Geraniol
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| Geraniol[1] | |
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3,7-Dimethylocta-2,6-dien-1-ol |
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| Identifiers | |
| CAS number | 106-24-1  |
| ChemSpider | 13849989 |
| UNII | L837108USY |
| EC number | 203-377-1 |
| ChEBI | CHEBI:17447 |
| ChEMBL | CHEMBL25719 |
| Jmol-3D images | Image 1 |
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| Properties | |
| Molecular formula | C10H18O |
| Molar mass | 154.25 g mol−1 |
| Density | 0.889 g/cm3 |
| Melting point |
15 °C, 288 K, 59 °F |
| Boiling point |
229 °C, 502 K, 444 °F |
| Solubility in water | Insoluble |
 (verify) (what is:  / ?)Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) |
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| Infobox references | |
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 that is insoluble in water, but soluble in most common organic solvents. It has a rose-like odor and 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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[edit] Use
Research has shown geraniol to be an effective plant-based mosquito repellent.[2][3] 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.[4]
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.[5]
[edit] Biochemistry
The functional group based on geraniol (in essence, 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.
[edit] Reactions
In acidic solutions, geraniol is converted to the cyclic terpene alpha-terpineol.
[edit] Health and safety
Geraniol should be avoided by people with perfume allergy.[6]
[edit] Related compounds
- Citral, the corresponding aldehyde
- Nerol, the double bond isomer
- Rhodinol, a related terpene alcohol
- Geranyl pyrophosphate
- Geranylgeranyl pyrophosphate
[edit] See also
[edit] References
- ^ Geraniol, The Merck Index, 12th Edition
- ^ Barnard, D.R., and Xue, R. (2004). "Laboratory evaluation of mosquito repellents against Aedes albopictus, Culex nigripalpus, and Ochlerotatus triseriatus (Diptera: Culicidae)". J. Med. Entomol. 41 (4): 726–730. doi:10.1603/0022-2585-41.4.726. PMID 15311467.
- ^ UF entomologist develops safe, effective alternative to DEET insect repellents, Univ. of Florida, 1999
- ^ R.G. Danka, J.L. Williams and T.E. Rinderer (1990). "A bait station for survey and detection of honey bees". Apidologie 21 (4): 287–292. doi:10.1051/apido:19900403. http://www.apidologie.org/index.php?option=com_article&access=doi&doi=10.1051/apido:19900403&Itemid=129.
- ^ What's in a cigarette? at about.com
- ^ Survey and health assessment of chemical substances in massage oils
