Geraniol

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Geraniol[1]
Geraniol
Geraniol-3D-balls-B.png
Identifiers
CAS number 106-24-1 YesY
ChemSpider 13849989 YesY
UNII L837108USY YesY
EC number 203-377-1
ChEBI CHEBI:17447 YesY
ChEMBL CHEMBL25719 YesY
Jmol-3D images Image 1
Properties
Molecular formula C10H18O
Molar mass 154.25 g mol−1
Density 0.889 g/cm3
Melting point −15 °C (5 °F; 258 K)[2]
Boiling point 230 °C (446 °F; 503 K)[2]
Solubility in water 686 mg/L (20 °C)[2]
Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
 YesY (verify) (what is: YesY/N?)
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 scent 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.

Use[edit]

Research has shown geraniol to be an effective plant-based mosquito repellent.[3][4] 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.[5]

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.[6]

Biochemistry[edit]

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.

Reactions[edit]

In acidic solutions, geraniol is converted to the cyclic terpene alpha-terpineol.

Health and safety[edit]

Geraniol should be avoided by people with perfume allergy.[7]

Related compounds[edit]

See also[edit]

References[edit]

  1. ^ Geraniol, The Merck Index, 12th Edition
  2. ^ a b c Record in the GESTIS Substance Database from the IFA
  3. ^ 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. 
  4. ^ UF entomologist develops safe, effective alternative to DEET insect repellents, Univ. of Florida, 1999
  5. ^ 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. 
  6. ^ What's in a cigarette? at about.com
  7. ^ Survey and health assessment of chemical substances in massage oils

External links[edit]