Geraniol

Geraniol[1]
Names
IUPAC name
(trans)-3,7-Dimethyl-2,6-octadien-1-ol
Identifiers
106-24-1 YesY
3D model (Jmol) Interactive image
ChEBI CHEBI:17447 YesY
ChEMBL ChEMBL25719 YesY
ChemSpider 13849989 YesY
ECHA InfoCard 100.003.071
EC Number 203-377-1
2467
PubChem 637566
UNII L837108USY YesY
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
Flammability code 1: Must be pre-heated before ignition can occur. Flash point over 93 °C (200 °F). E.g., canola oil Health code 0: Exposure under fire conditions would offer no hazard beyond that of ordinary combustible material. E.g., sodium chloride Reactivity code 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g., liquid nitrogen Special hazards (white): no codeNFPA 704 four-colored diamond
1
0
0
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N verify (what is YesYN ?)
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

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 it.

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]

See also

References

  1. ↑ Geraniol, The Merck Index, 12th Edition
  2. 1 2 3 Record in the GESTIS Substance Database of the IFA
  3. ↑ Barnard, D.R.; 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; 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. ↑ MSDS - Geraniol at www.sigmaaldrich.com, Accessed June 24, 2014
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