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{{chembox
{{chembox
| Watchedfields = changed
| verifiedrevid = 477215677
| verifiedrevid = 477215677
| Name = 2-Undecanone
| Name = 2-Undecanone
| ImageFile = 2-undecanone.svg
| ImageFile = 2-undecanone.svg
⚫
| ImageName = 2-undecanone
| ImageSize = 200px
⚫
| PIN = Undecan-2-one
⚫
| ImageName = 2-undecanone
⚫
| OtherNames = Methyl nonyl ketone (MNK)<br>Nonyl methyl ketone<br>Methyldecananone<br>2-Hendecanone<br>Undecanone<br>IBI-246
⚫
| IUPACName = Undecan-2-one
⚫
|Section1={{Chembox Identifiers
⚫
| OtherNames = Methyl nonyl ketone (MNK)<br>Nonyl methyl ketone<br>Methyldecananone<br>2-Hendecanone<br>Undecanone<br>IBI-246
⚫
| ChEBI_Ref = {{ebicite|correct|EBI}}
⚫
| Section1 = {{Chembox Identifiers
⚫
| ChEBI_Ref = {{ebicite|correct|EBI}}
| ChEBI = 17700
| ChEBI = 17700
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII_Ref = {{fdacite|correct|FDA}}
Line 15: Line 15:
| DrugBank = DB08688
| DrugBank = DB08688
| SMILES = O=C(CCCCCCCCC)C
| SMILES = O=C(CCCCCCCCC)C
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 7871
| ChemSpiderID = 7871
| KEGG_Ref = {{keggcite|correct|kegg}}
| KEGG_Ref = {{keggcite|correct|kegg}}
| KEGG = C01875
| KEGG = C01875
| PubChem = 8163
| EC_number = 203-937-5
| ChEMBL = 1236582
| 3DMet = B00364
| InChI = 1/C11H22O/c1-3-4-5-6-7-8-9-10-11(2)12/h3-10H2,1-2H3
| InChI = 1/C11H22O/c1-3-4-5-6-7-8-9-10-11(2)12/h3-10H2,1-2H3
| InChIKey = KYWIYKKSMDLRDC-UHFFFAOYAV
| InChIKey = KYWIYKKSMDLRDC-UHFFFAOYAV
Line 27: Line 31:
| CASNo_Ref = {{cascite|correct|CAS}}
| CASNo_Ref = {{cascite|correct|CAS}}
| CASNo = 112-12-9
| CASNo = 112-12-9
| RTECS = YQ2820000
| RTECS = YQ2820000
}}
}}
| Section2 = {{Chembox Properties
|Section2={{Chembox Properties
| C=11|H=22|O=1
| C=11 | H=22 | O=1
| Appearance = Colorless or pale yellow liquid
| Appearance = Colorless liquid
| Density = 0.829 g/cm³, liquid
| Density = 0.829 g/cm<sup>3</sup>, liquid
| Solubility = 0.00179 g/100 mL (25 °C)
| Solubility = 0.00179 g/100 mL (25 °C)
| MeltingPtC = 15
| MeltingPtC = 15
| BoilingPtC = 231
| BoilingPtC = 231
}}
}}
| Section7 = {{Chembox Hazards
|Section7={{Chembox Hazards
| ExternalMSDS = [http://msds.chem.ox.ac.uk/UN/2-undecanone.html External MSDS]
| ExternalSDS = [http://msds.chem.ox.ac.uk/UN/2-undecanone.html External MSDS]
⚫
| NFPA-H = 1
| EUClass = Flammable ('''F''')<br />Irritant ('''Xi''')
| NFPA-H = 1
| NFPA-F = 2
| NFPA-F = 2
| NFPA-R =
| GHSPictograms = {{GHS09}}
⚫
| NFPA-R =
| GHSSignalWord = Warning
| RPhrases = {{R50}} {{R51}}
| SPhrases = {{S23}} {{S24}} {{S25}}
| HPhrases = {{H-phrases|400}}
| PPhrases = {{P-phrases|273|391|501}}
| FlashPtC = 88
| FlashPtC = 88
}}
}}
| Section8 = {{Chembox Related
|Section8={{Chembox Related
| Function = [[Ketone]]s
| OtherFunction_label = [[Ketone]]s
| OtherFunctn = [[Acetone]]<br />[[Butanone|Butan-2-one]]<br>[[3-Pentanone|3-pentanone]]
| OtherFunction = [[Acetone]]<br />[[Butanone|Butan-2-one]]<br>[[3-Pentanone|3-pentanone]]
}}
}}
}}
}}


