Geraniol

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 = Insoluble

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 which is insoluble in water, but soluble in most common organic solvents. It has a rose-like odor, for which it 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. [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 bees 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 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 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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Look at other dictionaries:

  • Géraniol — Structure du geraniol Général Nom IUPAC (2E) 3,7 dimethylocta 2,6 dién 1 ol …   Wikipédia en Français

  • Geraniol — Géraniol Géraniol Structure du geraniol Général Nom IUPAC (E)3,7 diméthyl 2,6 octadién l ol trans 3,7 diméthyl 2,6 octadién 8 o …   Wikipédia en Français

  • Geraniol — Nombre (IUPAC) sistemático …   Wikipedia Español

  • geraniol — GERANIÓL s.n. Alcool component principal al uleiului de trandafiri. [pr.: ni ol] – Din fr. géraniol. Trimis de gall, 16.06.2002. Sursa: DEX 98  geraniól s. n. (sil. ni ol) Trimis de siveco, 10.08.2004. Sursa: Dicţionar ortografic  GERANIÓL s. n …   Dicționar Român

  • géraniol — [ ʒeranjɔl ] n. m. • 1900; de géranium et (alco)ol ♦ Chim. Le plus important des alcools terpéniques doublement insaturés. Le géraniol donne leur odeur aux roses. ● géraniol nom masculin Alcool monoterpénique présent dans de nombreuses huiles… …   Encyclopédie Universelle

  • geraniol — ge*ra ni*ol, n. [See {Geranium}.] (Chem.) A terpene alcohol ({C10H18O}) which constitutes the principal part of the oil of palmarosa and the oil of rose. Chemically it is 3,7 Dimethyl 2,6 octadien 1 ol. It has a sweet rose odor. MI11 [PJC] …   The Collaborative International Dictionary of English

  • Geraniōl — (Lemonol, Rhodinol) C10H 18O, Hauptbestandteil des Palmarosaöls, des deutschen und türkischen Rosenöls, findet sich in beträchtlicher Menge auch im Geranium , Zitronell und Lemongrasöl, in geringer Menge in vielen andern ätherischen Olen, teils… …   Meyers Großes Konversations-Lexikon

  • Geraniol — Geraniol, s. Geraniumöl und Riechstoffe, künstliche …   Lexikon der gesamten Technik

  • geraniol — geranìōl m <G geranióla> DEFINICIJA kem. C9H15CH2OH, dvostruko nezasićeni terpenski alkohol mirisa ruže, sastojak mnogih eteričnih ulja ETIMOLOGIJA v. geranij + ol …   Hrvatski jezični portal

  • geraniol — [jə rā′nē ôl΄, jə rā′nēōl΄] n. [< ModL Geranium (see GERANIUM) + OL1: so named because deriv. from geranium leaves] a terpene alcohol, C10H18O, found in many essential oils and having an odor resembling roses: used in perfumery …   English World dictionary

  • Geraniol — Strukturformel Allgemeines Name Geraniol Andere Namen 2,6 Di …   Deutsch Wikipedia

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