3D model (JSmol)
CompTox Dashboard (EPA)
|Molar mass||154.253 g·mol−1|
|Melting point||−15 °C (5 °F; 258 K)|
|Boiling point||230 °C (446 °F; 503 K)|
|686 mg/L (20 °C)|
|NFPA 704 (fire diamond)|
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
|what is ?)(|
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.
Uses and occurrence
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 is also commonly used as a insect repellent, especially for mosquitoes.
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.
Health and safety
- Citral, the corresponding aldehyde
- Nerol, the double-bond isomer
- Rhodinol, a related terpene alcohol
- Geranyl pyrophosphate
- Geranylgeranyl pyrophosphate
- Linalool, the isomer derived from transposition of the allylic alcohol
- 8-Hydroxygeraniol, produced by action of geraniol 8-hydroxylase
- "Geraniol". The Merck Index (12th ed.).
- Record in the GESTIS Substance Database of the Institute for Occupational Safety and Health
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- Piancatelli, Giovanni; Leonelli, Francesca (2006). "Oxidation Of Nerol To Neral With Iodosobenzene and TEMPO". Organic Syntheses. 83: 18. doi:10.15227/orgsyn.083.0018.
- "MSDS – Geraniol". Sigma-Aldrich. Retrieved June 24, 2014.