geraniol

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,{{Cite web |title=Духи с запахом розы - Лучшие розовые парфюмы с фото - Описания духов с ароматом розы - Розовая парфюмерия. |url=https://duhiroza.ru/ |access-date=2025-04-14 |website=duhiroza.ru}} 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.{{cite journal |first1=R. G. |last1=Danka |first2=J. L. |last2=Williams |first3=T. E. |last3=Rinderer | title = A bait station for survey and detection of honey bees | journal = Apidologie | volume = 21 | issue = 4 | pages = 287–292 | year = 1990 | doi = 10.1051/apido:19900403| url = https://hal.archives-ouvertes.fr/hal-00890837/file/hal-00890837.pdf | doi-access = free }} It is also commonly used as an insect repellent, especially for mosquitoes.{{Cite journal|last1=Müller|first1=Günter C.|last2=Junnila|first2=Amy|last3=Kravchenko|first3=Vasiliy D.|last4=Revay|first4=Edita E.|last5=Butler|first5=Jerry|last6=Orlova|first6=Olga B.|last7=Weiss|first7=Robert W.|last8=Schlein|first8=Yosef|date=March 2008|title=Ability of essential oil candles to repel biting insects in high and low biting pressure environments|url=https://pubmed.ncbi.nlm.nih.gov/18437832/|journal=Journal of the American Mosquito Control Association|volume=24|issue=1|pages=154–160|doi=10.2987/8756-971X(2008)24[154:AOEOCT]2.0.CO;2|issn=8756-971X|pmid=18437832|s2cid=41927381 }}

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.Holcombe, Luke (9 January 2018) [https://aggie-horticulture.tamu.edu/vitwine/files/2018/03/Wine-Faults.pdf "Wine faults"] {{Webarchive|url=https://web.archive.org/web/20210916114943/https://aggie-horticulture.tamu.edu/vitwine/files/2018/03/Wine-Faults.pdf |date=2021-09-16 }}, p. 11.

Geranyl pyrophosphate is important in biosynthesis of other terpenes such as myrcene and ocimene.{{Ullmann|first=M.|last=Eggersdorfer|title=Terpenes|doi=10.1002/14356007.a26_205}} It is also used in the biosynthesis pathway of many cannabinoids in the form of CBGA.{{cite journal | vauthors = Fellermeier M, Zenk MH | title = Prenylation of olivetolate by a hemp transferase yields cannabigerolic acid, the precursor of tetrahydrocannabinol | journal = FEBS Letters | volume = 427 | issue = 2 | pages = 283–85 | date = May 1998 | pmid = 9607329 | doi = 10.1016/S0014-5793(98)00450-5 | doi-access = free | bibcode = 1998FEBSL.427..283F }}

In acidic solutions, geraniol is converted to the cyclic terpene α-terpineol. The alcohol group undergoes expected reactions. 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.{{OrgSynth|title=Allylic Chlorides from Allylic Alcohols: Geranyl Chloride|first1=Gilbert |last1=Stork |first2=Paul A. |last2=Grieco |first3=Michael |last3=Gregson |year=1974|volume=54|page=68|doi=10.15227/orgsyn.054.0068}}{{OrgSynth | author = Jose G. Calzada and John Hooz | title = Geranyl chloride| volume = 54 | pages = 63 | year=1974|doi = 10.15227/orgsyn.054.0063}} It can be oxidized to the aldehyde geranial.{{OrgSynth|title=Oxidation of Nerol to Neral With Iodosobenzene and TEMPO |first1=Giovanni |last1=Piancatelli |first2=Francesca |last2=Leonelli |year=2006|volume=83|page=18|doi=10.15227/orgsyn.083.0018}} Hydrogenation of the two C=C bonds over a nickel catalyst gives tetrahydrogeraniol.{{OrgSynth|title=Asymmetric Hydrogenation of Allylic Alcohols Using BINAP–Ruthenium Complexes: (S)-(−)-citronellol|first1=Hidemasa |last1=Takaya |first2=Tetsuo |last2=Ohta |first3=Shin-ichi |last3=Inoue |first4=Makoto |last4=Tokunaga |first5=Masato |last5=Kitamura |author6-link=Ryoji Noyori |first6=Ryoji |last6=Noyori |year=1995|volume=72|page=74|collvol=9|collvolpages=169|doi=10.15227/orgsyn.072.0074}}{{cite book |doi=10.1002/14356007.t11_t01 |chapter=Flavors and Fragrances, 2. Aliphatic Compounds |title=Ullmann's Encyclopedia of Industrial Chemistry |date=2015 |last1=Panten |first1=Johannes |last2=Surburg |first2=Horst |pages=1–55 |isbn=978-3-527-30673-2 }}

Geraniol is classified as D2B (Toxic materials causing other effects) using the Workplace Hazardous Materials Information System (WHMIS).{{cite web|url=https://www.sigmaaldrich.com/US/en/product/aldrich/163333 |title=MSDS – Geraniol |publisher=Sigma-Aldrich |access-date= Feb 15, 2022}}

Geraniol was first isolated in pure form in 1871 by the German chemist Oscar Jacobsen (1840–1889).{{cite journal |last1=Jacobsen |first1=Oscar |title=Untersuchung der indischen Geraniumöls |journal=Annalen der Chemie und Pharmacie |date=1871 |volume=157 |pages=232–239 |url=https://babel.hathitrust.org/cgi/pt?id=uva.x002457983&view=1up&seq=244 |trans-title=InvestIgation of Indian oil from geranium [grass] |language=German}} 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 … ){{cite book |last1=Semmler |first1=F.W. |title=Die ätherischen Öle |trans-title=The Volatile Oils |date=1906 |publisher=Von Veit & Co. |location=Leipzig, Germany |volume=1 |page=292 |url=https://archive.org/details/b28089595_0001/page/292/mode/2up |language=German}} 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. Using distillation, Jacobsen obtained geraniol from an essential oil produced in India which was obtained from the so-called geranium grass.(Semmler, 1906), p. 491. 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.{{Cite book |last=Askinson |first=George William |url=https://books.google.com/books?id=ToXYI1IIcN4C&pg=PA154 |title=Perfumes and Their Preparation |date=1892 |publisher=N.W. Henley |pages=123-124, 154 |language=en}}

The chemical structure of geraniol was determined in 1919 by the French chemist Albert Verley (1867–1959).{{cite journal |last1=Verley |first1=Albert |title=Sur la constitution du géraniol, du linalool et du nérol |journal=Bulletin de la Société Chimique de France |date=1919 |volume=25 |pages=68–80 |url=https://babel.hathitrust.org/cgi/pt?id=iau.31858002467680&view=1up&seq=78 |series=4th series |trans-title=On the chemical structure of geraniol, linalool, and nerol |language=French}} The chemical structure of geraniol appears on p. 70.

• Citronellol
• Citral
• Nerol
• Rhodinol
• Geranyl pyrophosphate
• Geranylgeranyl pyrophosphate
• Linalool
• 8-Hydroxygeraniol
• Geraniol 8-hydroxylase
• Bergamottin
• Perfume allergy

{{reflist}}

• [http://gmd.mpimp-golm.mpg.de/Spectrums/3a24b562-4124-4405-af12-a5ab43c97740.aspx Geraniol MS Spectrum]
• [http://www.thegoodscentscompany.com/data/rw1006991.html Geraniol properties, animations, links]

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Category:Perfume ingredients

Category:Monoterpenes

Category:Primary alcohols

Category:Alkene derivatives

Category:Flavors

Category:Insect repellents