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Adding local short description: "A monoterpenoid and alcohol that is the primary component of rose oil, palmarosa oil and citronella oil", overriding Wikidata description "chemical compound" (Shortdesc helper)
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{{Short description|A monoterpenoid and alcohol that is the primary component of rose oil, palmarosa oil and citronella oil}}
{{Short description|a monoterpenoid and alcohol that is the primary component of rose oil, palmarosa oil and citronella oil}}
{{chembox
{{chembox
| Verifiedfields = changed
|Verifiedfields = changed
| Watchedfields = changed
|Watchedfields = changed
| verifiedrevid = 443834400
|verifiedrevid = 443834400
| Reference = <ref>{{cite book|entry=Geraniol|title=The Merck Index|edition=12th|title-link=The Merck Index}}</ref>
|Reference = <ref>{{cite book|entry=Geraniol|title=The Merck Index|edition=12th|title-link=The Merck Index}}</ref>
| Name = Geraniol
|Name = Geraniol
| ImageFile = Geraniol structure.png
|ImageFile = Geraniol structure.png
| ImageSize = 200px
|ImageSize = 200px
| ImageName = Geraniol
|ImageName = Geraniol
| ImageFile2 = Geraniol-3D-balls-B.png
|ImageFile2 = Geraniol-3D-balls-B.png
| ImageSize2 = 200px
|ImageSize2 = 200px
| OtherNames =
|OtherNames =
| IUPACName = (2''E'')-3,7-Dimethyl-2,6-octadien-1-ol
|IUPACName = (2''E'')-3,7-Dimethyl-2,6-octadien-1-ol
| SystematicName =
|SystematicName =
| Section1 = {{Chembox Identifiers
|Section1 = {{Chembox Identifiers
| IUPHAR_ligand = 2467
|IUPHAR_ligand = 2467
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
|ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 13849989
|ChemSpiderID = 13849989
| InChI = 1/C10H18O/c1-9(2)5-4-6-10(3)7-8-11/h5,7,11H,4,6,8H2,1-3H3/b10-7+
|InChI = 1/C10H18O/c1-9(2)5-4-6-10(3)7-8-11/h5,7,11H,4,6,8H2,1-3H3/b10-7+
| InChIKey = GLZPCOQZEFWAFX-JXMROGBWBZ
|InChIKey = GLZPCOQZEFWAFX-JXMROGBWBZ
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
|StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 1S/C10H18O/c1-9(2)5-4-6-10(3)7-8-11/h5,7,11H,4,6,8H2,1-3H3/b10-7+
|StdInChI = 1S/C10H18O/c1-9(2)5-4-6-10(3)7-8-11/h5,7,11H,4,6,8H2,1-3H3/b10-7+
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
|StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = GLZPCOQZEFWAFX-JXMROGBWSA-N
|StdInChIKey = GLZPCOQZEFWAFX-JXMROGBWSA-N
| CASNo_Ref = {{cascite|correct|CAS}}
|CASNo_Ref = {{cascite|correct|CAS}}
| PubChem = 637566
|PubChem = 637566
| ChEMBL_Ref = {{ebicite|correct|EBI}}
|ChEMBL_Ref = {{ebicite|correct|EBI}}
| ChEMBL = 25719
|ChEMBL = 25719
| CASNo = 106-24-1
|CASNo = 106-24-1
| EINECS = 203-377-1
|EINECS = 203-377-1
| UNII_Ref = {{fdacite|correct|FDA}}
|UNII_Ref = {{fdacite|correct|FDA}}
| UNII = L837108USY
|UNII = L837108USY
| ChEBI_Ref = {{ebicite|correct|EBI}}
|ChEBI_Ref = {{ebicite|correct|EBI}}
| ChEBI = 17447
|ChEBI = 17447
| KEGG = C01500
|KEGG = C01500
| SMILES = CC(=CCC/C(=C/CO)/C)C
|SMILES = CC(=CCC/C(=C/CO)/C)C
⚫
}}
⚫
|Section2 = {{Chembox Properties
⚫
|C=10 |H=18 |O=1
⚫
|Density = 0.889 g/cm<sup>3</sup>
⚫
|MeltingPtC = -15
⚫
|MeltingPt_ref = <ref name=GESTIS>{{GESTIS|ZVG = 491258}}</ref>
⚫
|BoilingPtC = 230
⚫
|BoilingPt_ref = <ref name=GESTIS/>
⚫
|Solubility = 686 mg/L (20&nbsp;°C)<ref name=GESTIS/>
⚫
|LogP =3.28<ref name="chemsrc">{{Cite web|url=https://www.chemsrc.com/en/cas/106-24-1_125147.html|title=Geraniol_msds}}</ref>
⚫
}}
⚫
|Section3 = {{Chembox Hazards
⚫
|NFPA-H = 0
⚫
|NFPA-F = 1
⚫
|NFPA-R = 0
⚫
}}
⚫
|Section4 =
⚫
|Section5 =
⚫
|Section6 =
}}
}}
⚫
| Section2 = {{Chembox Properties
⚫
| C=10 | H=18 | O=1
⚫
| Density = 0.889 g/cm<sup>3</sup>
⚫
| MeltingPtC = -15
⚫
| MeltingPt_ref = <ref name=GESTIS>{{GESTIS|ZVG = 491258}}</ref>
⚫
| BoilingPtC = 230
⚫
| BoilingPt_ref = <ref name=GESTIS/>
⚫
| Solubility = 686 mg/L (20&nbsp;°C)<ref name=GESTIS/>
⚫
| LogP =3.28<ref name="chemsrc">{{Cite web|url=https://www.chemsrc.com/en/cas/106-24-1_125147.html|title=Geraniol_msds}}</ref>


