Geraniol

Geraniol

Geraniol[1]
Geraniol
Names
IUPAC name
(trans)-3,7-Dimethyl-2,6-octadien-1-ol
Identifiers
 Y
ChEBI  Y
ChEMBL  Y
ChemSpider  Y
EC number 203-377-1
Jmol-3D images Image
PubChem
UNII  Y
Properties
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]
686 mg/L (20 °C)[2]
Hazards
NFPA 704
1
0
0
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
 N  (: Y/N?)

Geraniol is 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.

Contents

  • Use 1
  • Biochemistry 2
  • Reactions 3
  • Health and safety 4
  • Related compounds 5
  • See also 6
  • References 7
  • External links 8

Use

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

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

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

Health and safety

Geraniol is classified as D2B (Toxic materials causing other effects) using the Workplace Hazardous Materials Information System (WHMIS). Geraniol is considered a severe eye (and moderate skin) irritant.[7]

Related compounds

See also

References

  1. ^ Geraniol, The Merck Index, 12th Edition
  2. ^ a b c Record in the GESTIS Substance Database of 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.  
  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.  
  6. ^ What's in a cigarette? at about.com
  7. ^ MSDS - Geraniol at www.sigmaaldrich.com, Accessed June 24 2014

External links

  • Geraniol MS Spectrum
  • Geraniol properties, animations, links