Geraniol

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Not to be confused with Geranial.
Geraniol[1]
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Geraniol
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Names
Preferred IUPAC name
(2E)-3,7-Dimethylocta-2,6-dien-1-ol
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
DrugBank
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EC Number
  • 203-377-1
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KEGG
UNII
  • {{#property:P3117}}Lua error in Module:EditAtWikidata at line 29: attempt to index field 'wikibase' (a nil value).
  • 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]
log P 3.28[3]
Hazards
NFPA 704 (fire diamond)
NFPA 704 four-colored diamondHealth 2: Intense or continued but not chronic exposure could cause temporary incapacitation or possible residual injury. E.g. chloroformFlammability 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
2
1
0
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Geraniol is a monoterpenoid and an alcohol. It is the primary component of citronella oil and is a primary component of rose oil and palmarosa oil. It is a colorless oil, although commercial samples can appear yellow. It has low solubility in water, but it is soluble in common organic solvents.

Uses and occurrence

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Geraniol is used in medicine, perfumery, and food industry.[5][6]

In addition to being found in rose oil, palmarosa oil, and citronella oil, it also occurs in small quantities in geranium, lemon, and many other essential oils. With a rose-like scent,[6] it is commonly used in perfumes and in scents such as peach, raspberry, grapefruit, red apple, plum, lime, orange, lemon, watermelon, pineapple, and blueberry.

Geraniol is produced by the scent glands of honeybees to mark nectar-bearing flowers and locate the entrances to their hives.[7] It is also commonly used as an insect repellent, especially for mosquitoes.[8]

The scent of geraniol is reminiscent of, but chemically unrelated to, 2-ethoxy-3,5-hexadiene, also known as geranium taint, a wine fault resulting from fermentation of sorbic acid by lactic acid bacteria.[9]

Reactions

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Geranyl pyrophosphate is an intermediate in the biosynthesis of other terpenes such as myrcene and ocimene.[10] It also participates in the biosynthesis of many cannabinoids in the form of CBGA.[11]

Geraniol undergoes a variety of reactions to give useful derivatives. it can be converted to the tosylate, which is a precursor to the chloride. Geranyl chloride also arises by the Appel reaction by treating geraniol with triphenylphosphine and carbon tetrachloride.[12][13] It can be oxidized to the aldehyde geranial.[14] Hydrogenation of the two C=C bonds over a nickel catalyst gives tetrahydrogeraniol.[15][5] In acidic solutions, geraniol is converted to the cyclic terpene α-terpineol.

Health and safety

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Geraniol is classified as D2B (Toxic materials causing other effects) using the Workplace Hazardous Materials Information System (WHMIS).[16]

History

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Geraniol was first isolated in pure form in 1871 by the German chemist Oscar Jacobsen (1840–1889).[17][18] Using distillation, Jacobsen obtained geraniol from an essential oil produced in India which was obtained from the so-called geranium grass.[19] This essence, after which the compound was named, was a 50% cheaper substitute for the essence of the proper geranium flower with a similar, although less delicate, odor.[20]

The chemical structure of geraniol was determined in 1919 by the French chemist Albert Verley (1867–1959).[21]

See also

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References

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  1. ^ Lua error in Module:Citation/CS1/Configuration at line 2172: attempt to index field '?' (a nil value).
  2. ^ a b c Record in the GESTIS Substance Database of the Institute for Occupational Safety and Health
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  9. ^ Holcombe, Luke (9 January 2018) "Wine faults" Archived 2021-09-16 at the Wayback Machine, p. 11.
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  16. ^ Lua error in Module:Citation/CS1/Configuration at line 2172: attempt to index field '?' (a nil value).
  17. ^ Lua error in Module:Citation/CS1/Configuration at line 2172: attempt to index field '?' (a nil value). Jacobsen named geraniol on p. 234: "Danach ist dieser Körper, das Geraniol, isomer mit dem Borneol … " (Accordingly this body [i.e., substance], geraniol, is isomeric with borneol … )
  18. ^ Lua error in Module:Citation/CS1/Configuration at line 2172: attempt to index field '?' (a nil value). From p. 292: "Von dem Geraniol ist zu erwähnen, daß … erst Jacobsen (A. 157, 232) brachte im Jahre 1870 über den Alkohol, den er Geraniol nannte, nähere Angaben, er stellte die Formel C10H18O auf, ohne weitere Konstitionsangaben zu machen." (It should be mentioned about geraniol that … Jacobsen (A. 157, 232) first gathered in 1870 more detailed data about the alcohol, which he named geraniol; he established its [empirical] formula C10H18O, without providing further data about its chemical structure.) See also: § 49. Geraniol C10H18O, pp. 439-493. On p. 439, two hypothetical structures of geraniol are proposed.
  19. ^ (Semmler, 1906), p. 491.
  20. ^ Lua error in Module:Citation/CS1/Configuration at line 2172: attempt to index field '?' (a nil value).
  21. ^ Lua error in Module:Citation/CS1/Configuration at line 2172: attempt to index field '?' (a nil value). The chemical structure of geraniol appears on p. 70.
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