⚫
'''Geraniol''' is a [[monoterpenoid]] and an [[alcohol]]. It is the primary component of [[rose oil]], [[palmarosa]] oil, and [[citronella 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. The [[functional group]] derived from geraniol (in essence, geraniol lacking the terminal [[hydroxyl|−OH]]) is called '''geranyl'''.
⚫
}}
⚫
| Section3 = {{Chembox Hazards
⚫
| NFPA-H = 0
⚫
| NFPA-F = 1
⚫
| NFPA-R = 0
⚫
}}
⚫
| Section4 =
⚫
| Section5 =
⚫
| Section6 =
⚫
}}

⚫
'''Geraniol''' is a [[terpenoid|monoterpenoid]] and an [[alcohol]]. It is the primary component of [[rose oil]], [[palmarosa]] oil, and [[citronella 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. The [[functional group]] derived from geraniol (in essence, geraniol lacking the terminal [[hydroxyl|−OH]]) is called '''geranyl'''.


==Uses and occurrence==
==Uses and occurrence==
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It is a byproduct of the metabolism of [[sorbate]] and, thus, is a very unpleasant contaminant of [[wine]] if [[bacteria]] are allowed to grow in it.{{explain|date=March 2020}}
It is a byproduct of the metabolism of [[sorbate]] and, thus, is a very unpleasant contaminant of [[wine]] if [[bacteria]] are allowed to grow in it.{{explain|date=March 2020}}


== Biochemistry ==
==Biochemistry==
Geraniol is important in [[biosynthesis]] of other [[terpene]]s. For example, [[myrcene]] and [[ocimene]] are formed by dehydration and isomerization of geraniol.<ref name=UllmannEgg>{{Ullmann|first=M.|last=Eggersdorfer|title=Terpenes|doi=10.1002/14356007.a26_205}}</ref>
Geraniol is important in [[biosynthesis]] of other [[terpene]]s. For example, [[myrcene]] and [[ocimene]] are formed by dehydration and isomerization of geraniol.<ref name=UllmannEgg>{{Ullmann|first=M.|last=Eggersdorfer|title=Terpenes|doi=10.1002/14356007.a26_205}}</ref>


== Reactions ==
==Reactions==
In [[acidic]] solutions, geraniol is converted to the cyclic terpene [[terpineol|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.<ref>{{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}}</ref><ref>{{OrgSynth | author = Jose G. Calzada and John Hooz | title = Geranyl chloride| volume = 54 | pages = 63 | year=1974|doi = 10.15227/orgsyn.054.0063}}</ref> It can be hydrogenated.<ref>{{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}}</ref> It can be oxidized to the aldehyde [[Citral|geranial]].<ref>{{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}}</ref>
In [[acidic]] solutions, geraniol is converted to the cyclic terpene [[terpineol|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.<ref>{{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}}</ref><ref>{{OrgSynth | author = Jose G. Calzada and John Hooz | title = Geranyl chloride| volume = 54 | pages = 63 | year=1974|doi = 10.15227/orgsyn.054.0063}}</ref> It can be hydrogenated.<ref>{{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}}</ref> It can be oxidized to the aldehyde [[Citral|geranial]].<ref>{{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}}</ref>


== Health and safety ==
==Health and safety==
Geraniol is classified as D2B (Toxic materials causing other effects) using the [[Workplace Hazardous Materials Information System]] (WHMIS).<ref>{{cite web|url=http://www.sigmaaldrich.com/MSDS/MSDS/DisplayMSDSPage.do?country=CA&language=en&productNumber=163333&brand=ALDRICH&PageToGoToURL=http%3A%2F%2Fwww.sigmaaldrich.com%2Fcatalog%2Fsearch%3Finterface%3DAll%26term%3Dgeraniol%26N%3D0%26mode%3Dmatch%2520partialmax%26focus%3Dproduct%26lang%3Den%26region%3DCA |title=MSDS – Geraniol |publisher=Sigma-Aldrich |access-date= June 24, 2014}}</ref>
Geraniol is classified as D2B (Toxic materials causing other effects) using the [[Workplace Hazardous Materials Information System]] (WHMIS).<ref>{{cite web|url=http://www.sigmaaldrich.com/MSDS/MSDS/DisplayMSDSPage.do?country=CA&language=en&productNumber=163333&brand=ALDRICH&PageToGoToURL=http%3A%2F%2Fwww.sigmaaldrich.com%2Fcatalog%2Fsearch%3Finterface%3DAll%26term%3Dgeraniol%26N%3D0%26mode%3Dmatch%2520partialmax%26focus%3Dproduct%26lang%3Den%26region%3DCA |title=MSDS – Geraniol |publisher=Sigma-Aldrich |access-date= June 24, 2014}}</ref>