'''2-Undecanone''', also known as '''methyl nonyl ketone''' and '''IBI-246''', is an oily [[organic chemistry|organic]] liquid manufactured synthetically, but which can also be extracted from oil of [[rue]]. It is found naturally in [[banana]]s, [[clove]]s, [[ginger]], [[guava]], [[strawberries]], wild-grown [[tomato]]es, and the perennial ''[[Houttuynia cordata]]''.<ref name=gcmsav>{{cite journal
'''2-Undecanone''', also known as '''methyl nonyl ketone''' and '''IBI-246''', is the [[organic compound]] with the formula CH<sub>3</sub>C(O)C<sub>9</sub>H<sub>19</sub>. It a colorless oil. It is usually produced synthetically, but it can also be extracted from various plant sources, including from essential oil of [[rue]]. It is found naturally in [[banana]]s, [[clove]]s, [[ginger]], [[guava]], [[strawberries]], wild-grown [[tomato]]es, and the perennial leaf vegetable ''[[Houttuynia cordata]]''.<ref name=gcmsav>{{cite journal
| last = Liang
| last1 = Liang
| first = Minmin
| first1 = Minmin
| last2 = Qi
| last2 = Qi
| first2 = M
| first2 = M
| last3 = Zhang
| last3 = Zhang
| first3 = C
| first3 = C
| last4 = Zhou
| last4 = Zhou
| first4 = S
| first4 = S
| last5 = Fu
| last5 = Fu
| first5 = R
| first5 = R
| last6 = Huang
| last6 = Huang
| first6 = J
| first6 = J| title = Gas chromatography–mass spectrometry analysis of volatile compounds from Houttuynia cordata Thunb after extraction by solid-phase microextraction, flash evaporation and steam distillation
| title = Gas chromatography–mass spectrometry analysis of volatile compounds from Houttuynia cordata Thunb after extraction by solid-phase microextraction, flash evaporation and steam distillation
| journal = [[Analytica Chimica Acta]]
| journal = [[Analytica Chimica Acta]]
| volume = 531
| issue = 1
| volume = 531
| pages = 97–104
| issue = 1
| pages = 97–104
| publisher =
| year = 2005
| url = http://ir.rcees.ac.cn/handle/311016/23180
| location =
| doi = 10.1016/j.aca.2004.09.082
| year = 2005
| bibcode = 2005AcAC..531...97L
| url =
| doi = 10.1016/j.aca.2004.09.082|display-authors=etal}}</ref>
| display-authors = etal
| access-date = 2024-02-02
| archive-date = 2020-09-14
| archive-url = https://web.archive.org/web/20200914184859/http://ir.rcees.ac.cn/handle/311016/23180
| url-status = dead
}}</ref>


==Uses==
==Uses==
2-Undecanone is used in the [[perfumery]] and [[flavoring]] industries, but because of its strong odor it is primarily used as an [[insect repellent]] or [[animal repellent]]. Typically, 1&ndash;2% concentrations of 2-undecanone are found in dog and cat repellents in the form of a liquid, [[aerosol spray]], or gel.
Because of its strong odor it is primarily used as an [[insect repellent]] or [[animal repellent]]. Typically, 1&ndash;2% concentrations of 2-undecanone are found in dog and cat repellents in the form of a liquid, [[aerosol spray]], or gel. 2-Undecanone is also used in the [[perfumery]] and [[flavoring]] industries.


