Geraniol
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Preferred IUPAC name
(2E)-3,7-Dimethylocta-2,6-dien-1-ol | |
Identifiers | |
3D model (
JSmol ) |
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DrugBank | |
ECHA InfoCard
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100.003.071 |
EC Number |
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KEGG | |
PubChem CID
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UNII | |
CompTox Dashboard (EPA)
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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) | |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Geraniol is a
Uses and occurrence
In addition to
Geraniol is produced by the
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.[7]
Reactions
In
Health and safety
Geraniol is classified as D2B (Toxic materials causing other effects) using the Workplace Hazardous Materials Information System (WHMIS).[14]
History
Geraniol was first isolated in pure form in 1871 by the German chemist Oscar Jacobsen (1840–1889).[15][16] Using distillation, Jacobsen obtained geraniol from an essential oil which was obtained from geranium grass (Andropogon schoenanthus) and which was produced in India.[17] The chemical structure of geraniol was determined in 1919 by the French chemist Albert Verley (1867–1959).[18]
See also
- Citronellol
- Citral
- Nerol
- Rhodinol
- Geranyl pyrophosphate
- Geranylgeranyl pyrophosphate
- Linalool
- 8-Hydroxygeraniol
- Geraniol 8-hydroxylase
- Bergamottin
- Perfume allergy
References
- The Merck Index(12th ed.).
- ^ a b c Record in the GESTIS Substance Database of the Institute for Occupational Safety and Health
- ^ "Geraniol_msds".
- ^ "GERANIOL - Cameo Chemicals - NOAA". Retrieved 26 June 2021.
- .
- S2CID 41927381.
- ^ Holcombe, Luke (9 January 2018) "Wine faults" Archived 2021-09-16 at the Wayback Machine, p. 11.
- ISBN 978-3527306732.
- PMID 9607329.
- .
- .
- ; Collected Volumes, vol. 9, p. 169.
- .
- ^ "MSDS – Geraniol". Sigma-Aldrich. Retrieved Feb 15, 2022.
- ^ Jacobsen, Oscar (1871). "Untersuchung der indischen Geraniumöls" [InvestIgation of Indian oil from geranium [grass]]. Annalen der Chemie und Pharmacie (in German). 157: 232–239. 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 … )
- ^ Semmler, F.W. (1906). Die ätherischen Öle [The Volatile Oils] (in German). Vol. 1. Leipzig, Germany: Von Veit & Co. p. 292. 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.
- ^ (Semmler, 1906), p. 491.
- ^ Verley, Albert (1919). "Sur la constitution du géraniol, du linalool et du nérol" [On the chemical structure of geraniol, linalool, and nerol]. Bulletin de la Société Chimique de France. 4th series (in French). 25: 68–80. The chemical structure of geraniol appears on p. 70.