== Related compounds ==
==Related compounds==
* [[Citral]], the corresponding aldehyde
*[[Citral]], the corresponding aldehyde
* [[Nerol]], the double-bond isomer
*[[Nerol]], the double-bond isomer
* [[Rhodinol]], a related terpene alcohol
*[[Rhodinol]], a related terpene alcohol
* [[Geranyl pyrophosphate]]
*[[Geranyl pyrophosphate]]
* [[Geranylgeranyl pyrophosphate]]
*[[Geranylgeranyl pyrophosphate]]
* [[Linalool]], the isomer derived from [[transposition (mathematics)|transposition]] of the [[allylic]] [[alcohol]]
*[[Linalool]], the isomer derived from [[transposition (mathematics)|transposition]] of the [[allylic]] [[alcohol]]
* [[8-Hydroxygeraniol]], produced by action of [[geraniol 8-hydroxylase]]
*[[8-Hydroxygeraniol]], produced by action of [[geraniol 8-hydroxylase]]


== See also ==
==See also==
* [[Perfume allergy]]
*[[Perfume allergy]]


== References ==
==References==
{{reflist}}
{{reflist}}


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


{{Transient receptor potential channel modulators}}
{{Transient receptor potential channel modulators}}

Revision as of 20:17, 3 March 2021

Geraniol[1]
Geraniol
Names
IUPAC name
(2E)-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
KEGG
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]
log P 3.28[3]
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 component of rose oil, palmarosa oil, and citronella 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. The functional group derived from geraniol (in essence, geraniol lacking the terminal −OH) is called geranyl.

Uses and occurrence

In addition to 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, 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.

Geraniol is produced by the scent glands of honeybees to mark nectar-bearing flowers and locate the entrances to their hives.[4] It is also commonly used as an insect repellent, especially for mosquitoes.[5]

It is a byproduct of the metabolism of sorbate and, thus, is a very unpleasant contaminant of wine if bacteria are allowed to grow in it.[further explanation needed]

Biochemistry

Geraniol is important in biosynthesis of other terpenes. For example, myrcene and ocimene are formed by dehydration and isomerization of geraniol.[6]

Reactions

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.[7][8] It can be hydrogenated.[9] It can be oxidized to the aldehyde geranial.[10]

Health and safety

Geraniol is classified as D2B (Toxic materials causing other effects) using the Workplace Hazardous Materials Information System (WHMIS).[11]

Related compounds

See also

References

  1. ^ "Geraniol". The Merck Index (12th ed.).
  2. ^ a b c Record in the GESTIS Substance Database of the Institute for Occupational Safety and Health
  3. ^ "Geraniol_msds".
  4. ^ Danka, R. G.; Williams, J. L.; Rinderer, T. E. (1990). "A bait station for survey and detection of honey bees" (PDF). Apidologie. 21 (4): 287–292. doi:10.1051/apido:19900403.
  5. ^ Müller, Günter C.; Junnila, Amy; Kravchenko, Vasiliy D.; Revay, Edita E.; Butler, Jerry; Orlova, Olga B.; Weiss, Robert W.; Schlein, Yosef (March 2008). "Ability of essential oil candles to repel biting insects in high and low biting pressure environments". Journal of the American Mosquito Control Association. 24 (1): 154–160. doi:10.2987/8756-971X(2008)24[154:AOEOCT]2.0.CO;2. ISSN 8756-971X. PMID 18437832.
  6. ^ Eggersdorfer, M. "Terpenes". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a26_205. ISBN 978-3527306732.
  7. ^ Stork, Gilbert; Grieco, Paul A.; Gregson, Michael (1974). "Allylic Chlorides from Allylic Alcohols: Geranyl Chloride". Organic Syntheses. 54: 68. doi:10.15227/orgsyn.054.0068.
  8. ^ Jose G. Calzada and John Hooz (1974). "Geranyl chloride". Organic Syntheses. 54: 63. doi:10.15227/orgsyn.054.0063.
  9. ^ Takaya, Hidemasa; Ohta, Tetsuo; Inoue, Shin-ichi; Tokunaga, Makoto; Kitamura, Masato; Noyori, Ryoji (1995). "Asymmetric Hydrogenation of Allylic Alcohols Using Binap-Ruthenium Complexes: (S)-(−)-citronellol". Organic Syntheses. 72: 74. doi:10.15227/orgsyn.072.0074; Collected Volumes, vol. 9, p. 169.
  10. ^ Piancatelli, Giovanni; Leonelli, Francesca (2006). "Oxidation Of Nerol To Neral With Iodosobenzene and TEMPO". Organic Syntheses. 83: 18. doi:10.15227/orgsyn.083.0018.
  11. ^ "MSDS – Geraniol". Sigma-Aldrich. Retrieved June 24, 2014.

External links

Retrieved from "https://en.wikipedia.org/w/index.php?title=Geraniol&oldid=1010101959"