Research from North Carolina State University has shown that it may be useful as a [[mosquito]] repellent, as effective as, or even more effective than, [[DEET]].<ref>[http://www.sciencedaily.com/releases/2002/06/020611070622.htm Mosquitoes Repelled By Tomato-Based Substance; Safer, More Effective Than DEET], ''Science Daily'', June 2002</ref><ref>{{cite journal | journal = Pesticide Broadcast | author = Stephen J. Toth, Jr. and Wayne G. Buhler | volume = 12 | issue = 5 | year = 2002 | title = North Carolina State University Scientist Discovers Mosquito Repellent in Tomatoes | url = http://ipm.ncsu.edu/current_ipm/Broadcasts/broadcast06-02b.html}}</ref>
It has been investigated as a mosquito repellant, like [[DEET]].<ref>[https://www.sciencedaily.com/releases/2002/06/020611070622.htm Mosquitoes Repelled By Tomato-Based Substance; Safer, More Effective Than DEET] {{Webarchive|url=https://web.archive.org/web/20230928005519/https://www.sciencedaily.com/releases/2002/06/020611070622.htm |date=2023-09-28 }}, ''Science Daily'', June 2002</ref><ref>{{cite journal | journal = Pesticide Broadcast | author = Stephen J. Toth, Jr. and Wayne G. Buhler | volume = 12 | issue = 5 | year = 2002 | title = North Carolina State University Scientist Discovers Mosquito Repellent in Tomatoes | url = http://ipm.ncsu.edu/current_ipm/Broadcasts/broadcast06-02b.html | access-date = 2009-01-24 | archive-date = 2008-05-13 | archive-url = https://web.archive.org/web/20080513030943/http://ipm.ncsu.edu/current_ipm/Broadcasts/broadcast06-02b.html | url-status = live }}</ref>


==Chemical properties==
==Chemical properties==
2-Undecanone is a [[ketone]] that is soluble in [[ethanol]], [[benzene]], [[chloroform]], and [[acetone]], but its large carbon chain renders it insoluble in water. Like most [[methyl]] [[ketone]]s, 2-undecanone undergoes a [[haloform reaction]] when in the presence of a basic solution of hypochlorite. For example, the reaction between 2-undecanone and [[sodium hypochlorite]] yields [[sodium decanoate]], [[chloroform]], and [[sodium hydroxide]].
2-Undecanone is a [[ketone]] that is soluble in [[organic solvents]] but insoluble in water. Like most [[methyl]] [[ketone]]s, 2-undecanone undergoes a [[haloform reaction]] when in the presence of a basic solution of hypochlorite. For example, the reaction between 2-undecanone and [[sodium hypochlorite]] yields [[sodium decanoate]], [[chloroform]], and [[sodium hydroxide]].


:CH<sub>3</sub>CO(CH<sub>2</sub>)<sub>8</sub>CH<sub>3</sub> + 3 NaOCl → CH<sub>3</sub>(CH<sub>2</sub>)<sub>8</sub>COONa + CHCl<sub>3</sub> + 2 NaOH
:CH<sub>3</sub>CO(CH<sub>2</sub>)<sub>8</sub>CH<sub>3</sub> + 3 NaOCl → CH<sub>3</sub>(CH<sub>2</sub>)<sub>8</sub>COONa + CHCl<sub>3</sub> + 2 NaOH
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* ''The Condensed Chemical Dictionary (10th Edition)'', Gesner G. Hawley
* ''The Condensed Chemical Dictionary (10th Edition)'', Gesner G. Hawley
* [http://www.thegoodscentscompany.com/data/rw1021151.html 2-Undecanone] from The Good Scents Company
* [http://www.thegoodscentscompany.com/data/rw1021151.html 2-Undecanone] from The Good Scents Company
* [http://www.albochem.com/wps/wp-content/2009/01/mnkmsds.pdf MSDS for 2-Undecanone]
* [http://www.albochem.com/wps/wp-content/2009/01/mnkmsds.pdf MSDS for 2-Undecanone]{{Dead link|date=March 2019 |bot=InternetArchiveBot |fix-attempted=yes }}


{{DEFAULTSORT:Undecanone, 2-}}
{{DEFAULTSORT:Undecanone, 2-}}
[[Category:Dialkylketones]]
[[Category:Alkanones]]
[[Category:Insect repellents]]
[[Category:Insect repellents]]

