- Geraniol
Chembox new
Name = Geraniol
ImageFile = Geraniol structure.png
ImageSize = 200px
ImageName = Geraniol
IUPACName = 3,7-Dimethyl-2,6-octadien-1-ol
Section1 = Chembox Identifiers
CASNo = 106-24-1
EINECS = 203-377-1
SMILES = CC(C)=CCC/C(C)=C/CO
Section2 = Chembox Properties
Formula = C10H18O
MolarMass = 154.25 g/mol
Density = 0.889 g/cm3
MeltingPt = 15 °C
BoilingPt = 229 °C
Solubility = InsolubleGeraniol is a monoterpenoid and an
alcohol . It is the primary part ofrose oil ,palmarosa oil, andcitronella oil (Java type). It also occurs in small quantities in geranium,lemon , and many otheressential oil s. It appears as a clear to pale-yellow oil which is insoluble in water, but soluble in most common organic solvents. It has arose -like odor, for which it is commonly used inperfume s. It is used in flavors such as peach, raspberry, grapefruit, red apple, plum, lime, orange, lemon, watermelon, pineapple and blueberry.Use
Research has shown geraniol to be an effective plant-based mosquito repellent. [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.] [ [http://www.napa.ufl.edu/99news/nodeet.htm UF entomologist develops safe, effective alternative to DEET insect repellents] , Univ. of Florida, 1999.] On the other hand, it can attract bees as it is produced by the scent glands of
honey bee s 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. [ [http://quitsmoking.about.com/cs/nicotineinhaler/a/cigingredients.htm What's in a cigarette?] at about.com]Biochemistry
The
functional group based on geraniol (essentially geraniol lacking the terminal -OH) is called geranyl. It is important inbiosynthesis of otherterpene s. It is a by product of the metabolism ofsorbate 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. [ [http://www2.mst.dk/udgiv/publications/2006/87-7052-278-2/html/kap07_eng.htm Survey and health assessment of chemical substances in massage oils] ]
References
ee also
*
Citral , the corresponding aldehyde;
*Nerol , the double bond isomer;
*Rhodinol , a related terpene alcohol.
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