lacking the terminal −OH) is called geranyl. In addition to rose oil, palmarosa oil, and citronella oil, it also occurs in small quantities in geranium, lemon, and many other essential oils. With a rose-like scent, it is commonly used in perfumes. It is used in flavors such as peach, raspberry, grapefruit, red apple, plum, lime, orange, lemon, watermelon, pineapple, and blueberry. Geraniol is produced by the scent glands of honeybees to mark nectar-bearing flowers and locate the entrances to their hives. It has been considered as a mosquito repellent. It is a byproduct of the metabolism of sorbate and, thus, is a very unpleasant contaminant of wine if bacteria are allowed to grow in it. Geraniol is important in biosynthesis of other terpenes. For example, myrcene and ocimene are formed by dehydration and isomerization of geraniol. In acidic solutions, geraniol is converted to the cyclic terpene α-terpineol. The alcohol group undergoes expected reactions. It can be converted to the chloride with thionyl chloride. It can be hydrogenated. It can be oxidized to the aldehyde geranial. Geraniol is classified as D2B (Toxic materials causing other effects) using the Workplace Hazardous Materials Information System (WHMIS).