Latest revision as of 17:46, 19 June 2024

2-Undecanone
2-undecanone
Names
Preferred IUPAC name
Undecan-2-one
Other names
Methyl nonyl ketone (MNK)
Nonyl methyl ketone
Methyldecananone
2-Hendecanone
Undecanone
IBI-246
Identifiers
3D model (JSmol)
3DMet
ChEBI
ChEMBL
ChemSpider
DrugBank
ECHA InfoCard 100.003.579 Edit this at Wikidata
EC Number
  • 203-937-5
KEGG
RTECS number
  • YQ2820000
UNII
  • InChI=1S/C11H22O/c1-3-4-5-6-7-8-9-10-11(2)12/h3-10H2,1-2H3 checkY
    Key: KYWIYKKSMDLRDC-UHFFFAOYSA-N checkY
  • InChI=1/C11H22O/c1-3-4-5-6-7-8-9-10-11(2)12/h3-10H2,1-2H3
    Key: KYWIYKKSMDLRDC-UHFFFAOYAV
  • O=C(CCCCCCCCC)C
Properties
C11H22O
Molar mass 170.296 g·mol−1
Appearance Colorless liquid
Density 0.829 g/cm3, liquid
Melting point 15 °C (59 °F; 288 K)
Boiling point 231 °C (448 °F; 504 K)
0.00179 g/100 mL (25 °C)
Hazards
GHS labelling:
GHS09: Environmental hazard
Warning
H400
P273, P391, P501
NFPA 704 (fire diamond)
NFPA 704 four-colored diamondHealth 1: Exposure would cause irritation but only minor residual injury. E.g. turpentineFlammability 2: Must be moderately heated or exposed to relatively high ambient temperature before ignition can occur. Flash point between 38 and 93 °C (100 and 200 °F). E.g. diesel fuelInstability (yellow): no hazard codeSpecial hazards (white): no code
1
2
Flash point 88 °C (190 °F; 361 K)
Safety data sheet (SDS) External MSDS
Related compounds
Related Ketones
 Acetone
Butan-2-one
3-pentanone
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
checkY verify (what is checkY☒N ?)

2-Undecanone, also known as methyl nonyl ketone and IBI-246, is the organic compound with the formula CH3C(O)C9H19. It a colorless oil. It is usually produced synthetically, but it can also be extracted from various plant sources, including from essential oil of rue. It is found naturally in bananas, cloves, ginger, guava, strawberries, wild-grown tomatoes, and the perennial leaf vegetable Houttuynia cordata.[1]

Uses

[edit]

Because of its strong odor it is primarily used as an insect repellent or animal repellent. Typically, 1–2% concentrations of 2-undecanone are found in dog and cat repellents in the form of a liquid, aerosol spray, or gel. 2-Undecanone is also used in the perfumery and flavoring industries.

It has been investigated as a mosquito repellant, like DEET.[2][3]

Chemical properties

[edit]

2-Undecanone is a ketone that is soluble in organic solvents but insoluble in water. Like most methyl ketones, 2-undecanone undergoes a haloform reaction when in the presence of a basic solution of hypochlorite. For example, the reaction between 2-undecanone and sodium hypochlorite yields sodium decanoate, chloroform, and sodium hydroxide.

CH3CO(CH2)8CH3 + 3 NaOCl → CH3(CH2)8COONa + CHCl3 + 2 NaOH

See also

[edit]

Notes

[edit]
  1. ^ Liang, Minmin; Qi, M; Zhang, C; Zhou, S; Fu, R; Huang, J; et al. (2005). "Gas chromatography–mass spectrometry analysis of volatile compounds from Houttuynia cordata Thunb after extraction by solid-phase microextraction, flash evaporation and steam distillation". Analytica Chimica Acta. 531 (1): 97–104. Bibcode:2005AcAC..531...97L. doi:10.1016/j.aca.2004.09.082. Archived from the original on 2020-09-14. Retrieved 2024-02-02.
  2. ^ Mosquitoes Repelled By Tomato-Based Substance; Safer, More Effective Than DEET Archived 2023-09-28 at the Wayback Machine, Science Daily, June 2002
  3. ^ Stephen J. Toth, Jr. and Wayne G. Buhler (2002). "North Carolina State University Scientist Discovers Mosquito Repellent in Tomatoes". Pesticide Broadcast. 12 (5). Archived from the original on 2008-05-13. Retrieved 2009-01-24.

References

[edit]
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