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Geraniol

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Geraniol[1]
Geraniol
Names
IUPAC name
(trans)-3,7-Dimethyl-2,6-octadien-1-ol
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.003.071 Edit this at Wikidata
EC Number
  • 203-377-1
UNII
  • InChI=1S/C10H18O/c1-9(2)5-4-6-10(3)7-8-11/h5,7,11H,4,6,8H2,1-3H3/b10-7+ checkY
    Key: GLZPCOQZEFWAFX-JXMROGBWSA-N checkY
  • InChI=1/C10H18O/c1-9(2)5-4-6-10(3)7-8-11/h5,7,11H,4,6,8H2,1-3H3/b10-7+
    Key: GLZPCOQZEFWAFX-JXMROGBWBZ
  • CC(=CCC/C(=C/CO)/C)C
Properties
C10H18O
Molar mass 154.253 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 (fire diamond)
NFPA 704 four-colored diamondHealth 0: Exposure under fire conditions would offer no hazard beyond that of ordinary combustible material. E.g. sodium chlorideFlammability 1: Must be pre-heated before ignition can occur. Flash point over 93 °C (200 °F). E.g. canola oilInstability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogenSpecial hazards (white): no code
0
1
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 checkY☒N ?)

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 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]

See also

References

  1. ^ Geraniol, The Merck Index, 12th Edition
  2. ^ a b c Record in the GESTIS Substance Database of the Institute for Occupational Safety and Health
  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.{{cite journal}}: CS1 maint: multiple names: authors list (link)
  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. ^ MSDS - Geraniol at www.sigmaaldrich.com, Accessed June 24 2014
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