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| Geraniol | |
|---|---|
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| IUPAC name | 3,7-Dimethyl-2,6-octadien-1-ol |
| Identifiers | |
| CAS number | [106-24-1] |
| EINECS number | |
| SMILES |
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| Properties | |
| Molecular formula | C10H18O |
| Molar mass | 154.25 g/mol |
| Density | 0.889 g/cm3 |
| Melting point |
15 °C |
| Boiling point |
229 °C |
| Solubility in water | Insoluble |
| Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) Infobox references |
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Geraniol is a monoterpenoid and an alcohol. It is the primary part of rose oil, palmarosa oil, and citronella oil (Java type). It also occurs in small quantities in geranium, lemon, and many other essential oils. It appears as a clear to pale-yellow oil which is insoluble in water, but soluble in most common organic solvents. It has a rose-like odor, for which 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.
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Use
Research has shown geraniol to be an effective plant-based mosquito repellent.[1][2] On the other hand, it can attract bees as it is produced by the scent glands of honey bees to help them mark nectar-bearing flowers and locate the entrances to their hives.
Although geraniol and other flavor compounds are found naturally in well aged tobacco, geraniol is listed in a 1994 report from cigarette companies as one of the 599 additives to cigarettes to improve their flavor.[3]
Biochemistry
The functional group based on geraniol (essentially geraniol lacking the terminal -OH) is called geranyl. It is important in biosynthesis of other terpenes. It is a by product of the metabolism of sorbate and thus is a very unpleasant contaminant of wine if bacteria are allowed to grow in wine.
Reactions
In acidic solutions, geraniol is converted to the cyclic terpene alpha-terpineol.
Health and safety
Geraniol should be avoided by people with perfume allergy.[4]
References
- ^ Barnard, D.R., and Xue, R. Laboratory evaluation of mosquito repellents against Aedes albopictus, Culex nigripalpus, and Ochlerotatus triseriatus (Diptera: Culicidae), J. Med. Entomol. 41(4):726-730, 2004.
- ^ UF entomologist develops safe, effective alternative to DEET insect repellents, Univ. of Florida, 1999.
- ^ What's in a cigarette? at about.com
- ^ Survey and health assessment of chemical substances in massage oils
See also
- Citral, the corresponding aldehyde;
- Nerol, the double bond isomer;
- Rhodinol, a related terpene alcohol.
Wikipedia content modification information:
- This page was last modified on 19 June 2008, at 20:38.
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